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The Biggest Surprises After Retirement – WSJ Readers Weigh In

Retirement Surprises

Retirement can present a number of surprises. The Wall Street Journal article below is an interview of several readers where they were asked what surprised them most. If you are planning to retire, or know of a friend, colleague or neighbor who is planning retirement, feel free to pass this along. Of course, if they need financial guidance on how to make sure they navigate a successful retirement, please let them know that Total Wealth Planning offers a complimentary no-obligation, introductory meeting.   Sending our best, David Wilder.

Enjoy the interviews below:

Randy Catron
Randy Catron with his cousin’s dog on the “first day of school” last year.

The biggest surprise is, even after I’ve “retired,” how much I am working my side gigs (subbing in two school districts with special-ed kids, working security at Texas Motor Speedway, and working as a cycling coach).

I am having to track how much money I make to stay under the earned income limit in my first (partial) year on Social Security and balance the school and speedway requests for my time. My wife still works full time, so I feel like when she’s working, I should still work. But we have enough saved, and adequate income streams so that we could both not work and be OK, financially. But “cutting the cord” from work has been difficult, at least for the first couple months.

Randy Catron, Denton, Texas

Ellen Mannos
Ellen Mannos, photographed by her husband.

Trying to embrace retirement with the same momentum and energy as work proved to be the wrong strategy for me. I rolled out of bed setting the stage to immediately do five different things. “I’m ready to go!” I said to myself. But it wasn’t happening. Presently I am doing one thing—effectively, joyfully, thoughtfully and with serious passion.

Career mobility was exciting during those years, yet retirement took me to a whole new place I had not considered. Mental, social, physical and spiritual needs took on a whole new importance. New friendships developed, old ones got stronger or were outgrown. Some family members became closer, others proved otherwise. Health issues suddenly surfaced, got resolved, lingered or were dealt with. The nonfinancial aspect of retirement is what matters most to me. It’s not a final destination but the beginning of a new journey which I’m just beginning to come to grips with and—I think—starting to enjoy!

Ellen Mannos, Chicago, Ill.

Jed Berliner
Jed Berliner on Cape Cod.

I STILL cannot get around my 45-year-old mental block against spending retirement savings.

I haven’t begun yet, even though I’m 71 and not yet forced into the mandatory withdrawals. Social Security, part-time income and having no office rent or utilities keep me on an even keel. It’s the anticipation of having to withdraw beginning next year that I’m struggling with.

Jed Berliner, Hampden, Mass.

Keller Arnold, right, and her husband Adrian Costello
Keller Arnold, right, and her husband Adrian Costello at the Monterey Bay Aquarium in California.

There are too many positive things about retirement to list here, but one negative surprise was the feeling of the absence of structure. I quickly realized that for decades, my day, week, month were structured with meetings, trips and deliverables, and that I was psychologically dependent on that structure to keep motivated. I was very deliberate about my calendar and it was my North Star.

As fun as it sounds to be completely free of these constraints—and it was fun for a few months—it can be a little shocking after decades of structure. After a few months of retirement, I created my own (albeit looser) structure and goals which is working well for me after two years of retirement. And it evolves. It’s a sort of a lighthearted version of skills I learned while working—priorities, goals, plans. Some may say that sounds like “work.” The difference is that I choose these things—they aren’t chosen for me.

Keller Arnold, Yardley, Pa.

Harry B. Hartman and his wife, Molly Hartman
Harry B. Hartman and his wife, Molly Hartman.

“After 5 years totally retired, my favorite saying is “I’m so busy now, how did I ever have time to go to work before?”

Hobbies, family, friends, and especially grandchildren. Blessed. Amen.”

Harry B. Hartman, Elburn, Ill.


Sadly, we could only afford to retire by leaving California. Happily, we love living near Lexington, Kentucky, a blessing. After decades of running our own small business, my wife got zero Social Security, she had to get a “job” for 5+ years to qualify. Although while in California, we could not find a doctor to take Medicare, in Kentucky, it’s not a problem, so that’s another blessing.

—Bob Clunie, Versailles, Ky.

Frank Balestrery
Frank Balestrery

The first big surprise (of the century): Covid-19. It disrupted everything. It wrecked the economy, families and pulverized the healthcare system. It’s not over yet. I expect the rest of my retirement years will be affected by it, in some way. For example, I expected to do more traveling during retirement; perhaps some of that will have to be curtailed.

The second: inflation. The quote attributed to Einstein, that the “most powerful force in the universe is compound interest” has a flip side: inflation. And, although intellectually I was fully aware of the reality that prices go up, when actually dealing with it in real time on a fixed income has been a bit of an eye opener.

Frank Balestrery, Tracy, Calif.

Steve Conrad
Steve Conrad, photographed by his wife.

Surprise! Surprise! Thank you, Wall Street. The recent years have seen such a broad market rally, that the plans my wife and I always had have been expanded to include much more travel. In fact, we just got back from a two-week Mediterranean cruise on a small ship filled only with fully vaccinated people.

Start saving and investing early, stay the course, and find something you enjoy that can fill your time and social calendar. We both play bridge and have many bridge friends. And, these days, I teach bridge on cruise ships. We have died and gone to heaven, so to speak. We are having a wonderful retirement with time for children and grandchildren.

—Steve Conrad, Manhasset, N.Y.

Rick Orlemanski with his wife, Karen Orlemanski, and their dog, Molly
Rick Orlemanski with his wife, Karen Orlemanski, and their dog, Molly.

Biggest positive surprise: how much I enjoy retirement. Several retirees that I knew warned me that I would be bored in retirement. I planned on doing consulting after retirement, but quit consulting a couple of months after retirement because I was enjoying retirement so much. Biggest negative surprise: how much I had to pay for Medicare coverage. I thought that I had taken everything into account when planning my retirement. The amount that I pay for Medicare coverage and Medicare supplemental coverage exceeds what I paid monthly for health insurance when working.

Rick Orlemanski, Cary, N.C.

Lisa Summins
Lisa Summins on a trip to New Jersey in September.

After a lifetime of working and saving, I have attained a very comfortable retirement. I do enjoy not having to rush out the door in the morning, and I savor my coffee and crosswords. What surprises me is an underlying anxiety that, despite my smart investments and assurance from my financial adviser, I might exhaust my savings as I am no longer replenishing via salary. It is strange not to be earning.

Lisa Summins, El Paso, Texas


The number of new things that need doing rises exponentially: family responsibilities, board memberships, community responsibilities, religious responsibilities, college responsibilities, part-time jobs explosion, reuniting with old friends, financial management, genealogy, hobbies, home improvement, reading catch-ups, old projects arriving from the back burner, traveling, health & medical issues, sports training and competitions, reconciliations, new technologies to learn, moving, finally learning that musical instrument, inheritances, bucket list stuff, organizing, spousal reconnection, personal growth projects, etc. etc. etc. HELP!

Douglas Herz, Bay Area, Calif.

Ted Sward
Ted Sward, hiking in Colorado.

My first surprise was what I call the “retirement time trap”: this feeling that you’re leaving a full-time job behind, so you’re going to have hours and hours on your hands. Paradoxically, you find so many things to do that you can be super busy. In my case, I’m just as busy now as when I was employed full-time. So much so that recently I’ve even stopped describing myself as retired, because when people hear that they think you’re golfing every day. Since my wife, Julie, works, and my son is in high school, I tell folks I’m a stay-at-home dad since that’s much more descriptive of my new responsibilities.


What were your biggest surprises in retirement? Join the conversation below.

Another surprise just dawned on me recently even though I retired in May of 2019. A close friend retired before me, and he started a big car restoration project right away. I couldn’t understand why, after retiring, he didn’t make more progress on the car. He kept getting distracted, helping his neighbors and friends with small stuff like fixing their weed-eater. Then, I realized that when I was working full time, I had the opportunity to help people every day. Once retired, my opportunities to help people were less frequent. As it turns out, helping other people is a lot more rewarding than working on your own projects, which is why my friend’s car still isn’t finished after five years. And my garage is still not as organized as I’d like, but I’m finding reward and meaning in helping others with less discretionary time than me.

Ted Sward, Glendale, Mo.

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