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Who has the best advice on retirement? Retired people. Here’s what they have to say, from the practical to the down-and-dirty.

I am a student of retirement. In the process of earning an M.B.A. and becoming a Certified Financial Planner, I’ve had many outstanding instructors. But some of my greatest teachers have been the retirees I have befriended or coached over the years.

They have the best advice on retirement, from the practical to the down-and-dirty. Luckily for me (and now for you), those with experience are willing to share. Privacy regulations forbid me to use their real names or locations, but here is what they have to say:

Love at first sight

You wouldn’t know when you first meet her that she was widowed toward the end of her teaching career and had to rearrange everything she imagined retirement to be, letting go of the life she built with her husband. “The initial phase was difficult,” she admitted. “Everyone seemed part of a couple.”

Over time, she felt ready to meet new people and even explored different places to live by renting a month at time in some tempting areas. She found the idea of community a perfect way to make new friends and still have her own home.

Carol has settled into an active over-55 community and taken up pickleball. “I never thought I would love retirement this much!” she said.

Plus: This couple retired 2 years ago on about $27,000 a year. Here’s how that’s going

On second thought

“Don’t get me wrong, retirement is good, but it is not a challenge,” said Jerry, a recent retiree who confided that he “missed work.”

When I asked him to explain, he said he liked the challenge and the comfort of having a place to go every day. “I really did not think I would miss it,” he said. “In retrospect, I liked my job more than I thought. I guess I picked the perfect career.”

Another indifferent retiree, John, said that after 10 years of leisure, “I am ready to go back to work!” Only too delighted to retire at age 60, he and his wife had traveled and had fun with their grandchildren. John said he had felt ready to leave work when he did and had planned the next stage financially. Yet, at age 70, he was ready for a job. “I miss the routine,” he said, “and the camaraderie.”

“There needs to be a time limit on retirement,” he mused, “then a fitting job to go back to for someone of my experience and age.”

Retirement magic

The magic age of retirement was not so simple for Maureen and her husband. She retired at age 67, as the couple had longed planned. But even though they had a mutually agreed succession plan in place and money set aside to enjoy life, Steve could not let go of his business.

Despite Maureen’s encouragement, then frustration, then downright anger at his refusal to quit the business, he hung on tight. She felt he unilaterally broke their mutual pact to retire and accused him of “ruining my retirement.”

Finally, after years of debate, some therapy and heartfelt conversations, the longtime married couple have a new plan. They take much longer vacations together — three to five weeks each trip, enjoying each other’s company and visiting all the places they had talked about with their retirement plan.

When they return home, he goes back to work. She admits this is not what she (or they) had envisioned but accepts that you cannot get someone to change if they do not want to make a change.

“Be prepared to be flexible, even with long-held dreams,” Maureen said.

Think twice before moving

“If you think you want to live somewhere else, rent first. And do not forget to consider what you are leaving behind in the excitement of moving forward.”

That is sound advice learned from painful experience:

While preparing to retire from his medical partnership in Michigan, Sam and his wife took a trip to Florida, where they found and quickly bought a house. He soon stepped away from his business and started enjoying their new home in the Villages, a retirement community northwest of Orlando. She, meanwhile, flew back and forth between Florida and Michigan during her last few years of work for a large technology company. The arrival of COVID gave her reason to work from home, in Florida.

Related: Being snowbirds was harder than we thought—don’t make the same mistakes we made

The warm weather was appealing but they had acted too fast, the impending retirement feeding the sense for a need for action. Yet, they learned within a year that they wanted to be home in Michigan, near their grandchildren and her aging mother.

Sam’s advice for future retirees? “Don’t jump too soon, even if you have the money,” he said.

They found a new house by a lake near their children and her mother. “The grandchildren love to come and play, and I can help my Mom as needed,” she said. “Florida is a place we vacation now, rather than live — and we like it that way.”

Don’t miss: The dilemma for many retirees who have paid off their mortgage: sell or stay?

Changing relationships

“I never thought I would live this long,” said Thomas, a healthy 75-year-old. “I am happy to have family around, but my friends are all sick or worse, dying.”

Medical professionals recognize that social isolation is a health risk for aging. Illness, divorce and death all contribute to the loneliness many older adults feel. A Pew Research report in 2020 found that 27% of Americans aged 60 or more lived alone, and that older people in the U.S. are more likely to live alone than older people elsewhere in the world.

For Thomas, the late-in-life breakup of his marriage — what lawyers refer to as a “gray divorce” — meant rearranging the retirement he planned.

See: ‘There’s a lot of lonely people out there.’ Is loneliness killing you?

Medical issues

It is not uncommon for people to tell their financial planners, “We have the time and money to travel, but my health is declining rapidly.”

People are more likely to be diagnosed with a chronic disease after age 65. Many older adults face more than one such condition. For good reason, these illnesses are called great disruptors.

“Physical health affects so much of your retirement plan,” Karen said. “Tell people to travel while they can, even before their day of retirement. Health does not last forever.”

Hobbies and activities

Roger was financially prepared for retirement. He knew what he loved to do — “Fly fish and wood working.” He stocked his wood shop with everything he needed and updated his fishing gear with the latest and greatest the field had to offer before he retired.

He came to see me two years after he had retired. “How is the fishing?” I asked.

“I don’t know,” he replied. “I gave it up.”

He had started taking pilot lessons. “Tell people, hobbies shift in the retirement years.”

Also see: 3 common retirement dreams that can become big disappointments

Medicare and healthcare costs

“We are somewhat healthy, but still paying too much on medical,” Mary and Bert once told me, shaking their heads in agreement. “I need hearing aids and dental work,” Bert said. “That adds up quickly.” They do indeed add up quickly but Medicare does not cover them.

“We thought at least our glasses would be free in retirement,” Mary paused and then added, “Medical insurance is costly.”

Gratefully, they have the funds to buy extra coverage for such common goods but wish they could use that money as planned: for “extras” or giving to their grandchildren.

An introvert’s dream

Betty is an introvert and retirement suits her perfectly. “I love not having to go somewhere each day,” she said. “I still see friends in my lifelong community, but I have time to sew, write and bird watch.” Most important, she added, “I am not rushing places anymore.”

She is fortunate to have a defined-benefit pension from a former employer — and acknowledges as much. “From the financial end, I admit having worked for an agency which provided a pension, makes it easier,” she said. “I know how much money I have coming in each month. I own my own home and live simply.”

Retirement is full of surprises

“Our life has been turned around. We have no regrets but some days are really hard and I would rather be off on a cruise with friends than prepping dinner for two middle-schoolers.”

Sally and Joshua adopted their two grandsons. Now they are raising a second family. They are not alone. A Rand Corp. study found a host of factors — including mental illness, substance abuse, prison or death — that increase the chances of grandparents raising their grandchildren.

Read: Grandparents: Forget everything you ever knew about taking care of babies

Retiring soon? Talk with people who have already taken that step. Keep your retirement expectations realistic. Most of all, embrace opportunities for new experiences.

C.D. Moriarty, CFP, is a Vermont-based financial speaker, writer and coach. She can be found at 

This article is reprinted by permission from, ©2023 Twin Cities Public Television, Inc. All rights reserved.

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