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I love GitHub but this post doesn't provide much coherent advice.

"Optimizing for happiness" seems like a hard idea to argue against. The author defines happiness as:

"I'm a hacker; I'm happy when I'm building things of value, not when I'm writing a business plan filled with make believe numbers."

That's a pretty narrow definition. The rest of the article implies that what the author really means by happiness is freedom and lack of stress. He writes:

"When there are fewer potentially catastrophic events on the horizon, you'll find yourself smiling a lot more often."

That's actually an argument against doing a startup at all. Startups are extremely stressful and freedom-limiting endeavors. Servers crash in the middle of the night. Smart people launch competitive products that try to kill yours. Users get pissed at you for removing their favorite feature. In my experience there are always catastrophic events on the horizon in a startup.

Personally, I try to optimize for things like excitement, challenge, personal development, impact, and fun. Raising a VC round may or may not contribute to these, depending on a lot of things.

Are startups necessarily stressful or freedom limiting? Somebody recently emailed me and invited me to speak in Europe. I started saying "Thanks but..." before I realized "Wait, if I wanted to, I could totally go. I have the money, and a week or two delay of launch won't kill anyone."

As for stress, I think my most stressful moment in six months was an unexpected outage. I recovered in ten minutes. Other than that, laundry causes me more stress.

If it's a corporate conference, you should ask them to pay your travel expenses.

They may say no, but you'd be surprised how often sponsoring companies and organizations will say yes to that kind of thing.

Are startups necessarily stressful or freedom limiting?

That's an interesting question.

In my model of human psychology, when a person is passionately driven to achieve an ambitious goal, he gets stressed out about obstacles that stand in the way. Does passion necessarily cause stress? I think so, but if you know a way to have passion without stress, please let me know.

As for being freedom-limiting, startups take a lot of time, and you generally have cofounders, investors, employees, and (hopefully) users relying on you. These external factors are big responsibilities. Does responsibility necessarily limit freedom? I think so, but I would be interested in counterexamples.

Thus, if you want to avoid stress and limits on freedom, you would have to avoid passion and responsibility. I suppose you could start something not very ambitious, that you aren't very passionate about, avoiding cofounders, investors, employees, and users. I would have a hard time calling such an endeavor a "startup".

I don't think Tom equates happiness to lack of stress, or to freedom in the context you seem to describe. My understanding of Tom's advice to "optimize for happiness" is more along the lines of "optimize for self-determination". Historians seem to analyze "the pursuit of happiness" in the Declaration of Independence similarly -- basically, as a right to self-determination.
What's cause and what's effect?

Is GitHub a great product because the founders optimized for happiness or where they only able to optimize for happiness because they had a home-run product on their hands?