[chasing]

You seem like a good guy and I agree that balancing work and lifestyle is crucially important -- especially in an industry like ours that tends to like to grind people into the ground with mirages of fame and fortune. [Edit: Mixed metaphor. Sorry.]

But. You come off as someone who has just barely started thinking about these issues. You're being wildly overly simplistic about how freelancing works in real life. And using the skydiving billboard as a trigger makes it sound like "living your dreams" means doing extreme sports and hanging out on the beach. Which is fine, but kind of shallow and definitely not the end-all be-all of a well-lived life.

[pbreit]

I didn't get that sense at all. What I took away from the post was a) in sad of packing your days with work now so you can do the things you want in 20-40 years, structure your life so you can do those things now and b) freelancing could be an option (but its not easy).

[rhizome]

It makes sense if you take a step back and see this as a play for the ol' "blog to book deal" business model. Jumble up your thoughts and experiences, slice and dice them into a couple hundred posts and maybe it'll look like sales-in-waiting to some acquisitions editor.