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How to monetize what you love

There’s a guy–a young guy–who stands outside the Whole Foods at Union Square with a cardboard sign:

“I need money for weed.”

He looks able bodied. He’s clearly entrepreneurial. Ballsy. And, for many passersby, charming; I’ve seen plenty of them pass him a five dollar bill or larger.

But he pisses me off.

He pisses me off because he reminds me that I don’t have this figured out. He’s obviously succeeded at working smarter, not harder. He gets to work outside when it’s sunny. Stay inside when it’s not. He meets lots of people. A good many of them think he’s funny. After a little bit of “work,” he makes money. He’s succeeded at getting people to fund what he loves.

How do you monetize what you love?

It’s a question that lots of friends and I have been talking about lately, or that they seem to be exploring in posts on their blogs. I hope you didn’t come here for an answer because I just don’t have it… yet. For six years now I’ve lived without a “real” job (meaning a 9-to-5), but in many ways, I work harder than ever. I love what I do, but I’d like to be able to take on fewer projects that pay better. And I’d like to spend less time in front of the computer, a desire that’s especially strong right now because summer is in the air. I know that even asking the question confirms just how privileged I am– I have as many choices as I have ideas (and there are hundreds), even though some of those choices are less feasible because of other life circumstances (like being married to someone who can’t travel because of his immigration status).

But back to the matter at hand: how to monetize what you love. While I haven’t figured out yet what works best for me–it’s a complex decision that involves taking into consideration the work I love, the money and lifestyle I want, the ethics and obligations implied by each option–I’ve been reading about people who are experimenting with lots of exciting monetization models, and I’ve concluded we’re living in a pretty exciting time.

  • There’s the author who put together his own book tour, rejecting the traditional dog and pony show put on by publishers (the idea being that he’d sell books, make more authentic contacts, and develop a more loyal/lasting readership);
  • There’s the whole “pay as you wish” end-user concept (tried out by restaurants, PASTE Magazine, and Radiohead, to name a few);
  • There are artists who decided to paint small and sell at reasonable prices in order to get their inventory moving;
  • There are home cooks and chefs who forego the ridiculous overhead of a restaurant, creating an entirely new niche with home meals (this isn’t the first time I read about this phenomenon-wish I could find that article, but it’s the most recent thing I’ve read about this idea);
  • And there are chefs who share the rent for a Brooklyn restaurant that changes its name and its menu (and its staff) every night (can’t find that original article either).

And these are just a few of the ideas.

How many of these options were really and truly open to our parents’ generation?

If you know what it is you love to do, it’s only a matter of time before you figure out the best way to monetize it.

I’d love to know about your successes and your struggles with monetization. Feel free to share in the comments.