If you haven’t heard the stories first-hand, you probably “know somebody who knows somebody” who thought they were embarking on their dream retirement only to end up disillusioned, bored, depressed and/or bitter.

It happens—but why does it happen to some people and not to others? More important, what can we learn from the people who hate retirement so we can avoid their fate? Bottom Line Personal asked Ernie J. Zelinski, author of How to Retire Happy, Wild, and Free…


Maybe retirement isn’t for everyone. It’s tempting to look at unhappy retirees and conclude that some folks just aren’t cut out for retirement. And that may be. But what definitely is true is that certain personality traits are conducive to a happy retirement…

Creativity. This doesn’t mean that you’re good at quilting or drawing or writing music. It means that you’re inquisitive about the world, love trying new things, are a lifelong learner and are good at keeping yourself amused. People lacking creativity often feel adrift when their lives become unstructured during retirement.

Self-sufficiency. The happiest retirees are people who never looked to others to rule their lives, and they don’t blame external forces—spouse, employer, government, society—when things go wrong. They’re self-directed, taking full responsibility for their choices, and when something isn’t working, they take action to make it better.

Freedom-loving. We all imagine that we thirst for freedom, but the truth usually is closer to John Boyd Orr’s assertion that if you give people a choice between a sandwich and freedom, most people will choose a sandwich. People who have forged their own way in life, nonconformists and eccentrics tend to be happiest in retirement. Those who thrive in corporations, rigid institutions and highly structured hierarchies might struggle.

Outgoing personality. Isolation can destroy your happiness during retirement. People who make new friends easily tend to be much happier ­retirees than those who are naturally more withdrawn.

All these traits are somewhat innate, but they’re all subject to improvement.


Fulfill your basic human needs. Each of us has three simple needs that are filled by a career—purpose, structure and community. After retirement, it falls to you to meet those needs. People who hate retirement usually fail to create a set of circumstances in which those needs are met.

Purpose. During your working years, your sense of purpose takes care of itself—earn enough money to pay off your house, raise your family, educate your children, save for retirement, grow the business, beat the competition, etc. The day you retire, those priorities fall away, and you’ll be miserable if you don’t replace them with a new mission. So many unhappy retirement ­stories hinge on lack of purpose. We’ve all heard of the hard-charging executive who despises retirement because it lacks intellectual challenge or diminishes the status that the job provided.

Structure. You rise at the same time every weekday, commute to work, commute home, go to sleep at the same time, take Saturday and Sunday off. When you’re grinding away at the rat race, the prospect of a retirement blissfully free of such routine can be enticing. But many retirees find that a total lack of structure is soul-crushing. Those who fail to create new routines and structures are in danger of depression and unhappiness.

Community. Even introverts need people. When life is most hectic, you might dream of retiring to a mountain cabin, blissfully isolated from the world. But if you’re cut off from friends and family, the mental health effects of social isolation come creeping in. The happiest retirees are those who have close ties to friends and family.


You’ll need to adjust. Even people who are cut out for retirement usually experience a dip in happiness once the new reality sets in. That’s normal…and often temporary. Do what you can to pave the way for a happy retirement, take the transition in stride, and move on.

Mistakes to avoid…

Counting on your work friends. Sociologist and author Jan Yager calls relationships with coworkers “workships,” not friendships. It’s rare to forge true friendships with colleagues that last into retirement.

Overthinking your purpose. Your new post-retirement purpose doesn’t have to be noble or selfless—it just has to be a reason to get out of bed in the morning. Your mission might be to rescue puppies…or perfect the art of leisure. Failing to find a purpose—any purpose—is a recipe for unhappiness.

Embracing inactivity. You might feel exhausted by the time you get to leave your job. But when retirees embrace their inner couch potatoes, things can quickly fall apart. They enter a cycle in which the less they do, the less they feel like doing…and both their physical and mental health suffer.

Make sure you’re getting exercise every single day…and look out for passive activities such as watching TV, gambling and shopping. There’s nothing wrong with these things in moderation, but they can drag you down if you overindulge.

Overburdening your spouse. Many couples adjust poorly to suddenly having their partners there all the time every day. It’s great if you and your spouse share interests and activities, but it’s also crucial that you spend time apart and have other friends to share experiences with.

Over-relying on your children. Some retirees assume that their emotional needs will be met through their children and grandchildren. But that’s a gamble—your kids might be too busy for you…or they might even decide they don’t like you. A retirement-home resident seemingly blessed with several children who never call might be lonelier than another who has one or two good friends who visit every day.

Miscalculating your dreams. I see this most often when it comes to travel. A couple imagines that when they retire, they’ll spend their time traveling. Then they retire, take one trip, and never travel again. Now what? This usually happens to people who hadn’t traveled during their working years—it was a glamorous, hazy, “someday” ideal, and when they tried it out for real, they found they didn’t love it after all. This also can happen with other hobbies, pursuits and lifestyle choices. Plan to do the things in retirement that you know—from experience—you’ll enjoy.

Relocating blindly. Some folks run into trouble by moving somewhere they’ve never even been because it sounds so great. Once they get there, they hate it. Never plan to retire somewhere you haven’t visited several times at different times of the year for prolonged periods.

Being afraid to spend the kids’ inheritance. After having deferred their dreams for their whole adult lives and sacrificing for their children, some retirees continue to deny themselves simple pleasures in their golden years because they feel guilty about spending the money their kids will inherit. Your hard-earned money is yours, and while you probably don’t want to blow all of it, you deserve to enjoy yourself in the years you have remaining. Successful retirement is about making yourself happy, so spend your money on the kinds of experiences that bring you joy. Although it’s hard to admit, you might develop resentment if you don’t splurge on yourself at least a little.

What To Do Today

If you’re still working: We think, read and talk a lot about financial retirement planning, but we pay scant attention to the social and emotional side of this exciting stage of life. The unhappiness of so many retirees can be traced back to what they did and didn’t do during their working years. Fostering friendships, developing hobbies and interests, building good exercise habits, visiting potential retirement destinations, working on self-reliance, creativity and social skills—all of these things will set you up not just for financial success, but for real happiness in retirement.

If you’re already retired: Take stock of your level of happiness. Have you provided for purpose, structure and community? Have you made one or more of the common retirement mistakes listed above? It’s never too late to get back on track. By taking responsibility for your own destiny, you still can make your retirement the happiest time of your life.

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