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.

Rejection Challenges

One of my New Year’s resolutions this year was to conquer my fear of rejection by getting rejected at least 100 times trying 100 different things. I have done quite a few things to that end: I’ve taken several Improv classes, and I’ve tried a couple of self-directed rejection challenges here and there. Admittedly, I haven’t kept great track of where I am out of 100 different ways to get rejected, and I still have a moderate fear of rejection which is currently manifesting itself as a resistance to putting my work as a self-employed individual into the world for real feedback.

In an effort to fight back and make real progress toward this goal before the year ends, I’m trying something a little different with November: I’ve asked six friends to each give me five rejection challenges of varying difficulties for 30 challenges total, enough to do one a day for each day in November.

Why am I doing this?

The short version is that I read Rejection Proof (affiliate link), a book about Jia Jiang’s mission to get rejected once a day for 100 days and everything he learned from the experience. Reading his book made me realize that I am acutely afraid of rejection, judgment, and just plain looking silly; that that fear limits me; and that I also could potentially learn a lot from being rejected a whole bunch of times. The longer version of the story is that this is part of a larger campaign to challenge my fears and cultivate courage–topics about which I’ve written a (at time of writing unfinished) series of posts.

Of course, the goal isn’t to reach a point where I completely disregard others’ opinions–that’s called being a sociopath, and I certainly don’t want to get there. The hope is, however, that a lessened fear of rejection, and a weaker preoccupation with what others think of me will lead to a greater sense of self-acceptance, a higher degree of authenticity in all of my interactions, and the courage to ask people for what I really want.

What is a rejection challenge?

Loosely described, a rejection challenge forces me into a scenario where I need to ask someone for something to which the answer could be “no” (or, equivalently, to which the answer could be something I don’t like or maybe don’t want to hear, e.g. negative feedback). The challenges I have here are all over the place ranging from simple and easy requests, to requests that are just completely ridiculous and awkward, to requests that require me to bother people I wouldn’t otherwise bother, to requests for things that I might actually feel somewhat emotionally invested in. These challenges are designed to make me cringe, and I imagine that they will be extraordinarily cringeworthy (and/or just amusing) to watch.


By asking friends for challenges rather than coming up with them myself, I’ve added some very acute social pressure to actually follow-through, and by publishing this post, I’m adding some additional public accountability to the mix. I’ll be making every effort to do one of these challenges every day, and if I can figure out how to make it work, I may even vlog them on YouTube so everyone I know can make fun of me (in a sense, this is its own rejection challenge). At the very least, you can expect that I’ll write about the more interesting or informative experiences.

The Challenges

Without further ado, here are the challenges rank ordered by approximate relative difficulty scored out of 10:

  1. 2: Smile, make eye contact with, and ask for a high-five from every person you encounter while walking down 2 blocks of street (or equivalent distance in a mall).
  2. 3: Ask a waiter to take you to the kitchen and meet the chef/see how things get made.
  3. 3: Ask a homeless person if they will eat dinner with you.
  4. 3: Ask a homeless person to tell you their life story.
  5. 4: Ask to make your own sandwich at Subway.
  6. 4: Go to a mattress store and ask to take a nap in one of their beds.
  7. 4: Go to a convenience or grocery store and ask to speak over their intercom system.
  8. 4: Go to a burrito joint and ask if you can come behind the counter and call out a few orders.
  9. 4: Ask to help prepare something in a food truck.
  10. 4: Call the office of the Mayor of San Diego and ask for a meeting.
  11. 5: Challenge a stranger on the street to an impromptu chess game.
  12. 5: Ask 3 strangers if they will play a quick game of Simon Says with you.
  13. 5: Ask to walk a stranger’s dog.
  14. 5: Ask a running stranger if you can jog with them.
  15. 5: Ask 2 people to jump into the Pacific Ocean with you.
  16. 5: Offer to autograph a stranger’s hand with a sharpie.
  17. 5: Try to sell a roll of paper towels to a mall stall vendor or street-side vendor.
  18. 6: Ask 3 strangers if they can text you a screenshot of their phone’s home screen.
  19. 6: Ask someone if you can create chalk art in their driveway.
  20. 6: Ask 10 people on public transit (or at the beach!) what they’re listening to and try to turn it into a conversation.
  21. 6: In a crowded place, ask a stranger if they’d be willing to pose with a potato mango as if they were in the Lion King while you take a picture.
  22. 6: Ask a stranger to join you as you walk like a crab for at least 1 block on a fairly busy sidewalk (or until you pass at least 3 people, whichever happens last).
  23. 6: Ask a stranger to swap shoes with you for a block.
  24. 7: Carry a rubber chicken around, and ask a random stranger if they will kiss it.
  25. 7: Ask someone to give up their seat for you on public transportation. (Bonus: Do this when there are empty seats around them.)
  26. 7: Ask a stranger to apply sunscreen to your face.
  27. 7: Try to convince a stranger to feed you a banana.
  28. 8: Spend at least 30 minutes busking in a crowded place. Explicitly walk up to someone at the end of a performance and ask for some money.
  29. 8: Go to a karaoke bar, a stand-up venue, or something similar. Perform, and then explicitly ask a stranger from the crowd for feedback afterwards.
  30. 9: Apply to be a chef on Feastly. If approved, host a pop-up kitchen event and cook for a bunch of strangers through Feastly. Ask them for their honest opinions after the meal.

Closing Thoughts

Are some of these challenges incredibly socially awkward? Yes. Do some of them force me to break social norms? Absolutely. Will they get me in trouble? I’m really hoping not. Are all of these completely realistic rejection scenarios? Of course not. Do I think they’ll teach me something anyway? Definitely.

Regardless of whether they are realistic or contrived, socially acceptable or socially awkward, all of these challenges will put me in situations that make me at least a little bit uncomfortable. As I’ll elaborate in a soon-to-be-published post, learning to act in spite of that discomfort and that fear is an important part of what I’ve learned to call courage.

Wish me luck!


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Interested in keeping up with the challenges? Please consider subscribing to be the first to know as new content comes out!

Have a great rejection challenge idea? Tell me about it in the comments below, and I may end up doing it later this year!

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Self-Awareness: The Everyman's Superpower

This is the second post in a three-part series on Fear and Courage. While this post is designed to stand alone, you can get caught-up by reading Fear: The Invisible Prison of the Mind.

If you could be dipped into a vat of radioactive liquid and granted any comic book superpower, what would you choose? The ability to fly? Invulnerability to everything but Kryptonite? Laser vision? Personally, I’d love to be able to learn how to do anything perfectly after watching just once. Since, unfortunately, I’ve never met a vat of radioactive liquid that wouldn’t also kill you 10 times out of 10, however, I want to talk about a superpower that all humans are born with, but don’t always fully utilize: self-awareness.

Self-awareness is our ability to examine our own character, emotions, motives, and desires. It’s an important part of any good definition of what separates humans from machines and artificial intelligences (at least for now). In a lot of senses, self-awareness is also what differentiates humans from animals: rather than continuously react to our environment, we seem to have the ability to step out of situations, self-examine, and proactively choose a response. We literally have the ability to think about our thoughts–otherwise known as metacognition in psychology–which, when you think about it, is pretty damn mind-blowing. (No pun intended.)

Our self-awareness plays an important role in our lives on multiple levels: it’s what allows us to identify our emotions, it’s what gives us the choice in how we respond to events in our daily lives, and it’s what allows us to ask deeper questions about our lives and our motivations. Developing a sense of self-awareness can be helpful for understanding and promoting virtually any quality of mind: among other things, it allows us to understand when and why we feel lazy so that we can foster discipline; it allows us to understand when and why we despair so that we can learn to persevere; and it allows us to understand when and why we feel afraid so that we can cultivate courage.

Developing self-awareness requires that we question ourselves and our motives. We must first acknowledge that virtually every action we take represents a choice, conscious or subconscious. Then we must ask ourselves why we choose what we choose, and ask why again and again until we understand the deeper motivations behind our choices. This process can, however, be difficult, and, for some, it can be downright terrifying to question deeply. Sometimes in the short-term this process leads to more questions than answers, and the ensuing uncertainty can be overwhelming. Ironically, it takes a certain amount of courage to even ask ourselves questions like “what does it mean to live a good life?” because occasionally we’ll find that the answers aren’t congruent with the how we’ve chosen to live our lives. Sometimes it’s easier to banish the questions and change nothing than to acknowledge that we are not living way we hope to. In the long-term, however, giving ourselves license to ask these questions even when we don’t have the answers or don’t like the ones we find builds self-awareness and helps us to lead more authentic, and therefore happier lives.

Self-awareness of Fear

While self-awareness can help us understand and identify complex emotions, most of our emotions can be generalized as extensions of two primary emotions: hope and fear. Ultimately, therefore, our choices are made from either a place of hope or a place of fear. For example, someone who has had a bad romantic experience, and lets that experience color all of their future romantic entanglements may make choices out of the fear of being hurt again rather than the hope that they will find a love that is fulfilling and true. Similarly, someone who has tried and failed to accomplish something may choose to give up out of the fear that they will continue to fail rather than the hope that they will eventually succeed.

The essential question we seek to answer when confronting fear is: what would I do if I weren’t afraid? If self-questioning and self-awareness come easy to you, answers to this question may come naturally. If not, don’t fret–I have another trick up my sleeve for you to try.

Sometimes fear is so deeply ingrained in our psyches that we struggle to connect with our hopes, and so can’t imagine an alternative to fear. When this happens, we can either wait it out–all emotions are transient, including fear, and so will pass if we don’t give them time and don’t actively hold on to them–or we can use a mental exercise called visualization. Both options are often paired with a meditation practice, but a full overview of the power of meditation and how to start your own practice is out of the scope of this post. (Check back in the future for a separate post on that topic.) For now, this simple exercise should suffice for the purposes of combating our fears and reconnecting with our hopes:

  1. Find a comfortable place to sit down where you won’t be bothered or interrupted, and where you won’t feel subconscious about what you’re doing.
  2. Sit comfortably, but erect. Leave your hands comfortably on your legs or in your lap. Keep your eyes open for now.
    1. I’m going to ask you to close your eyes so you can visualize without sensory distractions, but if you’re too comfortable you might fall asleep (been there, done that), and if you’re not comfortable enough you’ll be distracted by your posture.
  3. Take 10 slow, deep breaths in through your nose and out through your mouth, paying attention to the physical sensations of the air filling your chest and lungs.
    1. The purpose of the breathing is to relax and calm you. Paying attention to the physical sensations grounds you in the present, and helps you to focus your mind and your senses on what you’re doing rather than on random thoughts or on the world around you.
  4. Return to breathing normally in and out through your nose and close your eyes. Maintain your focus on the breathing by thinking “in” as you breath in and “out” as you breath out. Do this 10 times before you move on.
    1. We’re now lowering the focus on the breathing, but still trying to maintain it as a loose touch point to keep you present and grounded in the exercise. Closing your eyes helps to block out additional visual distractions as we ease into it.
  5. Recall a time when something really good happened that made you feel powerful or unstoppable (e.g. I often think back to hearing the news that I landed my first job out of college).
    1. We’re going to take this feeling, and use the human brain’s awesome power to replay and reexperience memories of emotions as if you were experiencing the same thing now. Essentially, if you’ve ever been in a state of mind where you felt less afraid because you felt powerful, you can always get back there by visualizing and replaying those emotions.
  6. Imagine that feeling embodied as liquid sunlight. Everything it touches, it soothes, cools, and infuses with that feeling of power. Visualize that liquid sunlight entering and then sort of filling the body from above your head, starting with each of your toes, then up your legs, then your stomach, torso, arms, and finally filling your head until it overflows out of you.
    1. As you visualize the feeling filling your body and overflowing, what it’s actually doing is permeating through your mind, amplifying that replayed emotion and fixing it squarely in your mind.
  7. Now, with your eyes still closed, stop focusing on the visualization, and just let your mind do whatever it wants for the next 20-30 seconds.
    1. This time is so that your mind can just get used to resting and being in that emotional space we’ve just created.
  8. Open your eyes to conclude the visualization. Now that you hopefully feel less afraid, ask yourself whatever question you were struggling with again and see what answers you come up with.

Even just having the self-awareness to recognize that we are influenced by fear loosens its hold on us. However, once we know that fear manipulates our actions, we have two choices: we can accept the fear and the boundaries it creates in our lives–sometimes in the face of unacceptable real risk or danger, this is preferable and rational–or we can decide that something we value is more important than avoiding fear.

In accepting fear, it’s worth pointing out that as we build more courage our perspective of what is too terrifying, too risky, or too dangerous can change. What’s impossibly scary today could be very manageable in the future, and the only way to really know is to cultivate courage so you have as much perspective as you can when faced with something that scares you. However, there is a difference between courage and recklessness: courage is facing fear and taking a potential risk when fear is irrational or when something we value or hope for is truly more important than the danger we expose ourselves to; recklessness is putting ourselves and others in real danger just for the sake of it and without principle or reason to guide us. Courage is a virtue; recklessness is a vice.

Cultivating courage, however, will be the topic of next week’s final post in this series. Stay tuned for that, and in the meantime in the comments below tell me: what would you do if you weren’t afraid?

Other Resources

Disclaimer: this section may contain affiliate links where, at no additional cost to you, I receive a small amount of compensation for things you purchase through links on this website. I never list things here that I don’t personally use and believe in, and the money goes toward supporting this site and allowing me to continue writing.

The 7 Habits of Highly Effective People is one of my favorite books, and contains much of what powers my personal philosophy today. The first time I read it, it blew my mind, change my perspective, and ultimately altered the course of my life. The first habit, Be Proactive, has a lot of echoes to the concepts of self-awareness. Stephen Covey claims that the space between stimulus and response is what makes us human and gives us choice. I’ve expanded on this concept to place self-awareness in this space.




Headspace LogoHeadspace is a mindfulness and meditation app that’s gained a lot of popularity recently. Despite my parents insisting that I try various forms of meditation for years before I found it, Headspace is what really got me into meditation. Rather than frame meditation as a spiritual practice (which it does not have to be), Headspace frames it as a set of mental exercises that help us to learn and maintain different states of mind.



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Fear: The Invisible Prison of the Mind

I was about about two-thirds of the way to the top of a rock climbing wall when I realized I was too tired to keep going, and too tired to climb down. A slack rope snaked up the wall beneath me and hooked into several anchor points before finishing in a knot at my waist. Looking down the 30 or so feet to the ground, I felt myself break into a cool sweat. I had two options at this point: intentionally fall anywhere between 10 and 15 feet before my partner below trapped the rope and arrested my fall–perfectly safe, in theory, in the controlled environment of an indoor climbing gym–or live the rest of my days on this wall.

As stupid and melodramatic as it sounds, I seriously considered what it would be like to spend the rest of my life right where I was. The idea wasn’t pretty–how would I get meals? how would going to the bathroom work? would I ever find true love up here?–but in that moment I wanted nothing more than to not have to take that fall. That singular fear overrode all else, leaving me completely paralyzed.

In fact, I’m writing this from that same climbing wall–no, of course not. Obviously I eventually made it down the wall. I wish I could say that in my moment of panic, I gave myself a rallying pep talk and confidently leapt off the wall. Unfortunately, instead, I spent another 5-10 minutes up there wondering why I had ever been born and why on earth I had decided that coming up this wall was a good idea in the first place. Then, with a bit of a whimper, I individually unwrapped each of my fingers until I was no longer holding on to the wall and I fell.


* * *


Fear is one of our oldest and most primitive emotions. Once upon a time, fear kept us alert, and kept us alive; it was our sixth sense, the superpower that prevented us from becoming food for sabre-toothed tigers, giant flesh-eating kangaroos, or demon ducks of doom. Over time humans evolved and moved up the food chain, and all of these predators went extinct. Our fears, however, did not.

Everyone is afraid of something. Personally, I’m afraid of a lot of things. There are physical fears–spiders and heights–and there are psychological fears–failure and rejection. While there are certainly many things to legitimately fear in the modern world, just as many of the things we commonly fear are not life-threatening. These fears are vestigial, but they are often nevertheless pervasive and pernicious. Sometimes they affect our lives in conscious and obvious ways: the fear of physical things like spiders and heights may lead us to go out of our way to avoid these things, even when our rational mind knows there’s no actual danger; the fear of failure might make you afraid to quit your job and follow a dream, or even just to take risks at work; and the fear of rejection might make you afraid to talk to someone attractive, or even just to be authentic with yourself.

Psychological fears can also control us in more subtle but no less nefarious ways. The greatest deceptions are the lies we tell ourselves to justify avoiding the things we fear the most: you might convince yourself that what you dream of doing instead of holding a stable, traditional job, is whimsical, irresponsible, or impractical, when really you’re just afraid that if you tried you might fail; or you might convince yourself that someone you find attractive is “out of your league,” when really you’re just afraid that if you made your interest known they might reject you. Because we are afraid, we let these things stop us from being authentic, from living with integrity, and doing what we really want to do–perhaps, even, doing what we were really meant to do.

Ironically, despite the Western Democratic ideals of Liberty and Freedom, many of us unwittingly live in the invisible prison of the mind constructed by our fears and insecurities. Whether we are aware of them or not, our fears define the limits of our realities, and in order to become all that we can be we must learn to see them, to challenge them, and ultimately to overcome them.

The mission to escape the confines of this mental cage and other forms of emotional inertia is what led to my being on that climbing wall despite a lifelong fear of heights and of falling. I eventually did get to the point where I could confidently leap from the wall, and not let fear stop me from getting to the top. In facing that fear, and a few others, I’ve cultivated the courage to face larger and more life-altering fears like the fear of failure.

In the process, I’ve learned that courage cannot exist without fear anymore than light without darkness. I’ve learned that courage isn’t so much about banishing fear, as it is about accepting it so completely and so thoroughly that it loses its hold on us. I’ve learned that mastering courage means learning to re-frame fear in real time so that we can act with clarity, confidence, and integrity in defiance of its influence. As I continue to push the bounds of my comfort zone, I’ve found that my perspective of what’s possible has naturally shifted, leading to a sense of greater fulfillment, a more authentic life and disposition, and a more consistent belief in hope rather than fear. Now I want to share with you how you can have that, too.

What are you afraid of? What are the lies you tell yourself to avoid those fears? What would you do and who would you be if you weren’t afraid? Tell me about it in the comments below, and stay tuned in the following weeks to learn how to recognize fear, cultivate the courage to conquer it, and live the life you’re meant to. Until then, in the words of Nelson Mandela, “May your choices reflect your hopes, not your fears.”

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2017 New Year’s Resolutions

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.
    Chiubaka.com Google Analytics September 2017

    Number of new users by day at Chiubaka.com 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
    Chiubaka.com Amazon Affiliate Metrics September 2017

    First income! Amazon Affiliate metrics for Chiubaka.com 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 Chiubaka.com, 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 DanielChiu.com, but thought better of it as it would require a reasonably large overhaul of existing content. Instead, opted to just redirect DanielChiu.com to Chiubaka.com, 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 Chiubaka.com 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.

How Busy People Learn Languages

The two biggest myths of language learning are that it takes years to learn a language and that you need a lot of time to do it. In fact, many languages can be learned in a year or less with a time investment of no more than an hour a day, but this doesn’t happen learning languages the way most of us have been taught.

As an aspiring polyglot, I’ve tried learning languages in just about every imaginable way: I took Latin classes in grade school, I tried night school Japanese at a local university, I’ve had private Chinese tutors, I completed the Duolingo tracks for both Spanish and French, and I even spent an entire summer at a Chinese immersion program run by the famed Middlebury College. Some of these things worked better than others, but most have either felt inefficient or unsustainable; classroom and self-taught curriculums often require large time investments and don’t emphasize real-life conversational fluency, and immersion, while great, doesn’t teach strategies to retain hard-earned progress long-term.

If, like me, you’re a busy person without all that time and energy to spare, you can’t afford huge time investments with low long-term returns. Fortunately, there are strategies and techniques used by successful polyglots that can take you to fluency quickly and maintain that fluency with minimal effort. I’ve personally been able to use many of them to get myself from beginner to intermediate/upper-intermediate in French in under a year.

Disclaimer: as a fledgling writer and aspiring digital nomad, I do sometimes receive compensation for sale or use of products and services mentioned on my blog. I do, however, only mention products and services I have used personally and strive to always provide my honest opinion positive or negative. I will never compromise the integrity of the content on this blog for financial gain.

The Shortest Path to Conversational Fluency

Trying to speak a new language can be embarrassing!

Trying to speak a new language can be embarrassing! (Image Source)

When it comes to conversational fluency, the real problem with most approaches is that they don’t force you to confront what’s really holding most people back in foreign language conversations: fear of rejection and sounding stupid. Instead of challenging themselves in a difficult and potentially embarrassing situation, most people retreat into book studies, telling themselves that if they just memorize a little more vocabulary or if they just keep studying those conjugation tables, they’ll be ready soon. Except that soon almost always turns into never, and even when it doesn’t no amount of book studying can save you when you panic and your mind goes blank. (If you read last week’s post, you may recognize this as a form of emotional inertia: talking to people in a new language and risking sounding like a lobotomized second grader is terrifying, especially for recovering perfectionists like myself, so it’s easier to just avoid that situation altogether.)

When you force yourself into real conversations with native speakers, you start to overcome the anxieties that make these situations scary. As a result, you begin to open yourself up to more opportunities to learn by speaking to people in new and different contexts. Furthermore, the quickest way to learn the vocabulary and phrases you actually need to carry on conversations is, well, trying to have conversations. (Captain obvious saves the day!) Each time you have a new conversation, it highlights new areas for directed growth toward your weak areas. (Contrast this with the sort of shotgun approach taken by most structured curriculums.) Didn’t know how to say “hello,” “thank you,” or “how are you”? Go memorize them. Couldn’t figure out how to express a thought or opinion? Figure out how to say “I think that…”. Struggled to answer a certain question about your life? Prepare an answer offline that you can practice and deliver the next time someone asks. Your conversations may last as little as 10 seconds before switching to English, but over time you should be able to push this further and further until you’re having full and rich conversations in your target language.

Learning Mindset

It's all about the mindset.

It’s all about the mindset. (Image Source)

With the right mindset it’s almost never too soon to start talking to people in your new language. In fact, Benny Lewis, an accomplished polyglot and author of Fluent in 3 Months, encourages people to start having foreign language conversations in their first week of learning. The trick is to remember that the goal is to understand and be understood without reverting to English for as long as possible, and that failing and making mistakes is totally OK. In the beginning, everything is fair game–pointing to objects, bizarre and convoluted hand gestures describing abstract concepts, or interpretive dances–just try not to revert back to English in fear or frustration. Don’t let yourself get caught up on the mistakes you’re making–the words you mispronounced, the grammar you botched, or the vocabulary that left you when you metaphorically shit yourself–instead remind yourself that perfection takes time and practice, and that even native speakers make mistakes sometimes. Your speech may be broken, and you may sound like you were repeatedly dropped on your head as a child, but so long as the gist of your meaning is somehow getting across, you’re doing great. You don’t need years of classroom instruction, you just need, as with most goals, a few ounces of courage to get started, a dash of discipline to consistently keep at it, and a pinch of perseverance to help you through the most embarrassing moments.

Immersion programs work so well because they give you no choice but to fall into this mindset, and then force you into uncomfortable situations where you don’t know what to say or how to say it. Conversely, some of the more popular language learning tools like Duolingo aren’t as helpful because they give you the illusion of progress without actually dragging you into real conversations. This isn’t to say that things like Duolingo don’t work–if you spend enough time with a tool or set of tools, you’ll eventually reach a certain level of fluency, but then, if you spend enough time trying to crack a coconut open with toothpicks, you’ll eventually succeed. (Don’t quote me on that–I’ve, uh, probably, never actually tried this.) Don’t get me wrong, I love Duolingo–I think what they’re doing is great, their product is moving in the right directions (chatbots are beginning to help close the conversational fluency gap), and I love their mission of providing free language education for all, but having graduated from two of their language tracks, I can attest that it never took me to a sense of real fluency in either language. Tools like these are great supplemental resources, but they’re not going to get you where you want to go on their own.

Language Exchanges

If we’re on the same page at this point, you’re probably thinking, “Great, thanks Daniel, I get that having real conversations is important, but I don’t know anybody who speaks Klingon, so what gives?” Fortunately, it’s a wonderful time to be alive and we have this amazing thing called the Internet (maybe you’ve heard of it?). The primary mechanism I use for having conversations with native speakers is called a language exchange, wherein I connect with someone on the other side of the planet who speaks the language I’m trying to learn and is trying to learn English, so we’re able to trade competencies. There are a lot of websites out there to help facilitate language exchanges, but the one I currently use is called italki. (Disclaimer: this is a referral link, so I do have a small incentive to advertise here. You and I would both receive $10 in italki credits if you take a lesson with one of italki’s very affordable–sometimes as cheap as $10/hr–community tutors. That said, I primarily use italki for the community, not for the tutoring, though both are great.) Through italki, I’ve connected with native French speakers in Europe and Africa. It honestly still freaks me out every time, but doing more of these was one of the improvement areas I identified for my French-learning goals during this year’s mid year review. Aside from italki, I’ve also found that there is a wealth of language-related meetups, so it’s usually not hard to find other language learners to practice with. If you’re feeling really brave (or really desperate?), it can be surprisingly easy to find people to practice with spontaneously in the real world as evidenced by this video of a couple polyglots speaking 12 different languages with random strangers in Ohio of all places.

Efficiently Learning Everything Else

If having real conversations is the strategy for getting us past our anxieties and identifying our areas for improvement, the next natural question is: what’s the best way to improve once we know what we need to improve? And how can we maintain our language gains with minimal effort?

Spaced Repetition

Spaced repetition allows you to review information efficiently.

Spaced repetition allows you to review information efficiently. (Image Source)

The answer to both questions is a memory technique called spaced repetition, which is actually already in use behind the scenes in some popular language tools like Duolingo and Memrise. Spaced repetition involves reminding yourself of a piece of information at an interval that optimizes your likelihood of remembering it without overexposing yourself to it, theoretically resulting in better long-term retention of the data each time you review it, while minimizing the number of reviews.

In practice, if you’re using spaced repetition with a deck of flashcards, rather than review those cards every day, the first day you would review all of your cards. Then tomorrow, you would go back and review your cards again, and you’ll save the cards you remembered correctly to review again in two days. The cards you didn’t remember correctly, you’ll review again the next day. Each time you successfully remember a card, its review interval increases exponentially (so if it had been two days since you saw this card, now you’ll snooze it for four days), and each time you fail to remember a card, it starts over in the process. Eventually, you won’t need to review some of these cards for months or even years. In order to avoid having to study hundreds of cards at a time, you can also break the deck up and just learn a few cards every day to keep things manageable.

There are a few software tools out there for automating the spaced repetition process, but the main two I’ve come across are Memrise and Anki. I personally prefer Anki because it’s more flexible and customizable and virtually every polyglot I’ve ever talked to uses it. It’s also free so long as you can get away without it on your mobile devices. It is however, a lot less sexy and modern-looking than Memrise. Of note, Gabriel Wyner also has a Kickstarter out for a new language learning app, which promises to be a solid competitor to these existing options. (In fact, many of the tips in this section originate from Gabriel’s book Fluent Forever, which likely does them better justice than I can.)

So what is it we’re actually using spaced repetition to memorize? Well, truthfully, you can use this to memorize anything (I’m looking at you, future doctors and lawyers), so long as it comes in small, quizzable chunks. That said, for learning a language, the main things you’ll want to memorize are vocabulary and grammar, and primarily you’d be doing that through flashcards.

Memory Hacks for Flashcards

To get the most out of each flashcard, you’ll want to abuse a few memory tricks. First, every flashcard should have an image. We have visual memories, so associating a foreign language word with an image is much better for you than associating a foreign language word with an English one (which would more-or-less sets you up for translating word-by-word in your head later on). It can be fun to Google image search foreign words because sometimes the subtle differences in the connotation of the word as it’s natively used and its English translation become apparent. (Gabriel Wyner calls this “spot the differences” in Fluent Forever.)

Second, choose an image that is really provocative. Our minds tend to remember things that are really out there: really strange, really funny, really sexy, or really violent. (No joke, I have some pretty racey flashcards–it doesn’t help that a non-trivial number of French words turn up unexpectedly sexual image search results.)

Last, if you can, write a word or short phrase that reminds you of a memory you have that is somehow associated with the vocabulary in question. When this card comes up, try to remember what this phrase was as well. Since our memories operate as sort of associated networks of information, the more connections you’re able to make between a new word and other new or existing memories in your mind, the easier it will be to remember.

Learning Vocabulary

When it comes to learning vocabulary, you need to get yourself to the point where you’re picking up new vocabulary words in the wild–as opposed to from a list–as quickly as possible. This ideally means finding new words and sentences to learn from in their natural contexts–from easy reading, from watching YouTube videos in the target language, or from playing video games in the target language, for example. Unfortunately, the shortest path to getting to this point does involve memorizing vocabulary from lists, but not the lists you’re used to finding in your textbooks. Instead, you’ll want to grab a list of the most frequently used words in your new language. This works because the most frequently used words in a language appear disproportionately often in context so, for example, by learning the 600 most frequent words in a language you can actually learn most of the words you’ll expect to see in the wild, which will typically leave you able to guess at the meaning of most simple sentences, even if you don’t recognize all of the words.

It’s typically not terribly hard to find a list for your language free and available on the Internet, but I personally bought a frequency dictionary for French and don’t regret the investment. I’m also a big fan of Gabriel Wyner’s frequency lists, as they offer a more visual and thematic experience.

When it comes to vocabulary, one of the really important points is that you make your own flashcards. There’s an abundance of existing flashcard stacks on the Internet for any language you could want to learn, but the experience of creating the flashcards in the first place, if done right, is a valuable first step in establishing a concept in your memory. For each word, you’ll want to create at least a couple of flash cards using as little English as possible: 1) picture of something on one side, word itself and other info (like gender, pronunciation, similar words, or relevant memories) on the other side; 2) word on one side, picture and other info on the other side.

If you use Anki, check out Gabriel Wyner’s Anki card templates and use Forvo to grab native speaker pronunciations for words and sentences you make flashcards for.

As a bonus tip here, for languages with those pesky gendered nouns, you can actually shove this information into your visualization centers by associating a descriptive verb with each gender. For example, I like to use “freezing” for feminine words and “burning” for masculine words, so if the word is “farm” and it’s feminine, I’ll picture the image of the farm that I have on the card, but with everything frozen over. Anything that creates a provocative image when combined with the images on your cards will do–melting, shredding, eviscerating (disemboweling? ._.)–let your imagination run wild :).

Learning Grammar

The mechanisms behind learning grammar are similar to that of learning vocabulary. Use all the same memory hacks, but generally use sentences rather than words now. For grammar, it’s easiest to use a sentence you’ve either written yourself or found somewhere and create a blank in the sentence that you have to fill. For example, if I’m trying to learn a verb conjugation, rather than make myself a flashcard for the second person singular of that verb, I’ll just create a sentence flashcard that implies second person singular and leaves a blank for the verb form. I’ll usually give myself the verb infinitive, since the goal here isn’t to test if I know the word, but rather the form of the word that fits here. You can also do the same thing for other grammatical constructs like learning which preposition to use. Eventually, you can also use fill in the blank sentences to learn vocabulary words.

Again, I would check out Gabriel Wyner’s Anki card templates for this if you use Anki.

Learning Pronunciation

Some example minimal pairs difficult for English learners.

Some example minimal pairs difficult for English learners. (Image Source)

Some languages have pronunciation systems or just consonants and vowels that are really different from English. For example, Mandarin Chinese has a tonality system that English speakers find excruciatingly confusing, and French has some very, very subtle pronunciations that sound similar. Sometimes you’ll find yourself staring dumbly at a native speaker who insists that two things that sound exactly the same are actually completely different words or phrases. (Fun fact: these words/phrases are actually called minimal pairs.)

Don’t worry, you’re not dumb. You really can’t hear it. When we’re young, our brains automatically learn to cluster the sounds of our native language into vowels and consonants we recognize. Some languages have slightly different sound clusterings that other languages get easily confused because they get lumped into a sound clustering that we do recognize. But don’t lose heart, it is possible to train one’s ear and one’s tongue to hear and say these sounds.

I recommend checking out Gabriel Wyner’s resources for minimal pairs. He even has Anki-based pronunciation trainers for most languages, which I’ve found helpful for French.

Keep it Fun

The Alchemist by Paulo Coelho in French.

The Alchemist by Paulo Coelho in French.

When it comes to learning a language, don’t forget to be creative and keep it fun! Search for new and interesting ways to immerse yourself in the language. I try to read easy books, I watch TV, and I play video games in French. I’ve even changed the native language of my phone to French–Siri now only does things for me when I talk to her in French and my pronunciation is sufficiently non-shitty–and have gotten used to things like navigating app interfaces in French or having Google Maps tell me how to get where I need to go in spoken French.

Don’t stay chained to a textbook or to flashcards! Your ultimate goal is to be able to function in your new language the way you function in English–don’t forget to find pleasurable ways to do that. Just remember to occasionally make yourself a flashcard or two when you encounter a new word or sentence structure you didn’t know before ;).


I spent my whole life learning languages the wrong way, and up until recently have always felt frustrated by the slow pace of progress or the inability to hold on to a new language over time. Much of that has changed for me after discovering the techniques described in this post, none of which any of my language teachers in school ever bothered to teach me.

With regular conversations in my target language, I’m able to get a better sense of how actually fluent I feel, and with all of the memory hacks I’m able to download a huge amount of information into my brain pretty quickly. While I can’t guarantee the same results for everyone, and you definitely get more out of a language the more time you put into it, I’ve personally put less than an hour a day on average into learning French this year and, though my written and spoken communication still lag behind a bit, I’m able to pass diagnostic tests placing me into intermediate and upper-intermediate French levels. By the time my spoken French skills catch-up–hopefully in the next few months–I expect I’ll be fairly conversationally fluent!

I hope this information will help inspire you to pick up a new language or finish learning a language you started in the past. It doesn’t take years, and it doesn’t require chaining yourself to a textbook for multiple hours a day!


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This was just an overview of some of the language learning methods and hacks I’ve learned this year.

If you found this fascinating or helpful, please consider taking a moment to react to this post on social media, or even share it with your friends.

If you have questions about any of this, please leave a comment on the post, and I’ll get back to you as soon as I can!

Lastly, you can expect more posts on this blog outlining smart ways to accomplish common goals in the near future. Become an email subscriber to be among the first to know when new posts come out!

Further Reading

Fluent in 3 Months: How Anyone at Any Age Can Learn to Speak Any Language from Anywhere in the World breaks down a lot of the barriers that people run into when trying to learn languages: fear of jumping into conversations, the belief that they just don’t have a talent for language learning, and the idea that one has to fly halfway across the world to really get exposed to a new language. This book is the basis for this blog post’s section on “The Shortest Path to Conversational Fluency,” and also contains a number of cool memory hacks and language learning tricks that I didn’t have space to cover in this blog post. I’d also recommend checking out Benny Lewis’ website and blog.


Fluent Forever: How to Learn Any Language Fast and Never Forget It is an excellent and comprehensive resource for language learners. Many of the memory hacks and techniques outlined in this post under “Efficiently Learning Everything Else” come from this book. It’s also worth giving Gabriel Wyner’s website and blog a look, and checking out the Kickstarter he’s running for the Fluent Forever App.




Emotional Inertia

The natural human reaction to discomfort is avoidance–if I don’t feel like doing something, I just won’t; if I hate being rejected, I’ll just stop meeting new people; or if I’m afraid of getting hurt, I’ll just play everything safe. Left alone, our instinct is to pursue what’s easy and what’s comfortable, often trading long-term growth and fulfillment for short-term safety and gratification. Over time, this tendency creates a psychological momentum that keeps us rooted where and who we are–a concept I call emotional inertia.

Emotional inertia is responsible for most of the behaviors we consider stereotypically average: the people who say they’re going to do something–start a business, write a book–and then never do; the people who choose the stability of a 9-5 desk job over the chance to discover and pursue their passions; the people who give up at the first sign of struggle rather than persevere. There’s nothing objectively wrong with being average, or comfortable, or safe, but I will argue that it is less satisfying; if you’ve ever wondered if there’s supposed to be more to life, odds are you’ve succumbed to emotional inertia, and that’s OK–most of us do at one point or another, and every extraordinary individual was average in some way before becoming exceptional.

The truth is being average is a choice and it’s one that we often subconsciously make each and every day. It’s the habit of reacting through our lives rather than proacting. It’s the mode of conceding control to our emotions–our fears, our doubts, our insecurities–instead of taking control with our minds. It’s the practice of waiting for things to happen to us instead of acting to make them happen. When we exist this way, life lives us, not the other way around.

The development of emotional inertia is subtle, but its effects are pervasive. Each time we make a promise to ourselves and break it, emotional inertia grows. Each time we betray the calling of our souls for what is safe and comfortable, emotional inertia swells. Each time we give up without giving it all we’ve got, emotional inertia expands. Eventually we convince ourselves of the highest forgery: that we were never capable in the first place, so we were right not to try.

Emotional inertia leads us to choose comfort over courage; to choose what is fun, fast, or easy over what is right; and to choose to simply profess our values rather than practice them. We combat it by putting virtue into practice. In the immortal words of Marcus Aurelius, “The impediment to action advances action. What stands in the way becomes the way.” Each time we take action in defiance of sloth, we develop discipline. Each time we press forward despite our fear, we cultivate courage. Each time we endure even though we’ve taken a beating, we promote perseverance. Though some people have an affinity for one or more of these qualities, none are innate. Like muscles, each must be individually strengthened and maintained. The choice to do so is always ours.

The beautiful irony of emotional inertia, however, is that it works both ways: it creates an ennui that prevents us from starting, but also fuels an internal resolve that keeps us from quitting. Like a boulder rolling down a hill, we gain momentum as we go and it gets easier, and easier to persist. Still, the struggle is constant and perfection is forever elusive. Yet the promise of pushing that potential to its peak is staggering: mastery over our internal worlds, power to control our perceptions rather than let them control us, courage to dream, discipline to execute, and perseverance to rise again boldly when we fall.

This vision of mastery is what I strive for every day. It’s what inspired me to train for and complete an Ironman triathlon, it’s what motivated me to start pushing myself past my fears, and it’s ultimately what impelled me to take responsibility for my own future by quitting my job. None of these things has been easy. There have been times when I couldn’t get myself excited to do what I needed to do; there have been times when I turned around and went home instead of facing a fear I set out to break; and there have been times when I have wondered if it would be better to just give up, to quiet my inner voice, and go with the flow. But I haven’t. And I won’t. Because ultimately I choose to see what I’m capable of, not in terms of wealth or fame, but in terms of inner strength and character.

While I won’t begrudge those who prefer safety and comfort, I do believe you deserve to become all that you can be. So what’s holding you back? What are you avoiding? What fears do you let control you? Will you rise again? And which destiny will you choose?

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Further Reading

The 7 Habits of Highly Effective People by Stephen Covey is one of my favorite books, and likely the book that has most strongly influenced my personal philosophy. The first habit, “Be Proactive” is a major theme in this post. The other six habits were, in my opinion, equally profound. Nothing in this book is non-obvious, but putting principle into practice is one of the hardest things we can do as human beings. This book is one of my guides for doing so.

The Obstacle Is the Way by Ryan Holiday is an entire book written about the philosophy behind Marcus Aurelius’ immortal quote, “The impediment to action advances action. What stands in the way becomes the way.” This is book about grit, about courage, and about perseverance as understood through Stoic philosophy and the expressed in the lives of many of history’s greatest figures like Demosthenes Amelia Earhart, Ulysses S. Grant, John D. Rockefeller, and Steve Jobs.

Rising Strong by Brené Brown, a renowned vulnerability researcher now of Ted Talk fame, is an inspiring book about resilience. This book is the source of a quote I’m often fond of paraphrasing: “Integrity is choosing courage over comfort; choosing what is right over what is fun, fast, or easy; and choosing to practice our values rather than simply professing them.” Like this quote, the rest of the book is written beautifully, and contains extensive grounded theory research on the process of being brave, falling, and getting back up. This is actually Brené Brown’s third book, and her other two The Gifts of Imperfection, about vulnerability and shame, and Daring Greatly, about courage, are both also well worth a read.

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.
        • Chiubaka.com, 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.

There’s a little less than 6 months left in 2017, which means I’m due for a check-in on my annual goals. This is just a reflection on goal progress over the last 6 months and on how I can do better in the next 6. For more context on the goals themselves (e.g. why I even care about doing some of these things), see the original post.


At a high-level, I think I’m generally moving in the right direction for most of my goals. There are a few where I’ve honestly made very little progress, and there a few where I’ve already hit my stretch goals. If I had to grade myself, I think I’d give myself a C+.

Qualitatively, I do feel generally more confident and less afraid and je peux parler une petite peu de francais :).

For the rest of 2017, I should try to do a better job of tracking metrics for my goals and try to establish more goal-related habits and routines to help me make consistent daily or weekly progress on some of the longer term goals.


Green below means an objective or key result is done. Red means it hasn’t been done or is at risk. For mid year, it’s a good sign to be averaging yellow on all of these.

  • Conquer my fears and insecurities by cultivating courage.
    • Do at least 150 things total that scare me this year. (Does not have to be 150 unique things if appropriate level of fear is still present.)
      • I haven’t done a very good job of tracking this, but I think I’ve probably completed on the order of 30-50 fear challenges this year, especially since this overlaps with rejection challenges. Some of my favorites include:
        • Committing to leaving the safety and comfort bubble I’ve built for myself in Silicon Valley. (I leave at the end of July.)
        • Learning to lead climb and passing my lead climbing certification test.
        • Night diving in San Diego. (Though I was with friends, so it
        • admittedly wasn’t as freaky as it could have been.)
      • Risk Mitigation: Track challenges more consistently. Figure out how many of these I really need to do each week in order to stay on track, and try to hit those numbers rather than worry about the yearly numbers.
    • Conquer my fear of failure.
      • Figure out what I would do if I weren’t working at Palantir.
        • I admittedly have taken none of the steps to network with people in various professions or problem spaces that I had set out to at the beginning of this year, but much of what I’ve learned about myself recently tells me that this isn’t the right time for any of that. Nevertheless, I have enough clarity now to say that I know generally what I would do for at least a year post-Palantir.
      • Stretch: Take a leave of absence from work or quit and do my own things for 3-6 months or leave my current job to work on something more risky.
        • While I haven’t yet committed to leaving my job, I have asked Palantir to send me to France and, while I intend to keep an open mind about this, I do have a timeline along which I am mentally committed to leaving lacking any large changes.
    • Conquer my fear of rejection.
      • Get rejected at least 100 times trying 100 different things.
        • I haven’t done a very good job of tracking this, but don’t think I’ve hit 50 unique things so far. I’d guess I’ve done on the order of 20 different rejection challenges of varying difficulties including:
          • Asking several attractive women out on a date.
            • I only ever do this when I’m genuinely interested and want to get to know someone better.
          • Going on some dates with attractive women.
            • Again, I only ever go on dates when I’m genuinely interested.
          • Attending a speed dating event.
          • Asking for a kitchen tour at Joya in Palo Alto.
          • Asking random strangers at the mall for a high five.
          • Asking strangers on University Ave if they’d be willing to take a picture with me.
          • Generally trying to get to know co-workers that I otherwise have no reason to talk to (e.g. sitting with a random new group of total strangers at meal time).
        • Risk Mitigation: Track challenges more consistently. Figure out how many of these I really need to do each week in order to stay on track, and try to hit those numbers rather than worry about the yearly numbers.
      • Complete at least Foundation Level 2 improv at BATS.
        • Finished this one in March!
    • Conquer my fear of sharks.
      • Go swimming in a shark cage.
        • I actually think I wouldn’t be afraid to do this today. The issue is more around time and money–I think last I checked shark caging is pretty ‘spensive.
      • I haven’t done much on this front other than swim Alcatraz despite knowing there are great white sharks in San Francisco Bay.
      • Risk Mitigation: Put together a fear hierarchy for exposure to sharks which I can use to gradually combat my irrational fear/anxiety when around them.
    • Conquer my fear of spiders.
      • Hold a tarantula in my hand without freaking out.
        • Most of the issue here is that this goal is, itself, entirely too hard for me to tackle from the outset. I definitely need smaller, more realistic goals leading up to this and I’ve failed to define those so far.
      • I’ve done very little on this front.
      • Risk Mitigation: Put together a fear hierarchy for exposure to spiders which I can use to gradually combat my irrational fear/anxiety when around them.
    • Conquer my fear of falling.
      • Go bungee jumping.
      • Go rock climbing outdoors.
      • Stretch: Go lead climbing outdoors.
        • I haven’t been climbing outdoors yet, but I did take a lead climbing class, and I do now have a lead climbing certification card at Planet Granite. This has done a lot to help me get over the fear of falling.
    • Conquer my fear of open water.
      • Complete an Alcatraz swim.
      • Complete scuba certification.
      • Stretch: Go on 2 additional dives after certification.
        • I’ve actually gone on 3 dives past my certification! Twice in San Diego, and once in Nice, France.
      • All of the key results have been accomplished for this one, but I’ve noticed that I am still irrationally afraid of swimming in open water alone. Large groups like a swim race aren’t a problem, and I strangely don’t feel a lot of fear while scuba diving (perhaps because I’m always with a guide?). I think I could plan to push myself further here, but I may leave continued progress on this one to next year in order to hit some of my other goals.
  • Become confident around attractive women.
    • Ask out at least one woman I find attractive each week in person.
    • Go on at least one Tinder date.
      • I haven’t gone on a single Tinder date :P. I did go on a Coffee Meets Bagel date, but I honestly find it hard to genuinely connect with a complete stranger over text. Pretty much all of the dates I’ve been on this year have been with people I met somehow in real life, and then asked out later either in person or by  message.
    • I realized pretty immediately after I wrote my resolutions that these key results are awful and needed to be altered.
      • “Ask out at least one woman I find attractive each week in person” is entirely too aggressive given my comfort level, given that I’m extremely picky, and given that I don’t meet new women that often.
      • “Go on at least one Tinder date” isn’t something that I can immediately control, nor is it necessarily a good proxy for the actual goal here.
    • Overall, I actually feel like I’m doing well here. At the beginning of this year, I felt like I had no idea at all what I was doing when it came to asking attractive people out, or being a normal human being (as opposed to a puddle) when talking to them, or dating them. At this point, I feel pretty comfortable with just being honest and just being myself. I’ve found that if I express my honest attraction to a woman directly and confidently, I can walk away feeling like I have paid her one of the highest compliments I can give regardless of whether or not she agrees to see me. I’ve also found that I’m very happy with who I am and how I communicate with others in my most natural of states–I’m usually a little sarcastic and dry, but overall I like to think I’m a fun and amusing person to hang out with–most of my anxiety around attractive women comes from being too worried about her perception of me and therefore failing to be present. Anyway, to summarize: I feel like I’m probably on the average side of dating ability now, whereas before I really just didn’t feel like I had any idea what I was doing. I’m still afraid of the idea of walking up to a total stranger and trying to get to know her from there and I’d like to feel like I can handle myself in that situation, but I’m doing OK.
  • Read more.
    • Learn to speed read.
      • Read a book about speed reading.
      • Watch speed reading lectures I have saved.
        • Didn’t do this, but am replacing knowledge-oriented key results with just time practicing at this point.
      • I haven’t been practicing consistently, but I did purchase some software (7 Speed Reading) which I think would get me to where I want to be if I just used it for 20-30 minutes regularly.
      • Risk Mitigation: Commit to doing 20-30 minutes of speed reading practice every other day.
    • Read at least 40 books.
      • So far I’ve read about 20 books, so I’m tracking well here. 80% of those books were read in the first 3 months of the year, however, so I have slowed down and that does present some risk to completing this.
  • Become a polyglot.
    • Become fluent in French.
      • Spend at least 1 hour each day learning French.
        • I was fairly consistently at 30-60 minutes for awhile at the beginning, but have been learning a little bit more passively since. So far I’ve memorized ~1000 of the most frequent French words, did a few language exchanges through italki.com, studied a grammar book and did a large number of exercises, and spent 10 days in France realizing that I still suck at talking to people. Right now I’m mostly doing things to increase my exposure to natural French language like playing video games (Skyrim aka Bordeciel is awesome for this haha), reading books, and watching TV.
      • Earn the DELF B2 French language qualification or higher.
        • I haven’t taken a super official test, but I do have a McGraw-Hill certificate stating that I passed one of their B2-level French diagnostic tests. This was probably the lowest test score I’ve had in my life (#asianproblems), but I passed… on the second try haha.
        • Stretch: Earn the DELF C1 French language qualification or higher.
      • Read Harry Potter in French.
        • I have the first book in French both on Kindle and on Audible and have done a few sessions where I read along while I listen, but progress is a little slower than I’d hoped. I’m actually having more success with L’Alchemiste by Paulo Coelho, perhaps because it’s one of my favorite books and I’ve already read it multiple times in English.
      • Risk Mitigation: Hoping to spend about 6 months in France starting in August. Ahead of that, I need to focus more of my attention on actually talking to native French speakers. Book studying is great, but not really what I need right now.
    • Future: Become fluent in Chinese (Mandarin).
    • Future: Become fluent in Japanese.
    • Future: Become fluent in Spanish.
  • See the beauty and strength of which my body is capable.
    • While I haven’t exactly let my fitness languish, and I’m still in pretty good shape, I haven’t made much real progress towards my goals here in the past few months.
    • Qualify for the Boston Marathon.
      • Strategy here was to break through to a 5K time that would extrapolate out to a Boston-qualifying marathon, then work up to the same for a 10K, then a half marathon, and finally a marathon. I’ve come close to the fitness level required for the 5K (~6:00/mi), but in boosting my run intensity I’ve struggled with knee injuries. I’ve spent much of the last few months in physical therapy, but if I’m being totally honest with myself I know I could also be doing more to speed my recovery so I can get back to racing. As is, this goal is at risk, and it’s looking increasingly unlikely that I’ll qualify for the 2018 Boston Marathon.
      • Risk Mitigation: I need to double down on my physical therapy exercises to make sure I can keep running in the long-term. Additionally, I’d like to try a few different things with my training. Boosting intensity on shorter distances is definitely helping my speed, but I think it could also do a lot for me to simply train back up to marathon endurance and continue competing in races to just chip away at my personal record.
    • Develop a 6-pack.
      • Still just have the 4 on top with no sign of the bottom 2 underneath the blubber.
      • Get down to 9% body fat.
        • Started at about 15%, still at about 15% :/. Finding that discipline with food is hard for me especially when the company I work for offers all-you-can-eat meals 3 times a day. (I know, I know… world’s smallest fiddle here…)
      • Do an abdominal workout three times a week.
      • Risk Mitigation: Well, my physical therapist has also recommended lower abdominal exercises, so I don’t have much excuse anymore here. I’d like to focus more on the diet aspect of this. It blows my mind that I was able to get myself to exercise for 20 hours a week to complete an endurance event, but not eating things is so hard. Ideally, I start planning my meals and combine calorie restriction with ketosis. I’ve also started experimenting with intermittent fasting as a method of achieving some basic calorie restriction and to help pull me into ketosis more quickly. Honestly, much of this is bro science, but the first step is building the discipline to hold to a routine long enough to determine if it’s working. Ketosis seems to work well for me since most of my guilty pleasure free calories come from carbohydrates like desserts and snacks… :(.
    • Stretch: Lift weights three times a week.
  • Improve my ability to regulate and compartmentalize thoughts and emotions, especially negative and anxious thoughts and emotions such as fear or insecurity.
    • I haven’t been amazing about the key results here, but I’ve found that through a combination of rejection challenges and self-administered cognitive behavioral therapy, many of the skills for doing this are becoming increasingly internalized.
    • The single most helpful thought for this has been remembering always that “this, too, shall pass.” This thought helps with not panicking when things aren’t going great, and helps provide perspective to not take feeling great for granted so I notice why I feel great when I do. I can then optimize for making things that usually lead to me feeling great happen more often.
    • Meditate for 20 minutes every day.
      • I’m a bit on and off with this. I have long streaks where I’m good about it, and long streaks where I’m not. I do best with this when I make it part of a routine and meditate early in the morning when it feels like I have all the time in the world.
      • Risk Mitigation: I’ve definitely found that consistently waking up early (6AM or 7AM) and meditating first thing completely kills the excuse of “I don’t have time” or “I don’t have energy.” When I actually wake up several hours before the work day, I feel like I have all the time and energy in the world to do these things.
    • Write in a journal at least once a week.
      • I’ve written a few journal entries, but mostly this tends to happen when there’s a lot on my mind and I just need to get it out of my head. So I haven’t been super consistent about this, but I’d also say that once a week is probably a bit too frequent.
  • Become more politically active.
    • Become more politically informed.
      • I have books picked out for all of these categories, but haven’t read them yet. I have, however, read a number of biographies of political and philosophical figures I admire including Martin Luther King, Bruce Lee, Joe Biden, and Ben Franklin.
      • Read at least 2 books about healthcare issues.
      • Read at least 2 books about global warming and environmental issues.
      • Read at least 2 books about education issues.
      • Read at least 2 books about immigration and globalization.
      • Read at least 2 books about economics.
      • Read at least 2 books about political theory and political philosophy.
      • Risk Mitigation: Not sure there’s much I can do here but read more, and focus more of my reading time on these books rather than whatever else appeals in the moment.