How to Retire

Dan Freedman talks about how to bridge the psychological gap between work and what comes next.


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The new year had hardly begun when I found myself opposite the boss at lunch, confronting the inevitable fact of life that no happily employed person likes to face. “Dan, what are your thoughts on ­retirement?”

I’m 66 years old, but still flying high at work, nowhere near out of gas even after 32 years as a journalist in the Washington press corps. Sure, I’d previously set the end of 2019 as a likely retirement date. But 2020, a presidential year, is beckoning. Don’t the newspapers for which I work need the wisdom and experience I’ve accumulated over a lifetime?

My boss told me how much he valued my work. But the signals were clear: It was time for the curtain to come down on this phase of my career.

I’m hardly the first person to go through such a rude awakening. And I realize this is about as soft a landing as anyone gets in today’s job-slash world, particularly in the media business. But I still left lunch feeling shaky and hurt and, most surprising for me, not a little scared.

Even though I had hoped to forestall the ax falling, I had been reading a lot about retirement during the past few months. Many of these stories called it a “second childhood.” But an equal number raised the specter of tedious days, too much channel surfing, no purpose in life, spouses increasingly irritated. “Twice as much time, half as much money,” is one common complaint.

But my bad feelings began to fade over the next few days as I faced the challenge of turning a potential tailspin into a kind of rebirth.

As opposed to many people, I was very fortunate in that money was not a real problem for me. If I behaved sensibly and prudently, cash flow would see me through many decades. But my problem was (a) having a lot of time on my hands (health permitting of course), and (b) what I was going to do with it.

I started my research with Nancy Schlossberg, who brings a long career as professor of counseling psychology and an expertise in “transitions and change” to bear on this topic. Now retired and living in Sarasota, she is the author of 10 books with titles like Revitalizing Retirement: Reshaping Your Identity, Relationships, and Purpose and Too Young to Be Old: Love, Learn, Work, and Play as You Age.

At the outset, Schlossberg recommends that you delve into your inner self and come to grips with your personality — your emotions and expectations. A little bit of self-knowledge can help you avoid the pitfalls of retirement. (See sidebar: “What’s Your Retirement Type?”) For example, one person she had interviewed, a former top executive, spent his first days in retirement helping his wife with the shopping. It didn’t go well. He actually started arguing with her about what kind of cereal she was buying. “Is this what my life has come to?” he asked. Clearly he needed to face the fact that he wasn’t going to change overnight from making major corporate decisions to puttering through a supermarket filling up the shopping cart.

Another disappointed Schlossberg subject was a woman who retired and had to confront her daughter’s expectation that she was available for babysitting at a moment’s notice. “You’ll need to renegotiate with your spouse and your children on what the boundaries are going to be,” Schlossberg says.

The bottom line: “Improvisation should become a way of life,” she says.

One piece of advice really stood out: Once a week, leave the house and go do something on your own.

As if following that suggestion, David Odess, 66, of Boynton Beach, Florida, who retired last year after a successful career in sales, took advantage of an almost clichéd part of retirement — the golf game — to get some advice before taking the plunge himself. He realized the retirees with whom he played were a font of information, interviewing them as they played. “‘What advice do you have for me?’” he would ask. “Every one of them had an opinion. But they all agreed on some fundamental points.”

Namely, you need to first accept that the mental grind of work is over, along with the constant highs and lows. Most felt that the key was not trying to replace a lifetime of work with any one commitment anytime soon. But at the same time, they warned about the temptation to just take refuge on a comfortable couch, TV remote in hand. Don’t go there, at least during the daytime. Without pressuring yourself, begin to think about what you really like to do — and do it. Stay busy. But not too busy. Beware of obsessively pursuing activities for fear that a day or hour or minute of down time is tantamount to doomsday.

And finally, one piece of advice really stood out: Once a week, leave the house and go do something on your own. Go to lunch, but not with your spouse. It’s “you” time, a chance to rediscover the individuality that may have gotten buried back in younger days by marriage, kids, and work.

“There’s no magic to it,” said Odess, who at the time of this writing was on a cruise with his wife.

Another good role model I met is Rosemary Parrillo, 67, of Marlton, New Jersey, who abruptly departed her job late last year when her company “rebranded” — tech speak for going in a new direction that doesn’t include you.

The first thing Parrillo said she’s going to do was … not much. Letting the dust settle a bit and settling into a new routine can be a beneficial alternative to frantically filling the days with busywork.

One of her first projects was organizing and writing down her mother-in-law’s classic Italian-American recipes for meatballs, oso bucco, sauce Genovese, and many others. Down the line, she also planned to do some writing. The secret, Parrillo says, “is finding the way to be undisciplined, but disciplined enough to say ‘I need things in life that organize me.’”

So there is a lot of yin and yang in retirement: Active, but not driving yourself nuts. Relaxed, maybe even a bit self-indulgent, but not to the point of out-and-out laziness. And trying to avoid pitying the person you see in the mirror.

It’s also important to just remember that if something isn’t working for you, you probably have the option to change it — an option that younger people rarely enjoy. Joe Bensi, a police detective in Chardon, Ohio, retired after 32 years on the force and — fearing that he’d be at sea in retirement — immediately took a job as a security officer with the local school system.

The detective’s life was stressful, but the school job was downright distasteful. School officials essentially assigned him the tasks they didn’t want to do themselves: Telling angry parents things they didn’t want to hear about their unruly children, dealing with truancy, or catching students who didn’t actually live in the school district.

It took his wife, Margaret, “to make me realize what it was doing to me,” Bensi says. After he quit the security officer job, he found “the biggest surprise is that I don’t miss working at all. I’m very happy to have retired when I did.” Now at 71, he happily does household chores on days that Margaret is working as a hospice nurse, so on days when they’re together, “we don’t have to spend time cleaning house, shopping, laundry.”

But what if you’re stuck? What if you can’t come up with anything you find deeply satisfying? Or you just need a jump start or some old-fashioned prodding?

Schlossberg advises a drop-in at your local area senior center, community center, or library. “Be open to what’s around you,” she says. “It could be something around the corner and you just don’t see it.”

Michael Brumas, 66, for instance, discovered a sport he had never heard of — pickleball, a hybrid of tennis, Ping Pong, and paddleball. It is growing in popularity among retirees, so picking up partners for impromptu games of doubles is never a problem. And the on-court socializing pays a dividend in the form of off-court get-togethers and potlucks with spouses.

“No matter how many books you read on retirement or retirees that you talk to, coming up with a retirement plan is something everyone has to do for themselves — there’s not a one-size-fits-all model,” says Brumas, who lives in McLean, Virginia.

So now it’s time to confront my own metaphysical fruit salad of emotion about retirement. Of course, those sideline interests I used to have can now go to stage center. Travel? Check, up to a point. Cooking? Check, as long as my waistline cooperates. Running? Check, although my days of running marathons are behind me. And I’m certainly fortunate to have three grandchildren close by. I can foresee happy trips to art lessons and dance classes, occasional bus-stop drop-offs and pickups, and lots of sideline cheering at their sports activities.

But thinking about Schlossberg’s suggestion of delving deeply into my emotions brought up memories from decades ago. In 1980, I drove with a friend from New York to Antigua, Guatemala, and enrolled in a Spanish-language school. It was an incredible experience — a colonial village under the shadow of a dormant volcano, living with a Spanish-­only family, intensive one-on-one lessons. After two weeks, I was thinking to myself in Spanish while showering. But I was there only four weeks, hardly enough time to gain mastery of the language. Suddenly I remembered that a friend at work had told me that a former girlfriend had taken Spanish at a school in Guanajuato, north of Mexico City. I googled it. What came up were videos of an enchanting colonial town, cobblestone streets, tolling church bells, and outdoor cafés — an Italian-style hill town just a few hundred miles from the U.S.-Mexico border.

I was transported. And I found myself almost ready to leave work right then — ahora mismo — and embrace my retirement destiny.

As my workdays begin to tick down, I’m a little surprised at how unagitated I feel. I’m not sure how long that will last. But I recall what Mike Brumas told me: “Successful retirees don’t wait for the world to come to them — they’re always on the lookout for new experiences and adventures to explore. And if something doesn’t work out, or isn’t interesting or fulfilling, you’re under no obligation to continue. This is your retirement, and you get to make all of the executive decisions.”

Dan Freedman is retiring after 32 years as a writer and editor for Hearst Newspapers in Washington, D.C.

This article is featured in the July/August 2019 issue of The Saturday Evening Post. Subscribe to the magazine for more art, inspiring stories, fiction, humor, and features from our archives.

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  1. I love this article and the accompanying retirement “types” box. I’ve read it aloud to friends and also made copies to pass along. Some of us have been in the retirement pool for quite some time, but I’m new to it and confess to the occasional panic attack. Your article made us all smile and nod in agreement, while offering sound advice and hope for happy and productive futures. My sincere thanks to Dan Freedman and Nancy Schlossberg. Wishing you both all the very best in every stage of life!

  2. This is excellent information and guidance for those of us lucky enough to even have the option of retirement in the first place, therefore having the need to pick out what your ‘retirement type’ is.

    Personally, I don’t know anyone who’ll EVER be able to ‘retire’ at all, Dan! The high cost of living is a really ugly reality for a lot of us folks that are members of ‘Generation Jones’ (late Baby Boomers born between 1955-’64) and those born after that, of course. MANY older Baby Boomers and those even older are not immune either, trust me.

    The fact I/they live in the long tarnished ‘Golden State’s Los Angeles has a lot to do with it, I know. Skyrocketing costs for worse and worse conditions. Even the once great weather here is largely gone with the wind. Before that though was the beginning of the end of the great post World War II middle class mobility and job security, going back to 1973; over 45 years ago.

    Even my own father, a successful, well-educated attorney had to keep working, up until the month before he passed away in January 2008 at 92. Yes, 92. I work 2 (secure) part-time jobs in accounts receivable avoiding the traps and fears of all of the eggs in one basket. In addition there’s no age discrimination, limits or other little corporate traps of horror.

    My condo is paid for thank God (!!), but I dare not turn down ANY additional opportunities to make extra money, like an extra $90 (cash or personal check ONLY—thank you) dog-sitting Kaluah (a Doberman) certain weekends. It ALL helps, and it all has to keep coming in; sorry. I could leave California any time I’d like, but checking out and starting over is a lot easier said than done.


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