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Hmmm, let's see...

If we really wanted to, we could make a very nice livelihood doing contract programming/consulting for let's say $100 per hour. That's roughly $200,000 per year. Not bad. Over 40 years, with compound interest, conservative investments, and a reasonable lifestyle, that adds up to, well a lot!

So why would anyone in that position take so much time away from earning to work on a side project, prototype, or startup? There could be many reasons, but the two biggest I can think of are:

- We work on something that pays nothing now because we have to. We don't ever want to wonder what would have been if we didn't.

- We invest time we can never get back in the possibility of a big pay day. That may or may not ever happen, but unlike OP, this is one lottery we're willing to play because it's more than luck; we do have significant influence on the outcome.

I think everyone overestimates their ability to influence the outcome. 85% of venture backed startups are no longer operating in 3 years. Startups are fragile critters, and those 85% presumably were larger high-aptitude and hardworking folk who all THOUGHT they'd at least make it the the "walking dead" group (which presumably makes up most of the remaining 15%).

A lottery is probably a bad analogy. It's probably more like a couple of hands of blackjack.

I think your first point is the winner. See Bezos' Regret Minimization Framework: http://www.youtube.com/watch?v=jwG_qR6XmDQ

I understand your point but I also think that no startup will be truly successful unless you are working on the startup because you want to and love what you do, not just because you have to, or because you want to get rich.

For me, when I say I "have to" work on my startup, I'm really saying that it's what I want and love to do, and if I didn't do it, I'd spend my whole life wondering and regretting choosing the "safe" approach. The safe path will always be available in the future, as long as I keep my skills current, so why not live a little dangerously until I know for sure whether I'm good at it?

I think you are right that people who hate the startup will not do well, but I have to seriously question your assumption that you have to enjoy yourselves _or_ want get rich.

In fact, I believe you must want to get rich, and enjoy what you do. If you don't want to get rich you won't have any incentive to get over the point that isn't fun and you won't build a big business.

It seems to me that regret (wondering what if...) isn't--or at least shouldn't be--a proper motivating factor for doing something as intensive as founding a startup.

As I see it, the reason to swing for the fences isn't to avoid the if only I had... scenario but because we each believe that we posses some innate greatness within ourselves and to not strive to reach that potential is more than just regrettable, it is a failure to live up to our own expectations.

I agree that there is something tragic in never being bold enough to find out what we are each capable of, but the avoidance of that tragedy isn't what should motivate someone, rather it is the desire to see if we have it within ourselves to succeed, to realize our own potential.

Perhaps my disagreement is just a matter of semantics and we are both approaching the same idea from different directions, but I don't think it's an arbitrary distinction irrespective of the context.

Being the richest man in the cemetery doesn’t matter to me … Going to bed at night saying we’ve done something wonderful… that’s what matters to me. -Steve Jobs

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