Should You Really Get Paid To Do What You Love?

Photo by Priscilla Du Preez on Unsplash

Ever since I’ve been, ahem, unemployed, I’ve been circling this question like a vulture.

I have always worked for systems and organizations. You know, the ones who offer benefits packages and 401k’s and who provide stale donuts on staff appreciation days. But I’ve always dreamed of working for myself.

I’m a serial, faux- entrepreneur.

I listen to Jenna Kutcher’s Goal Digger podcast and Cathy Heller’s Don’t Keep Your Day Job while I’m doing the laundry or playing chauffeur to my children’s endless, after school activities. I read Rachel Roger’s book, “We Should All Be Millionaires” in one sitting and caught myself agreeing, emphatically, aloud ( to the chagrin of my fellow coffee shop patrons).

I have always been enormously self-disciplined. I keep to a schedule. I have both a digital and a physical planner and trash-picked a conference room sized white board to keep track of my, “work projects”.

I’m a creative- there is no way around that. I’ve tried to deny it for too many years but it keeps coming around to bite me in the ass and as I’m quickly approaching the end of 30's, I think it’s probably time to just accept the part of me that I’ve refused to acknowledge as a real, legitimate thing.

But, to make it my profession as well?

Well, that’s a different story.

It gives me the same feeling as when my Nana used to warn me, “not to put all my eggs in the same basket”. There are quite a few things that have prevented me thus far from taking the plunge from the comfort and familiarity of the traditional 9–5. I’ll share them, because perhaps it’s the same for you.


I like to know when my paychecks are coming in. I like to wake up on the 15th and the 30th and know the amount that will mystically appear in my checking account. I like that I can automate bills, organize my grocery shopping trips and plan for emergencies and special expenses like birthdays and Christmases based upon the steady stream of income. Having been raised by a hardworking, single Mama, I know what it feels like to scrape funds together. Having the experience of being a young Mom and living through my own financial hardships sealed the deal: I will take financial security wherever I can find it. Even if it’s false. Even if it’s those special, “golden-handcuffs” everyone likes to talk about. Because not knowing when the money’s coming in freaks me the F out.


I read Greg McKeown’s, “Effortless” this summer with an online book club at The She Interviews and it absolutely blew my mind. There was something he said in the first Chapter that made me put the book down for 3 days. It was this particular quote that I mulled over and over:

“We are conditioned over the course of our lifetimes to believe that in order to overachieve, we also must overdo. As a result, we make things harder for ourselves than they need to be.”

I am an over-doer. If you’re into that kinda thing, I’m a pretty stereotypical Enneagram 3. I get my sense of worth from how hard I work, how much effort I put in, how many hours I log, and how much I sacrifice along the way. McKeown’s insight on how things can and SHOULD be effortless was a revolutionary thought- one I’m still chewing on, and how that might have something to do with my reluctance to commit to putting both feet in the fire to merge my passions with a paycheck.


This sounds a bit ridiculous at first, I’m sure. It did to me, too. I’ve lived my whole life thinking I never pursued a career in Musical Theater or Writing or International Relations or Academia or the Clergy or, anything, really, because I was too afraid I wouldn’t be good enough. But I think, it’s actually the opposite. Sometimes, you get so comfortable in your uncomfortableness the idea of venturing out and actually doing something different is more terrifying than staying where you are. Because, at least HERE, you know what to expect.

Should you get paid to do what you love?

Is there value and wisdom in keeping passions as, “hobbies” and leaning on a day job to provide secure income?

I’m still on the fence.

Are you?

A recovering know-it-all learning how to eat my words. Sometimes, literally.

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Jenny Vanderberg

Jenny Vanderberg

A recovering know-it-all learning how to eat my words. Sometimes, literally.

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