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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.


8 responses »

  1. I’m currently struggling with this concept. As a (relative) newbie to the freelance scene, I’m still working out exactly what I “love” to do within the field and defining my long term goals.

    Most recently, I’ve been forced to decide if my future was in magazines or in my freelance business. Weighing into that decision was what I wanted in my personal life (namely, my current relationship).

    Thanks for the post. Hopefully, we’ll both figure out the answers to our questions.

  2. I think the key to doing what you love and making money is to 1. find out what your passion really is and 2. find a way to market it in a unique way… Career Renegade by Jonathan Fields is book you should check out (or just check out 🙂

    • papertrail23

      1.’s never been my problem. (unless you count have several passions that are equally important).
      2.’s where I tend to get hung up. 🙂

  3. This is sort of off topic, but one thing that amazes me is the quality of some the “free” stuff out there that has a creator who isn’t the slightest bit interested in monetization.

    A case in point is the guy who does the Sounds in My Head Podcast. High-production cutting-edge music mixes every two weeks–for free. The only downside is when he takes vacations sometimes and leaves his subscribers in the lurch until he returns.

    • papertrail23


      I love that you took it off topic! Yes, I like examples of those kinds of folks, too. Gabriel Craig (who makes and gives jewelry away) is one. And a couple of collectives doing these cool things- Rooftop Films and Slideluck Potshow are two that come to mind.

  4. I’m still waiting for some epiphany. All I know is that when I leave this cubicle, I ain’t comin’ back.

  5. Great topic, Julie. I tend to be pretty cynical about this. I think it’s really hard to monetize what you love without cheapening or losing personal/intellectual control over it in some way.

    I think now there’s so much emphasis on monetizing what you love and directly making money from it, and making all of that happen via your own pull-yourself-up-by-your-bootstraps entrepreneurship, that people forget that in the past several centuries artists and innovators have nearly always a) been wealthy b) had patrons or c) lived in abject poverty.

    This is just to say that the whole do-what-you-love-and-the-money-will-follow thing isn’t necessarily a given, but more and more it seems to be painted as such. And I don’t know if I think that whole quest to use your passion to make money is necessarily a good thing.

    Really interesting topic.

    • papertrail23

      Sarah- In all seriousness, I was really thinking about the old-school system of patronage when I wrote this. I think “monetization” is just an overused contemporary word for something that artists have always tried to do. I’m just tired of living divided, you know? Between doing what I love and not making any money and between doing what I don’t really love and making enough to survive. 🙂


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