Losing Sight of the Shore

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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