Start-ups and Emotional Debt (2014)

If you go through life tinkering with projects, ideas and products without never really finishing something it gets demoralizing. You start feeling like a broken record talking about all the things you're going to do "some day". Not from a money point of view, but rather the joy of having created something special.

Sure you can stay in that cushy job and give up your dreams and delusions of grandeur, working away for someone elses vision, but you'll always have that nagging disappointment that you didn't follow through.

This might only apply for certain personalities, but for those I think it might be better to at least give it a shot rather than forever wonder what could have been.

The outcome is that I have nil joie de vivre, and have become a dour old fuck at the ripe young age of 31. I've gone from boundless enthusiasm and optimism when we started, even though we are now finally coming into our own and running the business less like asshats, to viewing the world through crap-stained glasses.

It's cost me friendships, relationships, my health, my sanity, and pretty much everything else that's actually worthwhile in life.

I suppose I do at least still have enough introspection and perspective to realise that it's not as bad as my wounded instincts lead me to believe, but it's a never-ending struggle to consciously adjust my perceptions.

If there's any moral to this story, it's to learn to not give two craps about other peoples' happiness as early as you can, and to learn to clamber over people and stamp on their faces to achieve your goals. Unfortunately, I can't get behind that ethic, so am doomed to forever feel that I'm letting people down - thanks, negativity bias, you sod.

This blind spot is the undercurrent to his whole essay. While there are definitely startup founders who can experience regret of an alternative life, the author completely ignores the opposite situation: the play-it-safe employee who has "friends & family" but has demons of "unfulfilled potential" constantly gnawing at him.

>, you should probably spend more time learning about your own brain, and trying to form enduring friendships, and less time worrying about money and start-ups and equity and things.

This assumes that one cannot create enduring friendships while in the act of building startups. People can pursue goals of becoming a Navy SEAL, climb Mt Everest, hunt for the Higgs-Boson, etc and cultivate friendships while spending time on activities that require intense focus.

>For whatever reason — maybe it’s generational — today’s founders feel the need to be the hero of their own inner narratives. For them, start-ups embody a kind of happy confluence of making a lot of money, changing the world, showing everyone how smart and wonderful they are, and, ultimately, becoming their awesome true authentic selves.

The author has a dismissive tone using phrases like "for whatever reason", "showing everyone how smart and wonderful they are", and "becoming their awesome selves". Sure, manipulate the reader by only describing caricatures of egotism.

The author doesn't mention the other legitimate sentiments such as, "I don't to be a cog in someone else's wheel", or "I don't want to optimize algorithms to make people click on ads"[1]

The author doesn't seem to acknowledge the existence of people who will not be fulfilled with friends unless they are satisfied with what they are doing with their life. A similar scenario is a family man who isn't fulfilled by settling into a domestic routine. He has children; at best, he loves them but at worst, he's apathetic and sees them as constant reminders of ambitions that were killed. The girlfriend/wife unexpectedly got pregnant and now he feels trapped.

[1]http://www.fastcompany.com/3008436/takeaway/why-data-god-jef...

Indeed, I've been managing my startup for 3 years and in the process have learned to hire, fire, sell software, test software, manage investors, and more. These are all skills I'd rather be getting now than later.

Different people are built for different organizations -- some do well in small groups, others are great in large, hierarchical structures. Both are important skillsets and knowing where you fit and will succeed is important.

I'd encourage people to read "Managing Oneself" by Peter Drucker to help decide if a startup or small company is, or is not, for you.

Like my parents and extended family, I fall into intensive training and skill-building when I feel like it, not for the pragmatic reasons I was told to believe. I'm not enterprising; although I've done some business, I am not a founder, certainly not in the SV sense of the term. I am content with a simple life with many friends, find little pleasure in making deals or drawing attention to myself, and at the end of the day, would like to focus on building the world through the esoteric, not the popular.

Valuable things for me are not something I can weigh or measure like assets and work hours; neither are they idyllic stories and images, or carnal pleasures. They're weird stuff, and nobody particularly cares about weird stuff except other weird people. And so the startup narratives ultimately fail to work for me; I don't want to allocate that level of commitment into the marketplace. It feels like a distraction, because the market values the popular and the practical, at any level. Everything else slips through the cracks, and I like slipping through the cracks. The way to hook me on a get rich quick scheme is to tell me that I'm slipping through the cracks and need only make one small change.

I didn't come to this conclusion without lots of attempts over the last decade, though. If I had genuinely wanted to pursue a popular, practical approach, I had many chances to do so. I convinced myself, like many a confused young person, that I did want this, and I took some of them, and the experience was worthwhile, but not enough to stick around for. Successes tended to feel empty; failures felt delusional. The biggest satisfactions usually came when I walked away after getting bored with the idea - yes, bored. Not after a definite, final, concrete answer, but after simply being unwilling to take the next step forward and drifting off. I know that some of those things I walked away from could work, could still work now. I don't care.

This is a step that my parents stop short of acknowledging. They still live with the burden of "being successful" as a universal, and their struggle as one measured against that universal, tearing themselves apart a day at a time as their behavior mismatches their expectations.

What do I actually do? Today I met someone I've only known for an hour or two outside of the internet. We had coffee, and I met some of their relatives. They were on vacation. We had no business together. We just sat and talked, with luxurious pauses and lulls in the conversation. For three hours. It was fine, and now I have a closer friend.

And that is me, that is the type of thing I do and like doing. But it's not rational thought. I felt and did, and rationalized after. As such the way forward for me is to fuck off with planning my professional career in any more than a broad "make a little, save a lot" conservative generality. If I do anything more risky or ambitious, it'll happen suddenly, because it always has, but in most respects I value inner life more.

And that is not you, dear reader. Maybe you're similar to me. Maybe you're more like a founder. Maybe take some personality tests(that are not Myers-Briggs).

"By developing “start-up skills” for four years, you are missing an opportunity to hone your skills as a writer, musician, engineer, architect, or whatever that secret aspiration was that you had before you decided it was necessary to make a lot of money first. It will be a regret that will not go away."

I did fully commit myself to build a company which gives me immense financial freedom and I definitely did not pursue some interests I wanted to. However, I have absolutely no regrets. Given a choice all over again, I'd choose building the startup without even thinking for a micro-second compared to wanting to pursue a career in music. Interestingly, now I can take private lessons on playing the piano when and where I feel like.

Money is definitely not everything and cannot singularly make you happy, but in today's world it's definitely the first thing you'd like to acquire to simplify getting most of the other things you want.