The perceived expectations of others

Raising money fucked me up (discussed on Hacker News) is a refreshing counter-perspective to posts and reflections by successful startup and business founders. While I do not doubt the general ability and competence of those people, a part of me could never shake the feeling that “In the end, you just got lucky, and all this post-facto analysis may as well be astrology”. I’m not sure how seriously to take this thought¹.

Here, the author is honest with themselves. without concern that this puts them in a less favorable light². Quoting:

I was excited about the idea we were working on at the time […], but in hindsight, being truly honest about my motivations, I mostly wanted to run my own thing. In a dream world I’d have had the “idea of my life” while working at PostHog or Doublepoint and have gone on to build that with maximum conviction but this wasn’t the case, so I got tired of waiting for a spark and decided to go out and make it happen, with the idea we were working on being our best bet at the time.

The common trope among founder stories “I had this fantastic idea and just HAD TO go build it, whatever it cost.” Refreshingly, not the case here! The author starts their own business just because they’ve always wanted to. Nothing wrong with that! But, admittedly, not so sexy or glamorous.

They go on to raise some money from investors, and then, things start to go wrong:

Anyway, so what happened is I found myself spending days with my head spinning, searching for ideas. I’m angry, I’m annoyed, and I’m not being super productive.

As I dug deeper into these feelings, I realized I was feeling pressured. We weren’t making that much money, we weren’t growing super fast. Then you look around and see “startup X gets to $1M ARR a month after launch” and shit like that and I’m feeling terrible about how we’re barely growing. I’m thinking people that I really respect and admire have placed a bet on me and I’m letting them down.

Except they’re not saying this, I am.

The imagined or perceived³ expectations of others. This has resonated with me.

Throughout my career, I’ve always had really high ownership roles, and have been actively involved in a couple 0 to 1 journeys. This led me throughout my career to get many comments about how great of a founder I’d be or how I have the “founder profile”. I led teams, I wore a bunch of different hats, I worked hard as fuck, and I always thought about the big picture.

Those traits led my former bosses to then invest in me, and now suddenly I have to, in my head, live up to all of this. I can no longer take solace in some excuse like “I could have been a founder but working full-time was the best financial decision (it almost always is) so I never started my own thing”. I set foot down a path from which there’s no return. I’ve begun my attempt. I can of course stop and try again later. But from now on, I’m either gonna be a successful founder, or I’m not. And if I’m not, I’ll have to deal with having broken with the expectations that people had of me.

Of course, I myself have never attempted anything like this, but I believe I understand the underlying feeling that’s being described here. I imagine anybody who was considered, growing up, to be “a bright kid” or equivalent would too⁴. I find this such a nasty psychological effect, which is why I so much appreciate somebody taking the courage of writing about it so cleanly and openly. This effect explains why so many bright kids go on to have miserable lives after school, why so many end up with ruined lives. It’s the pressure of forever having to live up to that label. It becomes a part of your identity. It means that failing at something is failing that image, and that is image is the image that you have grown to have about yourself. Humans don’t tolerate damage to their self-image well.In me, I have noticed that I don’t like trying new things, because I know that like everybody, I will be bad at them at first, which I find difficult to deal with. I can do afford to be like this because what I have found a career in which what I am good at is very valued, but I know and know of others who have not been lucky. Human psychology is rarely pretty, but if you know about such an effect, then perhaps you have a chance to handle it better, both within yourself and in the people around you.