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What Retirement? People Over 65 Are Launching Encore Careers and Finding Fulfillment Like Never Before

Published November 01, 2019

Ah, retirement. That time when you can finally kick back, relax and for once, simply do nothing.

Or is it?

A growing number of older Americans are challenging the idea of traditional retirement, as more retirees decide they want to keep working or pursue passions after leaving the rat race behind: the number of Americans age 65 and over who continue to work has doubled since 1985, according to a study by United Income. Some people simply need to keep a paycheck coming in to cover the bills, but many want some combination of rewarding work on their own terms and additional financial security. If this sounds like you, there are pros and cons to consider when pivoting to a second — or third or fourth — act later in life.

First, do some soul searching, career experts say.

“Ask yourself, what is it that you do well and enjoy doing, and find meaningful at this point in your life?” says Nancy Collamer, founder of and self-described “semi-retirement” coach. Don’t re-invent the wheel if you don’t have to, Collamer says. It’s much easier to get a venture off the ground using contacts you already have instead of starting from scratch in a new field.

Network, Network, Network

The network you’ve built up over your years in the workforce is your most valuable asset, experts says. Reach out to people you’ve worked with over time and ask them to get lunch or set up informational interviews. LinkedIn is your friend.

“That’s how you’re going to get a job,” says Chris Farrell, author of “Purpose and a Paycheck: Finding Meaning, Money, and Happiness in the Second Half of Life” — not by sending out cold applications online. Solicit feedback from people whose opinion you trust. Ask them what your strengths and weaknesses were on the job if you’re struggling to figure out what type of second career you want to segue into.

Don’t underestimate the support you can find through your college alumni association, local resources and trade associations, either, Collamer says. You can find free mentoring, online classes and workshops through organizations like the Small Business Administration. Look into a place like SCORE, which connects beginner entrepreneurs with business owners who have already built their own companies. It’s a good idea to join a community of other entrepreneurs so you don’t feel isolated working from home, Collamer says.

Get Financially Fit

“Debt is a dream killer,” says Kerry Hannon, a work and jobs expert and author of “Never Too Old to Get Rich: The Entrepreneur’s Guide to Starting a Business Mid-Life.”

The biggest stumbling block people have when they’re shifting careers or starting their own business is money,” she says.

If you’re starting a new career, you’re not going to make as much money as you did at your previous job, at least initially, Hannon points out. If you’re opening your own business you may not be able to take a salary at first (or only take a very small one) as you reinvest in the business.

“It often takes three years to make a really successful career switch,” Hannon says. “It’s not a sprint, it’s a marathon.” Create a budget for your new business just like you would for your household spending. Think about how you can cut back in other areas of your life to free up some cash flow. Could you relocate to a place with lower cost of living, for example?

Michael Lowe, 70, was a corporate lawyer for three decades, but became bored after a few years of retirement.

“There’s only so much yoga you can do,” he says. While trying to pass time, he discovered he loved learning how to make cocktails. He took a risk and set out to start Green Hat Gin, the first distillery to open in decades in Washington, D.C. Talk about a career pivot.

But Lowe was smart and went into business with his son-in-law, who had worked in the retail alcohol business and could provide the necessary connections to help get their venture off the ground.

He was prepared for the high start-up costs involved in building a distillery from scratch. Lowe couldn’t have pulled off the capital-intensive launch without enough savings: he contributed the majority of the roughly $1.5 million the partners needed to start the business. It took about a year for Green Hat to turn a profit. The partners also spent a few thousands dollars investing in training themselves: they signed up for a week-long apprenticeship program at the Dry Fly Distillery in Spokane, Wa., where they learned exactly how the distilling process works and what kind of commercial equipment they would need to buy.

Paul Dillon, 74, also retired from his corporate job to open up his own shop, Dillon Consulting Services, LLC., where he advises veterans and others on business strategies. For Dillon, part of planning a comfortable retirement as a budding entrepreneur was budgeting for potential gaps in income as he built the business, like Hannon suggests.

“It’s perfectly normal,” he says, of going through extended periods of time without a paycheck, or with smaller paychecks. Don’t get discouraged if you experience a dip in cashflow — it’s be to expected. Be prudent and factor plausible income drops into your business plan ahead of time, Dillon advises.

He also relied on his connections to cut expenses when working on his start-up. He asked favors from peers, like using empty office space at a professional connection’s company rather than paying to rent his own space in a building.

Though he still maintains an office in Chicago, now Dillon lives and works in Durham, N.C., an ideal place for certain retirees thanks to a reasonable cost of living and ample teaching opportunities at nearby universities. His well-planned relocation allowed him to stretch his second act even further by making a transition to academia: he is now part of the adjunct faculty at Duke University’s Sanford School of Public Policy teaching a course on veterans’ issues.

Prepare Physically and Mentally

Hannon says she often fields concerns about ageism. “Should I get Botox?” is a question she hears from retirees who are thinking about an encore career. Instead of worrying about what they look like, she counsels clients to focus on the presence they project when they walk into a room.

“Whether it’s walking or swimming, or what you’re eating and good nutrition, you have that energy and that can-do spirit,” she says. “You present a really positive image. People want to have you on their team, they want to work with you.”

And energy is key to running your own business. You’re not just the CEO, but the I.T. woman, the H.R. person and your own accountant, too. Plus, you need to have the stamina to pick yourself back up when you encounter bumps in the road. Be mentally prepared to encounter setbacks — they happen to every entrepreneur — so they don’t overwhelm you when they inevitably occur.

“It’s not a leisure activity,” Lowe says of running his distillery, which also has a tasting room and bar attached to it. “I’m more than full-time.”

Lastly, it may sound obvious but, do your research. It’s a step people can overlook in their excitement to create something of their own. You need to pinpoint opportunities for profit before you dive in head-first. Dillon says that’s some of his best advice for people striking out on their own.

“I would have spent more time thinking about and researching potential clients and avenues that I could go down,” he says. Having a network will help you meet people, but you can’t land a client if there’s no market for your services. “I would have benefited by spending more time planning before I started my own business.”

“It’s ok to be a dreamer, but be a practical dreamer,” he says.




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