Kiplinger

The Joy of Owning a Business in Retirement

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.

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