The last few months since my last entry in this series have been eventful, though, perhaps not terribly productive in a traditional sense. After a month of respite in California and then New York City, I have, at long last, made my way to France where I am endeavoring to reach conversational fluency in French while also making progress toward business profitability.

In the intervening months I have:

  • Become a licensed motorcyclist in the state of California

    A view of Half Dome in the distance in Yosemite Valley.

  • Organized a trip to Yosemite with many of my friends from Silicon Valley
  • Attended my sister’s graduation from NYU
  • Explored the wilderness in rural Pennsylvania
  • Stayed in Marseille, France for 2 weeks
  • Mastered driving a stick shift while driving thousands of kilometers across France to visit Lyon, Haut-Jura, Auxerre, Beaune, Dole, Dijon, Fontainebleau, Paris, Mont Saint-Michel, Tours, Amboise, and Chambord
  • Lived in Bordeaux, France for nearly 2 weeks
  • Taken on two small consulting projects with a potential third on the horizon
  • Attended 2 weeks of the summer mindfulness retreat at Plum Village
  • Gone from absolutely terrified to speak to anyone in French to being able to hold a reasonable conversation provided some effort on both sides

As is the nature of things, along the way many things have gone wrong including:

  • Having my prized Google Pixel 2 smartphone stolen while I watched the sunset in Marseille
  • Enduring a difficult and complicated breakup with my Vietnamese girlfriend (the circumstances of which, both for my privacy and out of respect for her, I won’t be elaborating on at this time)
  • Having my expensive and supposedly high quality Samsonite suitcase completely break in less than 6 months of—admittedly heavy—use


Fallingwater, a Frank Lloyd Wright house in rural Pennsylvania.

I, of course, have much to say about France in general, and the cities I’ve had the chance to get to know, but for concision—and for SEO :P—I’ve decided to separate these thoughts into a yet-to-be-written series of posts about what it’s actually like to be a nomad in different cities. In these posts I’ll aim to answer questions about the cost of living, finding internet and good places to work, securing housing, social outlets, and just cool things to see and do. I’ve found that there are lots of high-level resources like NomadList for nomads to choose new destinations, but there are never enough narratives to give life to the statistics, especially in less common and ostensibly less affordable destinations like the vast majority of Europe.

For now, it suffices to say that France is expensive and good internet is surprisingly hard to find. It doesn’t even begin to compare to how expensive it was in Silicon Valley, but it’s certainly 3-6 times more expensive than Southeast Asia, which I’m increasingly realizing has completely spoiled me. From a lifestyle perspective, I’ve found that since I’m not willing to pay 10€ for an average meal out, it’s advantageous to cook or buy simple picnic ingredients from grocery stores. In a funny way, I’ve been really pleased to find how much joy I can get out of a simple meal of bread, cheese, fruit, and a little bit of meat (<3€/meal). I find it liberating to learn how little I really need to be happy, which leaves me yet again questioning the typical American ethos of working hard for the sake of work or for the sake of money to purchase possessions which we often become convinced will somehow magically produce happiness and joy.

The view approaching Mont Saint-Michel during low-tide.

Despite its status as a first-world nation, internet infrastructure in France is surprisingly pitiful in comparison to Thailand and Vietnam. Perhaps this difference is more cultural than anything, but most French cafes are not very accommodating for those seeking a nice environment to hangout with coffee, power, and a good internet connection. Even those cafes which are more stereotypically configured for this use case (i.e. pretty much just Starbucks) have laughable speeds and questionable reliability. The coworking spaces are also typically much more expensive here (200-300€/month) than what I’ve become accustomed to finding in Asia (70-150€/month).

Learning French

I’ve spent much of my time on the ground here in France trying to take advantage of the immersive environment for learning French. On good days, I’ll find myself spending nearly 4 hours a day learning French with a mix of book studying, language exchange meet-ups, reverse and ladder trees on Duolingo, reading on LingQ (affiliate link!), listening to French podcasts (e.g. Coffee Break French), and re-watching my favorite Netflix series in French audio (sometimes with, sometimes without French subtitles).

Sometimes it’s hard to see the difference day-to-day, but reflecting on it I’ve realized my French has come a long way. When I got here, I experienced a sort of social anxiety around speaking to anyone because I was pretty terrified of embarrassing myself in French but didn’t want to speak English either. It used to be a big deal for me to even buy something small from a store in French and not go deer-in-headlights a little when someone asked me if I wanted a bag using a word for “bag” I had never learned before :P.

Now I’ve had a bit more experience and, though fast-talking native speakers still give me a lot of trouble, I’m finding I understand enough to hold reasonable conversations. I often have to stop and ask for a repetition or the meaning of a word or ask how to say a word in French, but I can do all of these things in French at this point. Sometimes I also still struggle with piecing my sentences together, but I’ve noticed that some sentences and sentence structures have become surprisingly fluent.

There’s a long way to go still, but I’ve been able to accomplish things like getting tourist information about a new city, teaching a child how to play chess, and holding a 45-minute introductory conversation with a fellow software engineer using nearly nothing but French. People are generally finding me understandable even when I struggle to express complex ideas. I think it’s fair to say that I’ve moved into a phase where I can now truly learn new words and phrases from real conversations with native speakers where we’re actually trying to get to know each other.

Plum Village

A close-up of the lotus pond in the Lower Hamlet of Plum Village.

I’ve just returned from 2 weeks at Plum Village, a Mindfulness Practice Center and Buddhist Monastery founded by the famous Vietnamese Zen Buddhist master Thich Nhat Hanh, a Nobel peace prize nominee (nominated by Martin Luther King, Jr.!) and an important advocate for peace during the Vietnam War. I was fortunate to find space at Plum Village—when I had checked originally it was completely booked. I ended up finding a way to nab a one-week stay in Plum Village, and then once I was there I found a way to extend my stay by an extra week.

A full accounting of my experience at Plum Village is also going to have to wait until next week. For now I’ll say that it was one of my goals this year to deepen my mindfulness practice, which is the primary reason why I made my way to Plum Village in the first place. All-in-all, my experience there was magnificent and I feel as if I view myself and the world differently in subtle but very important ways. I feel as if before I had only just scratched the surface of what mindfulness could do for me and now I’ve been exposed to its full potential. I’m more focused, more mindful, and more present than I ever was before. I’m increasingly aware of my own unmindful and potentially self-destructive habits and aware of important sources of unhappiness in my life which I’m now committed to resolving rather than perpetually avoiding. I feel more competent in handling my emotions and anxieties, including the stresses related to my current occupational choices. Time will tell how long these effects will stay with me.

Where I Am Now

The obelisk at the Place des Quinconces, near the center of Bordeaux.

I have returned to Bordeaux for a bit of sightseeing before I take a train to Lyon, the gastronomic capital of France, where I intend to spend my remaining 5 weeks in France before my Schengen tourist visa expires and I’m forced to migrate elsewhere. I’m excited to have my own apartment in Lyon after successfully negotiating the price down by ~25% from its listing price on AirBnB.

I haven’t made much progress on my own projects of late, and my lack of a live product continues to be a source of frustration for me. In the States, my time was focused on things I could only take care of while there or spending time with family. Since coming to France, much of my time initially was spent on dealing with the emotional fallout of my recent relationship or on learning French. The few times I’ve taken the time to open my code editor and start to work on Serenity, I’ve found it overwhelming to consider the amount of remaining effort to launch the product along with the potentially low likelihood of a successful outcome.

I must admit that prior to going to Plum Village, my mood had been fluctuating and occasionally visiting some deep lows. The combination of emotional stressors from my recent breakup along with the anxieties involved with having to speak French and starting to get back into my own work was a lot to handle, and I’d guess that I came the closest I’d ever been to wanting to abandon my present course. I knew the emotions would pass however, and, somewhat serendipitously, in my lowest week I had two people reach out to me in the same day asking if I’d be willing to consider some short-term work on a consulting basis. I’ve agreed to one, and am still working out the details of the other, which may involve my returning to Asia later this year. I’m also currently helping my little sister implement an online portfolio for her creative work so that she can use it as a resource to send to potential employers. Helping her get situated in her post-graduate life in this way was one of the gifts I offered her upon graduating.

La Cité du Vin, an ultra-modern museum all about the history and culture of wine in Bordeaux.

Having outside work recently has helped a lot to remind me that I have a valuable skill set in high demand and that I’m good at what I do. I’ve found it comforting to have a few more concrete and complete projects to show for my time (now almost a full year!) being self-employed. Combined with the emotional bolstering of my experience in Plum Village, I’m back in a good place and am excited for the challenge of learning to apply mindfulness to my unorthodox lifestyle.

The “Plan”

In my remaining 5 weeks in France, I’m hoping to wrap up work for my sister (her dream job was just posted, so we’re now operating on a clock), potentially take on another small project for an existing client, work out details for another potentially larger project for a new client, and attempt to launch Serenity to at least friends and family if not to public beta. All the while, it will continue to remain a high priority to make use of my time in France to improve my French.

I’m still exploring the possibilities, there’s a possibility that an opportunity will bring me back to Asia after France in mid-September or early October. I’m thinking that in the intervening time I may go to Morocco as originally planned, though I haven’t chosen a city yet (Essaouira maybe?). If I end up back in Asia, it probably makes sense to stay for a number of months, so I’m considering returning to Thailand, visiting India and Nepal, spending some time in Hong Kong or Malaysia, or even living in Taiwan or rural Japan for a few months to learn languages. If the opportunity doesn’t shake out the right way, I’ll likely spend 3 full months in Morocco continuing to work on my French before considering a return to France or moving on to South America.

I’m finding I plan less and less far ahead travel-wise, and this no longer makes me anxious the way it would have last year. In fact, the flexibility this sort of seat-of-pants traveling has afforded me seems to have far outweighed the possible price increases from last-minute bookings (at least on everything other than air travel).

Vietnam is a country with a rich but turbulent history. It’s lived through occupation by the Chinese, the French, and the Americans as recent as two generations ago. Foreign cultural influence and scars from not-yet-forgotten conflicts blend to make Saigon, known at its peak as the “Pearl of the Far East,” a complex and deeply interesting city.

Amongst digital nomads, however, its southern capital, Saigon (aka Ho Chi Minh City), is a polarizing and controversial place: some love it enough to settle here for months or years at a time, while others leave quickly and never give it a second thought. A short walk down any street obviates the reasons for this: one’s senses are swiftly overloaded–motorbikes whiz around, narrowly missing each other and any uninitiated pedestrians who dare to cross; the sounds of horns and honking are present at all hours of day, as are the clarion calls of street side vendors; smells of delicious meals from any number of amazing local joints waft through the air, mixing with and ameliorating the common odors of waste, vomit, and urine; heat and humidity compound with dust and debris to create an often hot, dirty, and uncomfortable environment.

To an outsider, Saigon can look and feel like untamed, unfettered chaos. And yet, in the time I’ve lived here I’ve found myself mesmerized by the energy of this city. It’s chaotic, yes, but it makes me feel alive. So much so, in fact, that I decided early in my stay here to skip spending the month of April in Penang, Malaysia, and instead extended my time in Saigon to two months. (There are, of course, other good reasons for having done this: the time, financial, and mental costs of switching locations every month turn out to make 2-3 months a more ideal amount of time to spend in each place when also trying to get work done.)

Unlike Chiang Mai, which, despite being the second largest population center in Thailand, had a distinctively “small town” feel to it, Saigon is a true, full-blown city, and it turns out to be the first city I’ve ever lived in for any real amount of time. I’ve been surprised by how much I enjoy the city lifestyle here–in the past I’ve always preferred sleepy college towns and quiet suburbs with easy access to nature. While Saigon doesn’t have much to offer tourists passing through for

Bánh xèo–a savory crepe-like Vietnamese dish

just a few days, it does have a slew of interesting coffee shops, bars, and live music venues for the slower-paced traveler or longer-term expat to experience. There’s also a lush variety of foods to sample from all over the country–Vietnamese food is, as it turns out, much more diverse than the typical phở and bánh mì sorely under representing this cuisine in the States–certainly more than one could experience in weeks, months, or even years here.



Cost of Living

Despite being a city, Saigon is quite affordable, making it a prime location for potential expats and digital nomads. A month’s rent in a serviced apartment close to the city center runs typically between $300 and $400/mo, while meals can be found for anywhere between $.75 (street food) and $30/meal (an upscale restaurant). A membership at a good coworking space with a flexible desk runs $90/mo. Braver travelers can rent a motorbike for ~$60/mo or purchase and re-sell for around $250. By my estimation a nomad really looking to save, or an entrepreneur seeking to extend her runway could live a decent life in Saigon for under $700/mo (less, even, if you’re willing to pinch pennies).

People and Community

Frustrated and angry bloggers sometimes give Vietnam and the Vietnamese people a bad wrap. Personally, I’ve had a lot of great experiences with both Vietnamese locals and the expat community in Saigon, so I feel I have a responsibility to set the record straight.


Some people hear stories about swindlers and hustlers in Vietnam–people who will overcharge tourists because they don’t speak the language, for example–and imagine that all Vietnamese people are liars and cheats. Of course, as is the case anywhere one might go in the world, these people do exist, and one should exercise caution and common sense when traveling. These people are, however, far from a majority. Most Vietnamese people I’ve met–business owners, students, Viet Kieu–have impressed me with their kindness, their generosity, their work ethic, and their optimism. One student even befriended me, showed me around, and came back to help me when my motorbike broke down during a long road trip back to Saigon. I would honestly not have known what to do without his help.

As an American, I find it especially encouraging how little animosity anyone ever showed me despite the fact that the Vietnam War (known in Vietnam as the American War) happened so recently–if anything there was a distinctly pro-American sentiment, especially among the younger generation. Though war is terrible, I find myself hopeful knowing that in just a few generations two peoples that were previously in conflict can so easily forgive and forget the transgressions made by their forebears.

To be fair to all involved, however, as an Asian American I likely have a different experience in Asia than other Western travelers do. Everywhere I’ve visited in Asia so far I’ve been mistaken for a local until I opened my mouth to speak, and since most Asian cultures have similar customs and values, my pseudo-Asian upbringing helps me relate to these people more naturally.

Entrepreneurs and Expats

One of the initial reasons I chose Saigon is because I read that it has more of an entrepreneurial community than some of the other hubs for digital nomads like Chiang Mai. Saigon is, indeed,  home to an up and coming tech scene in one of the fastest growing economies in the world. There is, however, still much room for the entrepreneurial scene in Saigon to grow and evolve–it doesn’t yet have the same energy, infrastructure, or prevalence as it does in Silicon Valley.

Nevertheless, there are at least a few pockets of very interesting people. In my opinion, Start Coworking Campus, where I chose to both live and work for the majority of my time in Saigon, is one of those places. Admittedly, I didn’t know much about Start when I booked my room there in December–I chose them because I wanted to try something new with coliving, and because their marketing promised a heavy emphasis on community, which can be hard to find while moving around. I was super pleasantly surprised by Start, and I honestly can’t rave about them enough. They deliver well on their promise of community, with daily community lunches and plenty of events throughout the month.

Most, but not all, of the people I met at Start were somehow related to tech, though not all of them were actually nomads. Saigon is home to quite a few long-term expats–sometimes former nomads–many of whom form a consistent backbone for community at Start despite a constantly rotating cast of travelers. After just a few weeks there, I really felt that I knew all of the regular faces, and after two months I felt that I had made some cool friends with whom I hope very much to keep in touch. Over lunch and during random breaks throughout the day, I’d often find myself engaging in deeply interesting conversations about a wide variety of topics, including political theory, global economics, philosophy, and current trends in tech. I can’t be sure because I haven’t yet seen that much, but I have a strong hunch that communities like this are pretty rare to find.


Just as I’ve been searching for a sense of community while abroad, I’ve also been experimenting with dating and romantic companionship. When I left the States to become a nomad, I expected that doing so meant I’d realistically have to put romance on hold until I settled back down in a single place. I felt that the odds of finding someone right for me while abroad, and the difficulty of pursuing something serious or long-term while moving around simply left real romance out of the question, but perhaps there was no reason not to experiment anyway. Much to my surprise, this turned out to just be the latest in what’s becoming a long string of false assumptions I made about traveling and the nomadic lifestyle–it didn’t take me long to fall in love with a beautiful, intelligent, and deeply reflective local Vietnamese entrepreneur.

When I landed in Vietnam, the differences in the dating scene struck me almost immediately–whereas in Chiang Mai and Silicon Valley I’ve often found dating frustrating, I quickly had four dates scheduled for my first week in Saigon. For the first time in my life I felt like I had more dating prospects than I could possibly have time to talk to, a complaint I normally only ever hear from my girl friends. It also felt easier than ever to open conversations and get dates scheduled.

Some of the difference could perhaps be attributed to me and a general mindset shift on dating: in the interest of putting myself in uncomfortable situations and learning more about dating, I decided to be more open-minded about first dates and made it a goal to quickly push for an in-person meeting with any girl I messaged back and forth with. Most of this, however, is likely attributable to Saigon and its particular dating pool: I tend to be more popular with Asian women, and densely populated international cities tend to have more young single women who speak English confidently enough to communicate. (By contrast, Chiang Mai was a much smaller city notably lacking in English-speaking confidence.)

Despite having more options than ever, I met the woman who would become my girlfriend on literally the second night I was in Saigon. In fact, she was the first date I went on in my new city, and probably the first local Vietnamese woman I’d really interacted with.

As is becoming more and more cliché these days, we met on Tinder. My expectations were pretty low, and our pre-date conversation barely had an ounce of substance to it, but I wanted to push myself out of the comfort zone so I asked her on a date anyway. To my surprise, she agreed to a hastily scheduled date for later that same night, and not two hours later I found myself walking anxiously to a craft brewery in the center of town.

I remember being terrified on my way to our first date–not because I felt nervous about impressing her, but because a couple of things she had said and done left me super confused about what to expect. Most of my pre-date anxiety centered around the fears that she wouldn’t look like her photos (this happened to me in Chiang Mai), that I’d get stuck in an awkward conversation with a weirdo or, worse, that I’d somehow get murdered. (Hey, I’m not proud of that thought, but I was in an entirely new city and my brain was running wild with catastrophic worst-case scenarios :P.)

When I walked in I was pleasantly surprised to find a woman whose beauty and personality would be hard to fully and accurately portray in still photography. She was funny and made me laugh easily (she’d later tell me that she thought I was laughing way too hard at her shitty jokes, but I honestly found them that funny). It turned out we’re both tech entrepreneurs–her as a designer and a product manager, me as a jack-of-all-trades software engineer–and could understand each other’s careers and daily job struggles. She shared a lot of my interests as well, and it quickly became apparent that we had extremely congruous mindsets, perspectives, and worldviews.

In short, I wasn’t sure what to expect at first but I was totally and completely blown away by the time I parted ways with her nearly four hours later. In fact, I was so blown away that I was almost scared in the opposite sense from before–things just seemed too uncannily similar and way too good to be true. I felt like either I had been super thoroughly stalked or the perfect woman had somehow just manifested before my eyes.

For awhile now, I’ve professed my belief in the law of “fuck yes or no”–if my gut doesn’t scream “fuck yes” about someone I don’t pursue them further. At that point, however, I’d never experienced a true “fuck yes” after a first date with a total stranger, and I’d been on enough first dates to begin to wonder whether or not the bar for going on a second date had been set too high–after all, maybe sometimes one just needs a couple of lukewarm experiences before a deeper connection can occur. My first date with this girl proved to me that the bar for second dates was, in fact, not set too high. She was a total and complete “fuck yes,” and now that I know that that’s possible I don’t think I’d ever want to settle for less.

Though I did go on dates with a few other women, I very quickly lost interest in anyone but her. She continued to be a “fuck yes” for me for many, many more dates and I’m now proud and excited to call her my girlfriend. She understands, challenges, pushes, and inspires me all in ways I didn’t know I could expect from a partner. Meeting her and choosing to enter a committed relationship with her has also tested some of my self-perceptions and my worldview.

Some of my past dating experiences left me questioning both my adequacy and my competency to meet and charm a potential partner through the silly, awkward dance we call modern dating. In particular, the last time I dated someone with serious intentions, through no purposeful fault of either party, it left me feeling like I didn’t know what I was doing, and like experiencing the kind of connection I hoped for with someone I found extremely attractive might be impossible for me without further growth. With my new girlfriend, though, I’ve come to realize that I am already enough, and that, with the right person, it should always feel that way. I shouldn’t need to feel like I have to constantly pursue someone to win their approval–the attraction can and should be mutual enough that a connection develops smoothly and naturally on its own.

Wanting something real and serious with my new girlfriend does leave me with new questions about where and how love fits into my larger worldview, however. Much of my personal philosophy centers around maximizing authenticity and growth. These are easy things to solve for independently, when one has no responsibilities or other people to consider, but they become complicated when a romantic partner enters the picture. Prior to coming to Saigon and meeting my new girlfriend, I thought that I might travel around the world and work for myself for a few years, chasing growth and adventure wherever it waits to be found. I thought I’d have at least a few years before I might meet anyone serious (I never expected to fall in love on the road).

Having found her though, I find myself faced with the serious question of returning to Saigon to spend more time with her in the near future. I know that successful relationships occasionally require sacrifice and compromise, so I find myself asking what I can and can’t authentically compromise on. If being with her means sacrificing some amount of travel and exploration, can I justify that at this point in my life? But even as I consider giving up on growth from exploration, I find myself wondering how our relationship might allow us to help each other grow and become even more authentic versions of ourselves. If we’re not careful, though, could it do just the opposite?

I also find myself asking questions about the implications of falling for a foreign woman in a land far away from where I previously called home, though I know it’s too early to be thinking super long-term about such a young relationship. Before meeting her I always just assumed I’d probably meet a nice American woman some day, and we’d probably settle down in the States. I never really had a good reason to think this, it’s just one of those assumptions that fills a space and goes unchallenged for a long time. Now, however, that idea is being questioned and replaced with a more globally inclusive idea of what it might mean to settle down with someone someday.

Some of these questions frighten me, and I don’t have great answers to most of them. I am, regardless, excited to find myself and my perspective being pushed in new and completely unexpected ways–ways they never could have when I was just an unattached solo traveler. My girlfriend and I are long distance right now, as I’m back in the States and still have plans to travel to France for at least 3 months before I might consider returning to Asia. Though I know the distance will be hard, and relationships are an art, I’m very much hoping that she and I will have a chance to explore answers to these questions together, one step at a time.


Saigon is a large city, organized into 12 numbered districts and several more named ones–this sometimes gives running around the city an oddly Hunger Games-like feeling–but even so is less of an adventure-driven place than Chiang Mai, with fewer grand, iconic, and touristy things to do. It does, nevertheless, make for a great homebase to explore the South of Vietnam, and if you’re willing to dig a little bit there are fascinating and beautiful remnants of a culture extant in Saigon before much of its recent history, which hauntingly feels as if it is slowly slipping away as the younger generations forget. Since I spent a lot of time dating in Saigon, I also found that it can be a very romantic city, though many of the city’s best spots are hidden away off street level, and would have been very difficult for me to find without a local.

The many districts of Saigon

Live Music

Saigon turns out to be a city full of music, and there are quite a few cool places to go for different kinds of music. My personal favorites were the places where they’d sing old Saigonese songs from before the War. Most of the music in this time period is incredibly beautiful even not being able to understand the music, and really creates the sense of haunting nostalgia I alluded to earlier.

Cafe Vừng ơi, Mở ra

17 Ngô Thời Nhiệm, phường 6, Quận 3, Ho Chi Minh City, Vietnam

In English, the name of this place translates to “Open, Sesame.” My now girlfriend brought me here on our fourth date and it blew my mind. To find this place, one has to walk through a pretty sketchy alleyway, then through a rather nondescript door and up several flights of stairs. I like to joke with my girlfriend that she brought me here to murder me, but then thought better of it and took me to hear some live music upstairs instead. Step through the door here and you’ll be transported to a different world, full of candle light and beautifully romantic music. The artists and the music here are top notch and they play a mix of beautiful Vietnamese classics and popular romantic songs in English.

Le Saigonnais

9 Thái Văn Lung, Bến Nghé, Quận 1, Hồ Chí Minh, Vietnam

This one’s hard to find because it’s not actually listed on Google Maps, but it’s in the same building as the Bâng Khuâng Café at the address listed above. This place is truly a window into old Saigon, even down to the furniture and decorations. Many of the patrons here are Saigonese people who either lived in the old days themselves, or remember them wistfully. There is almost an underground resistance-like vibe to this place, as if this is where people would meet to plan the second coming of Old Saigon. The music here is, of course, beautiful, and they play mostly classic Vietnamese songs from Old Saigon.

Craft Breweries

Saigon has a burgeoning craft brewing scene, which is heavily influenced by American expats and packed with loads of interesting, delicious beers. My favorites were:

Heart of Darkness

31D Lý Tự Trọng, Bến Nghé, Hồ Chí Minh, Vietnam

I’m biased because I also met my girlfriend here, and we went back to hang out a few times, but it does have the most cozy, intimate, and well-decorated vibes of any of the breweries I visited in Saigon. My personal favorite here is th Eloquent Phantom Imperial Stout.

East West Brewing Co.

181 – 185 Lý Tự Trọng, Phường Bến Thành, Quận 1, Hồ Chí Minh, Vietnam

I actually had their beers here a couple of times before I went to visit their brewery. The venue is nice–a well-decorated and mood lit warehouse with seating on the roof for those willing to climb the stairs. I’m not usually that into Belgian beer styles, but their Belgian Blonde and Belgian Darks are both very good, and their Independence Stout is fantastic.

Pasteur Street Brewing

144 Pasteur, Bến Nghé, Quận 1, Hồ Chí Minh, Vietnam

Pasteur Street is iconic in Saigon as one of the first craft breweries to crop up there. There beer is quite good, and they try some interesting things there–I tried a dark beer here with jalapeno and other distinctly Mexican flavors. The place itself, though, is, unfortunately kind of sterile, so I wouldn’t personally recommend hanging out here.

Weekend Adventures

Some of my favorite memories from Vietnam are from riding long distances on the back of my trusty motorbike on my way to some weekend adventure somewhere. While I didn’t spend all of my weekends in Vietnam off on adventures, there were quite a few memorable ones.

Mekong Delta

The Mekong Delta actually describes a very large region in the South of Vietnam. Many people, myself included, initially make the mistake of thinking that it’s a single place or attraction that one can visit. In reality, you could drive for nearly 8 hours from Saigon and still not reach the end of the Mekong Delta.

That said, one of the most popular attractions in the Mekong Delta are the floating markets–markets run on clusters of small boats in wide rivers connecting trade between villages that until very recently had no easy road access to each other. The most widely publicized place for tourists to see the floating markets is Cần Thơ, though many of the locals will express that they feel the markets here are overly commercialized for tourists.

I personally didn’t have time to venture further into the Delta than this–Cần Thơ is already a 5 hour drive out of Saigon–but I enjoyed both the drive there and the tour I took of the markets. I would love for my tour to have spent more time moving in and through the market itself so that we as passengers could participate in it a little bit more, but it was nevertheless a very cool experience to have coffee and phở made and then served to me on a boat.

If I had more time, I would have considered going to An Giang province, further into the Delta, in search of a more local floating market and the Trà Sư forest.

Đà Lạt

Đà Lạt is an old French vacation spot nestled in the mountains to the East of Saigon. It’s a ~7 hour bus ride to get there from Saigon, but it’s a worthwhile break from the city routine. Temperatures in Đà Lạt are usually quite a bit cooler than Saigon, and this time of year a typical day in Saigon is humid and hot (90+ degrees F). People are much more laid back in Đà Lạt, and if you plan for it there’s plenty of nature to explore.

Cu Chi Tunnels

The tunnels are an old remnant of the war located about an hour north on the outskirts of Saigon. It’s interesting to experience, and it’s one of those

A cramped entrance to the Cu Chi Tunnels

things that you “should” do while you’re in Saigon, but I honestly felt a bit

underwhelmed by them. I got the idea pretty fast after 20 minutes, did find the engineering behind the intricate tunnel systems fascinating, but then was quickly over it. If traveling on your own by motorbike, however, one can keep driving north to find more interesting and less staged things. I ended up at a very colorful buddhist temple overlooking a large lake and had a good time.


Having fewer touristy things to do in Saigon did help to make it a more productive setting, though this was perhaps balanced out by wanting to spend time on my new relationship. My overarching goals have not changed much over the past couple months: the aim right now is to launch a functional product and create product offering that might net me recurring paid customers or money in the bank. As expected, my previous consulting engagements have mostly wound down, leaving most of my time available for my own projects.

On average,

Serious mode: engaged.

I spent about 6+ hours working each day, and though I do think I’ve accomplished some important things in the last couple months, I am feeling more and more behind on the actual feature development required to launch my initial product offering.

I had a Facebook Ads credit expiring at the end of March, so invested time in a marketing experiment to spend the credit on. My goal was to create the marketing site that I think I will use when the MVP of the product launches–past versions of the site advertised moonshot feature sets that likely would not exist for many months past my initial product offering. Doing this required me to think very critically about what will and won’t be in my MVP, and raised a lot of concerning questions for me about how I will differentiate my product from my competitors in its early stages. (I won’t have a mobile app for some time, and don’t plan for one in the MVP, and whether or not to include some of the cool differentiating features before launching the product has been a topic of some internal debate.)

In the process of doing research on my audience to improve my marketing copy, I concerningly learned that the potential market for my product is much smaller than I originally thought. Unfortunately, in total, the number of people interested in Getting Things Done on Facebook in the US is below 50k. For English-speakers globally, that number is still only about 200k. Unexpectedly, the largest market segment for my product appears to be Italian women

Facebook Audience Insights for GTD in the USA

(600k), so I may actually want to consider translating my product into Italian in the future. (For those wondering, I used Facebook Audience Insights to find this information.)

Given the success of Getting Things Done and David Allen, I previously just assumed that my total market was somewhere in the millions, which meant I hadn’t been thinking super critically about market saturation for my ads or other experiments. With millions of people potentially interested in my product, I didn’t care much if I alienated a few thousand in the process of refining my product offering. My thought has also always been that I would really only need Serenity to hit 1000 paying customers for it to be a huge success, a number which I previously thought would be a very small percentage of the overall market. Now that I know the market is an order of magnitude smaller than I thought it was I need to think more carefully about how I expose the product to the market at every stage, and I’m a bit more pessimistic about the lower and upper bound earning potentials for this project.

Regardless, once I had a pretty a good idea of what my product roadmap looks like, I completed a design overhaul of the Serenity marketing website, split tested some of the information on the page, and added pricing information to the email sign-up page to loosely validate the price point I’ve proposed for my product. I wish I had thought of enticing people to give me their email addresses in exchange for a free month of hypothetical product usage before–this has turned out to be the simplest and most effective way to test my early pricing model.

The results of this experiment were positive–the ad click-through and on-page conversion rates were very reasonable, and I collected a fair number of email addresses despite the inclusion of pricing information. In retrospect, however, since Serenity is a product in an already crowded space, I could probably have just trusted my competitors’ pricing models (most of them do have recurring paying customers) and foregone explicitly validating pricing myself.

At this point it’s clear to me that I can make some money off of Serenity, but it’s not clear how much money, and it’s also not clear how much time I’ll need to invest in the product before the cash starts to flow. Even so, I’ve decided to move forward with the product for a few reasons: 1) the main investment I’m making in the product is my time and runway, both of which are still abundant 2) even if Serenity can’t get me to my income goals by itself, some relatively passive income is better than none and 3) I am actually very excited about the future of the product, and think it could have an important role to play in a larger suite of products I hope to create to help people set and achieve their goals.

My next milestone is to launch the product in public beta. Since the market is small and I don’t want to alienate potential customers, but I do want to start collecting signal about what is and isn’t working, I’ve decided that positioning the product as a free beta is more prudent than just slapping a payment portal on the thing and letting the market decide when it’s worth something. I will, however, be offering beta users the chance to pre-purchase subscriptions for the product at a significantly discounted rate, which should help me detect when the product is truly providing enough value that people are ready to pay for it.

By my current estimates, I’m a few weeks away from being able to launch the first beta version of the product in production. This month is going to be hectic, since I’m taking care of administrative things and spending a lot of time with friends and family while I’m briefly back in the States, but I am hoping to find a way to push to this milestone before the end of May. I’ll probably start reaching out to close friends and family to try out the product and give me feedback soon–if you’re reading this and that sounds interesting to you, please reach out :).


Things have been pretty good lately. For the most part, I haven’t experienced much fear related to self-employment in the last couple months. The low cost of living in Vietnam, has helped me to realize that if I live in the right places, I could continue working on my own projects almost indefinitely. While this revelation does wonders for any money- or survival- related anxieties I might have felt, it’s tended to have the opposite effect on self-discipline and self-motivation. Not having external deadlines and not having any real external pressure to deliver means that my motivation really has to come from within. Connecting well with my deeper, internal drive still doesn’t happen consistently, but I think it’s slowly getting better.

Meeting my girlfriend has, for the most part, helped here. Don’t get me wrong, I’ve certainly found myself sacrificing productive time to be with her, and she and I are trying to learn to balance that better going forward. But her belief in me does sometimes help bolster my belief in myself and, more importantly, some of the ideas she’s introduced me to–mainly the more secular sides of buddhism–have forced me to think a lot more about my fear of death.

It’s been a long time since I’ve thought of myself as someone who fears death, but when I really examined it I realized that my attitude towards the brevity of life is usually to shrug it off in a way that’s so dismissive it’s almost denial. In truth, I think that this is probably how most of us deal with the question of death, but it’s not necessarily the most healthy. Through buddhism, and to some degree through stoicism as well, I’m learning to embrace and accept the reality of my own impermanence, and the reality of the impermanence of any ego-driven legacy I might want to leave behind. While it is terrifying to remember that life is short, and that my stay here on Earth is really just a blink of an eye, it does provide a sobering reminder that, while I am still young and there is still time, there is no time to waste. There is a very real cost to spending my time doing or not doing something even if my savings could last me a decade or more some place in the world.

I’d say I’m optimistic. Most days, fear doesn’t visit anymore, and I do have some good tools for kicking myself back into disciplined focus when I find myself goofing off. Hopefully I can build that into a habit and use it to deliver my first product, and maybe many more.

It’s been about a month since I left the States, and, though I expect there will be many more twists and turns on my journey, I think I can already confidently say that leaving to travel was one of the best decisions I’ve ever made. Learning to balance work, tourism, and new friends has, indeed, been challenging. While overall productivity has slowed a bit, I can’t help but feel that my sense of growth and fulfillment have both accelerated.

Despite being on the learning curve, I think I did decently on my goals for the month. My consulting engagement has, unfortunately, stretched on a little bit, and I’ve only just recently reached a point where it no longer needs my focus full-time. I had hoped that I’d get back to my own projects and start making some non-consulting income in February, but alas that hasn’t been the way of things. I did, however, make a lot of great friends and a lot of great memories in Chiang Mai. Here are some of my favorites, pulled from my vlog:

Meet Squeaky, my trusty pink steed. See us in your rear view mirror and be afraid.

I’m in Ho Chi Minh City–aka Saigon–now (though I’ll wait until next month to write in-depth about this wonderful new city), and my plan for March is to buckle down and finish releasing my first product into the world. I’d ideally like to have my first paid customer before I leave Southeast Asia at the end of April, and more ideally would love to have my first paid customer before the end of this month. As was the case in Chiang Mai, however, while work is a high priority, I’m also hoping to find time to really experience Vietnam, and discover new ways to push my comfort zone. In particular, dating, which didn’t end up being a huge emphasis in February despite some of my efforts, seems likely to be a focus area for me in March.

Moving abroad has done wonders for my morale. Before I left, I had a lot of fears about traveling, especially while still trying to get my business ideas off the ground. I worried that I’d be isolated without friends out here, that it would be impossible to form meaningful relationships with people on such small timescales, or that living abroad would be devastatingly unproductive.

The reality has been almost completely the opposite of my fears. Though I was nervous about meeting new people abroad at first, I found that my fear of isolation really motivated me to push my social comfort zone. I’ve never been the social traveler hanging out with strangers in hostel lounges, so I arrived in Chiang Mai with the self-perception that I’m not the kind of person who usually meets other travelers. When I left Chiang Mai, however, I did so feeling confident in my ability to start new conversations, and connect with new people everywhere I went. It’s become something of a habit to make eye contact with people when I walk into a room, to smile, and even to ask them where they’re from.

Despite my short length of stay in Chiang Mai, I got to know some people very well. I’ve left feeling like I now have friends all over the world, who I hope to meet-up with as I make my way through and around the world. My roommates, Richard and Kat, in particular, have become close friends whose company and counsel I value very highly. I’ve also met, and gotten to know, other nomads from all over the world, working on various interesting things. I’m beginning to open myself up to the idea that, even in a short length of time, it is possible to create a meaningful and valuable connection with someone, and that it is worth my time to invest in these relationships despite their semi-transient nature.

Productivity has been up and down while traveling. Since I’ve been consulting an hourly rate, I’ve been tracking my time very carefully, and have found that I usually work about 6 hours on an average day. At first, I found this number disconcerting: I normally expect that I’m getting at least 8 hours of work done each day. In reality, however, with all of the breaks modern knowledge workers take for lunch and other things, 6-7 hours is probably closer to right for a business day. For me personally, being abroad has definitely meant more time spent out at lunch, especially when meeting new and getting to know new people. It’s also meant less time spent working after dinner, which is also prime time to be spending with new friends. For the most part, I’ve been able to find enough of a routine to stay on task–usually I’d work out of a coworking space for the entire day, or out of a coffee shop for the afternoon.

I have, however, taken a good amount of advantage of the flexibility that being self-employed provides: where necessary to accommodate travel activities, I’ve taken impromptu 3-day weekends or half days off. Calibrating my balance of all of this is something I certainly want to continue working on going forward. I think that as an explorer, the first time I visit a new place, there’s likely to be some overhead in my wanting to really experience and get to know the place. At this point, though, I feel that if I ever return to Chiang Mai (and I really hope to), it will be easier for me to focus on work.

Through traveling, though, I’ve also been exposed to a wealth of new people and perspectives. Chiang Mai is, itself, a very laid back place–the locals tend to live simple lives and prefer it that way, and the nomads are often also a little more chill in their working mindsets than I’m used to coming from Silicon Valley. Many of the Europeans I’ve met have helped me to understand how the American work ethic is often perceived by the rest of the world: there’s a subtle belief that Americans are willing to commit kind of a frenetic and, potentially, ill-conceived trade-off in quality of life against the desire to be productive and accumulate wealth. Some have even considered moving to the States for work, but thought better of it after learning of the insane hours and work expectations often implicitly upheld by employers in places like Silicon Valley and New York City. To be fair, I’m learning as well that American salaries are also often much higher than their global counterparts, but I’ve also heard enough to begin to question whether or not our quality of life improves proportionally. In fact, I’d say that my early conclusions are so far that we Americans may actually have disproportionately low quality of life when plotted against our wages–an average worker making minimum wage in America is actually making more than some of the highest paying jobs in some places, but isn’t able to afford many of the basic amenities that some people value. This, among other things, has deeply challenged my perspective, my worldview, and my workview.

Of course, it hasn’t been all sunshine and roses abroad. On my third or fourth day in Chiang Mai, I experienced an extreme amount of anxiety around my situation and my decisions–so bad, in fact, that I felt it necessary to do some research on remote therapy solutions, so I might be able to unpack my experience with an expert. I couldn’t believe that I’d left the States. I couldn’t believe that I was in a new country. I was scared that I couldn’t or wouldn’t adapt, that I’d find myself alone in a strange place. I was afraid that I’d just bet my career against the house, and that I’d never recover.

By the end of my first week, however, the crisis had passed. Quite counter to my fears, as time goes on I’ve been finding that travel has produced many of the growth side-effects I had hoped it might. I can feel myself becoming more comfortable with uncertainty, in part because I’ve placed myself in more unplanned scenarios, and gained more confidence in my ability to figure things out. Meeting other people like me–nomads and entrepreneurs making a living while traveling the world–who share my values has also helped me internalize a deeper sense of acceptance and contentment with my decision to leave the normal bounds of society behind. I think much of this still has yet to play itself completely out, as I am also still riding on the stability of a cash influx from my recent consulting project, but I’d like to think that my fears have started to quiet themselves, and that the way is becoming clear to achieve some of my business goals for the year.

Saigon promises to be a very different experience from Chiang Mai. The energy here is chaotic and frenetic–frenzied, even–but it makes me feel very alive. This month, I’m trying a stint in a co-working and co-living space in the heart of the city called Start, sort of an experiment for me with a new type of living situation. My experience has already been very positive, and I’m looking forward to new friends, new foods, and new avenues for growth!!

The adventure begins! (Not that everything before this hasn’t been its own sort of adventure.) I’m actually writing this while en route to Chiang Mai, Thailand, the first of 3 destinations in South East Asia. I’m going to be in Thailand for an entire month, and now that I’ve actually had time to stop, think about it, and do a bit of research, I’m really excited. Chiang Mai sounds like an adventure-seeker’s paradise: scenic hikes offering both cultural immersion and physical challenge and a flourishing food culture complete with street vendors in bustling night markets. So many new things to see and experience!!

I have to admit, though, that the jump abroad is bittersweet–most beginnings are also endings. While I’ve never found it terribly sexy to say out loud, I lived at home with my parents for a full 6 months. I hadn’t originally planned to spend that much time at home, and I had also mentally prepared myself to go a bit insane moving back in with my parents. While it wasn’t always perfect, and it did occasionally test the limits of my sanity, I’m surprised to find myself incredibly grateful for the experience. A wise friend pointed out that most people have already spent the vast majority of the time they’re going to spend with their parents by the time they leave for college, so getting to spend another 6 whole months with my parents was a rare opportunity to build a deeper adult relationship with them, and really get to know them better at a time in my life when I’m starting to be able to contextualize their experiences and their choices. While I’m excited to forge ahead, and ready for a new chapter, I can’t help but feel nostalgic that my time at home has, yet again, come to close.

So, how did I spend my time in January? I obviously completed my travel preparations, as I’m (finally) safely on my way to Thailand. I set up an LLC, opened a business bank account, and took care of a bunch of other little logistics to make everything work. It was a bit of a mad dash, and I was honestly packing and prepping virtually up until the last few hours before I left, but I’m off :). I also made significant progress on my first consulting project. I unfortunately wasn’t able to finish it out completely in January, but I’d say it’s 80% done. Now I’m kind of just hoping the last 20% doesn’t take 80% of the time as they say. I didn’t get around to slapping a payment portal on Serenity, but I did spend a few hours setting up a couple of unrelated experimental projects that will exercise my long-dormant artificial intelligence expertise (I have a Master’s degree in AI and Computer Security, but haven’t done much with either in a few years). In all honesty, dabbling with some new projects probably wasn’t the most objectively smart way to spend my time, but I’m nevertheless feeling really excited about the discovery that my AI fundamentals are strong enough to teach myself more and potentially to apply to future products.

Consulting has had an interesting positive effect on my morale. Working on a project for someone else temporarily removes a certain amount of the uncertainty and anxiety around being self-employed: there’s no question as to whether or not I’m wasting my time since value for work has already been pre-negotiated with the client. Knowing for certain that I do have a way to make money if I ever need it is also very comforting–I knew that consulting was a possibility in theory before, but now it’s more tangibly true.

There are also some really useful processes I go through when consulting that I think could be useful for my own projects. I’m finding that the drive to complete a project quickly, and to impress a customer has naturally re-activated some of the skills that I honed at Palantir, but which I haven’t been disciplined about applying when working for myself. In executing at a professional level for a client, I have to be good about planning, designing, and estimating the various project tasks, and then need to execute high quality work and show progress on a regular basis. Going forward, I’m hoping to treat my own projects as sort of mini-consulting engagements where I am my own client–I’m curious to see if doing so enables me to produce higher quality products more quickly.

February promises to be an action-packed month. With a little luck, this consulting project will only occupy me full-time for about another week, and past that will likely require my occasional attention as the project winds down. Once that’s done, my top priority remains slapping a payment portal onto Serenity and getting it out into the world. On top of all that, I have a hefty bucket list of things to do and eat before I leave Chiang Mai on March 4. It’s becoming increasingly clear that my biggest challenge in the coming months will be to successfully balance building a business with taking as much advantage of my exciting new surroundings as possible. I’m not entirely sure how this is going to work yet, but I’m excited to find myself naturally contemplating how to get things done more efficiently so that I can feel good about spending time adventuring. While there were sometimes troughs and crests of productivity at home, I think the call to adventure will apply constant positive pressure to make the most out of my limited time.

Should it interest anyone reading this, I’ve started to record some short vlogs about my adventures. My thought is that I’ll generally keep these short (~5 min max per day) and will do virtually no editing or post-processing on them. I’ll still be posting a broader update with reflections here on my blog once a month, and may start to do more in-depth travel posts about places or things I find really interesting, but for those interested in a video format at a (probably) higher frequency, consider finding me on YouTube. No hard feelings if not–both those videos and this blog are more a form of personal but public documentation of my journey for posterity than anything else.

In December I set out to get my first product, Serenity, off the ground and prototyped to a point where I’d feel comfortable putting it in front of close friends and family. I also wanted to complete my annual goal review and goal setting exercises for the New Year. It was a fairly productive month despite the holidays; I published my 2018 goals, and I ended up writing a lot of code. However, I didn’t quite get my end of year review into a publishable state (I did go through the entire exercise before writing out my new goals) and I’m still a little embarrassed to show Serenity to friends.

Unexpectedly, I also had a huge marketing breakthrough for Serenity in December,  managing to gather 80 email addresses with a $250 FB ads credit over ~a week. Even better, these numbers came from a split test, where I intentionally spent money on poorer performing ads to establish a baseline for comparison–running the best ad in the experiment over the entire budget will probably yield better results. This success provides clear signal that what I’m marketing addresses a need that people want solved, and that I potentially have an efficient channel to reach them. However, it doesn’t validate how much (if anything) people might pay for a solution.

Now that I have potential customers waiting for my product, I’m realizing that I’ve fallen into a common entrepreneurial trap: I don’t know how much product I need to build for it to be “enough”, so I keep delaying throwing something over the fence out of the fear that the product will be missing important features my potential customers will want. Left unchecked, I could easily build the product in a vacuum for months, extending the time needed to find my first paying customer while building features that may or may not provide real value. The answer to this trap is a slight execution strategy shift: rather than guess at what customers will want, or guess at how much product I need to provide before customers will pay, I should let the market decide. This means that my priority now is to create a “free trial” period and slap either a real or a mock payment gateway on the product. I can spend ~$50-$100 in ads to pay for a new cohort of potential customers, measure how long they stay engaged in the free trial, and see if anyone actually pays or indicates that they would pay at the end of the trial period. I’ll risk alienating some potential customers in the process, and I don’t want to throw buggy or unpolished pieces of the product over the fence, but I can and should post the product before it’s strictly “ready” in my own eyes.

My priorities for January, however, have shifted away from Serenity. I’m taking my first consulting project this month, and it’s likely this project will take most of my January bandwidth. Those who read my 2018 New Year’s Resolutions might be remembering how I said I’d be generally avoiding consulting projects this year and thinking me a hypocrite, so I feel the need to justify why I’m taking this project. Though the project is paying a decent sum of money, money isn’t the only consideration here. This project is actually for a friend, and is in the healthcare space, which is one of my stronger interest areas. I think this project provides some useful exposure and credibility-building experience in an industry I care about (and may get more involved in longer-term) while also bolstering my war chest. Also, while I do have enough money in the bank to potential weather no profits from my business for a year or two, even while traveling around the world, I’d be lying if I claimed that having a little extra cushion doesn’t put my mind a bit more at ease.

Since I’m also slated to depart for South East Asia on February 1, my priorities are as follows:

  1. Make sure all of my affairs are in order before I leave the country. (This includes things like making sure I’m happy with the legal structure for my business, taking care of my taxes, getting vaccines, and other logistics which I either cannot take care of while abroad or really must happen before I leave.)
  2. Execute on this consulting project. Try to wrap it up this month, if possible.
  3. Stretch: polish Serenity up a little bit, slap a free trial/payment flow onto it, and run my first cohort through the product to see if anyone bites.

I’m also making it a goal to get back to more consistently writing these updates closer to the actual beginning of the month, since I know I’ve been slipping on that.

Sanity-wise, there were some moments of fear in December, but mostly I stayed focused. Even through the fear, I stayed productive by maintaining a few touchstone habits like waking up early, meditating, exercising, and making my bed. I think my larger fear right now is less that I will fail, and more that I’m wasting my time or doing something that might not lead me to where I ultimately want to go.

Unlike much of the working world, I’m not really on the rungs for any predefined career ladder, and I know that some things do require that one build a track record and earn experience over time. I have been trying to think critically about what my narrative is and where what I’m doing leads me (or leads me away from, since every choice inevitably means not choosing other things). Some reflection on this has led me to the conclusion that taking some limited consulting projects tied to industries I care about helps me to continue to build a story for myself for working in those industries even if I don’t ultimately do tech in those industries (law or policy have been ideas I’ve played with for a little while).

I’m also realizing that entrepreneurship is and always has been one of the primary skill sets I’ve wanted to develop. I believe at our core, many entrepreneurs are passionate, empathic problem solvers. We’re the kind of people who get excited about making the world a better place by solving problems through the creation of businesses, services, and products. I think there are a lot of problems that can be solved this way (Elon Musk has inspirationally pushed the limit on this), though there are also some that can’t (e.g. policy).

For me, entrepreneurship is one tool in what will hopefully become an arsenal for a life spent working on the problems I care about most. I also believe that cracking the value creation cycle means that I won’t ever need to be tempted by money from sources outside myself, which I’m hoping will mean that I can maintain a higher level of personal integrity and authenticity (this is particularly important to me if, for example, I were ever to go into politics).

I mastered the technical implementation and execution aspects of software entrepreneurship a long time ago, but I still need to work on some of the surrounding skill sets, including learning to steer my own ship with confidence, crossing the marketing chasm between value and delivery of value, and designing products that people will love to use. Though it sometimes feels like I’m wasting time when I’m not writing code, or like I’m failing when I find myself gripped by fear, these are actually the moments when I’m learning and experiencing exactly what I need to right now.

October marked the beginning of the part of this journey through the “Trough of Sorrow.” It was like sailing into a section of the map ominously labeled “Here There Be Monsters…” True to analogy, October was littered with what felt like small failures–early marketing experiments flopped, there were moments when I let my fears consume me, and it didn’t seem like I made tangible progress toward having any working products. By contrast, November was a month of small victories–not enough to banish my fear, but enough to start learning to be curious instead of just afraid.

In a sense you could say that in October I saw the tip of an iceberg and, thinking myself clever, gave that iceberg an extremely wide berth, believing that it must extend for miles below the surface. In November I dove below the surface to find that the iceberg was exactly as it seemed from above, and that I put myself through a lot of extra misery for a false assumption.

In October, I had run a set of ads on a test marketing website I built for a product concept called Strive. I had launched some ads on Google AdWords and Facebook Ads and got exactly 0 email subscribers. When I actually examined the results in November, I realized that I had spent less than $10 between both ad platforms, and had only gotten ~25 actual clicks–not nearly enough data to draw conclusions from. I decided to up the ante and spent 10x the money on ads, hoping to get enough data to reach the truth. My new campaign performed much better. Without changing the test marketing site at all, I ended up with 6 email addresses for $59.18 in ads, which was surprising to me because the marketing copy is vague and the site has no screenshots to make the product real in any way. While it’s hard to quantify the value of the email addresses themselves, and hard to predict how many email subscribers will ultimately convert to paying customers, this did loosely validate the market need, and reset my expectations on how difficult it should be to get someone to leave an email address.

Despite some marketing success with Strive, I chose to divest from the project early on. I realized that the product wasn’t well-defined enough for me to have a sense for what to build and what would actually provide value, and I was coming to realize that the scope of the product was nebulously expanding to include other potential products. Instead, I broke Serenity off of Strive and started working on that, loosely piecing together a library of reusable code for marketing websites and web applications. Contradicting my October declaration that I would focus more on building than selling and designing, I actually found a good groove in November for designing with Figma. Wanting to improve on the marketing materials for Strive, I actually spent a good amount of time designing a few mock screenshots for Serenity to make things look a little more real. (App Launch Pad’s mockup generator was also invaluable here.)

I finished the Serenity marketing site in time to pour a friend’s unused Facebook Ads credit into the site to see how it would perform. Somewhat discouragingly, I found that $250 in Facebook Ads led to only 4 email sign-ups, with dismal click through rates and dismal on-page conversion rates. Rather than despair, however, this time I got curious and started designing some new experiments, including a salvo of Google AdWords ads to test different text copy.

When my AdWords experiments came back at a 3.61% click-through and a 10%+ email sign-up conversion, I started to realize something was up with my Facebook Ads. Though I’m still inexperienced, I’m coming to the conclusion that the kind of test marketing I’m doing works much better on AdWords than it does on Facebook. Part of this may just be a failure to target the right people with the right ads on Facebook, but it’s clear to me now that a user searching for a keyword on Google right now is a way stronger signal of potential interest than a user having liked some page in the entirety of the lifetime of their Facebook account. I’m also learning that Facebook is a more complex and harder to master ads platform, as there’s an order of magnitude more options to try and compare for any given ad, often making it difficult to declare a clear winner (e.g. where does the ad get placed? what image do you use? what specific audience do you target? what text copy do you use for your ads?).

I had a few other wins in November as well. While I’m still far from having a full MVP that I’d be willing to show-off here, the product for Serenity is beginning to take shape, and I’ll hopefully have something useful enough to show to some close friends before December is out. I also successfully finished all of my November rejection challenges!! It’s still on my list of things to do to write a longer debrief and reflection about my experience, but I think the most important thing I internalized is to get curious rather than upset when things don’t go my way.

Being honest though, despite November wins, I’m sometimes still finding much of this really difficult. It’s easier overall when things are going well, but that doesn’t mean there aren’t challenging days. I share this not because I want pity–remember, I chose this, so save your pity for someone who didn’t–but because it’s an important part of my truth. The world has enough manicured stories where the protagonist tries to air brush his past and pretend he was stronger in every moment than he really was. This is not one of them.

In my darkest moments, I’m frustrated and impatient. I’m now four months in and, while I do have some good learnings, the beginnings of a reusable library of code, and a few loosely validated ideas to show for it, I can’t help but feel like I should already have a complete product out and done by now, perhaps even have found my first paying customers. I keep expecting myself to fly, but it’s becoming more and more apparent that I’m just now learning to crawl.

In my darkest moments, I also worry about everything. I sometimes worry that I’m wasting my time and the best years of my life. I worry that my growth thesis is wrong, and that in the name of chasing growth, I’ve run away from other important things like commitment or responsibility. I worry that after a year or two of doing this I won’t have enough to show for it, and that I won’t know how to recover. I worry that I’ll lose touch with the people in my life who matter, that I’ll miss out on important events in their lives, and that I’ll fail to be there for them when they need me. I worry that while I’m out exploring the world and the depths of my own soul, the dating pool will thin and that I won’t ultimately find someone to share my life with. Trust me, if there’s a way to worry about something, I’ve worried about it.

The darkness sometimes leaves me feeling a little like Dr. Jekyll and Mr. Hyde–like there are two versions of me, and I don’t always know which I’ll be when I wake up in the morning.

One version seems fearless, unafraid, and undaunted. He embraces uncertainty, excited for the adventure of discovering his life one page at a time. He is optimistic, but not naively so. He understands that risk, pain, failure, and mistakes are all a natural part of the journey of life. He accepts them without worrying about them or overly identifying with them. He knows he can handle whatever life has to throw his way, and he trusts himself to make the best decisions he can in each situation. He has a will and a zest for life that is infectious–inspiring, even–to those he meets. He acts from a place of hope, not one of fear. He is unquestioningly the captain of his own soul.

The other version is anxious, fearful, and constantly worrying. He seeks certainty through a fragile sense of control over the future he’ll never truly find. To paraphrase my own words: the quest for certainty biases him towards defining things in blacks and whites, towards over planning and overthinking, and keeps him from fully embracing life which can so often be beautifully messy, gray, and uncertain. He fears that failure and mistakes imply that he is incapable or fundamentally flawed, and therefore doesn’t handle them well. He worries he won’t be able to handle what comes his way, he doubts himself, and he agonizes over every decision. He is terrified and his fear taints his experiences and his perspectives, desperately seeking comfort instead of adventure. He acts from a place of fear, not one of hope. Fear consumes his soul.

The fearless side of me knows that no adventure comes without struggle and unexpected challenges. He knows that hardship often means one is headed the right way because few things worth finding in life come easy, and that very few stories worth reading feature a perfect protagonist who experiences no hardship. By contrast, the fearful side sees hardship as a sign that he’s made a mistake. He sees monsters in these waters, not realizing that he is, himself, the only monster that might sink the ship. He thinks about turning back before he can no longer see the shore, forgetting that, in the words of Christopher Columbus, “You can never cross the ocean unless you have the courage to lose sight of the shore.”

That’s why my last major update for the month is that I’m forcing myself to lose sight of the shore. For better or for worse, I’ve booked myself flights to spend the majority of next year abroad, and in a sense there’s no turning back from that, at least not unless I feel good about abandoning a small wealth in cash and travel points. I leave February 1 for Southeast Asia (Thailand, Vietnam, and Malaysia, each for a month), returning only very briefly to the States in May before continuing on to France (most likely Marseille) for 3 months, then likely Morocco for 3 months.

While the fearless side of me smells adventure and can’t help but be excited, the fearful side of me is terrified by this. It’s not that I don’t love travel–I’ve been all over the world and experiencing new places and cultures is still one of my favorite things to do–but that I know this isn’t exactly the most sane business decision I’ve ever made. I don’t have a product yet. I’m not making any income yet. My pace is likely only to slow when presented with a new place to get used to, especially if there are interesting things to explore and I’m moving around every month. Sure, some of these places are cheap to live in, but they’re nowhere near as cheap as living at home. However, as I mentioned when I initially set out to do this, this has never been as much about starting successful businesses as it has been about personal growth and conquering a set of fears that clearly controls me. That obviously isn’t to say that I don’t intend to put my all into my business ideas, but it is to say that financial success has always been secondary to self-mastery (I don’t always remember this in my darkest moments). That this scares me so much tells me that I’m moving closer to the heart of my fear–the heart of the monster. In the end it will be me and the monster, and either I learn to tame him, or perhaps he and I will sink together.

Given the facts above, my goals for December are pretty simple. First, while I clearly believe some cliffs just need to be jumped off of that doesn’t mean that I don’t believe in checking, double-checking, and triple-checking my parachutes before doing so. Tangibly this means taking the necessary steps to prepare to leave the country including figuring out how to find cheap long-term rentals abroad, acquiring visas, renewing my passport, getting all of the proper vaccines, and gathering supplies/equipment I’ll need abroad. Second, since time is clearly running short and I really would like to have a real product before I leave the country, I’ll be putting my nose to the grindstone to make progress on Serenity. I’m aware that there are still clear open questions about the market viability of Serenity like whether or not people will actually pay for what I build and whether or not I can establish any sustainable growth channels. At this point, I’m going to build it anyway and if it fails I’ll learn, pivot, or work on something new. Lastly, I’ll need to find some time to write this month, at the very least to reflect on the year, my growth, and progress towards my 2017 goals so that I can define a new set of goals for 2018. If there’s time, I’d also like to reflect more thoroughly on what I learned from my November rejection challenges.

Welcome to the Trough of Sorrow

I want this to be an honest, raw, and vulnerable account of the ups and downs of my journey, so I’m not going to sugarcoat it: October was a challenging month, and it may be the first of many very challenging months ahead. When I say October was a challenging month, I don’t mean that I pushed myself particularly hard mentally or physically–I didn’t work 100 hour weeks, I didn’t lose sleep, and I didn’t solve any particularly challenging problems. Rather, I think October was an emotionally straining month as I began to truly acquaint myself with the realities and unique challenges of being self-employed.

I definitely did not accomplish everything I set out to at the beginning of October. By itself, I’m not overly upset about that; sometimes when I set a goal, I don’t achieve it on the first try despite my best effort, and I’ve found that applying extra self-criticism and pressure to the process is usually counter-productive. I am, however, candidly disappointed with the level of effort I put in this month, and I’m honestly a bit ashamed to admit it publicly. There were definitely a couple of days in there where I literally made no progress on any of my projects. Sometimes I was just distracted, and despite my best efforts couldn’t seem to get myself to produce a tangible work product. Other times, I found myself actively avoiding the work and over indulging in things like video games and Netflix. I’m not trying to give the impression that I’m on my own case because I couldn’t get myself to work over a weekend and indulged instead–the days I lost were during the business week when I had otherwise promised myself I would get work done. In short: I failed to consistently self-motivate in October.

As I ordinarily consider myself an extremely self-disciplined individual, of all the problems I expected to have in self-employed life self-motivation didn’t even come close to making the top 10. Initially, I was shocked, confused, anxious, afraid, and stressed out by my seeming inability to self-motivate. I struggled to understand what was going on, and the more I felt myself spinning my wheels in the mud, the more my morale dropped. Not only did I feel like I was failing, I felt like I wasn’t trying, and like I didn’t even know how to try.

While there were many factors, the two root causes I identified were an unexpected manifestation of the fear of failure and a lack of optimization around flow (aka the feeling of being productive or “in the zone” which may naturally boost productivity and focus).

At this point in my journey, I sit squarely in what Paul Graham of Y Combinator refers to as the “trough of sorrow.” This is the emotional rollercoaster portion of the journey when much of the initial enthusiasm and novelty of being self-employed have naturally worn off, but it’s too early to tell if anything is going to work. In theory, somewhere in here is also where the majority of unsuccessful entrepreneurs give up, succumbing to the pressures of emotional inertia rather than learning, pivoting, and persevering.

While books like The 4-Hour Work Week and The $100 Startup (affiliate links) are great for building a vision of what’s possible, they present what can feel like an overly rosy and optimistic view of the journey, and they’re glaringly silent about the trough of sorrow. Ultimately, I feel the right takeaway from these books is simply “it’s easier and more possible than most people think.” While I strongly believe this statement, I came into the journey knowing that it would likely also be harder than I had come to believe, and was under no illusions that there may be a significant amount of luck involved.

In October, I launched my first set of advertising experiments and managed to net a whopping 0 email subscriptions for the product I described. Despite the product being poorly described and not having screenshots, I expected giving up an email address to be a relatively low form of investment and was a bit discouraged by these results. I also had a couple of blogs posts totally flop from a metrics perspective, underscoring that I haven’t yet found the audience I may be writing for. September’s income from affiliate links turned out to be a fluke, and I haven’t been able to reproduce that in any capacity. In fact, I made more money in October (an impressive $10) by helping a friend sell mail-order rubber chickens than everything else I did on my own combined. (Actually, you should check out the rubber chickens haha–they make great gag gifts! You can use the offer code CHIUBAKA at checkout for 15% off.)

Having seen a few indications that early experiments might fail, the scary reality of the trough of sorrow is that I’m beginning to have enough data to validate “it’s likely harder than I think” but still not enough data to prove “it’s likely easier than most people think.” Standing where I am now, I absolutely understand why this is the crucible that makes or breaks entrepreneurs. Learning to navigate the trough of sorrow is going to be an essential part of my growth if I’m ultimately to succeed.

However, since I’m still learning to swim here, my unexpected response to early failure indicators was to freeze up. I discovered that faced with the possibility, perhaps even the likelihood, of failure I would naturally rather make no progress than to fully realize a potentially failed outcome. Despite all the years I’ve spent building my self-discipline, my intense fear of failure can still outweigh it if I’m not self-aware and proactive about countering it.

Doing things that remind me of my own power, skill, and self-efficacy helps to chip away at a sense of despair, hopelessness, or paralyzing fear by putting me in a mode where I start to think about what’s possible rather than what’s not. The opposite is also true: doing things that I’m not as good at, or that I struggle with contributes to a constrained sense of what’s possible, and therefore a stronger sense of fear that projects will fail.

I’m realizing that flow is an important part of what separates the things that make me feel effective from the things that don’t. Because flow is good for my morale, it’s important to my long-term productivity that I organize my time in ways that promote it where possible. Unfortunately, the way I set my priorities and built my routine for October didn’t take flow into account, so not only was I hit by a paralyzing sense of fear, but I also mostly engaged in activities that made me feel like I was struggling rather than crushing it.

In large part, flow seems to be the result of conscious competency–engaging in activities I’m good at and know I’m good at like writing or coding. In October, I didn’t spend much time in flow. Pushing to post a new piece on my blog every week forced me to spend more time writing than my energy naturally allows (I usually have about two good hours of writing time in the morning before my energy dips and putting sentences together eloquently becomes less natural). Additionally, my push to test market forced me to spend much of my time writing marketing copy or doing visual design for marketing websites–both tasks I can do, and do reasonably well, but which I haven’t yet put in the sweat to learn to do quickly.

The theory behind why I spend my time this way seemed sound at the time: the strategy was to grow the blog and use it as a cross-marketing tool for software products. I’ve since learned that the blog is unlikely to be a viable short- or even medium-term play. Simultaneously, the strategy for determining which products to work on came from the advice of a mentor, John Vrionis of Lightspeed Venture Partners, to sell, design, and build in that order. I 100% believe that selling, designing, then building is the best way to systematically de-risk a business idea–building something takes a lot of time investment, while generating early signal about market viability can be really simple. Unfortunately, since much of my consciously competent skills specialize on the building stage, delaying building for as long as possible, while strategically sound in abstract, leaves me with fewer daily sources of flow.

What am I actually doing about all this? Firstly, I’ve de-prioritized my blog. Apologies to any avid readers out there who may have noticed the slowdown–I’m still planning to write about topics that interest me, but I’ll be doing so without a real posting schedule (the one exception to this is that there will be at least one monthly set of posts in the Escape Velocity series as I continuously reflect, analyze, and plan to make this all work). I’d love to get to a point where I actually do have something worth publishing every week, but I’m not going to force it at the expense of quality and sanity.

I’m also now actively searching for the right personal balance between selling, designing, and building. Though I know it’s dangerous, I’ve been increasingly biasing toward engineering time because getting something tangible done builds more forward momentum than struggling with the rest. Since I’m taking an approach to engineering that involves building a toolset that should make it easier to build subsequent projects, part of my hope is certainly to bring the time cost of prototyping a new product so low that the risk of building without selling first is minimized. I won’t be putting all of my eggs in that basket, however, as I do need to start building the other skills.

Hopefully the shift in strategy will allow me to pick up momentum to use against any future paralysis I encounter while walking the trough of sorrow. Just in case, though, I’ve also decided to get serious about systematically desensitizing myself to the fear of rejection (failure is, in a sense, a form of rejection). While I don’t expect all of the learnings from my November rejection challenges to map directly to beating back the fear that threatens to hold my productivity hostage, I do think making a habit out of facing my fear will better equip me to counteract it when it comes up.

Based on these reflections, my new priorities for November are:

  1. Complete all 30 November rejection challenges.
    1. Even though it won’t directly lead to income, I am committed to following through on this, so will be making this a top priority.
    2. This will likely be taking the slot of my writing time for the month, so I probably won’t be publishing many non-rejection-related articles.
  2. Complete a prototype MVP for one of my products ideas.
    1. This may end up being rushed, but I will make sure to take the time to slow it down, and factor out re-usable pieces where possible.
    2. Should aim to at least be usable enough that I can start using it on a day-to-day basis, and potentially onboard a few close friends for feedback.
    3. Ideally: should also have a competent looking marketing website so I can start pushing ads to it, but this may be more than I can handle this month.
  3. Run more Google and Facebook ads experiments to refine ad copy, narrow target audience, and determine CPC.
    1. Aim to always have an experiment in flight. Go for impression volume rather than conversions to gather demographics data, and a large enough n to draw real conclusions.
    2. Ideally: should have enough data to design a useful experiment to push $250 worth of Facebook ads credits through.

Was October tough? Yeah, definitely. I have not, however, been beaten. I never asked for this to be easy. In fact, if I really thought this was going to be easy I’m not sure I’d have set out to do it in the first place. I may not always make predictable progress in the directions I want, but I am growing and learning from all of these experiences. I am facing my fears and insecurities on a daily basis. Sometimes they win, sometimes I win. No matter what happens, I am grateful for this opportunity to be in the ring rather than watching from the sidelines even if it means taking a few jabs to the ribs now and then.

Escape Velocity: First Income

The three weeks I had of September weren’t quite as productive as I’d hoped, but I did make my first $0.68 from Amazon Affiliate links, and I nevertheless learned quite a bit about digital marketing, how to run a blog, and how to keep myself efficient, motivated, and productive. Blog analytics suggest that people are actually engaging with the content I’m publishing, but I have some early concerns that the Amazon Affiliate model may not work long-term. In October, I’ll be committing to fewer, but more focused goals, and ideally applying my learnings from September forward to make them happen. I’ll primarily be focused on new content for my blog, boosting search rankings for my blog, and validating/implementing Strive, my first software product.

September Reflection

Milestones Reached

  • First income, however small, from a monetization tactic on my blog.
    • I made $0.68 from Amazon Affiliate links! This happened in my second week of self-employment, though the trend has unfortunately not continued week over week so far. My mother also jokingly remarked that I’d save $0.68 in a month if I just remembered to turn the lights off in the bathroom. Still, I remain optimistic that as the amount of content and links on my blog grows, and as readership numbers increase that I’ll start getting some more significant signal as to whether or not this will work.

Blog Metrics

Google Analytics

  • 408 unique users and 568 sessions. Google Analytics September 2017

    Number of new users by day at in September 2017.

    • There were two large anomalies, however: I got a strangely large number of views during the late evening hours from Canada one day that I still can’t explain, and I accidentally messed with the metrics by hitting the site with Google Pagespeed Insights over and over one day.
    • Regardless, this number is beyond my immediate social media influence, which indicates that my social media cross marketing strategies are working a bit, and that a few people have helped me out by sharing my posts.
  • 36.8% bounce rate (A “bounce” is when a user visits a webpage and then leaves without browsing any other pages on the same site. It’s usually a good indication that people either got there by accident or weren’t interested, though it’s important to analyze this along with session length.)
    • This is likely heavily skewed by the two anomalies mentioned above.
  • Average session duration of 3 minutes 32 seconds.
    • This is likely heavily skewed by the two anomalies mentioned above.
  • There’s about an even split between desktop users (55.6%) and mobile users (43.3%), so I need to make sure I keep checking that content works well on mobile.
  • The overwhelming majority of my users came from the United States (72.9%). The next closest country was… Ukraine (?!) at 11.8%.
    • Ukraine showing up here seems pretty sketchy. Either my writing has really caught on over there, or someone’s probably trying to do something malicious to my blog. Since the Ukraine traffic is relatively new in the last 7 days, perhaps it’s possible that the Ukrainian readers came for the language learning post? Otherwise, I really need to double-check my site security measures…
  • Post Popularity
    • The most popular posts were:
    • Relative post popularity suggests that the more philosophical topics like Emotional Inertia are so far less popular than practically applicable topics like how to learn languages. That or Sundays are really poor days to post blog posts (Emotional Inertia was published on a Sunday–all other posts on a Monday). I find this result a bit disappointing, and intend to keep playing with it–the philosophical posts are the ones that I actually really spend a lot of time and thought on.
    • Average time on page for each of the posts suggests that, on average people actually read through the entire post with the exception of Going Rogue, which on had an average time on page of 4:41.
      • This is actually really encouraging–the average time on page for the monstrous How Busy People Learn Languages post was a whopping 29:13, suggesting people actually found the post valuable enough to spend that much time on it. That, or a crapton of people just left their browser window open and walked away haha.
  • Acquisition
    • 47.5% of my traffic came from social media channels with a 21.13% bounce rate.
      • Facebook accounts for 72.31% of all new social media users and had a pretty low bounce rate of 16.10%.
      • Reddit was surprisingly the second most successful social channel with 19.49% of new social media users, but had a pretty high bounce rate of 42.50%
        • This suggests that my efforts to cross promote on Reddit are working, but that I might not be hitting the right communities with my content, or that my content is just naturally a lot more interesting to people who know me personally (probably currently true, and something I’ll need to fix if this is to keep growing).
      • Twitter did surprisingly poorly as a social channel, bringing in only 3 new users despite having received a retweet from a fairly large influencer in the language learning space.
    • 43.8% of traffic came from directly inputting my website into the browser’s address bar.
      • I find this pretty suspicious, but it’s also pretty unclear what actually constitutes direct traffic. I have a sneaking suspicious that either a bunch of these are somehow me, or there’s something going on here I don’t understand. I’ll have to monitor this number in the coming months to see how it trends.

Amazon Affiliates

  • 37 link clicks at a 10.81% conversion rate Amazon Affiliate Metrics September 2017

    First income! Amazon Affiliate metrics for in September 2017.

    • There was a spike of 21 clicks on September 29th that I can’t explain and looks seriously suspicious, though. Before this, the highest number of clicks in a single day was 3, and none of these clicks seem to have turned into conversions.
  • 2 items shipped for a total of $0.68.
    • Both items were Kindle e-books.
  • Surprisingly, there weren’t that many affiliate link clicks and no conversions after publishing How Busy People Learn Languages, which I admittedly wrote in part because the first item that made any earnings here was a copy of Fluent Forever (affiliate link). Ironically, since an average page view time of ~30 mins suggests people actually read the entire post, perhaps I did too good a job of explaining my methods and people didn’t feel there was much added benefit to buying either of the books? I’m going to choose to be proud of this rather than take advantage by purposefully limiting how much I say in future posts, but this is concerning because it does suggest that the affiliate link strategy may not work long-term.


  • Monetize my blog.
    • Create/update blog content.
    • Affiliate marketing.
      • Learned more about affiliate marketing in general.
      • Went through old posts and added affiliate links where I mentioned a book or product that I use.
    • Optimize blog for monetization and audience building.
      • Increase resolution on metrics I’m gathering for my blog.
        • Added a scroll event to Google Analytics, so I can track how far down the page people are actually reading. I haven’t actually spent much time interpreting the data here yet, though–mostly taking signal from bounce rate and page views per session.
        • Updated the Home page so relevant content is easier for new visitors to find, and so I can better track what people are actually reading.
      • Search engine optimization (SEO).
        • Read SEO 2017: Learn search engine optimization with smart internet marketing strategies (affiliate link).
        • Installed Yoast SEO plugin for WordPress.
          • This plugin is super powerful, and really well done. Tackles a lot of the points made in the book I read automatically and makes other SEO-related tasks really easy to do. I’m still getting my sea legs here, but am very happy this tool exists. I haven’t sprung for the premium version yet, but as it’s a one-time fee as opposed to a subscription I’m strongly thinking about it. I’m still not using all of the power in the free version yet, so will probably wait until I’ve mastered what’s available to me for free.
        • Fixed some performance issues with, which were likely hurting user experience and hurting SEO.
          • This was primarily solved by installing and configuring the free version of WP Fastest Cache.
      • Installed a plugin to connect WordPress to Mailchimp so that I can collect email addresses for people who want to subscribe to the weekly newsletter.
      • Considered re-branding my blog to, but thought better of it as it would require a reasonably large overhaul of existing content. Instead, opted to just redirect to, making it easier to tell people how to find my website.
    • Outreach.
      • Spent some time updating a few of my up-until-now-lesser-used social media accounts (Twitter, Quora, Instagram).
        • Was able to get a fairly well-known influencer in the language learning space to retweet one of my blog posts since I had mentioned him and his book, Fluent Forever (affiliate link), in a post.
      • Set up some Google Alerts so that I know if my name, or anything relevant to my blog comes up on the web.
  • Sell software to solve problems I have or am very knowledgeable about.
    • Read Give: The Ultimate Guide to Using Facebook Advertising to Generate More Leads, More Clients, and Massive ROI (affiliate link).
      • This ended up being less of a book about Facebook Ads, and more about marketing in the digital age in a social media context. Had some great points, which I hope to take to heart and test against other approaches.
    • Set up an account on Google Adwords.
      • This surprisingly and unfortunately ended up requiring a full hour on the phone with an agent.
    • Did some general research on what user stories are, why they’re helpful, and how to write good ones.
      • This will help me to focus my product vision on important user outcomes.
    • Strive, the platform for setting and achieving goals.
      • Did some research on the space of existing visioning exercises, and started experimenting with running visioning exercises with people I know.
      • Did some research on the existing psychological research behind goal setting.
      • Started building a test marketing website for Strive, but unfortunately did not complete it, and have not yet launched ads to test its performance.
    • Development
      • Bought a new laptop, and got my development environment running on it.
  • Spoke with a friend about her experience with due diligence in the growth equity and consulting industries.
    • This conversation gave me some insights into how to think about new potential markets and product opportunities.
  • Spoke with a friend about experiences with consumer products, consumer marketing, and consumer growth, and reached out to a few of my networks to learn more about these topics from friends who have experience with them.
  • Applied and got approved for a Chase Ink Business Preferred credit card, which, with its sign-up bonus and 3 points per $1 on things like online advertising, travel, Internet, and phone services, will help support my ability to live and work abroad in the near future.
  • Researched merchant bank accounts and came to the conclusion that I should definitely start with third-party payment processors like Stripe and PayPal. These typically have higher processing fees, but no monthly fee to hold the account open. They’re also much less of a hassle to set up and start using.

Not Done

  • Did not tackle low-hanging fruit for putting my blog out there (e.g. popular blog boards, etc.)
  • Completed 0 full iterations of a test marketing site for Strive. Made it part way through an iteration, but not finished to the point where I’m ready to launch ads for it yet.
  • Did not get to any serious development work on Strive.
    • Did not complete or scope out work for login functionality.
    • Did not complete basic execution functionality.
  • Did not finish migrating away from SquareSpace for test marketing websites.

Why didn’t these things get done?

I think primarily there was a failure to maximize my energy against my time in a way that kept me moving in the right direction along multiple types of work streams. In particular, most of what I didn’t get done this cycle is engineering work, which seems to have gotten dropped in favor of time to write and time to read. Part of this was waiting for my new laptop to arrive, as I expected to be doing most of my development work on it, part of this was also being overly cautious not to fall into the typical engineer’s trap of building before selling or designing a product, and part of this was just not blocking out time for it.

I ended up a little overcommitted, and since the activation energy to start writing or start reading was lower than getting back into engineering work, I chose not to start the engineering work. At a certain point toward the end of a few weeks, I ended up in emergency/disaster mode for writing and had to spend all of my time working on blog posts, even during times of day when the energy would have been better spent on something else (there were a few afternoons of staring at a blank or partially finished blog post going “derrrr”–writing is usually a morning affair for me).


Make Sleep Hygiene a Priority

I lost a day or two of productive time to not having gotten the sleep I needed and then not being able to translate a very limited amount of energy into outcomes. Sleep hygiene seems especially important when there isn’t external pressure which might force me to push through moments of extremely low energy or work on very small amounts of sleep. Getting myself into more of a regular sleep schedule has helped mitigate the risk that time and energy are wasted.

Wake Up With a Plan

You know that “lazy Saturday” feeling? The one you get when you wake up late on a Saturday morning without a real plan for how the day is going to go and you just kind of lounge your way through the day lackadaisically? It’s great on a weekend, but it turns out when you’re self-employed, you can get this feeling pretty much any day of the week if you’re not careful. When I worked for a company, I always at least loosely knew what other people were expecting from me the next day, and the structure and routine of my day was already loosely dictated for me: wake up by 8am, get to the office by 9am, work for most of the day, go home, lather, rinse, repeat.

As a self-employed individual, I find that if I don’t explicitly add structure to my day and a sense of what I need to do tomorrow so that I have a mission when I wake up, it can be easy to be lazy about getting my day started and moving. This usually means setting today’s priorities the night before and at least figuring out what the first thing I’m going to do in the morning is and when I plan to get started.

Optimize Energy for Different Task Types by Scheduling Chunks of Time Proactively

Primarily, I’m finding that my work now falls into three categories: writing/planning, reading/researching, and engineering/implementation. I found that without specifically and proactively chunking out time to do each of these at the right points every day, I’d naturally gravitate toward the easiest tasks to do–usually in the reading/researching category–at the risk of starving everything else.

I’ve started to get in the habit of actively chunking out 1-2 hour blocks of time on my calendar the night before to give my day structure ahead of time based on my stated priorities, and to make sure that I get a little bit of each thing done at the right time each day. For example, I now make sure the first hour or two of productive work every day is spent writing since I tend to get into flow with my ideas early in the morning when I feel like I have all the time and space in the world to think and play with the phrasings. Engineering work is well-suited for pretty much any other time, since when I really get into working on a problem I can get caught-up in it for hours. Reading makes a good after-lunch break, or something to mix in with blocks of engineering time so I don’t get burnt out of any single thing.

Over-committing Leads to a Lack of Focus

I found that when I over-committed myself in a given week that I’d actually end up a lot less productive than if I had given myself fewer, but more focused priorities. In the absence of this focus, I think I instead get a feeling of constant behind-ness no matter what I do, which often creates a counterproductive sense of stress rather than a helpful sense of flow. I’ve started to get in the habit of giving myself fewer, but more focused priorities for a given week, usually giving myself about as much or a little less than I think I can actually do, then setting a couple of stretch goals for myself. This works because things almost always take longer than expected, but if they don’t I get to build momentum around feeling like I made some stretch goals happen!

Be Wary of the Urge to Constantly Check Metrics and Social Media

One of the things I actually hate most about trying to seriously run a blog is how much more I have to engage with social media in order to cultivate outreach channels for ideas and content on my blog that I actually feel really passionate about and want people to read. I’m finding that it can get really easy to mindlessly check the blog’s metrics throughout the day and when I wake up, especially in the couple of days after publishing a new post. Additionally, I know that likes, reactions, and comments by people on social media are important in order for news feed algorithms to show my content to more people, but I really don’t like how fixated this can make me on social media or on the opinions and reactions of others. In fact, in general I think social media can be a very negative influence on people’s psyches since it encourages a fixation on what other people think rather than rewarding people for authenticity and vulnerability.

Both for my mental health and for my productivity, this is something I think I need to be very careful about, and short of making sure I’m responsive to people who comment and that I’m monitoring for potential problems with my blog, I think it would make sense to get into more of a regimented routine on this. For example, perhaps I only check once a day in the morning, and only really spend a significant amount of time analyzing the data and extracting insights once a week.

Keep Calm and Make Room for Time Off

Especially in a self-employed environment, I think it’s really important not to put too much stress and pressure on myself. That absolutely doesn’t mean I shouldn’t work hard, but it does mean that I should be careful about getting into a mentality where I don’t let myself take breaks, or expect myself to work every weekend, or always work late into the night. These kinds of things are exactly what I think creates a toxic culture in typical work environments, and I think if I’m not careful I can actually accidentally recreate that sort of toxic culture for myself.

This week, I almost pushed to finish the marketing website for Strive over this last weekend of September, but thought better of devoting my entire weekend to the task rather than giving myself a day or two to actually have no obligations, take care of some important personal life matters, and just plain recharge a little bit. I think there will be a time and place for grinding work out over weekends and during late night sessions, but killing myself just to meet a very arbitrary deadline which I clearly missed because I planned poorly the days and weeks before, seems like a very short path to burning myself out. Instead of doing this, I decided I’d make sure to really spend time to reflecting so I understood why I failed to have time for everything I wanted to get done and re-calibrate so that I don’t make the same mistakes on the next run.

October Planning


  1. Write a new blog post each week.
  2. Complete the test marketing website for Strive, and start running ad campaigns to validate the idea and its framing.
  3. Make significant progress on the MVP for Strive.
    1. Define user stories for each component of Strive.
    2. Determine the MVP feature scope.
    3. Implement MVP features for the execution component of Strive.
  4. Read more about the psychological field of goal-setting theory so I can pull research-backed ideas into Strive.
  5. Bring to the top of obvious search ranking key terms like my name and “Chiubaka.”
  6. Stretch: Continue talking to people in my network about their experience with consumer product marketing and growth.

Though I made my first few cents of income through my blog, it’s still too early to tell if the blog is going to work as an income stream. Nevertheless, the actual cost to run the blog so far isn’t much more than ~$10/mo, so other than the time it takes me to write the blog posts, which isn’t insignificant, it’s pretty cheap to keep running as an experiment. I’d therefore like to make it a priority to continue writing content for my blog. I’d also like to make it a priority to explore organic growth channels, which means I need to step up my SEO game and improve my blog’s search rankings.

Project-wise, I have a couple of immediate priorities, which include finishing the test marketing website for Strive so I can begin to collect data about the viability of the idea, and then to start actually implementing Strive. My actual MVP deadline for Strive is likely to be mid-November, so I have about 6 weeks to get something up. This is likely to take the majority of my time this month, and if for no other reason than that it helps me build momentum around project implementation, it’s likely to be time well-spent, even in absence of initial validation of the idea. Since one of my hopes is to make Strive a research-based project, however, I’ll also need to carve out a bit of time to continue reading about the psychological field of goal-setting theory. As a stretch, I’d like to continue talking to people in my network about their experience with consumer product marketing and growth, to help inform my strategy going forward.


* * *


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Further Reading

Disclaimer: As an Amazon affiliate I make a small percentage of the sale of the books below, all of which were mentioned in this post.

Give turned out to be more than just a book about Facebook advertisement. Give took me through how and why marketing has completely changed in the digital age. It explains the reasoning behind how people interact with ads in the modern world and how to successfully add value to people’s lives in order to build a relationship with potential customers that may eventually turn into a sale. This isn’t a great book to read if you’re looking for an in-depth understanding of the actual mechanics of Facebook advertising, but it does feel like a book that every modern day marketing professional should read at least once.




SEO 2017 is a pretty good overview of the ins and outs of Search Engine Optimization for the total beginner. I knew very little before reading this book, and felt like I came away with a good understanding of the space as well as the tools available for helping someone diagnose and fix common SEO problems. Some of this information can be found online rather than buying a book, but this book does caution that a lot of SEO information on random blogs is conflicting and out of date. If you’re interested in learning more about SEO, consider picking up this book or reading articles on Moz, one of the de facto leaders in the space.

It’s been two weeks since I quit my job to go it alone. I gave myself that time to rest and recover, making today the first day of actual self-employed life. I already know why I need to do what I need to do. Now it’s time to get down and dirty with the how, starting with clearly defining the goal conditions and milestones.


The primary goal is to reach self-sustained passive income (escape velocity) as quickly as possible. This is important because reaching a self-sustained state defuses the time bomb that’s currently my steadily dwindling war chest.

At an absolute minimum, this will require $2000/mo of average gross income with a very small time input, which I’ll define as one or two days of full-time dedicated work a week. This amount would be enough to keep me going in cheaper places abroad like Marseille, Lisbon, and certain cities in Morocco.

Higher monthly averages will allow me to sustain a more expensive lifestyle (e.g. in a city like Paris, Tokyo, or San Francisco), purchase things that I’d like to have or do (e.g. a really nice road bike, advanced scuba diving training, cooking school at Le Cordon Bleu), or save and invest my money to grow long-term wealth (e.g. IRA, investing in an index that tracks the market and beats inflation, or re-investing money in my own new or existing businesses). The obvious most ideal case is to be able to have all of the above while working less than a single full-time day a week to sustain it. I’m pulling this number out of my butt, but I’d guess that I’d need somewhere between $10000 – $15000/mo in average gross income to make this happen–this would leave me living comfortably, even luxuriously, most places while not having to compromise on funds to pursue personal growth, interests, and hobbies or compromise on long-term savings.

A good middle ground number for the kind of lifestyle I was used to while in Silicon Valley is probably around $5000/mo of average gross income, though this number assumes a minimal amount of long-term saving (maybe a little less than the $5500/year IRA contribution limit), and potentially some clever tax engineering (e.g. spending enough time abroad to qualify for the Foreign Earned Income Exclusion). This same number is likely sufficient for me to live just about anywhere in the world, though not necessarily luxuriously (and in some cases, not totally comfortably, but that’s alright; if comfort were the goal, I might not have quit my job :P).

The secondary goal is to take some risks, experience some failures, and learn a crap ton! This is actually much more important to me than making it out of all of this financially OK, but I figure much of this will come naturally from trying to make ends meet, so I don’t need to put an explicit focus on it.


Great, the goal is pretty clear. What are some of the ways I think I can build income quickly? Or, since income is really just a proxy for value, the better question might be: what can I do that’s valuable to other people? Where can I find the intersection of what people need, where my strengths lie, and what I’m passionate about?

Based on my strengths, skills, and passions here are a couple of high-level directions I can already take to start trying to create value:

  1. Monetize my blog.
    1. Writing and communication are two things that I excel at. I also enjoy thinking deeply about life and am not afraid to share the details of my own life for the benefit of others, so I believe that I have interesting and valuable things to write about.
    2. Time input for a blog is approximately the time it takes to post ~once a week, which isn’t a whole lot. Plus, I rather enjoy the process of writing and sharing :).
  2. Sell software to solve problems I have or am very knowledgeable about.
    1. I’m a professional software engineer by training and am well-versed in Silicon Valley methods for effective engineering and product management. I may have quit my job, but I do actually enjoy writing code and solving problems!
    2. At a certain point, my software will likely reach a relatively steady and stable state. By its nature, it runs itself without input, but I may occasionally need to do work to fix issues or scale infrastructure.
    3. Solving problems that I have myself probably isn’t a winning strategy if I wanted to build the next Facebook, Google, or SnapChat, but it works great if my win condition involves thousands of users rather than millions. This also greatly reduces the product management overhead–I won’t need to agonize about whether or not a product or feature solves a real need; I just ask myself if it effectively solved one of my own needs and market to people who are similar to me (there aren’t millions of such people, but there are certainly thousands).

Fortunately, if I operate along a theme the two methods above have synergistic properties. Even more fortunately, I do have a theme of helping people self-actualize and living with integrity.

Normally, profit for a consumer product boils down to whether or not the user acquisition cost is acceptably below the lifetime value of acquiring that user. The major factors in the equation are how much it costs to show an ad to a single user, what percentage of users actually click on the ad, what percentage of those users actually convert to paying customers, and how much money a typical customer pays over their lifetime use of the product.

Unfortunately, but predictably, there’s a humongous drop-off at every step: good ads lose about 95-97% of potential customers before they even click on the ad, and then from there every page a user has to go through to decide whether or not to purchase the product deters a similarly large number of people. All told, it wouldn’t be ridiculous if less than 1% of 1% of users exposed to my product actually purchased the product. The deficiency here is that a potential customer has no relationship with the product creator until the ad makes the first impression, and they’re making a purchase decision based on how much they trust you in the 30 seconds it took for them to click on your ad, read about your product, and check out your offering. Talk about judging a book by its cover, eh?

With a well-oiled blog, however, I can build a consistent audience of people who have already self-selected themselves as similar enough to me to find my content interesting. The more focused the theme and content of my blog, the more focused this self-selection will be. Now if I create a product that solves a need related to the theme of the blog, not only have I identified a bunch of people who are similar enough to me to likely be interested, but I’ve also had the opportunity to build a real relationship with them. I don’t have an exact number, but I think it’s safe to bet that conversion through this channel is likely to be much higher than 1% of 1%. Even better, if done right, marketing through this channel costs nothing and doesn’t feel intrusive the way traditional marketing does. There are tons of clever cheap and free ways to build readership on a blog, not the least of which is simply writing compelling content that resonates with people so that they share it with others.


Cool, the goal makes sense and I have a few workable ideas for how to get there. The next question is how do I break the goal down so that it’s more manageable?

Here are some milestones I’d like to hit organized by method:

  1. Monetize my blog.
    1. My blog is the first thing that comes in Google when someone searches my name.
      1. This will prove that I’ve established my online presence and that search engines are properly indexing my content. Right now I show up on the second page. Time to blow all those other Daniel Chius out of the water!!
    2. First subscribed user that I can’t claim to know personally (and doesn’t look like a bot).
      1. This will prove that something I’m doing is starting to work and that the content on my blog is actually compelling enough for people outside of my immediate social network to read on a regular basis.
    3. First income, however small, from a monetization tactic on my blog.
      1. This will prove that the monetization channels I’ve chosen can actually work, which means that income from my blog should begin to scale linearly with the number of regular readers on my blog.
      2. This will also prove that I can make money from my blog without “selling out.” I don’t really intend to fill the space on my blog with cost per click advertising. Instead, I’m hoping to use affiliate programs to make it easier for readers of my blog to buy products that I actually really believe in and have mentioned here.
    4. Generate enough Amazon affiliate purchases that Amazon decides to approve my affiliate application.
      1. I’m pretty sure Amazon affiliate purchases are going to be my main monetization channel, and I don’t think I get paid out until they actually approve the application, sooooo… this would be a big deal haha.
    5. Reach a point where I’m posting to my blog once a week or more and getting relatively consistent readership numbers without losing people.
      1. This will prove that I can consistently produce content that’s worth reading.
    6. Reach 100 subscribed users.
    7. Reach 1000 subscribed users.
    8. Reach 5000 subscribed users.
  2. Sell software to solve problems I have or am very knowledgeable about.
    1. First re-used piece of code between two projects.
      1. There are going to be some commonalities between many of the products I try to create (e.g. social login and payment integration), and I’m hoping to make my software modular so that each time I build a product I can reuse large chunks of it to make it quicker to build the next one.
    2. First successful test marketing page.
      1. I’ll be test marketing my ideas by creating offerings for products that don’t exist yet, then measuring how well they do when I funnel real ad traffic to them. In my mind, successful means that a) users actually took an action indicating that they would purchase based on the information they’ve seen and b) user acquisition cost falls below a reasonable pricing for the offering.
    3. First product launch.
    4. First paying customer.
      1. This is a big one. The biggest fear of every entrepreneur is that they’ll create something and nobody will care. This proves that I’ve created something that has some value for someone. Scaling that value from one user to n users is much easier than going from zero to one.
    5. First recurring paying customer.
      1. This proves that the product is compelling and sticky enough to generate recurring revenue (likely on a subscription basis).
    6. 100 recurring paying customers.
    7. 1000 recurring paying customers.
      1. Depending on pricing, this could be sufficient to push me over $5000/mo if each user pays $5/mo.

Actions and Timelines

This Week

  • Monetize my blog.
    • Create/update blog content.
      • Write this week’s post for my blog. (This is it!)
      • Write next week’s post for my blog.
      • Update the about page on my blog to clarify what this blog is about.
    • Affiliate marketing.
      • Learn more about affiliate marketing in general.
      • Go through and add Amazon affiliate links where books or products are mentioned in old posts.
      • See if affiliate programs exist for other products I love to use and use regularly to help me accomplish my goals.
    • Optimize blog for monetization and audience building.
      • Increase resolution on metrics I’m gathering for my blog.
        • Find a way to measure how far down the page readers scroll so I can decide whether or not my typical post length is too long (it probably is).
        • Re-work the home page so it isn’t possible for a reader to read the entirety of more than one post without me being able to track which posts they read.
      • Search engine optimization (SEO).
        • Learn more about SEO in general.
        • Figure out what I need to install/configure to optimize my WordPress blog for search engines.
      • Find a system for allowing readers to subscribe to my blog by email that I actually like using and don’t think is too intrusive.
        • Ideally, allows people to subscribe/unsubscribe by post category.
      • Outreach.
        • Do some research on best channels for increasing blog traffic.
        • Make sure I tackle all low-hanging fruit for putting my blog out there (e.g. make sure it’s indexed on popular blog boards, etc.)
        • Set up Google Alerts so I know if I or my blog are mentioned somewhere on the web.
      • Look into re-branding my blog.
        •, while fun and pithy, may not be the best brand for the theme I’ve chosen to blog about.
  • Sell software to solve problems I have or am very knowledgeable about.
    • Ideating and planning.
      • Brainstorm new product ideas.
    • Strive, the platform for setting and achieving goals.
      • Write-up a pitch, value proposition, and detailed execution plan document for Strive, a platform for setting and achieving goals.
      • Experiment with visioning exercises.
      • Do some additional research about the science behind effectively setting and achieving goals, as well as forming good habits.
    • Development.
      • Get my development environment setup on my home desktop computer.
  • Open a merchant bank account.

This Month

  • Monetize my blog.
    • Write a new blog post each week.
  • Sell software to solve problems I have or am very knowledgeable about.
    • Strive, the platform for setting and achieving goals.
      • Go through 2 iterations of a test marketing site for Strive, collecting data on performance by launching real ads.
      • Scope out work and effort for building an integrated social login backend for Django.
        • There’s an existing solution, but I’m not quite sure it does what I want it to do. I’d like to make it really easy for my products to allow a user to connect their Google and Facebook accounts and, if desired, authorize access to data integrations that may provide additional value.
      • Build login and basic execution functionality.
    • Development.
      • Migrate away from SquareSpace for test marketing websites and consolidate my own tooling/documentation for quickly creating these.
        • At $28/mo SquareSpace is a bit pricey for the purposes of test marketing, and as an experienced Web Developer I don’t think I get that much more out of their what you see is what you get interface for site building.
  • Reflect, re-evaluate, and re-strategize at the end of this month in order to plan appropriately for October. (You can expect this to be blogged as a progress update!)
    • Loosely speaking, I already know that I’m aiming to have a working and marketable MVP for my first product by the end of October, but will take new information into account when planning for this at the end of the month.


Since I mentioned living abroad in my last post, some people have been wondering when I’m actually leaving and where I’m going. Both are TBD at the moment.

I’m currently living in San Diego with my parents (I know, not sexy at all), and am planning to stay here until after my first product launch or, more ideally, after I acquire my first recurring paying customer. If I’m really lucky, I’ll leave the country shortly after Thanksgiving. More realistically, though, I’ll probably move abroad at the beginning of 2018 and stay abroad for the vast majority of the year.

Destination-wise, I’m still deciding, but am pretty certain my first destination will be Marseille in France, likely followed by Taghazout in Morocco, and maybe another stretch in Marseille (or elsewhere in France). I’m primarily prioritizing French-speaking countries so that I can finish learning French, since that was one of my goals this year. There are however, some other great options in Portugal, Eastern Europe, and South East Asia that are very affordable. I’ve found that Nomad List is a great resource for identifying candidate cities.

Further Reading

Stay Tuned!

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Effective today, I am leaving my full-time job to pursue my own aims. I have also decided to leave Silicon Valley and currently have no plans to return, though I remain open-minded about coming back in the future. Before you jump to conclusions, I have not left to start a startup, nor have I been struck by lightning inspiration–at least not in the senses that many people who know me might otherwise assume.

At the risk of oversimplifying, the short version is that I am going to attempt to create automatable small businesses while leveraging the strength of US currency to live affordably abroad with two ultimate goals:

  1. Create a source of passive income that will afford me complete dominion over my own time and energy or, more simply, true freedom.
  2. Fail as many times as I can in a short span to internalize the lessons of failure, and never again fear being crippled by it.

Some reading this will undoubtedly think that I’ve gone crazy. Others will say that this is an incredibly risky move and will assume that I either have an extremely high risk tolerance or am just plain foolish. From a traditional frame of reference, these concerns are justified: who in their right mind leaves a comfortable Silicon Valley tech job for a life of relative uncertainty and no guaranteed financial prospects? Why not at least stay in Silicon Valley and pursue the stereotypical startup dream?

On the contrary, however, I’m not that risk tolerant, and I’m (usually) not that foolish. In fact, despite how crazy this move may sound, I believe that it’s one of the few sane and sure courses available to me right now.

While I am extremely fortunate to have reached the highest rungs of Maslow’s hierarchy of needs, I find myself overall dissatisfied with my life course to date and the future it promises. Ostensibly, I have won, through some combination of luck and sweat, the freedom to choose my destiny and to self-actualize my dreams. I’ve come to realize, however, that on many levels I’m failing to do so, and that I’m not as free as I thought I was. Worse, even as I fail to self-actualize, I often think that I am succeeding.

The Paradox of Traditional Success

The paradox here comes from a received definition of success that I have come to take for granted: that to be successful one must seek achievement, prestige, and social exaltation. Looking around at my peers, this seems to implicitly be the most common definition of success, and it makes sense: after all, striving for these things is what motivated many of us to work and study so that we could attend the most prestigious academic institutions, and striving for these things is what likely motivated many of our early career decisions. We sit where few others have had the opportunity to sit, and because of that much of society holds us in awe and reverence.

Unfortunately, there are two controlling and potentially harmful pressures inherent in this definition of success: a drive towards conformity, and a fear of failure.


Pursuing prestige and achievement for their own sakes promotes conformity. We typically define prestige by what is desired but unattainable by the majority, so we as individuals don’t control what is considered prestigious. There is also usually a relatively established pecking order of prestige, with strong brands and selective opportunities typically dominating the field. Since the opportunities are few, and the majority agree on what is considered prestigious, when success drives us to seek prestige, we tend to conform to what society thinks is desirable and scarce. This outcome is unfortunate because it pushes many of what might be considered the best and brightest to trade their own desires, their own dreams, and their own originality for achievement and esteem in the eyes of the majority, sometimes even at the expense of their values.

Up until now, this has certainly been a theme in my life–I went to the most distinguished school I could, and took a job at the most prominent company that fit my skills and interests. Even in my most self-aware moments, I don’t know if I stopped to think whether I did these things because they were right for me, or if I did them because I knew society celebrates people who walk the prestigious path. Without thinking about it, my default mode became conformity motivated by a desire for prestige. Now that I’m capable of questioning it, I’m no longer willing to trade what makes me unique–or the chance to discover that–for prestige; I’m no longer willing to compromise on my values for an empty sense of accomplishment.

Fear of Failure

While conformity controls what we strive for, fear of failure influences how we get there. When approached correctly, failure can be life’s greatest teacher and an individual’s greatest ally. On the other hand, when handled inappropriately or outright avoided, failure can tear us apart from within, and it can drive a cycle of insecurity that encourages us to feed our egos instead of our souls. I’ve personally experienced failure both ways.

Most of us are conditioned to fear failure from a young age, and many of us will spend our entire lives doing everything in our power to avoid it. This reflex is a byproduct of the score-, test-, and grade-driven society that raises us. We’re subconsciously taught that the better we do on tests and the more pristine our resumes, the more we will be valued by colleges and, therefore, by society. At its extreme, we begin to confuse our perceived value to society with our sense of intrinsic self-worth. We come to believe the prime fallacy that failure is the antithesis of success, and that the less we fail, the better the life we will lead. Failure becomes our nemesis and our most potent fear. We allow this fear to define our sense of risk, often unquestioningly favoring well-paved roads to “success” over self-discovery, self-growth, and self-expression through finding our own unique ways through the world and living with integrity.

Try as we might, we cannot evade failure forever. Failure is a fact of life–in our careers, in our relationships, in our goals. The question, then, is not if we will fail, but when we will fail. Success should be defined not by the absence of failure, but rather by what we learn, who we choose to be, and the strength of character we display when we fail.

I cannot honestly say that I no longer fear failure–decades of accepting fear as truth cannot be reversed in the blink of an eye through a trick of the mind. Rather than succumb to that fear, however, I choose to face it, to embrace it, and even to seek it out. When I am done, I hope to have truly made failure my ally.

Redefining Success

I have chosen to reject any definition of success that finds its basis in conformity, fear, and ego. I refuse to measure my success in terms of material possessions, social esteem, and external validation. Instead, I have adopted a new definition based on my principles, values, and convictions: success means reaching my highest potential through application and embodiment of my principles, through cultivation of a character that is maximally aligned with my values, and through integrity to my convictions. I choose to measure my success in terms of growth, self-esteem, and internal validation. I hope that by doing so I will reach my highest potential, and that I will use that power to help others reach theirs.

A Good Life

This new definition of success comes from intense reflection on the perennial philosophical question, “What makes for a good life?” To find my answer, I imagined myself on my deathbed and tried to determine what I would need to do in order to feel satisfied with the life I lived.

External Validation

The first set of ideas that came to mind were stereotypical metrics for success: fame and fortune–things like wealth, material possessions, and the adulation of society and my peers. These metrics likely come from popular culture; the celebrities we adore have all of these things, and because they’re so high-profile we often assume that they’re among the happiest, most fulfilled, and most successful among us.

Thinking on it further, we often desire these things when we’re seeking external validation. We want others to respect us, to love and adore us, even to be jealous of us because when they do it props up our fragile egos. When we depend so heavily on the admiration of others, we don’t have to face the gargantuan task of learning to love ourselves. We seek status symbols in the form of material possessions because we think we can buy happiness or that net worth correlates with self-worth.

Worse, though, external validation is elusive and unreliable: we cannot control how others regard us just as we cannot control the many unpredictable factors that may or may not lead us to wealth. I’m not willing to take that chance with my sense of ultimate fulfillment.

Internal Validation

They say true happiness comes from within, and I agree: we become sustainably and self-reliantly content with ourselves when we cultivate sources of internal validation rather than external validation. I’ll even take it a step further and posit that the more internally validated we become, the closer we get to reaching our highest potentials–when we follow our internal compasses, we tend to grow most quickly and most authentically.

So what does it mean to be internally validated? In stark contrast with external validation, internal validation means loving ourselves, not in an egotistical or narcissistic way, but in an accepting and self-compassionate way. It means being able to derive a sense of self-satisfaction and self-motivation entirely from within rather than from without. In truth, I believe that what I call internal validation, when fully achieved, is what other philosophies refer to as “nirvana” or “enlightenment”: a complete sense of happiness, contentment, and fulfillment through mastery of the inner world.

How, then, do we become internally validated? We are most self-satisfied when we do, for lack of a less cliche phrasing, what feels right. Most of us, myself included, have certain principles, values, and convictions which help to define our sense of “rightness,” but which we don’t always follow. It’s easy to lose sight of these things because there are so many competing pressures in our lives: the pressure to conform; the aversion to natural human fears like failure, rejection, and regret; the default drive to seek comfort, certainty, and familiarity at all costs. It’s also surprisingly difficult to remember to regularly check-in with ourselves and be honest about our true motives.

By living a life that exemplifies and cultivates my principles, values, and convictions, I become more internally validated. When I do something because I hold conviction that it is the right thing to do, the outcome, which I often can’t control, ceases to matter. Instead, I’m happy because, given a choice, I acted with integrity to my values. I may not be able to control the fickle opinions of others or the whims of fate, but I can always control my character, my actions, and my reactions. I am much happier tying my ultimate fulfillment to these things than tying it to things outside my influence.

Of course, I’m not perfect, and I never will be. I also fully expect my values to change as I grow and experience more of life. I believe the pursuit is nevertheless worth it, and the wisdom I’ve accrued by living with authenticity and integrity is far more valuable to me than affluence or social acclaim. The pursuit of happiness seems to be an internal journey, not an external one, and that journey itself holds at least as much meaning as the destination.

Social Good

Those who know me well know that a sense of purpose for social good is an important part of my identity. For that part of myself, the idea of living my life solely to become internally validated–in a sense, a proxy for my own long-term happiness–feels selfish. Reconciling this took some thought, and I eventually amended my definition of a good life to include helping others become internally validated as well. This makes sense to me because it “feels right”–helping others is implicit in the principles of kindness, fairness, and compassion which I value highly–but it also stands to reason: if becoming more internally validated is how I maximize personal utility, then helping others reach that same state is how I maximize global utility.

There’s a bit of a paradox in the idea of helping someone else become internally validated, however. Is it even possible to help others become internally validated via external means? Though we can never directly create internal validation in others–that’s a task always left to the individual–there are two ways we can promote it:

  1. Free people from having to fight for basic needs, empowering them to have more choice and ability to meet their potential.
  2. Help people around us to feel, believe, and internalize a sense of personal worth and to feel, believe, and actualize their potential.

The first category is where the traditional “save the world” missions sit: existential threats like climate change or terminal disease may prevent a large number of people from reaching their potential by ending their lives prematurely. This category is also where social justice missions sit: a society that doesn’t provide equal opportunity or fair and equitable treatment to all regardless of their race, gender, or beliefs similarly prevents a large number of people from self-actualizing. Lastly, this category is where donation and direct acts of service fit: by donating our time, energy, resources, knowledge, or skills we can sometimes help fulfill the basic needs of others, giving them a better chance to meet their potential.

The second category is where we can make an impact in our everyday interactions with others. We’ve all met people who believed in us in ways that helped us affirm our belief in ourselves. These are the people who encourage us to grow, and who see our potential even when we struggle to. We all have the capacity to be those people in the form of, for example, a caring friend, a servant leader, a source of inspiration, a loving significant other, or an encouraging parent.

All that said, however, it’s important to remember that we can’t expect to be able to help others if we can’t help ourselves. This concept is similar to what we hear in every pre-flight briefing: that we should put on our own oxygen masks before assisting others with theirs. In order to help others reach their full potential and to maximize our impact, we must prioritize actualizing our own potential. If we’re not the best we can be, how helpful will we be in saving the world or leading a crusade for social justice? If we don’t believe in and pursue our own potential, what hope do we have of helping others believe in and pursue theirs? Of course, when possible, I believe in working on ourselves and contributing at the same time, but I don’t believe it’s healthy to deny our own growth needs when that’s not possible.

It’s also important to remember that contribution is contribution. There’s no value in comparing our contribution to others’; in reality, doing so turns social contribution into yet another status symbol arms race driven by our egos rather than our values. The only place where there is value in comparison is to ourselves: are we living with integrity and maximizing our ability to contribute in the ways available to us?

Walking My Path

Everything I believe and everything I’ve learned have led me to the crossroads I stand at now. Two years ago, as a computer science major at Stanford looking to go into industry, there were three obvious, socially-accepted paths after graduation: join a large, established, prestigious company like Google, Facebook, Dropbox, or Palantir; join a VC-backed startup; or start a VC-backed startup. These are the paths worse for wear, and though joining or starting a startup is certainly more financially risky, at this point it isn’t socially risky–doing these things still affords one “street cred,” and relative esteem in the eyes of one’s peers.

As a prestige-oriented individual, I never stopped to consider other options and, indeed, the doors laid open to me coming out of school reflected this. Now that I’m aware of my previous strong bias toward prestige, I can consciously counteract it, and in doing so I’ve had my eyes opened to a multitude of less conventional paths, some of which align more closely with my values and how I want to grow than the conventional ones. This doesn’t mean that I won’t ever return to a more well-trodden path, but it does mean that I don’t intend to do so unless I’m convinced there’s no better way to live my values and no quicker way to grow.

The path I have chosen this time signals a strong departure from what motivated me before, and a yearning to explore the road less traveled by. In the next chapter of my life, I hope to find financial independence while living and working with integrity. I plan to leverage my current skills, knowledge, and interests to create value for others, ideally in ways that help them self-actualize. Concretely, this means that I’ll be creating small products–most likely software-based–that can sustainably cover the cost of my lifestyle with minimal long-term time input. At the same time, I’ll be living abroad both to bring the cost of my lifestyle down and to satisfy my wanderlust.

I won’t lie and say that this doesn’t scare the crap out of me. By going it alone and changing my social setting I expect to experience extreme discomfort. I expect to fail, I expect to feel lonely, and I expect to feel afraid. I’m not arrogant enough to presume that the financial side of this is going to work–in the worst case I may blow my entire savings and fail to make a single cent. If it does work, however, I will win the ability to spend the vast majority of my time and energy in pursuit of my values without compromise. I will also have demonstrated to myself that I can create value on my own, and that if I ever need money to pursue my aims I’m capable of making it myself.

Regardless of the outcome, though, I expect to grow immensely–both in predictable ways and, if I’m lucky, in ways that will completely surprise me. Because my definition of success doesn’t correlate with financial gain, traditional definitions of risk don’t apply well here. Because I value maximizing growth more than I value maximizing comfort, this is the surest path I could choose. Because facing my fears requires cultivating a courage that upholds my highest values, I know that I’m living with integrity. I can only hope that that makes all the difference.

Walk Your Path

I’m not here to say that everyone who has ever taken a path that’s considered conformist or prestigious should immediately reverse course. I’m also not here to judge people for the paths that they have chosen–only they can really know why they made the choices they did. There are plenty of good reasons why people choose a more traditional path: sometimes that path truly does align with their strengths, interests, and values; sometimes that path offers growth and learning that can’t easily be found elsewhere; sometimes people are insecure and they just need something external to validate them so that they don’t give up; sometimes other responsibilities–to family, for example–require people to compromise and seek stability.

Whatever the reasons, the reasons themselves don’t matter to me; honest awareness of those reasons does. I ask that we have the courage to question our own motives. I ask that we compare our motives to our values, principles, and convictions. I ask that we be truthful and forgiving with ourselves when we find that we are not living with integrity. It’s never too late to start.

Your values and mine will likely not be the same–yours make you unique as mine make me unique. If we dare to follow our hearts where they lead us, we will walk unprecedented paths; paths full of adventure and challenge, growth and wisdom, success and failure that we will earn the right to call completely our own. It is my sincere parting hope that you find that path whatever and wherever it may be and that you walk it without regret, without shame, and without fear.

Thank You

Thank you for taking the time to read this. Much of this is very personal and, while I primarily write to inspire myself, I love hearing about how my ideas and my writing make other people think. If this resonated with you or, even better, if it didn’t at all, I would welcome a message, a phone call, or even just an anonymous comment below.

Further Reading

The thoughts, values, perspectives, and philosophies communicated here have been profoundly influenced by the following works, all of which have challenged my assumptions:

I believe the synthesis of these ideas is completely my own. No plagiarism or appropriation of ideas was intended.