Second Acts

By Beau Denton January 6, 2014

By choice and necessity, baby boomers are extending their working lives as entrepreneurs.

By Kim Hackett

For baby boomers, who have caused a social movement at every stage of development, it may come as no surprise that retirement is a new life phase that experts are calling an “encore.”

Encore is the period “between the end of midlife and anything resembling old-fashioned retirement,” says Marc Freedman, author of The Big Shift: Navigating the New Stage Beyond Midlife, who will be speaking in Sarasota next month as part of the Positive Aging conference presented by the Institute for the Ages. Freedman is the founder of, a nonprofit organization that helps people over 50 find meaningful work in the public and nonprofit sector. “We’re envisioning this chapter as a time when we make some of our most important contributions, for ourselves, for our world, for the well-being of future generations,” he says.

The encore years are a time to reinvent and give back. And for millions of boomers and those slightly younger and older, the encore years are a time when many decide to become an entrepreneur. About 25 million people—one in four Americans ages 44 to 70—are interested in starting a business or nonprofit venture in the next five to 10 years, according to a study by the Met Life Foundation and National organizations like and Senior Enterprise are springing up to help them with mentoring, education and sometimes venture capital, augmenting the help provided by the Small Business Administration and SCORE.

To be sure, much of this talk about “encore” years is about more than personal fulfillment. With average life expectancy reaching 80, many seniors are unprepared financially to live on Social Security benefits for 20 or 30 years. And many people over 50 who need to work experience hiring discrimination because of misconceptions about the abilities of older workers.

Freedman says that greater social acceptance of the concept of the “encore” life stage will break down barriers for people over 50, ensuring they have the support they need to traverse this next phase of life, whether it includes nonprofit, private-sector work, or starting a business. Freedman, who has been described by The New York Times as “the voice of aging baby boomers,” cajoles people to start using “encore” in casual conversations.  He wants people to ask one another, “What’s your encore?”

“I hope this conversation will soon be occurring around every water cooler and dinner table in America,” Freedman says.

“Encore” has picked up steam in academia, research and advocacy groups. The Wall Street Journal now features an Encore section on work and retirement.

“This is a living and growing movement,” says Elizabeth Isele, co-founder of Senior Entrepreneurship Works. “We’re empowering people to take charge of their lives.”

In 1998, living in Maine, Isele created CyberSeniors, a multilingual nonprofit computer training company that eventually trained more than 28,000 seniors in 24 states. She’s led numerous nonprofits over the decades and is now pushing public policy changes and forging connections between organizations to create an “entrepreneur ecosystem.”

That ecosystem is flourishing in Sarasota. Sarasota’s Institute for the Ages, established in 2009 to change the conversation about aging as one of deficit and decline to one about enhancing lives, is a lab for companies and services that want to tap into the needs of older adults.

In late 2013, the Institute launched, a web-based network to connect freelancers with companies seeking seasoned professionals for project-based work. The program started in Canada and the Institute is the first organization to bring it to the U.S.

When the Institute convenes a national convention here in February, entrepreneurship and encore careers will be a large part of the agenda. In addition to a keynote address by Freedman, Isele is leading a workshop on entrepreneurship with Bevon Rogel, who runs a Freedman-related Encore Academy in St. Petersburg to help seniors find meaningful work.

For Southwest Florida, which has one of the highest concentrations of seniors in the nation, the idea of an “encore” seems natural. As the rest of the country and world grays, branding this life stage as one that brings years, or potentially decades, more productivity and meaning to life has become an imperative.

Southwest Florida has plenty of boomers and seniors who have reinvented themselves, and we’ve found three examples.

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Bobby Brown and Cheryl James


When Bobby Brown’s friends heard his plans to open Nice Diggs Furniture in late 2007 with his wife Cheryl James, they told him he was making a mistake. Even a furniture salesman told him the timing was “the worst of the worst.”

“I didn’t understand his sales pitch,” says Brown, 54, with a laugh. “But we didn’t know what the ‘best’ was.” Now, with four employees, a 6,500-square-foot furniture showroom in South Venice and people inquiring about franchising, Brown is glad he ignored the advice. “We had a few sleepless nights, asking each other ‘What have we done?’” James says of the first year in business. “But we love it. It’s been an adventure.”

The couple had lived in the Venice area for just a year when they launched their business, so they never had a taste of the boom real estate years. Nor did they have any retail experience. Brown retired in 2006 as an employee assistance professional at General Motors, and James, a few years earlier, had retired as an employee assistance manager for another large corporation.

After retiring, they traveled, relaxed and enjoyed going to garage and estate sales, selling their finds through consignment stores. It was cumbersome, though, negotiating prices with sellers, and arranging one-on-one sales.  Then one day the couple spied a vacant storefront with a reasonable price. They signed a three-year lease with an opt-out clause and started selling their used and new furniture, glassware and “funky stuff.” Since then, Nice Diggs has morphed from a used furniture business to one that exclusively sells new merchandise. The showroom has aisles of wicker and rattan, bedroom sets, dinettes and accent pieces produced by local artists.

“There was a lot of trial and error and Midwestern work ethic,” Brown says about surviving his first year.

Nice Diggs did not have a big advertising budget, so to attract customers they resorted to an old marketing trick favored by car dealers up North—surrounding the parking lot with banners and giving away free hot dogs.  The couple worked seven-day weeks, 9 a.m. to 7 p.m., delivering furniture after the store closed. Sales steadily increased. Then summer hit. “We sold one vase in eight days,” Brown says.

Still they persisted, and through word of mouth, neighbors bringing in neighbors, and delivering what they had promised, the business grew. “Now manufacturers come knocking,” Brown says.

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Carl Cannova


Whenever Carl Cannova’s car backed up in traffic on I-75 because of an accident, his wife, Tommie, would listen to him complain about “rubberneckers.”

“Why doesn’t someone invent something to stop people from rubbernecking?” Cannova, 70, often asked.

After retiring in 2008 after heading up the western Florida division of Sysco, the world’s largest food services company with offices in Bradenton, Cannova decided to become that “someone.” He invented a portable screening system to shield accident and crime scenes. The SRN 1000—an abbreviation for “Stop Rubbernecking”—is a system of convertible screens and tripods that can be assembled in less than five minutes by just one person. The screening system has become a success more quickly than Cannova anticipated. A year into production, Cannova has sold about 100 of the $1,900 SRN systems to 11 Florida law enforcement agencies, as well as agencies in Maine, Idaho, Pennsylvania, Wisconsin and the U.K.

Coroners and first responders have also purchased the screens to protect the identities of victims. Cannova has had calls from Las Vegas casinos and amusement parks, who want the screens for security.

“When I was putting it together, I thought I might sell four or five,” he says. “With a thought and a dream” it has taken off.

The screening system controls wind, using magnets built into the fabric to stop it from flapping. Tommie Cannova makes the small sand bags that attach to the bottom of the tripods to keep the system secure. All the pieces fit into a customized golf bag so it is easy to tote around. Cannova projects sales will quadruple in 2014. Several family members are now working for the company full time, including Cannova’s son, Phillip, who is a vice president, and Tommie, who is the chief executive officer. Another son and daughter are working part time.

This is Cannova’s first invention. After retiring, he played golf and had lunch with friends. “My wife said, ‘Relax and enjoy retirement,’” he says.

Instead, Cannova invested $250,000 and spent two years developing a prototype, working with Sarasota design firm Robrady and local law enforcement. Most of the parts are made in the U.S. and the systems are assembled in Bradenton. The Manatee Sheriff’s Office was one of the first to purchase the SRN, giving Cannova some valuable feedback through several design changes.

“The system is durable, easy to travel with and set up,” says Manatee County Sheriff Brad Steube. “It is a crucial tool to provide privacy for victims and officers at several types of traumatic events.”

Tommie Cannova says this is not the retirement she envisioned after 48 years of marriage, four children and nine grandchildren. “I thought we’d be traveling and he would be playing golf,” she says with a laugh. “We enjoy doing this together. I’m excited to see how well received it has been and that we are doing something that is needed.”

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Sandra Hughes


When Sandra Hughes retired in 2008 after traveling the country and the United Kingdom for BoardSource, the highly regarded nonprofit consulting firm based in Washington, D.C., she planned to use her travel points and “live out of Hilton Garden Inns in Florence, Reykjavik, San Diego and a fourth to-be negotiated exotic locale,” she says.

But a routine exam changed her retirement plans. The pain Hughes felt was not a rotator cuff injury, as she suspected, but multiple myeloma—an incurable form of blood cancer. Hughes, then 66, abandoned ideas about Reykjavik and spent the next two years in chemotherapy, going through a stem cell transplant and enduring kidney complications. During a day in the hospital that she does not remember, nurses told her she was yelling, “I’m not supposed to be here; I’m supposed to be in Iceland.”

While Hughes managed her health with the support of family and friends, her plans were focused on preparing to die. “I had a do-not-resuscitate order and redid my will 90 times,” she says. She did not envision that she would again be conducting workshops on “selecting your next rock star board member.”

The life change began one day two years ago, when two young people contacted Hughes and asked her to help them become governance consultants.

At the time, Hughes’ health was stable, so she agreed to help the duo advance their careers, explaining her health limitations.

The mentoring gave Hughes purpose and her creative juices started flowing. “I had chemo-brain, and they got me to think again,” Hughes says. She started ordering books, becoming engaged and “got busy planning to live.” Hughes started accepting lunch invitations and social overtures from nonprofit colleagues, whom she had avoided while she was ill. She took on small consulting projects. Each assignment increased her energy.

While she no longer moderates five-day retreats, Hughes now works with about 15 nonprofits in Florida, most in the Sarasota-Manatee area, including the Community Foundation of Sarasota County, the Gulf Coast Community Foundation and the Patterson Foundation.  “Cancer forced me into doing things that I should have been doing before,” Hughes says. She guards her schedule and builds in work-free days.  She is honest with her clients about what she can and cannot do, and she now only works with positive people.

“Cancer changed my life for good,” Hughes says. “I’m a better person. I’m more real to clients, more accessible to family and friends.”


Seniors and baby boomers considering a business venture after decades of working as an employee face a whole new mindset and confront financial challenges at a later age that might not have been an issue earlier in their lives, says Elizabeth Isele, co-founder of Senior Entrepreneurship Works.

She advises people 50-plus to be honest about whether they have the entrepreneurial qualities of a positive attitude, resiliency, creativity and the passion to persevere. They’ll also need administrative and leadership skills—financial, communication and technology know-how as well as management abilities.

Be clear about your financial wherewithal to start a business. It is more difficult to replenish capital and rebuild your financial base at age 50 or 60 than at age 20 or 30, Isele says. How much money can you afford to lose and still remain comfortably solvent? What are the safest ways to bankroll a startup business at this point in your life? Be conservative. Don’t borrow more than you need. And always have an exit strategy for how and when you can repay debt.

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