You wouldn’t think that experts who spent their careers helping others plan their retirements could be surprised when it comes to their own retirements—but they often are. Bottom Line Personal asked these former retirement planners, researchers and writers to share what they’d failed to fully grasp until they’d experienced retirement themselves…

Financial Surprises

Medicare can take a big bite out of your retirement budget. I knew that Medicare Part B premiums increase for retirees who have substantial incomes—for 2023, these “income-related monthly adjustments” kick in when modified adjusted gross income (MAGI) tops $97,000, or $194,000 for married couples filing jointly. But I had not considered how substantial my premiums would be. My monthly Medicare Part B bill is $442.30…when you add in my wife’s Part B and our Part D premiums, we’re paying around $8,000 a year for Medicare. Some people pay even more—Medicare premiums can reach $578.30 per month, nearly $14,000 per year for a couple. Having sufficient income to trigger these steep Medicare premiums is, of course, a problem many people would love to have, but Medicare is expensive for people with modest incomes. Even the standard premium of $170.10 is more than $4,000 annually for a married couple.

Strategy: Before reaching retirement, determine how much Medicare will cost and build this into your budget.


Financial products that guarantee lifetime income are appealing after you stop earning. While you are still working, the goal of retirement planning is to get as much money as possible into 401(k)s or IRAs. But at its core, retirement planning is about replacing income you had been receiving from your job. Withdrawing money from 401(k)s or IRAs isn’t the most stable way to accomplish that. Annuities and other life insurance products offer income guarantees that investment accounts can’t. I have an annuity, but most of my retirement assets are in other investments—my plan was to invest my money myself and outperform insurance products. Now that I’m retired—and 2022’s stock market losses have provided a reminder of investment risk—the guaranteed annual income from annuities looks more attractive.

Strategy: Consider devoting 25% to 33% of your retirement savings to an annuity or other financial product that provides guaranteed annual income for life. Within five years of retirement start shifting assets into these financial products that guarantee income.


Unexpected macroeconomic events can undo even a carefully constructed retirement budget. The prices of everything—from groceries to gas to insurance—have shot up in the past year and will continue to rise. That can be devastating for retirees on tight budgets. Few retirement plans were constructed with the recent 8%-to-9% annual inflation rates in mind.

Strategy: If your retirement budget suddenly seems too tight for comfort and you don’t want to delay retirement or return to the workforce, look for ways to trim your spending. Ask merchants about senior discounts—a 10% discount essentially offsets the extreme inflation of the past year. Negotiate prices when you can. And before buying anything, consider whether you could make due with what you already have a little longer.


Lifestyle Surprises

There’s no way to know how long you’ll be physically fit and energetic. A friend climbed Mount Everest at age 70, while my knees make it hard to get up a flight of stairs. I had always known the day would come when I had to slow down. I assumed that by 10 years into retirement, I’d be content to do less. I was wrong!

Strategy: Everyone ages at a different pace. There’s a part of me that, like Dylan Thomas, wants to “Rage, rage against the dying of the light” but I remind myself to enjoy the bonus of still being alive. I consider it important to build social, physical and mental challenges into my day, but I accept that those challenges have become less ambitious.


The transition from “respected professional” to “not at all in demand” is frustrating. I planned to put my professional skills to use in retirement, but nonprofits weren’t interested in that—they wanted me only as a donor or as a board member.

Strategy: Create a role for yourself. Since no one was willing to offer me the retirement role I wanted, I started interviewing other retired people about their experiences, hoping that would help me figure out why I was struggling. Those interviews led me to write a book and then host a PBS special called Retire Smart, Retire Happy. After that, I was again in demand as a writer and speaker.


No longer making a contribution to other people’s lives takes an emotional toll. It’s easy to overlook how much satisfaction and purpose you derive from helping other people—and how much you’ll miss that when you retire. I was aware that this could be an issue, but I still was not emotionally prepared for it.

Strategy: Think about what your job provides you beyond the paycheck, then search for ways to replace these things in retirement. If you’ll miss helping others, perhaps continue to work part time, consult, mentor young professionals or teach classes related to your field.


Retirement is a lot of time. Plans like eating out, golfing, going to the ­theater and traveling fill only a few hours a week. The hard part is figuring out what to do with all the time between such events.

Strategy: One option is to not truly retire—remain professionally active even after you stop working. ­Employers now are desperate for qualified employees, and remote work often is an option. Or take your hobbies more seriously and dive deeply into them. I love opera and became active in opera-related organizations.

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