I've met plenty of people that took huge risks and wound up incredibly depressed. Many (most?) startup founders pour everything they have into that company. They give up money, time, health, relationships, other opportunities, etc. Most don't make it. Others will have a success on paper and then waste another year as a middle manager in a big company to get that earnout. Of course, that gets into the debate about whether they were working on the right thing at the right time -- survivorship bias is really strong on this topic.

I'm happy for your success. I assume it was earned with hard work. I hope it works out. A lot of startups with high valuations are feeling the crunch right now. Many of those will peter out and the founders will join the rest of those depressed by their life choices and/or feeling like victims of circumstance. There's far more to success than forgoing comfort and there's far more to happiness than success.

For my part, I co-founded and built two companies for ~4.5 years each: one in hardware and one in SaaS. The SaaS one was in the second batch of TechStars Boston. I had some success and I'm happy I did it. I learned a lot and it was generally fun. But, I trashed my health and wouldn't recommend others do it under the guise of happiness.

Nowadays I do industrial research on language VMs. I get paid very well. The work is gratifying. I have time for my kids, I'm learning things on the job. And I work with great people. I'll probably start another company some day because I like the variety of work and the thrill of the chase. My startup experience gave me a broad network and introduced new opportunities, but I'm only marginally better off compensation-wise than peers that worked a more conventional career. I'm almost certainly behind in terms of lifetime earnings. Many of them are impressed that I struck out and built multiple companies, but that has no real bearing on my happiness.

I'm not sure what being in the top 0.5% means without knowing the metric. If you love starting companies, have at it, but I can think of more challenging paths if you're looking to reach your full potential. Some of the smartest people I've ever met built the foundational technologies that allow SaaS to even exist while working for decades at the same company. I don't know how happy they are, but I know how impactful they've been.

I'm not sure what point you're alluding to here. I've met lots of people, some of whom I'd say took much greater risks than starting a tech company. I'm not sure if you're conflating conventional notions of monetary success with what the article is about, which is happiness.

Is your point that in order to take risks to be happy you need to be so cock-sure as to be closed minded? I tend to disagree and would probably characterize that as reckless as opposed to taking informed risks.