HAVE YOU EVER MADE MONEY DOING WHAT YOU LOVE?

IMAGE // Via EW.com

When I was a kid, having a TV in your bedroom was considered the Ultimate Luxury. Well, considered by me, anyway.

“Oh my Lord. You mean, you can watch 90210 right here?” I asked my friend Lindsey, gesturing to her bed. Lindsey was one of my rich friends.

“Yes,” Lindsey replied, bored, clicking through channels with her remote. “Sometimes I start watching something and just leave it on while I fall asleep.”

Oh my.  Just leave it on?  I found this notion outrageously glamorous. At my house, TV was a precious commodity, something you could only watch in a special room. It was doled out carefully at certain hours, when the best shows (Family Matters, The Fresh Prince of Bel-Air) were on. Having Cosby loll me gently to sleep each night while I blinked contentedly from my pillow was like a foreign country of awesome.

Lindsey lived in a bonafide mansion, and my mother always got a complex picking me up at her house. First she had to drive through the gate, then park next to a sprawling English garden, and then if these indignities weren’t enough, trudge up the flower-ensconced walkway to Lindsey’s magnificent front door. Had cell phones been around yet, I’m sure my mother would have texted me with a bright, “almost there! See u out front!” instead, but times being what they were, she had to put up with the regular, rose-scented reminder that we didn’t live the way Lindsey’s family did, and probably never would.

I had a lot of rich friends growing up, and I can remember totally idolizing the  way they lived: the TV’s in the bedroom, the country club memberships, the exotic car phones. But what you idolize and what you know are by their very nature so categorically different, and it’s funny how the “what you know” side of things often ends up being your preferred life course. For example, Ross and I don’t even own a TV! Anywhere in our house! I don’t tell you that smugly (ok…maybe a little); I just bring it up to illustrate how your environment shapes your cravings. These days, ever since the big quitting my job decision*, I think about money constantly, to reassure myself over and over again that Ross and I will be OK. But that’s an important distinction, right? It’s security I crave, not riches. I’m shallow and greedy in many ways, but my 12-year-old fantasies of the High Life are teeny tiny compared to the sheer joy of paying all my bills on time.

Anyway, I got to thinking about all this because I’m giving a talk tomorrow at the Texas Conference for Women – which features some truly FABULOUS speakers like Brené Brown and Gretchen Rubin, whose roster I am beyond honored to join – called ”How to Make Money Doing What You Love.” I like giving talks like these, because what can I say, I’ve got a teacher streak in me. But at the same time, I sometimes feel a little disingenuous doing so. I mean, what the hell do I know?

“Tolly, shut up! You just quit your job to do things you love,” I can hear you saying. Ok, true. And let me tell you, I am off-the-wall pumped about it; I turned in my yoga teacher training application on Sunday, and nearly skipped down the street!

But. Back to the matter at hand: how does one make money, doing what they love?

This isn’t a philosophical pondering; this is an honest question I am posing. Because in my talk, I’m not going to give a prescription. I gave a prescription for such-and-such at my last social media talk, and it honestly rang a little false to me. So instead, I’m going to tell stories. Tell people what’s worked for me, then tell people what’s worked for others.

So!  Let’s chat. If you leave a comment in the comment section, I will absolutely use it in my talk, because I’m trying to harvest as many examples as possible. Here are some questions for you:

A) Have you ever made money doing what you love? What was it?

B) Have you ever known somebody who has made money doing what they love?

C) How did you/they get this money-making venture off the ground? Old fashioned fundraising? Do a Kickstarter? Get a loan from the bank? Get help from Mom and Dad or a spouse? Develop a little somethin’ somethin’ on the side while tending to a day job?

D) Did you/they fail first? Or, was your/their first shot at monetizing a passion a resounding success?

E) How about business? Sometimes creative types have great ideas, but lack instincts on the business side of things (here I am describing myself). How did you/they learn how to set revenue goals, invoice clients, register your biz at the DBA, etc?

F) What would you/they recommend to someone who wants to make money doing what they love?

Please share your answers in the comment section!

I would love to share your thoughts in my talk tomorrow, especially because I know some of you are badass entrepreneurs. Maybe you’re such a successful entrepreneur, that you’re watching TV right now — from your bedroom!

*Thank you for your supportive, encouraging, and downright touching responses last Thursday! You guys were seriously making me emotional, and I mean that in a really, really good way. I am excited about the change, truthfully a wee bit scared too, but mostly excited — and that is due in large part to you sharing your experiences with me, and telling me over and over again that I can do it. I won’t let you down!    

  • http://twitter.com/kjsouthernbelle Katie

    I am so excited you’re on the roster with Brene Brown and Gretchin Rubin…this is HUGE!!! Congrats, my friend!

    Ok, I’m working on make money doing what you love. Can’t currently comment on your list of questions. BUT what I think I’m going to do is develop something on the side and once up and running I can quite the 9 to 5′er. I have a dog to support ya know.

    Good luck tomorrow!

    • http://www.austineavesdropper.com Tolly Moseley

      Katie! That is great news. I have been so curious about you and your new hatching of a little side gig — I know you’ve been wanting to switch things up career-wise for a while. We should get together sometime and chat about it.

      Oh, and, guess what?! There’s a silks show on Nov. 30 and Dec. 1 you should come to!! I have 2 pieces. :-)

  • Melissa Mora

    I make money doing what I love. I love to sew and design, and I recently quit my job to go full time designing and selling PDF sewing patterns. Prior to that, I spent a year building a blog audience and designing a couple patterns on the side, learning the ins and outs of the software I needed to use, all while working a day job as a teacher. The investment was pretty minimal, and came from our savings. As I began to sell patterns, that money was reinvested in my business. I did/do a lot of googling and reading of IRS/state websites to find out about the business side of things, but since I’m a creative girl with a love of rules and organization, that part of it hasn’t come too hard to me.

    • http://www.austineavesdropper.com Tolly Moseley

      Wow! That is really inspiring to hear, Melissa. What’s the website for your blog/sewing patterns?

  • http://www.facebook.com/akilah.hughes Akilah Hughes

    This post is lovely and everything I’m all about. I still don’t have a tv in my room, but hulu is pretty much doing the trick! And yes, I’m getting to a point where I’m making money doing what I love, but it certainly is difficult to sustain!

    xo – Akilah

    http://www.itsakilahobviously.com

    • http://www.austineavesdropper.com Tolly Moseley

      Very cool, Akilah! What is it that you do?

      (And yeah…we “cheat” and watch Netflix on our laptops all the time. ;)

  • hipstercrite

    Congrats, Tolly! Sounds like a great conference! Wish I could be there!
    After leaving my job as personal assistant in LA and moving to Austin to “work on my writing”, I was surprised after three years of staying focused, I was able to surpass my goal of “working on my writing” and actually become a paid writer. It still surprises me that people commission my services. I’m waiting for everyone to wake up one day and go, “Wait a minute! She has no idea what she’s doing!” Though my posture and ass have suffered greatly from working at home, it’s very invigorating to do what I love most. Austin is the sort of town where if you have goals and stay focused on seeing them through, there are plenty of opportunities available to you. I feel very lucky to live in this wonderful town and meet so many wonderful people.

    • http://www.austineavesdropper.com Tolly Moseley

      I echo your sentiments so much, Lauren. There’s a long culture here of contractors and freelancers, which I think makes career trajectories like yours not only possible, but a wise move. It also makes me hope that Austin can be a forerunner someday in healthcare for contractors … ah, dreams!

      Anyway, my fellow writer, you know I’m going to call you soon for a “networking” coffee (or drink. ;) You’ve been warned!

  • http://twitter.com/TheSimplifiers The Simplifiers

    just sent you an email with my bits of advice and answers! -Mary of The Simplifiers: Event Planning + Personal Concierge

  • http://www.facebook.com/elizabeth.mack.16 Elizabeth Mack

    oui!! Doing what i love every day, as terrifying as it was to take the leap from a “real job with benefits”, it’s equally energizing and exciting! Successful business? jury is still out…if success is measured in profits, but let’s go back to the “doing whaty i love” part. score! Thank you for being the inspring woman YOU are! :)

    • http://www.austineavesdropper.com Tolly Moseley

      @facebook-100002994637530:disqus, let’s have coffee soon! In my yoga biz daydreaming, I’ve stumbled on some cool social media companies that may be beneficial to FreeStyle, too. And PS, I will probably hit you up for advice soon on taking a trip to Paris…one of my girlfriends and I are currently trying to manifest that. ;)

      • http://www.facebook.com/anita.erickson.754 Anita Erickson

        Went this April, amazing, of course. We stayed at the Hotel Langlois; rooms were huge and it was intimate and not super-expensive (but still elegant).

  • http://www.facebook.com/anita.erickson.754 Anita Erickson

    A) Have you ever made money doing what you love?
    What was it?

    I’ve been really lucky to have been the first
    employee at three startups, so some of what I love is simply
    entrepreneurship. But with launching Red
    Chair Market this summer, I’m actually combining entrepreneurship with a topic
    I’m passionate about; furniture and interior design! It makes work even better when I get to look
    at beautiful things all day, although my husband’s pretty nervous about me
    spending so much time in furniture stores.

    B) How did you/they get this money-making venture
    off the ground? Old fashioned fundraising? Do a Kickstarter? Get a loan from
    the bank? Get help from Mom and Dad or a spouse? Develop a little somethin’
    somethin’ on the side while tending to a day job?

    We are lucky in that the two main skills needed for
    our business, web development and marketing, are under our roof at home. So we started our business with a small loan
    from Mom. My husband is working
    full-time and coding at night and I’ve just picked up a part-time job to fund
    more advertising. We hope to bootstrap for a while longer before we need to go
    after formal funding.

    D) Did you/they fail first? Or, was your/their first
    shot at monetizing a passion a resounding success?

    We’ll let you know! We’re giving ourselves about
    a year to make it happen.

    E) How about business? Sometimes creative types have
    great ideas, but lack instincts on the business side of things (here I am
    describing myself). How did you/they learn how to set revenue goals, invoice
    clients, register your biz at the DBA, etc?

    I learned much of the business and operations side
    in my previous roles with other startups.
    I encourage “creative types” to find a small startup to work for and to
    get in there and ask as many questions as possible from the “management types”. Understand the basics of accounting, finance,
    operations, legal; it can be boring but terribly important.

    F) What would you/they recommend to someone who
    wants to make money doing what they love?

    As above, find a small company to work for and
    become a sponge. Learn everything you
    can from people who have different roles than you. Then go for it, and remember that your first
    business is unlikely to become Facebook, so plan for some small success but
    hope for the home run. Everything you
    learn the first time around will make you more successful the second.

  • http://www.facebook.com/anita.erickson.754 Anita Erickson

    Tolly, how did it go??

  • http://www.austineavesdropper.com Tolly Moseley

    @48123d2578c6765d0c375675fd779a68:disqus !! I am so glad you commented. Ever since we met at Freelance Austin, I’ve always been so into what you do — your freelance public radio stories. It’s an incredibly unique biz, and I’d still love to take you out for lunch sometime and talk more about it. Have you ever thought about pitching KUT for your own show, now that they are building in more programming? (What with their split into 2 stations and all.)

    Anyway, such good advice here. You and Mary both recommended the City of Austin’s small biz development program, which I would love to go to (and bring my husband, also an entrepreneur. He teaches school-of-rock style music lessons to kids). With media, I definitely feel like I’m much more in the independent contractor mode, but with yoga — especially with a specific product offering I want to develop — I know I need to do all the big girl businessy things, like draw up a business plan, get Quickbooks, etc.

    So. I think we tried to establish this on Twitter sometime, but I flaked out! Lunch sometime, m’dear?

  • Lindsay

    Yes, definitely! We have much to talk about and apparently much in common. My husband is also a music teacher with a school-of-rock approach, but at a school. The middle school kids just did a fair rendition of Ice Ice Baby at an assembly.

    Are you free on Friday? I’ll be out of town much of next week.