Here's what I'm trying, and have advised my 23-year-old brother-in-law to try also.
I've determined that I need to earn $1500 after taxes in order to meet my committed expenses and have some to save/invest. But rather than try to find a single job that pays $1500, I've decided to try the multiple-streams-of-income theory. (Steve has an article on this, but I can't remember the title.)
Any day now, I'll find a part-time job that pays at least half of what I need ($800 or so). Then I'll try to generate $100/mo from 6-8 other sources, seeing how I can turn my hobbies into income. What I have so far:
Hobby: Music
Income Stream: 1-2 singing gigs each month
Hobby: Spreadsheets (I know this makes me sick and wrong):
Income Stream: designing spreadsheets that people can download for a small donation; computer consulting
Hobby: Photography
Income Stream: 10-15 prints or 1-2 framed pictures sold each month
Hobby: Coming up with wacky ideas
Income Stream: Consulting for people who need brainstorming help
Skill: planning and organizing
Income Stream: Business consulting for operations departments
Skill: doing something exactly the same way every time
Income Stream: business consulting for entrepreneurs who've read
E-myth
Obviously, these won't all be making me $100/month instantly. I'll be living off of my savings for a while, and my family will recieve homemade Christmas gifts this year. But none of these is especially outrageous. Selling one picture/month? One gig/month? If I can charge $1/idea, I only have to come up with 100 ideas/month. They're very realistic goals.
And while none of them is (right now) passive income, it is income that I got by doing things I enjoy. And as I get more experience, I'll learn how to tweak them into passive income.
To help with your brainstorming, here's what I'm recommending to my brother-in-law
Skill: Basketball
Income stream: coaching? Tutoring?
Skill: Guitar
Income stream: gigs, teaching
Skill: Comedy
Income stream: stand-up, freelance marketing
Skill: Magic tricks
Income stream: children's birthday parties
Skill: Outdoor sports
Income stream: tour guide
If anyone wants help brainstorming ideas for
your hobbies and skills, PM me. (I won't even charge you.

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