[martythemaniak]

Before you regret something you didn't do, ask yourself whether you understand that thing well enough to regret it. Why did you want to do a startup?

For example, one popular reason is "I'm my own boss", but that's largely wrong. If you're trying to make money, you have bosses. Going from a salaried job means going from one or a few bosses to many, many bosses. Depending on the startup, these could be a multitude of consumers, a few big clients and/or investors. These bosses will not tell you directly what to do, but will rather stop paying you, or never pay to begin with if you don't do what they want out of you.

You needs and wants about what you want to do is probably very different from what your bosses will pay you to do, and adjusting your needs/wants/ideas to what will pay is what we call "finding product-market fit". Yes, new markets arise, and sometimes someone extraordinary will mold the market to themselves, but largely you'll be molding yourself to the market.

This is not to say being your own boss is BS - you still get plenty of autonomy and are the final decision maker. The layers between you and the market are extremely thin, so the highs are higher and the lows are lower.

[wpietri]

One point I love about having many bosses is that the more numerous they are, the more you can get away with ignoring any single one. When I was consulting, I always tried to keep a few gigs going at different levels. That way if one client wanted something insane or dangerous, I could say, "Gosh, so busy!" and move along.

Paradoxically, having the ability to say no meant I didn't have to say it very much. When a client wanted something foolish, I could say confidently, "I don't think that's in your best interests," and explain why without fear.

[buboard]

This doesnt match my experience. Your users/clients are not bosses, they are optional. It's a qualitatively different experience from having "2 levels of bosses"