Whenever I discover a startup I like, or an entrepreneur I admire, I look into their story. The founder in me wants to know: what it was like in the beginning? Ideally, I’d like to find a video of them when they were young or some essays they wrote sharing their journey—as it was happening. But instead, what I usually find a is a key-note speech they gave recollecting their story. The ups and down are there, but it doesn’t fully capture what it was like. So the only real artifact we end up with is a picture of them in their early twenties, smiling, next to an extinct desktop computer.

Why don’t more entrepreneurs share their journey as it happens? I imagine not everyone who’s succesful cares about eventually motivating others to do the same. I, however, wanted to be a motivational speaker before I wanted to start a startup (yes, really), so sharing the ins and outs and ups and downs of starting a company is something I always thought about doing. I want my story to be feel real. Yet, I’ve been working on a startup for a year now and have yet to share a single experience.

I’m planning on changing that going forward. In fact, I’d like to start by explaining why I’ve found it difficult to share my journey.


The most obvious reason is that a startup is all consuming. I spend the majority of my days brainstorming and coding and learning. It’s a contionous cycle that doesn’t leave room for much else. That’s not to say that I don’t have any spare time—spending an entire day working productively is a challenge of it’s own. But there’s so much work to do in a startup that it’s hard to mentally block out time for anything else. Even as I write this, I can’t help but feel that I don’t have the time to write it; that I should be working on my startup, not this frivolous post.

Though it’s not like I haven’t already taken any time to write out my thoughts. I have various notes, journal entries, and half-finished posts I’ve recorded. But there doesn’t seem to be a platform geared towards sharing this sort of thought-in-progress information. Social media platforms like Twitter don’t provide enough context for the sharing to be meaningful, and blogging platforms like Medium give too much weight to each post for me to comfortably share unpolished thoughts. So sharing my journey always feels like something I have to go out of my way to do.

But if I’m honest, the hardest part of sharing my journey isn’t the lack of time or appropriate platform, it’s having the confidence to be candid about my experiences. Starting a startup is objectively hard, sure. But what makes it subjectively harder is a lack of perspective. I’m a single founder, and I don’t know many other programmers or startup founders. So there’s no way for me to truly know whether what I’m struggling to create is genuinely a hard problem to solve, or I’m just ill-fitted to solve it. Without that perspective, there’s an inherent inferiority involved in sharing my struggles. As if I can’t just be a human being—I need to know whether or not my experiences are justified for them to be worth sharing.

It’s enlightening to consider the irony of struggling and success: while you’re trying to make it, you feel inferior for struggling more than others; but after you’ve made it, you feel superior for having had to struggle more than others. This paradox explains why the majority of founders only share their failures after-the-fact: their success finally justified their struggle, and made it a story worth telling.

In theory, whether there’s merit in sharing one’s struggle should be determined by one’s trust in things eventually working out. In practice, these two thought processes don’t happen together. I started working on a startup because I’m ambitious and believe I can achieve something big; only after did I realize how hard it would be to make that happen. But since I now spend the majority of my time working, I rarely have time to reconsider my initial assumption: could I actually do it?

What’s most unsettling about this question, isn’t that the answer might be no—that would at least give me peace of mind. But that there’s no way to truly know the answer without living through the truth of it. So as long as I believe in what I’m working on, it’s pointless to question my ability to do it—there’s only one way to find out!

Yet, in preemptively sharing my journey, that’s exactly what I’m asking someone to do. Implicit in what I’m sharing is the question: is he actually capable of doing it? So that’s what makes sharing the journey hard: it forces me to slow down and openly embrace this uncertainty.

But slowing down to capture these details and share them is what’ll make the experience real years from now. Being open in the face of uncertainty is skin in the game. So despite my ego resistance to doing that, I’d like to start sharing more of my journey. Because I’d like you to see me not just for who I become, but for who I am, in it’s entirety.