How to Become a Gig Entrepreneur

By Lynne Beverly Strang

Jim Glay, Owner of Crash Boom Bam

After Jim Glay abruptly lost his sales manager position at age 59, he spent a year looking for another job. When no prospects materialized, he decided to go another route: turning his life-long passion – playing the drums – into a business.

Today, Glay is the CEO of Crash Boom Bam, where he sells pieces from his expansive collection of vintage 1960s drum sets through an online store. He also brokers sales for other drum collectors and performs as a drummer a few times a week with rock and jazz groups.

Glay was among the “gig entrepreneurs” – i.e., people who earn an income by turning skills and talents into gigs or freelance work — featured at Boomer Boot Camp, a July 2017 workshop sponsored by BoomerWorks and AARP Virginia.

I had never heard of the term “gig entrepreneur” before the workshop. But as a freelance writer and an author, I fit the description. So I joined the mostly 50-and-older professionals who filled a Northern Virginia church meeting room to hear the ins and outs of finding gig work.

Changing demographics, risk-averse employers and a trend toward outsourcing are factors behind the tighter job market for boomers, said Purposeful Hire’s Shira Harrington. As a result, interest in gig entrepreneurship has never been higher, as evident by the strong turnout for the boot camp.

Lanes and Tribe

For those interested in gig work, the first step, said Harrington, is to define your “lanes” (professional skills that can be repurposed into short-term gigs or a long-term business) and “tribe” (the industry, mission or sector where you can solve challenges and have an established network).

Harrington outlined three ways to enter the gig market: FCO or fast-cash options (focus groups, Uber, AirBnB, etc.) for those who need money in a hurry; on-demand gig work (project-based assignments such as freelance writing or event planning); and small business ownership.

Participants in the July ’17 boomer boot camp

How much money can you make from gig work?  It depends upon you and what you’re offering.

Gig entrepreneurs have unlimited earning potential but “you have to get into the frame of mind that says it is possible,” said Harrington.

In addition, an unfulfilled need has to exist no matter which route you choose. “People are only going to hire if you can solve an urgent problem,” she said.

No More Gold Watch

Micro-businesses with five or fewer employees are now among the top providers of employment, noted Angela Heath, founder of TKC Incorporated. “We, as baby boomers, have to think very differently,” she added. “There is no more gold watch.”

“You cannot live to be 45-plus and not have something to offer the economy.” — Angela Heath, founder of TKC Incorporated

Like Harrington, Heath believes the future is bright for gig entrepreneurs. “You cannot live to be 45-plus and not have something to offer the economy,” she said.

From Heath’s experience, people often overlook everyday skills – such as organizing, painting or home decorating – that have value and can be converted into a business. “With technology, the doors are swung wide open,” she said.

Still, first-time gig entrepreneurs may find it challenging to get a foot in the door. “When it comes to gig work, you have to be tightly focused at the beginning,” said Bizstarters’ Jeff Williams, whose clients include Glay of Crash Boom Bam.

Once people know you’re capable, they’re likely to come back to you for other jobs since it’s time consuming to find good help, he added.

Williams pointed to himself as an example. “I have probably picked up one-third of the income I enjoy today from work I never expected to do,” he said.

Getting Started

If gig entrepreneurship appeals to you, note these five things that Heath says you’ll need to get started:

1) Answers for your questions – Reach out to organizations or people who can provide technical information about your industry. Two places to look: Trade associations and LinkedIn.

2) A way to manage fear and doubt – These emotions are inevitable when you start a business. To cope, join a supportive community, do research and product testing, get feedback on your idea and analyze/prepare for worst-case scenarios.

3) Accountability – Line up someone who will keep you focused on your top priorities. A family member, a business partner or a marketing consultant may be candidates for this role.

4) Support – Find others to do the aspects of your gig work that you can’t, or don’t, want to do. Bartering can be a great way to exchange needed services.

5) A willingness to ask, seek and knock – Be prepared to market yourself and make “an ask.” And you can’t ask just one time. As Heath put it, “If you don’t bring it, somebody else will.”

Here are a few resources that might be helpful:

Articles20 Gig Websites; Top 10 Gig Websites.

Books – The Gig Economy by Diane Mulcaly; The Gig Solution: How Boomers Can Earn Executive Fees Doing Project Work by Spunk Burke; What’s Next? Follow Your Passion and Find Your Dream Job by Kerry Hannon.

Coaching – Williams and Heath offer coaching programs especially for older entrepreneurs. BizStarters’ Start Your Business NOW! e-course, normally $199, is $99 for a limited time. Limit-less: Uncover the True You and Profit, TKC Incorporated’s five-session live course, runs July 26-August 23, 2017.

Organizations – BoomerWorks,,, SCORE and the U.S. Small Business Administration offer various types of information – such as research, downloads, webinars and templates – for aspiring and new entrepreneurs.

The bottom line? Gig entrepreneurship can be ideal if you want independence, flexibility and an income without certain responsibilities (such a payroll) associated with other forms of entrepreneurship. Like any business owner, you’ll need focus, tenacity, a plan and a willingness to do without.

But you’ll be working for yourself.  And that’s a great feeling.


About Lynne Strang

I'm a freelance writer who helps organizations and individuals meet their marketing and communications goals. I am also the author of "Late-Blooming Entrepreneurs: Eight Principles for Starting a Business After Age 40." To learn more, please visit my website:
This entry was posted in Business, Career Changes, Careers, entrepreneurs, Entrepreneurship, Leadership, Retirement, Success and tagged . Bookmark the permalink.

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