3 Keys To Happiness in Retirement

WE LIKE TO ESCAPE the Northeast’s cold each winter, so we just spent 10 days in Sarasota, Florida. Like many others when they’re on vacation, we found our noses pressed against the windows of real-estate offices, perusing the listings and musing about whether we’d want to live there.

Fantasizing about the future is fun and free, but it can also be dangerous. It’s how folks end up buying timeshares and second homes during wonderfully relaxing vacations. But vacation, of course, isn’t real life. When you live somewhere, what seems special quickly becomes unremarkable. You stop noticing how cute Main Street is—because you’re hustling to get to the grocery store before the after-work crowd.

This is also the reason I’m skeptical of those lists of the best places to retire, which are often built around a quantitative assessment of things like crime, tax burden, weather, medical care and so on. Yes, those are important issues. But I don’t think they’re the keys to a happy retirement.

So, what should we focus on? I’d zero in on three factors—the same three factors that I think are crucial to happiness for everybody, retired or not.

Purpose. We won’t spend our retirement simply being. Instead, we’ll be doing. But what will we do each day that’ll make our retirement meaningful and fulfilling? That notion got me to thinking about categories of doing: exercise, hobbies, learning, reading, writing, chores, watching TV, volunteering, worship, working part-time, socializing, cooking, eating out, live entertainment, visiting museums, travel and so on.

Some of these activities—chores, reading, writing, worship, watching TV, cooking—can occupy our time no matter where we live. Location doesn’t much matter. But others depend on the community we’re in. How many theaters, museums and live music venues are nearby? How many decent restaurants? If we want to get outside and exercise, what are our choices? How close are the nearest airport and train station?

Each of us will have a different list of activities we want to engage in. But the crucial thing is to focus on the doing, not the being. We won’t be happy for long simply sitting on the deck and admiring the gorgeous view.

Friends and family. Next, there’s the all-important issue of social connections. We may not want to see others every day. But there’s great joy in spending an occasional evening with family and friends.

Will that be possible wherever we choose to retire? If we head to parts unknown, we’ll likely make friends—eventually. But it’s worth pondering how easy we find it to make new acquaintances, and how easy it’ll be for family and old friends to visit.

And, of course, there will likely be a time when our physical or cognitive deterioration demands help from others. That help can be purchased. But it’ll be a lot cheaper and probably more pleasant if at least some of that help comes from those we love.

Financial contentment. I think money—if used thoughtfully—can buy happiness, though I don’t think it can garner as much happiness as, say, a great night’s sleep or an hour spent at the playground with a grandchild. Good health and social connections are so much more important to happiness than money.

Instead, I believe money is most useful in helping us to avoid worry, especially worries about not having enough money. Yes, that’s the great irony of money: We should accumulate it mostly so we don’t have to think about it.

What does that mean for retirement? I think there are two key implications. First, we should organize our financial life with an eye to minimizing money concerns. That might mean downsizing to a less expensive home so we have ample breathing room in our monthly budget. It might also mean delaying Social Security, buying income annuities and holding plenty of cash so our monthly income is less dependent on the vagaries of the financial markets.

Second, if we move in retirement, we shouldn’t move to an area where we’re surrounded by far wealthier neighbors. Even if we have more than enough money for a comfortable retirement, we may find ourselves comparing our lifestyle to those around us—and suffering a gnawing sense of dissatisfaction.

Jonathan Clements is the founder and editor of HumbleDollar.

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