I wish we as a valley entrepreneur culture valued this more.
I quit my fulltime job at a startup recently, with the goal of starting my own company. I spent a bunch of time having fairly in depth conversations with potential cofounders. Really sharp people, many of which who had solid, well validated business ideas with significant investor interest.
But I couldn't fully commit. In the end, I realized it was because deep in my heart, I wanted to have a great life now, not at some unspecified (and uncertain) point way in the future. So I decided to focus on building a business that generates solid cash flow and which doesn't require a 60 hour workweek for me to maintain, once I get it up and running.
The process of going around and explaining my decision to everyone who I had been talking with awkward. If you liken the process of finding a cofounder to dating leading up to marriage, then the process of "breaking up" was akin to going around to all of the girls you're dating and telling them you're gay. "We're both attracted to different things", and, "I respect your lifestyle choice" were common phrases:) People were supportive in a "That's nice for you, I'm glad you're following your heart, but I would never choose that" sort of way.
It's a shame that the valley culture is so focused on big, home run hit businesses. We're now in an era of entrepreneurship where very solid cashflow businesses can be created with very little capital, and significantly lower risk than a big homerun hit business. Yet, as a community, we treat them like the uncle whose lifestyle everyone accepts but no one wants to talk about. A lot of the advising, incubators, and accepted best practices all center around taking funding and growing as big as possible as quickly as possible, above all else.
If any "lifestyle" entrepreneurs want to grab a cup of coffee sometime and swap advice and/or encouragement, drop me a line - my contact info is in my profile.
37Signals is not the typical lifestyle business. A business you've never heard of, or which you frequent without paying much thought, is the typical lifestyle business. No one will make a movie about such a business, or be in awe at its growth rate, or fund a bunch of competitors to get into the space. It certainly has its pluses and minuses, but if you are an ambitious kind of character who loves the clang of battle, there's a reason that a lifestyle business seems like a defeat.
Finally, it's not much easier to build a lifestyle business that actually makes more money (and hence provides more freedom) than your alternatives. If you have such talent, you could probably make more of an impact either at a big company or by joining/founding a top startup.
But don't despair, my friend, - people like you have a community: http://www.micropreneur.com/ Note that it's paid forum. I'm still reading the book ( http://www.startupbook.net/ - endorsed by patio11 ) right now, and when I'm done I will join that forum, too. I already met the author/organizer and he's totally the kind of guy who would attract the kind of people you want to rub shoulders with.
There's also going to be nice conference for people like you: http://www.microconf.com/
I am attending, and so should you. Doubting your own sanity is the single biggest risk factor in your micro-business.
I've been talking about starting a bootstrapper's group at the hacker dojo, something focused on those of us who are not focused on getting investment. 'cause like I said, the technical people understand what I'm doing, but it'd be interesting to talk to other people about the business side of my lifestyle business.