For the first time ever, someone acquired my product. I did not receive a life-changing amount of money in exchange—no where even close. But it was nice to have built something and receive recognition of its value. Reflecting on the experience of living through the full lifecycle of a product—from inception to (micro-)exit, I've refined my conception of conviction.
I used to think conviction meant the complete removal of doubt. Because, well, isn't that the marker of a successful entrepreneur? If you're going to make it, you need a level of unwavering belief in your vision that can only be rivalled by the likes of a Steve Jobs. (I blame popular media for this.) I remember one time when I felt possessed with that kind of absolute conviction. I acted on it, racing headlong towards building my vision and...eventually I crashed spectacularly. To keep it short: The market didn't care about my vision and my execution was abysmal. That failure left scars...and ever since, I've been disillusioned by unquestioned belief.
For a long time, I was the skeptical founder. When I began my search for a new founding idea, I couldn't help but question everything: every hunch, every assumption, every decision. My algorithm for doubt was endlessly looping: Is the problem worth solving? Is the market big enough? Would anyone actually pay for it? Is this idea venture-scale? etc. Of course, doubt—when moderated—can be a helpful ally. It can ask the important, guiding questions. It can act as your compass, preventing you from traveling down roads that lead to a dead end, or off a cliff. But an excess of skepticism can linger over every decision. The overthinking becomes over-protection. Like a parent so afraid of their child getting hurt that they never let them leave the house.
In my case, doubt cast a shadow on everything. And Instead of steering me in the right direction, it became the enemy of progress. When I asked myself if I'm good enough to get traction in an industry, I would convince myself otherwise. When I asked myself if this market was big, I would conjure numbers to show that it wasn't large enough to support a venture-scale company. In cases where it was big enough, I would conclude that there was too much competition for an upstart to make a successful entry. With every question and every decision that would allow me to take one step forward, there was a plausible counter-argument for why I shouldn't take that step. I was spinning my wheels under all the relentless questioning.
The dam finally broke when I got fed up with the paralysis of analysis. I asked myself, Why was I so agreeable with my self-doubt? If my faith can lead me astray, why couldn't my self-doubt?
So, I tried to just accept it—That doubt will always exist and I can't eliminate it. That all my choices carried a non-negligible, irreducible risk of turning out bad. When I was contemplating the product that would eventually get bought, I decided that as long as there was some baseline intuition (which happened to come from personal experience) telling me there was a possibility of success, I would move forward. As I started building, the doubt was still buzzing in the background. Is this worth it? Do you really think someone will want this? Am I the right person to make this work? Doing my best impression of a practiced meditator, I let these thoughts come and go. At times, they sharpened my focus. But they would also chip away at my confidence. I stuck to my conscious decision to ignore them. Nothing was going to stop me from shipping my product, except feedback from the market.
I persevered long enough through the nagging presence of my reservations—from ideation to sale—to get some reward from the market. The financial reward is a pittance, but I'm thankful to have received something even more valuable: Proof that one can succeed despite the ambient self-doubt.
I'm not the only one who's dealt with this kind of self-apprehensiveness. I've met plenty of founders who struggle with it, especially those who are exploring. These founders are brilliant people but armed with mental models and heuristics for analyzing markets, they can convince themselves out of pursuing anything. Some haven't had the lived experience of conviction, while others have had strong conviction but still got burned. Sometimes, a co-founder can be an effective counter-balance. Other times, they can only reinforce your doubt. The reality is, when you're searching for a meaningful opportunity, you're faced with so much ambiguous and conflicting evidence that it's easy to rationalize giving up. I've found clinging to gut and intuition—rather than rigorous analysis—helps me persist past the initial uncertainty. Blind faith or whatever it maybe, you need something to help you stick to an irrational decision long enough to gather evidence to know whether it was a good decision or not. But when do you know? When should you stop? I truly don't know. There's no clean answer to when you should listen to the mounting negative feedback. But I do know it shouldn't be determined by unfounded self-doubt.
So where does that leave me? I'm not the naive dreamer anymore, nor the paralyzed skeptic. I'm somewhere in the middle I suppose. I think I've developed a healthier way of coping with my inner doubt, thanks to this whole experience. One where I peacefully co-exist with the fear of the unknown, accepting the better parts (e.g. avoiding delusion), ignoring the rest, so I can make progress. When I start spinning from overthinking, I step back and try to ground myself in something simpler, like a gut feeling. That's what got me through this time—not a grand epiphany or a foolproof plan, but a quiet refusal to let doubt call the final shot. As I write this post, I have to admit, I'm worried. Worried that my message is useless—and convoluted—and plain obvious. Should I just scrap this copy and write about something else? My gut's telling me that somebody out there might resonate with my message so I should just publish it, and see if that's true.