Entrepreneurship as an Encore Career

Thinking about retiring? Then it’s time to start a business. Americans over the age of 55 have the highest rate of self-employment

By Deborah Jeanne Sergeant

Do you know what you’ll do once you retire? If you’re like many baby boomers, you’ll be working in some way or another. According to a Pew Research Center study released in 2016, 18.8 percent of Americans 65 and older — numbering almost 9 million — work full- or part-time, up from 12.8 percent or 4 million in 2000.

For many baby boomers, their labor won’t be for someone else once they retire from their career position. In “The Multistage Life and Self-Employment in the On-Demand Economy” posted in March 2017 by Small Business Labs, “Americans over the age of 55 have the highest rate of self-employment of any age cohort.”

Many factors account for the entrepreneurial bug biting. For Leslie Rose McDonald, losing several human resource specialists jobs caused her to think that she could provide a useful service in career development and helping other adults transition. She specializes in helping baby boomers shift gears to new careers.

It wasn’t easy to start out on her own to found what eventually became Pathfinders CTS, Inc. in Liverpool. Knowing human resources is one thing; starting a business entails a lot more. That’s why McDonald sought out experts in the area whom she trusted for mentoring and advice.


McDonald followed advice she often shares with others, “Is there some yearning in the background?”

By establishing her own career transition firm, she could truly help others while leveraging her experience in human resources.

“It’s about looking at your heart for something you’re passionate about,” McDonald said.

But once a would-be entrepreneur has established what to do, it’s time to think about why.

If it’s for the money, it’s especially important to consider the up-front investment. Consulting, writing and similar home-based work may require $1,000 or less investment. Opening a major franchise location often requires hundreds of thousands — and much more time involvement and a longer return on the investment. Be honest with yourself as to how much of your time and financial resources you want to commit.

The ongoing financial commitment and the timeliness for the return on investment represent huge factors for baby boomers who want to start businesses. Will the business make money in time to recoup the investment?

For some people, taking over an existing business represents the way to go. It already has an established customer base, vendors and business systems in place; however, you may find that you don’t like the direction the business is going or how the processes work. Revamping a business may prove more difficult than starting from scratch.

For those who are financially comfortable, an encore career could enhance their legacy.

Many baby boomers simply feel bored doing nothing in retirement and find fulfillment in operating their own business.

Another example, Jane Falter of Rochester transitioned from working in human resources to offering professional coaching as a way of parlaying her years of experience into a successful small business. Falter was a little young to retire at the time and thought that starting her own business at this point would allow her to finally accomplish her dream that previously “I didn’t have the guts to do.”

She advises soon-to-be retirees to examine themselves for “some sort of skill that may indicate what they want to do.”

That may be completely different from what you’ve been doing, such as a weekend hobby you’d like to make profitable or, like McDonald and Falter, a half-step away — with some education needed. Falter has furthered her education to learn coaching and effective resume writing.


Falter advises would-be entrepreneurs to network with others in their desired industry and in business/entrepreneurial groups.

It takes time to establish and grow a business. Falter said that about five years is right. To help soften the effect, you can establish networks and work at it part-time before retirement.

“Start planning, if you still have a job,” Falter said. “It takes more resources that you initially may estimate.”

Regardless of what type of business you run, Falter thinks that the most difficult part is marketing. She always keeps her eyes open for opportunities and encourages entrepreneurs to “follow your gut.”

While marketing experts produced a professional online presence for her, she realized it was too stiff and formal for her. She wrote her own and felt that it was more authentic (though if writing isn’t your forte, a proofreader may help you).

“It has to be deeper than what you do but who you are,” Falter said.