The book is a light intro into the field of Self-Determination Theory and it's filled with examples of people following their passion for 6 months before flaming out because no one will pay them for the thing they like to do.
Another way to put it is that making money takes practice just like playing the piano does. You're probably not going to wake up one day and realize that an empty calendar is exactly what you need to learn how people will pay you for something that nobody told you to build.
http://37signals.com/svn/posts/1985-making-money-takes-pract...
http://www.inc.com/magazine/20110301/making-money-small-busi...
In fact, there are so many examples of this working. Its a mindset: a person with non-entrepreneurial temperament can't imagine trying it, I get that. They go so far as to project their non-risk-taking onto others and claim they're making a mistake.
I think of it this way: entrepreneurs are swimming off the beach, splashing and surfing and diving and sailing small boats. A cruise ship comes by, people leaning over the rail and shouting "Get out of the water! You're getting all wet! You'll drown! The tide might go out! There may be sharks and stingy jellyfish!"
You can try to calm them, tell them "It's ok, I know how to swim, the water is not that bad, come on in with us!" But its pointless; they will stay on their cruise ship and shout and shake their heads. And that's ok.
I left law school a couple of years ago with a lousy plan to post on American craigslist listings, advertising LSAT tutoring. American rates were far higher than what I could charge in Montreal, Canada.
That plan was a total failure. But I was determined not to go back on the path that I was on. I wrote blog posts about the LSAT, and stayed in touch with people in my field. Eventually, an opportunity to be listed on the major blog in the niche came up, and later a chance to write explanations for the LSAT in return for royalties. I also set up a relationship with a company to teach classes for them, something I could not have done if I had still been in school full time.
I'm still doing all the things I started in the first dismal 3-4 months after leaving school. I couldn't be happier with how things worked out. If I had just tried it on the side, I never would have gotten so deep into things, and would have missed the opportunities I got. I HAD to find opportunities, because I had left myself no easy road back.
I like Neil Gaiman's moving towards the mountain metaphor. I had two objectives: earn recurring revenue, and earn enough in the meantime not to need to take a job. I just kept looking for opportunities that would move me in the direction of those twin goals.
Almost everything good that happened to me in the early (and later) days came as the result of talking to people. I emailed a few of the leading blogs in my niche. I cold-called a small company that taught the LSAT, and offered to help them expand to Montreal.
There were about five people writing explanations for the author of the leading blog. I contacted all of them. One of them founded a startup in the niche. I worked with them for a while, and still have a good relationship with them. That wouldn't have happened if I hadn't said hi. Talk to people.
Always look for opportunities. I got into Reddit early last year. I thought, "too bad there's no LSAT subreddit, I could post my stuff there". Eventually reframed that thought as "why don't I start a subreddit for the LSAT?". That subreddit has now become very popular within the LSAT niche, and it's been very helpful being the moderator there.
Think about what skills would help you towards your goal. "If I could do this, what would I know how to do? How would I do it?". I've learned book publishing, enough html/CSS to run a website on Wordpress, and some basic programming which has really helped speed up web page creation.
Nothing needs to be permanent. Don't say no to an opportunity if it's not what you want to be doing in five years. Is it useful to you today? I also do SAT tutoring. It doesn't hold much interest for me long term, but the money helped me through several rough patches.
Hope that helps. Think about what you want to achieve, and what skills you have to offer that will help you reach those goals.
And 'burning your ships' usually isn't quite as drastic and irreversible as it appears anyways.
Let me use friendships and social circles as an analogy. I've had periods in my life where I felt stuck socially. I kinda liked my social circles, I kinda liked my friends, but I yearned for something new or better. I didn't know exactly what though.
At first I tried to go to meetups and activities to meet new people. That worked at first, but it turned out to be very difficult to keep up. Because if I had the choice of meeting a bunch of perfectly fine friends on a Friday evening after a busy week, why would I opt instead for a bunch of strangers that one day might, or might not, become new friends? So at some point I just moved to another city, which for me was not such a huge deal, but still a pretty big step. And it worked very well. I had to go and make new friends. And it turned out that I didn't lose the old friends, not the ones that mattered anyways. In fact, those old friendships got a new shine and freshness.
That said, I did try a less drastic approach at first, and perhaps that's generally a good idea. But there's no substitute for forcing a change, because doing so incrementally can be quite difficult.
So, don't worry: I'm not just sitting around. I've been working on a small side project which is nearing completion, and I have another couple that I'd like to start. Plus, there's another long-term project I would like to do as a learning exercise in game design & development over the course of a few weeks. I should be able to get some time for that very soon. Furthermore, I'm a busker on the London Underground, which some people do for a full-time job and I hope to dedicate more time to (I have a financial goal there, too) which includes learning new songs and becoming a better performer. Finally, I do have a short-term (3-4 weeks) freelance project which is looking to be greenlighted coming up, which in itself will also be a learning opportunity.
The point is, there's loads of learning happening - and I'm really excited about all of that!
"I'd love to just leave my job, but I don't see why setting aside some solid hours each week isn't enough to get something off the ground." - I did this for about a year and a half and I just don't find it satisfying anymore, but I think part of that was because of the job I had.
It could be that this is just a short path of personal discovery, and I quickly change my mind - but I kind of want to find out for myself. For a long time, the whole "But Dan, you don't have a startup that is taking up more time than you can handle right now!" thing bugged me but the truth was, a large part of me wanted to quit for a whole multitude of other reasons, which I hope I have expressed somehow, at least between the lines.
Anyway, everybody has their own path. Mine, perhaps, seems a bit foolhardy at times, but I've been through some rough patches in life and come out the other side a better person, so even if this turns out to be a huge mistake, I do hope I look back at it and say, "well, that was a useful learning experience."
But I don't think it will be a huge mistake ;)
Thanks again, I appreciate the realistic viewpoint and honest opinion.
Sure, finding a job that is both rewarding and non-all-consuming such that you can work on side projects too (ignoring any IP ownership issues) is a great solution, but not everyone is in that situation.