Today I filed the Board Resolution for my company (thanks SimpleClosure). It's surreal and yet so very mundane. It's just another docusign -- like what I imagine that signing divorce papers of a long-dead marriage or a death certificate of a loved one who's been ill for a while feels like. On a technical basis, it's just step 31 out of 126 to shutting down a company. It's an event that I knew was coming for at least the last six months. On an emotional level, after letting myself having a minute to feel it, it's a culmination of a 5-year journey, from that fateful sit down. It's the journey of convincing myself to go through with it, falling in love with a problem, finding a co-founder, raising funds, building a team, launching products, myriad pivots, and finally the realization it's not going where it needs to and letting go. It is growth and a shattering of dreams. It is hard-earned, incomparable experience and a heartbreak. Startup and parenthoods are roads one gets on without truly thinking what lies ahead (thank God forthat, otherwise the human species would be long extinct). In the end, it's invariably 100x harder than anything one imagines. I struggle to answer the question: "are you happy that you did it?", because it's a question that doesn't make sense. Let's face it, if this was a unicorn startup, there would be a very easy answer to it, backed by a plump bank account. Seeing that this is one of the 95% of startups who don't fall into that category, the question is harder. The reality that much like a parent, I'm not the same person I was when I started the startup. This is not unlike parenthood. I often hear child-free folks asking the question -- but are you *really* happy that you did it? Not just saying? Look at you, you're covered with snot (or driving around kids), is this really what you wanted? How come virtually all say "yes" to this question? Surely some must regret it. The reality is that when a parent is asked "are you happy that you did it" the person answering the question is a *parent* with love and appreciation for their child, successful or unsuccessful as they might be. It's not the counterfactual non-parent who chose to not have kids. That person doesn't exist. Philosophically I guess, the thought experiment could be: go back to Iz in 2021. Open a crystal ball, and show him two futures: * Future A: A counter-factual where he doesn't do a startup. * Future B: The current point in time Which one would 2021-Iz choose? [1] This is difficult to ascertain not only because we don't know what future A might look like, but more importantly because I no longer know what 2021-Iz would want. I'm 2025-Iz, with 2025-Iz experiences and worldview and value system. And that Iz, almost by definition, values the startup experience tremendously. Like parenthood, this too seems to be almost a universal refrain from founders, even those who were unsuccessful. I know many founders -- successful and unsuccessful, and I literally can't remember a single one who said they regret it. Many may regret it *financially*, many may regret it from *lifestyle sacrifice* standpoint (this usually sounds like: "if I were to do it again, I would do it differently"), but I know literally none who regret the *totality* of the experience. Maybe it's copium? Maybe it's cognitive dissonance? Whatever it is, it's made of the same material as parenthood retrospective :) [1]