How to Turn Your Hobbies and Passions Into Hard Cash

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Last month I watched as my husband’s van, carrying 30 large mixed-media pieces bound for Missouri, Montana, Colorado, Texas and Nevada, pulled out of our Tennessee driveway. Instead of my artist husband at the wheel, it was our friend Karen Poole.

Poole, 72, retired from Blue Cross/Blue Shield in 2016, after 28 years there. When she decided she wanted to earn some extra money post-retirement, she took a cue from two of her primary passions — learning new things and helping others — and became a certified Enneagram practitioner. (The Enneagram is a tool that helps people understand their motives, strengths and weaknesses.)

She also works a few evenings a week at a funeral home, greeting mourners and guiding them to the correct reception rooms. In her spare time — what there is of it — she loves nothing more than to load up artists’ vans, and ferry their work hundreds, and sometimes thousands, of miles away, to galleries, businesses, art festivals and private homes.

“I love to travel, and I like to drive, so this gives me the opportunity to visit unfamiliar parts of the country, see incredible art and meet interesting people,” she says. And it’s all free. Her gas, hotel and meals are paid for by the artist, who also pays her an hourly rate.

I myself am no stranger to non-traditional money-making endeavors. In my mid-30s, I left my master’s-level job as a therapist and psychological examiner to pursue painting and writing. Ten years later, I left the art festival circuit to finish writing a book, and a few years after that, at age 51, I took a part-time job editing a monthly magazine for a nonprofit. Eight years later, I was laid off (thanks, COVID-19), after which I decided to level up my freelance writing game. The money isn’t reliable or plentiful, but I’m passionate about the work I do.

María Tomás-Keegan is a certified career and life coach, and the host of the Tips for the Transition/A Career Roadmap podcast who specializes in helping people do just that — move between careers. Having made a transition herself at age 61 following a corporate layoff, Tomás-Keegan understands the challenges, fears, doubts and obstacles that often stand in the way of moving from one kind of work to another. But, she says, whether women are seeking to transition from one full-time career to another, or from retired/not employed to working on a part-time basis, it can be done.

I asked Tomás-Keegan how women can begin to think about shifting from whatever career they had (or didn’t have) to finding money-making endeavors that are personally satisfying.

“Start by reflecting on what brings you joy and fulfillment outside traditional work structures,” she advises. “What hobbies, interests or dreams have you put on hold? How can these be translated into viable income streams? It’s about reimagining your skills and experiences in a new, entrepreneurial light.”

Janice Costa, 60, is a prime example of doing just that. After a decade working in the corporate arena, she left to run a dog vacation business.

She describes it this way: “I rent out a hotel with property and bring together 125+ dog lovers and their canine BFFs to enjoy dog sports, vet seminars, games, activities, classes and some charitable initiatives to raise money for dog-related non-profit organizations. I am thrilled to have turned my passion for dogs into a career.”

Caitlin Kelly, 66, of Tarrytown, New York, uses her foreign language skills to teach French to a homeschooled teen. And Susan J. Tweit, 67, of Santa Fe, New Mexico, is a scientist by training who started a Substack called “Year of Spiritual Thinking” that is steadily gaining subscribers.

“I never thought I'd be writing about something I've always kept private (spirituality),” she says. “Much less that people would actually pay to read my weekly missives.”

These transitions that can mean less money but are more fulfilling are “fantastic opportunities to align your professional life with your deepest passions and values. The emotional rewards of pursuing work that resonates with your soul are immeasurable," according to Tomás-Keegan.

Of course, starting a new business or marketing what was a hobby or passion can easily fall under the rubric of “easier said than done.” In addition to a growth curve, there is a learning curve. And there may be significant self-doubt or anxiety.

Don’t be afraid to ask questions. How have others done what you want to do? While some people you talk to might see you as competition, there are plenty of others who are happy to mentor up-and-coming small business people.

The transition from doing what you’ve always done to doing what you are passionate about starts with giving yourself permission to make your happiness a priority.

For me, going from laid-off editor to busy freelance writer took time, lots of encouragement from my husband and my writers’ group, and no shortage of coffee. Along the way, there were (and are) missteps, mentors, miseries, successes, joys and rejections. But unlike any other job, I am always aware that I am following my passion — and I am my own boss!

And following your passion is like having your headlights on bright in the deepest, darkest night.

 
Have any of you earned money by pursuing a passion? Let us know in the comments below.