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!