The Joy of Owning a Business in Retirement – Kiplinger’s Personal Finance

Editor’s note: Welcome to “The Retirement Happy Hour,” a lifestyle series that explores how people find happiness in retirement, featuring the personal stories of real retirees. Plus, scientific research that reveals how we can all start living a happier, more meaningful life right now.

If your work offered the most important elements to make you happy in life – a sense of purpose, the flexibility to generally live on your terms, financial security and good health – would you ever want to retire?

That’s the question I came away with after speaking with and learning about small-business owners in their 50s or older, known as encore entrepreneurs.

Take for example, the story of Dawn Fleming, 60, a former attorney turned vacation rental entrepreneur.

Like millions of people, Dawn and her husband were hit hard by the 2008 financial crisis. Three properties they owned went into foreclosure, and they struggled to find work. After two rough years, the couple moved from California to Florida to start over and rebuild their finances. But instead of taking the traditional road to retirement, they threw caution to the wind and purchased an oceanfront home on Isla Mujeres, Mexico, in 2016 and converted it into a micro-hotel called Castillito del Caribe.

Now, Dawn says, they manage various business interests while “living the dream in paradise.”

As people generally live longer, healthier lives, some say the definition of retirement is changing. It might be more accurate, though, to say more people are just rejecting the idea altogether. When I asked about potential business risks impacting their retirement, Dawn said, “We don’t feel at risk as we don’t believe in retirement.”

Rather than work toward a retirement that is all rest without work and responsibilities, many older adults want to leverage their skills and pursue their passions to live their best life. And many are doing that by starting their own businesses.

The prevailing image of entrepreneurs as 20- or 30-somethings leading tech startups is deeply flawed. The reality is that more than 50% of U.S. small businesses are owned by people 55 and older, according to a survey by SCORE, a nonprofit that provides volunteer mentorships to small-business owners.

Still, when considering the potential responsibilities of owning a business — manufacturing products, market research, marketing, the occasional disgruntled customer, etc. — is it worth it as a retirement activity?

Most older entrepreneurs say “yes.” A survey from Guidant Financial found 77% of baby boomer small-business owners said they feel happy.



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