The 4 Secrets to a No-Regrets Retirement

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Posted by The Savvy Retiree on February 12, 2020 in Live Better

I’ve recently been collecting lots of stories about retiree regrets for a screenplay I want to write.

These regrets, I think, offer a particularly poignant insight because: Here’s this collection of people who are looking at the sunset of life, and they’re analyzing all the choices they made over a lifetime—the paths they took and those they didn’t—and they’re distilling all that analysis into cogent, pointed thoughts that, if you pay attention, can serve as a roadmap to your own richer retirement.

Here are a few retiree regrets that I think are especially notable:

I wish I’d traveled more.

Travel isn’t for everybody, I realize that. And I realize I’m totally biased, given my ongoing effort to push past 100 countries (67 so far). But I also know that lots of people say they can’t wait to retire so they can travel…and then they retire, and put off traveling for whatever reason.

And one day they wake up and they can’t travel because of health or mobility or money issues.

So travel as soon as you feel the desire. Don’t wait. Explore your town, your state, your region. You don’t have to get on an airplane to gain the benefits of new discoveries and connections. If you’re worried about the money, use any of the many hacks my colleagues and I write about all the time that can reduce travel costs dramatically, such as housesitting in some destination you really want to visit.

I wish I hadn’t waited to start the career I wanted.

For better or worse, a job defines who we are and, often, how we feel about ourselves. Which is why too many people I know feel bad…they hate their job and what they do.

Yet too few choose to change. Inertia and fear hang heavy.

But life is a one-time offer. Makes no sense to spend years and decades unhappy for one-third of every day.

One of the primary messages I regularly address is working at what you love. Maybe you don’t make as much money…maybe you make more. Either way, daily happiness has no price. I was earning an income in the U.S. almost double what I earn in Prague. But my happiness now—doing what I love to do, where I love doing it—is immeasurably greater.

So pursue your passion. Again, this is a topic my colleagues and I research and write about every day because we want to encourage you and help you to find your happiness while you still have years to enjoy it.

I wish I hadn’t bought that house.

A retirement dream home is a goal for many people. And certainly it can be a worthy goal.

But lots of retirees who’ve trod that trail regret it. Because while a house might be a sign of stability, it’s also an immovable weight tying you to one place and imposing certain costs you cannot escape. And shedding that weight can be expensive if you wake up one day and realize, “This isn’t where I really want to be.”

Maybe it’s better to be a renter, at least when you’re a retirement newbie. The cost structure is more flexible, as is location. You might think you’ll love living on the beach in South Florida…until you face the hurricane insurance costs and the traffic that piles up in snowbird season.

Renting lets you get a taste of a place to figure out if it’s really for you. If it’s not, you can easily relocate and try somewhere else.

That goes for renting overseas, as well.

My colleagues and I (at both The Savvy Retiree and International Living) constantly write about retiring overseas as a way to bring a sense of adventure to retirement, while radically reducing your costs to stretch your nest egg farther than it will go in the U.S. But you shouldn’t dive into some location where you once vacationed just because it was fun. Visiting and living are two totally different creatures. When you’re outside the tourism bubble, local life moves a lot differently.

If you think you want to live in Portugal’s Algarve region, or near the beach in Costa Rica, rent a place for a few months and interact with the daily economy. You will quickly determine if that’s a destination where you can build a happy, comfortable life. And if not, don’t write off overseas living altogether. Instead, go try a different place. You have the flexibility to do so.

I wish I had something to retire to.

This, to me, is The Big Regret.

I can’t tell you how many times I’ve interviewed pre-retirees who insist the greatest luxury they anticipate is the ability to just do nothing.

OK, not to be unintentionally judgmental, but who wants to do nothing all day? For decades? Might as well be dead, frankly. Doing nothing all day long, six feet under, accomplishes the same thing.

Retirement should be a time to experience all that you couldn’t when work and family consumed your days. The retirees who wish they had something to retire to say that, in hindsight, they would have used the years running up to retirement to map out a strategy for their retired life—maybe start a business or find a side-hustle they enjoy just to stay physically and mentally active. To feel like they still mean something to the world.

Some say they wish they’d found daily structure once in retirement, be it volunteering or even a menial, part-time job. I once talked to a woman who held a Ph.D. and who’d spent her career in research. And in retirement…well, she absolutely adored working for a neighborhood green-grocer because it kept her engaged with customers, it kept her plugged into her community, and it allowed her to have fun with much younger employees who kept her apprised of the current cultural zeitgeist. “You know,” she once told me, “that’s how I learned about Game of Thrones. That’s why I got HBO.”

The money was absolutely irrelevant to her. In fact, she told me, “I’d work for free, just because it gives me something to do and makes me feel wanted and useful.”

So if nothing else, find a purpose to your retirement. No matter what it is, no matter what you get paid. Feel useful. Feel happy. Feel engaged.

We all have regrets. That’s life. But you don’t have to add to those regrets in retirement.

Written by Jeff D. Opdyke