BookWatch: Before you move to a new town in retirement, check the local Walmart – and 5 other hard-learned lessons

United States

Cost of living. Quality of life. Tax environment. Climate. We know all about these smart tips for finding the perfect retirement destination. And they are smart. But what if life’s circumstances, unforeseen pandemic effects or plain old shortsightedness force us down another path? 

Which describes my situation, living in a little Southern town, far from where I thought I’d be at this age, hours away from that sugar-sand beach and that cute downtown full of wonderful restaurants and those younger relatives there to help in a pinch. So how dare I give advice?

Didn’t your parents always tell you to learn from your mistakes? They were right. So I offer a few tips to guide you as you look for paradise. And please remember: these tips are offered with humility and even fear, conscious that I am only a Google search away from some old-timer who has exhausted the thrill of Pickleball and may want to come after me with some choice adjectives. Or a paddle.


Don’t choose a retirement spot based mainly on weather. There’s a reason the word “change” now appears regularly after “climate”. My little town, once a bastion of the sweetest springs and autumns, is now the newest version of Hurricane Alley in the fall and historically unheard-of cold in the winter.

Another point: endless sunshine can be too much of a good thing. After an amazingly brief period, you find yourself itching for a blizzard.

The waterfront

Beware your love of beachfront property. How many of you have actually lived on or near a beach? And since you’ve had your hip/knee/shoulder surgery? Is the beach really enjoyable now? Or did basting in suntan lotion and sand somehow lose its appeal about the time your swimsuit began to fit poorly?

Plus, the sun also goes down. Every day. After sunset, a view of the ocean can be much like a view of your spouse’s aging backside: either ominous or dull.


Even if you hate the idea, make a tour of the nearest Walmart in your proposed retirement paradise–if the place has one. (And if it doesn’t, be warned. Walmart does far more market research about its locations than you ever will and knows from where it invests.)

A Walmart walk-through will tell you almost all you need to know about the locals: how they shop, their attitude toward cleanliness, their degree of contentment, hidden issues of class and taste. 

And if there’s no self-service checkout, be very afraid. You’ll never get back those hours spent waiting for Uncle Cy to unload his cart.

Trial runs

Everyone always tells you, “Take a trial run or two to your dream location”. In this case, everyone might well be wrong. On my three trial runs to my little town, the locals couldn’t have been more solicitous—or more cunning. I had no idea that, with every portion of banana pudding, they were sizing me up as a potential civic asset–new “meat” for the Historical Preservation Board or church vestry.

But I’m not a complete idiot. I needed only a few months to spot those committees embroiled in endless arguments over when to hold the annual chili cook-off. 

Memory Lane

Oh, the potholes and wrong turns on Memory Lane! I had visited the South many years ago and, as they so often do, fond recollections of those visits clouded my judgment. Towns change. You change. The charming bar where I first fell in love is now a laundromat. The lovely Victorian B&B where I stayed on a past vacation is now a rundown rental.

Understand in advance that you will resist everything I’m now telling you. As I did. Memory is funny—and tragic–that way.

NewSouth Books

Politics and religion

Don’t think you can forever hide your own political or religious beliefs and live peacefully as a blue minority in a red state/county/town. Or vice versa. 

It would be beautiful to think so, but after keeping quiet during a few years’ worth of social occasions, you will inevitably explode and throw a glass of something in someone’s face and then face months of awkward meetings in the produce section of the grocery store. Take this advice to heart. Please. 

Finally, all of the above is simply another way of saying “Know thyself.” Or don’t lie to thyself.

In my little town, so unlike so much of my life experience, I’ve become much more practiced at self-appraisal—and compromise. I’ve figured out how to avoid certain civic groups without incident. I’ve learned why I don’t want to join the country club but am pleased as punch to be in the church choir. I’ve learned when to express a political preference—and when not to.

I even took advantage of all the free time available in a small town to publish a book about my oddball retirement. And the neighbors are still speaking to me. There is, after all, still something to be said for Southern hospitality.

D. B. Tipmore is the author of “My Little Town: A pilgrim’s portrait of a uniquely southern place” and has recently retired in southern Alabama. So far, his degree of assimilation includes owning a bush hog and making a mean spaghetti casserole.

Now read: MarketWatch’s Where should I retire columns