The When, Why, but Mostly Where to Retire
Sooner or later, it will happen.
The desire to retire will sweep over you. "That's it; I'm done," you'll say. "I'm out of here."
For some, this realization happens after 30 years. For others, it happens on Day 2. You may not retire immediately, but you will start thinking about it. In fact, you'll find you can't stop thinking about it.
Of course, wanting to retire is not the same as being financially able to retire. Not quite. You probably haven't thought of this before, but when you stop working, your paychecks stop, too. Even with your balanced portfolio of World's Fair souvenir teaspoons and Pokemon cards, maintaining your current lifestyle could be difficult.
And then there's that other little problem. You know you can't stay, but you don't know where to go.
This is the time you start reading articles like "How to Choose Where to Retire" at roadscholar.org.
If you are still employed, the rankings may rankle. Is "Cultural Stimulation" really your No. 1 concern and "Cost of Living" No. 14? Unless those Pokemon cards are Secret Rare and Ultra Rare, you may look at the situation differently.
But, hey, it's the end of your career, so let's start at the beginning.
No. 1: Do You Tell Your Company You're Leaving?
Breaking up is hard to do. You'll feel guilty informing your manager that they're losing their best employee. They will definitely beg you to stay and offer you a big fat raise if you do. And you may agree to stay on another five or 10 years, just to be nice.
This is why it is so important to keep your retirement plans secret. Sooner or later, your manager will notice you're no longer attending meetings or answering your phone, but by that time, you'll be long gone.
(Because you are a caring person, you'll want to keep the memories alive by taking some momentos, like that spiffy microwave in the break room and the Italian-design couch in the reception area. Be sure to throw in a file cabinet or two. They make wonderful souvenirs.)
No. 2: Is Everyone Going to Midland, Mich.?
According to U.S. News, Midland is the most popular retirement city in 2026. And no wonder. Midland has an Applebee's and a Subway, both of which are open until 10 p.m. Either bistro would make a perfect location for you and your fellow retirees to sit around and complain about the jobs you no longer have. Afterward, you can jump on your snowmobile and zoom off to your $206,176 median-priced home.
If you are the kind of odd duck for whom life in Midland does not thrill you with excitement, you can retire to Green Valley, Ariz., the No. 1 choice from the roadscholar.org article. You'll be happy to hear there is a Subway in Green Valley, but the nearest Applebee's is 20 minutes away.
Deal breaker? We'll see you in Midland.
No. 3: Spin the Globe
In the rare case when neither Midland or Green Valley appeals, consider going international. Choose a place where no one speaks English. This will keep you blissfully unaware of what is going on in the world. As long as you never learn the local language, you'll be constantly lost and confused, but, boy, will you be happy.
No. 4: Do You Tell Your Partner You're Retiring?
Most retirees obsess about when to tell their manager they're retiring. My question is -- when do you tell your partner? It does seem unfair to put all the stress of such an important decision on the person you care about the most, which is why I recommend keeping your retirement on the down low, at least for the first two or five years.
This won't be easy since someone so close to you will eventually notice that you are always relaxed and content. Tell them it's a phase.
No. 5: Retire in Place
Considering all the factors, there's no question that the best place to retire is where you are currently employed. All you have to do is stop working and stay on.
Your Cost of Living will be minimal. There's no rent and as long as you can subsist on office coffee and what you can pilfer from the breakroom fridge, your food expenses will be zero.
Sooner or later, some smartypants manager will discover you are no longer working and make you leave the office, which is totally unfair.
On the positive side, it does give you something to complain about at Applebee's.
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Bob Goldman was an advertising executive at a Fortune 500 company. He offers a virtual shoulder to cry on at info@creators.com. To find out more about Bob Goldman and read features by other Creators Syndicate writers and cartoonists, visit the Creators Syndicate website at www.creators.com.
Copyright 2026 Creators Syndicate, Inc.
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