Let’s Get Started with Jill Smith Entrekin


Let’s Get Started with Jill Smith Entrekin



The Happiest Retirees podcast debuted on September 19, 2023, and Jill Smith Entrekin was our very first guest. As the new kids on the podcast block, it was essential to start strong, and Jill’s performance was the bulging bicep we needed to flex our mission of helping families retire happier.

What makes Jill a happy retiree? Let’s get into it.

Born in the small town of Thomaston, Georgia, she taught high school literature for over thirty years. One can only imagine the number of young minds she inspired. Yet even more impressive than her career is what she’s done since.

After three decades of teaching others how to write, she put down the blackboard chalk and picked up her pen. She’s now published two books, with a third, Bonnie Mac’s Cafe, coming soon. James Taylor, the host of Writers in Focus, said that her evocation of growing up in the ’60s in rural Georgia was as good as any he’d read, including best-selling novelist Ferrol Sams.

Having enough savings may be the foundation for a happy retirement, and Jill had that in order. But it takes knowing what you want to do with your new life to build something beautiful. Jill took the time and did the soul-searching. Once the dust settled, she figured out that she wanted to be the one putting original words on the page rather than showing others how to do it. It was her turn. She told me, “I decided, alright. This is the best time in my life to do what I’ve always dreamed I wanted to do. So, I got started.”

Jill makes it look easy, but don’t let that fool you. It was not. She dealt with extreme loss. Her sister died young from juvenile diabetes, and in 2020, her husband, Dana, passed away after a four-year battle with Lewy Body Dementia. She also stared down the fears and challenges anyone faces after leaving a career and wandering into the unknown.

How did she manage to come out the other side? She relied on the encouragement and support of family and friends to give her that extra boost of courage to go for it. I find that some of the most affable and talented folks can be quite hard on themselves. Unlike the braggadocious bores who never bother with self-reflection, they ask, “Why me?” It’s that humble instinct that makes them such empathetic stewards of society. And though the self-critical impulse pushes them to excel, it can also prevent them from owning the greatness they undoubtedly possess. Jill had the goods. She just needed to believe it.

Sometimes, a nudge from a loved one can take us from “Why me?” to “Why NOT me?” Perhaps that’s one reason we have found that the happiest retirees average three close social connections, belong to at least one organized social group, and travel at least once per year with friends. A glance at Jill’s social calendar would show she meets these marks and then some.

Why else does Jill get an A+? Is it because she’s just plain fun? I can honestly say none of my high school teachers ever wore a black dress with a red “A” to teach Nathaniel Hawthorne’s The Scarlet Letter or a straw hat and overalls to introduce Mark Twain’s Huckleberry Finn. So, yes, she’s definitely more fun than most. But it goes deeper than fun. She’s curious about the world and craves an exploration of its beauty.

As Wes Moss says, “Curiosity may have killed the cat, but a lack of curiosity kills happiness in retirement.” The happiest retirees average about three and a half core pursuits—the hobbies that get them out of bed in the morning. The unhappy ones tend to have less than two. Jill has so many it would take a while to list them. In fact, she had to skip her beloved yoga class to sit down for our interview.

Many people think the recipe for a happy retirement is simple—quit working and start relaxing. In reality, that recipe is likely to land you in the soup. Life is full of flavor, but only if you live it. Jill put it perfectly when she told me, “You have to make a niche for yourself. You have to find these things to do. And you’re not going to find them sitting on your rear end in front of the TV.”

Jill Smith Entrekin knows who she is at heart—a Southern girl who’s eaten Georgia peaches and climbed magnolias all her life. Retirement is not the time to stop being who you are. It’s a magnificent opportunity to foster who you’ve always been.

Listen to Jill. It’s time to get started.

This information is provided to you as a resource for informational purposes only and is not to be viewed as investment advice or recommendations.  This information is being presented without consideration of the investment objectives, risk tolerance, or financial circumstances of any specific investor and might not be suitable for all investors. This information is not intended to, and should not, form a primary basis for any investment decision that you may make. Always consult your own legal, tax, or investment advisor before making any investment/tax/estate/financial planning considerations or decisions.  The views and opinions expressed are for educational purposes only as of the date of production/writing and may change without notice at any time based on numerous factors, such as market or other conditions.


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