__Years ago, I read a wonderful book called *Stumbling on Happiness* by Harvard psychologist Daniel Gilbert. Chapter after chapter, he humorously describes the many ways our minds fail us when trying to pursue a happy life. (Come for the insights, stay for the perfect Shakespeare quotes at the beginning of each chapter.)__

In the end, he said the lesson to be learned is very simple: If you want to make better decisions, talk with people who have made the decision you’re considering and see how it worked out for them.

In last Friday’s roundup, Joseph included a *[Wall Street Journal* article](https://www.wsj.com/articles/retirement-regrets-investments-relationships-b67a1080?st=0x9x57ulgc1glx5&reflink=desktopwebshare_permalink) filled with priceless lessons learned from retirees who wish they could have a do-over. Here’s what we can learn from them.

__Set goals to pursue in retirement.__ After retiring, Jim Pilzner quickly discovered there’s only so much golf one can play and so many lunches one can go on. “I would counsel my younger self, and any other active, achieving person to recognize what drives them and what success really means,” he said.

Recognizing that taking action and learning new things were two significant sources of motivation before he retired, Pilzner, at age 78, is now studying for a degree in political science and history.

__Plan your retirement date carefully.__ Of course, this one is far easier said than done. For many people, having enough money for retirement is the main driver of the decision. However, it’s easy to let “enough” become an ever-moving target.

Jay Holt retired at age 64, hoping to spend more time pursuing his favorite hobby: polo. But two years after retiring, he was injured to the point where he can’t play anymore. Now he regrets not retiring earlier.

As someone once said, retirement is typically marked by three distinct periods: the go-go years, the slow-go years, and, ominously enough, the no-go years. No one knows how long they will be in good health, so timing retirement to be able to maximize the go-go years is difficult. Still, it’s worth considering.

On the other hand, Arthur Parmentier wishes he had worked a few *more* years instead of retiring at age 65. “Had I waited two more years or maybe three, I would have been quite comfortable, but right now, I’m living on Social Security and trying not to touch my IRA,” he said.

__Keep relationships in mind.__ Some people dream of retiring to a different climate or even a different country. For many, that works out just fine. For others, it’s only after they move that they realize how difficult it is to form new friendships.

While Dan Roberts and his wife, Robin, didn’t move in retirement, he wishes he had maintained relationships with former colleagues. Their son and his family used to live just two hours away but then moved to New Zealand. Roberts said if he had kept in touch with former co-workers he might have been able to do some contract work, which would have given them the financial freedom to visit their son’s family more often.

“We miss our grandchildren terribly,” Robin said.

__Questions worth asking__

What will you do in retirement? When should you retire? And how can you best plan for retirement in a way that will foster connection with the people who matter to you most of all? Again, these are not easy questions to answer. But they’re worth asking. And they’re worthy of lots of time in prayer.

*[Image](https://soundmindinvesting.com/img/asset/Y2xvdWQvcmV0aXJlbWVudF9sZXNzb25zLmpwZw==?fit=crop-1-55-1&w=1660&h=896&s=b6a5f49235e75487e8ea3b8741250daf) used with permission. *

Since 1990, do-it-yourself Christian investors have relied on SMI for proven strategies and trustworthy guidance.

Sound Mind Investing

Retirement

What will you do in retirement? When should you retire? And how can you best plan for retirement in a meaningful way?

INVESTING | Jun 9, 2025

Invaluable Retirement Lessons From Those Who Learned the Hard Way

By: Matt Bell

Since 1990, do-it-yourself Christian investors have relied on SMI for proven strategies and trustworthy guidance.

You May Also Like