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.
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
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.
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.