Merlin Mann (Back to Work / Episode #120 / "Egg MacGuffin") on rehearsing versus doing_
You haven't spent your life rehearsing on how to be happy with what you've got. You spend your life rehearsing what's going to happen when this big, fantastic Mr. Roarke scenario comes down and you're finally never going to have to worry about anything again.
And then later_
I don't think you are going to get a lot accomplished by sitting around and being envious of other people and I don't think you are going to get a lot accomplished by hoping you are going to hit a number one day.
How ironic would it be if what you did turned out so great you actually made some money from it... instead of working that backwards and saying all I need is all of this money and then I can finally be happy and make something.
I think he touches on something that can apply to many aspects of life. Whether it's never being satisfied with material possessions or happy with life, in general. The fact is, whether it's "if I get this iPhone I will be happy" or "if I [INSERT ANYTHING] I will never have to worry about [ANYTHING] again", the feeling is temporary and you will have new challenges to deal with or new gadgets to lust over or some other new thing that is super appealing to you. The grass is always greener on the other side and it's even more so if you get comfortable and stop growing and challenging yourself.
And then there's the classic question that's supposed to help you discover your true calling_ "If you won the lottery, what job would you want to do?" But in reality, you're setting yourself up to believe that's the only option for that dream to come true. I see the appeal in the lottery or any windfall, but when it comes down to it you have a 1-in-175 million chance to hit the Powerball jackpot. The odds of hitting any other lottery aren't much better (how does 1-in-5 million sound?!)
As much as you hear about the high rate of small business failure, you have better odds of success at that, by far. Yes, it costs more. (Though that cost is continually dropping due to technology.) Yes, it's more work. And far, far harder work. But, that dream job will be reality and you'll have a real chance at turning that dream into something that can support yourself and your family. It's the active pursuit of your dream versus continually dreaming, hoping, and rehearsing for that windfall. [1. And, please, PLEASE, charge money for your service/site/whatever. Make a decent living and work hard to build it up into a sustainable long-term business. Relying on an acquisition from Google/Facebook/Yahoo/Microsoft/whomever is no different than rehearsing for that lottery win.]
So... what would you do if you won the lottery? What can you start doing now to make that a reality?