I can understand how you feel, after 4 years of hard work and total commitment would you really be ready to make that sort of commitment again? The thought of it can be daunting.
Oh, I’d make the commitment again in a heartbeat. I will write until I drop dead. The question is whether I would ever get any other payoff from my effort outside of the process itself. Will I get an agent? Will I get published? Will anyone ever recognize my effort in any appreciable way?
I don’t have any goals to sustain myself completely on a writer’s income, but an extra $5k or $10k a year wouldn’t hurt. I’m a very introverted person and I hate all the marketing and networking stuff but you can’t avoid it these days. I’m not looking forward to that, either.
I think that this Flannery O’Connor quote is the one that I was thinking of:
(I remembered it from Harlan Ellison’s introduction to Prayers to Broken Stones.
Reminds me of a buddy of mine who teases us relentlessly for doing anything with NaNoWriMo. He also makes fun of poetry, not because some poets aren’t brilliant, but because most aren’t. I’d like to think I’m a little softer. But I still laugh.
Shared interest certainly works.
Through my love of chess, I’ve met people I wouldn’t normally get to know:
- Gary Kasparov (World Chess champion)
- Steve Davies (World Snooker champion)
- Derren Brown (TV illusionist.)
If you’re talking about deliberately meeting, and the billionaire lives locally, there are often clubs and membership fees can be quite reasonable. Then there are trade associations. Through one such I’ve met many wealthy and powerful people.
They are both Furries, and the protagonist recognizes the voice of the billionaire at a party.
Googly Eyes Wide Shut.
I ran into Cuban at a trade show. Met plenty of famous/wealthy folks at trade shows like NAB, CES and SIGGRAPH. For instance, I went to a party at SIGGRAPH for NYIT alums and met Ed Catmull and Alvy Ray Smith. Not names the average person would know, except they co-founded PIXAR, and presumably made a nice chunk of change from that.
Occasionally, cruise ships are overbooked and a billionaire ends up sharing a stateroom with a reporter. Neither of them is pleased, but the resulting friendship is among the finest.
Shared interests. They both breed hostas and go to groups organized around that. They are in the same AA chapter. They both like to restore old cardboard jigsaw puzzles.
Or the billionaire hires the lay person. Maybe the billionaire needs a sound engineer when he’s designing his living room. Or has a piece of jewelry or a musical instrument custom made.
See, that one is so ridiculous that it would distract me from the rest of the story. 
This is the type of thing I could carry as a writer, I am well accustomed to doing service work for wealthy people.
Warren Buffet picks up breakfast at McDonslds every morning. So hang out at McDonalds.
Or not.
If you do, you do. If you don’t, neither did Margaret Mitchell.
I am a neighbor of one of the vacation homes of one of the real life billionaires others have mentioned in this thread.
And previously I have met several socially though sailing. Often I knew far more about their sailboat and sailing skills before I ever learned they were well off.
I know people who do shows for kids birthday parties and they get calls for all kinds of kids, rich and poor.
Then their is always the Howard Hughes scenario.
Very true - I do computer support work for half a dozen millionaires.
Really, even with all the action and detective work?