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How to Turn a Hobby into a Business

Some people change plans after they retire; others make change itself their plan

By Chris Farrell

Editor’s note: This article is part of Navigating Change, a Next Avenue initiative made possible by the Richard M. Schulze Family Foundation and EIX, the Entrepreneur Innovation Exchange.

Courtney Burton has spent most of her career in the retail industry. She was a merchant for several major companies, including Target, CVS, Albertson's and Lane Bryant. For the last 11 years of her retail career, she represented small companies selling private label products to Target.

A woman standing on stage singing into a microphone. Next Avenue, hobby into business
Courtney Bruton, for many years a retailing executive, has changed into a jazz singer, something she has wanted to do for most of her adult life  |  Credit: Courtesy of Courtney Bruton

She also had a side-gig for more than two decades in the Twin Cities: Singing old school jazz with Beasley's Big Band. "That's my sweet spot," she says. "I have become an advocate for keeping this uniquely American art form alive."

Burton decided to retire in 2018 at age 60 for several reasons (although "next chapter" is a more apt term than "retire"). She wanted to leave her job on her own terms and timetable. Her mother was "at the end stage of her dementia journey."

The Challenge of Changing Careers

But the primary motivation for retiring was her desire to turn her passion for music and side-hustle as a singer into a full-time career. Her financial planner told her the numbers worked if she kept getting professional engagements. Her career coach said she was ready emotionally to make the transition. "I still have my voice," she says. "I don't know how long this is going to last. I got to do it now."

She embraced the music business in 2019. In addition to regular shows with Beasley's Big Band, she's also creative director and lead vocalist for her jazz ensemble, Court's in Session. She also has a side-hustle focused on another activity with high personal returns — career coach. Burton's practice is geared toward individuals looking to make a life transition, including career development, changing occupations and retiring.

"I still have my voice. I don't know how long this is going to last. I got to do it now."

Her music business was interrupted by the pandemic of 2020 and, like many entrepreneurs, she had to quickly pivot. Burton took advantage of time away from live performances to build an infrastructure for her music business. She relied on coaching for income.

At age 65, she finds coaching and music are now about equal in time for her. "I love creating nurturing, safe spaces for people to experience humanity, whether it be their own or someone else's," she says. "I do that in the coaching practice, and that's really the essence of my music business."

We know that plenty of older adults pursue various creative endeavors in their spare time (think of your aging neighbors and 50-plus colleagues). The web-automation company Zapier estimates 40% of Americans had a side-hustle in 2022. Gallup found that 61% of those surveyed said hobbies were extremely or very important to them.

The thought of turning hobbies, creative passions and side hustles into a business in the second half of life is an attractive option to consider. For one thing, the activity is meaningful with high personal returns. For another, you understand the product or service. Finally, the time spent on your passion has revealed insights into what potential customers want and need.

Being Your Own Boss Is Exhausting

That said, the transition toward building a full-time creative business isn't easy. There is a big difference between, say, intermittently selling homemade salad dressing at farmers' markets and running a full-time salad dressing company, or making a little money on the side by occasionally doing paid DJ gigs for friends and making a living as a DJ.

"Maybe you think it isn't about money, but at the end of the day you don't want to lose money doing it."

Starting a full-time enterprise requires much work, planning and financial and emotional commitment. Sometimes a creative passion that has given personal satisfaction for years along with extra income should remain a hobby. Nothing wrong with that.

"It starts with what any entrepreneur should start with. What are your goals? What do you want to get out of it?" says Donna Marie De Carolis, founding Dean of the Charles D. Close School of Entrepreneurship and the Silverman Family Professor of Entrepreneurial Leadership at Drexel University in Philadelphia. "Maybe you think it isn't about money, but at the end of the day you don't want to lose money doing it."

You'll want to develop a business plan and figure out how you'll make money selling your services or product, of course. There are also several practical steps to take that don't cost money (beyond the price of buying coffee, wine and maybe a meal) but do require an investment in time. De Carolis strongly recommends tapping into your network early on to get their insights into your business idea. Actively reach out and solicit their suggestions and criticisms.

Ask for Advice — and Use It

Research your business prospects by learning from surrogates, entrepreneurs already engaged in the activity you want to pursue full-time. Many successful entrepreneurs are remarkably willing to share what they have learned about their business. You might also consider pulling together an advisory board — two or three people "who will work with you as you go through this journey," says De Carolis.

The number crunching, business plan, marketing strategies and other basics are critically important because they improve the odds your enterprise will succeed. (Check out this column's sidebar with its 15-point list of to-dos.) So are the high personal returns — the sense of purpose and meaning — that come from transforming a passion into an encore career. Just ask Marshall Vanderburg, aged 68.


Vanderburg had several careers in Colorado working for local government, a software company and a small business serving nonprofit organizations and local governments. He and his wife raised two daughters and many Airedales in their home in Denver. He is now a farmer and writer.

Next Step: Winegrower

Specifically, Vanderburg is in his third year as winegrower with a modest 125 vines on land in North Fork Valley in central Colorado. He writes about his experiences growing grapes and Colorado's burgeoning wine industry on his website, Wine Encore. He works hard and it's clear from our conversation that he's having a blast. "I always enjoyed learning new things," he says. "The part of how I'm spending my time learning is so rewarding."

"I always enjoyed learning new things . . . spending my time learning is so rewarding."

Let's back up for a moment. Vanderburg worked in the retail and commercial wine business as a young adult in college and immediately after graduation. He moved to Denver as a Vista volunteer after graduating from the University of Oklahoma.

In 2008, inspired by a friend who has a winery in California, he began making his own wine. Ten years later he wanted his own operation. He and his wife bought some land in the wine growing area of North Fork Valley. He grows Pinot Noir and Riesling since both grapes are suitable for the area's climate.

The work is physically hard and there have been weather-related setbacks. The vineyard is a bootstrap operation financially, at least so far. He's working on a business plan that would let him sell wine with the aim of covering his costs. "That's my goal," he says.

Mentors for a Mid-Career Rookie

Several experienced mentors in the Valley have helped him along in his wine-making adventure. "There's nothing better than learning from someone doing what you want to do," he says. "I spend a lot of time with people a lot more knowledgeable than me."

The entrepreneurship and creativity among older adults looking to turn their passions, hobbies and side-hustles into full-time enterprises is exciting. Traditional barriers between leisure (fun) and work (hard) crumble.

The embrace of entrepreneurship in the second half of life by so many older adults reflects the deep desire that our work makes a difference to ourselves, our families and our community, even if only in small ways. "Finding purpose in life matters," says Vanderburg, adding that "it doesn't matter what age you are." He's spot on.

Photograph of Chris Farrell
Chris Farrell is senior economics contributor for American Public Media's Marketplace. An award-winning journalist, he is author of the books "Purpose and a Paycheck:  Finding Meaning, Money and Happiness in the Second Half of Life" and "Unretirement: How Baby Boomers Are Changing the Way We Think About Work, Community and the Good Life." Read More
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