Forty-two stories above ground, Jon Gottlieb traced his bicycle route. From his vantage point by the pool, on his building’s roof, he could see the stop sign where he turns right, the road he hates crossing, the park he rides through and the tunnel that leads to the Lakefront Trail bike path.
Gottlieb, 75, rode this route at least five times a week through the 13 years since he moved into the Lincoln Park building, the tail end of a five-decade commitment to cycling. For half a century, the retired railroad services manager tracked his mileage on bicycles and compiled it in a spreadsheet. Mark Mattei, who serviced Gottlieb’s bikes for 36 years, said it was clear that Gottlieb was honest about his mileage.
In 2020, he passed 100,000 miles on his bike. In 2023, he hit 110,000. Last week, Gottlieb prepared for two-wheel retirement as he geared up to ride his 115,000th mile. He reached his final threshold Friday.
“You gotta quit somewhere,” he said.
With his serious cycling days behind him, Gottlieb faces a life unstructured by a goal. He’s retired, happily married and financially comfortable. But like others on the older side of the baby boomer generation, he’s not quite sure how to spend his days without reaching toward something.
Some experts say that Americans tend to identify themselves with their careers, which leaves them feeling lost in retirement. Others, though, have found that baby boomers, especially the younger ones, are much better at finding fulfillment outside work than their parents were. As the last of the baby boomers reach retirement age, they have to manage more than financial stability — they’re figuring out what fulfillment looks like.
The baby boomer generation was born in what Gottlieb called “the backwash of the Second World War,” or the years 1946 through 1964. According to the Alliance for Lifetime Income, the United States is facing its greatest “retirement surge” ever, as more than 11,000 Americans turn 65 every day. For people who can afford to retire, and aren’t burdened by serious health issues, rebuilding a routine is usually the toughest challenge retirement offers.
“There’s a lot of detriment when the structure that you normally have gotten from your occupation is no longer there, and it’s kind of that rug being pulled out from underneath you,” said Michael Wolf, a professor at Northwestern’s Feinberg School of Medicine who researches aging.
For people who connect their identities to their jobs, Wolf said, retirement is gutting, as they experience a loss of identity and self worth. The happier retirees Wolf sees in his work are typically those who figure out what brings them joy ahead of retirement.
“You need to be able to not think of retirement as something like going cold turkey from work,” Wolf said. “You need to envision it as a staged process.”
Jon Gottlieb, dressed to celebrate the 115,000 mile accomplishment, maneuvers his bicycle over a crosswalk in Chicago, Aug. 1, 2025. (Antonio Perez/Chicago Tribune)
‘Desire to find a balance’
Stacks of vintage toys block nearly every window on the first floor of Mattei’s house in Lincoln Park. Two wooden chairs are the only furniture on the floor, unless you count the dozens of display cases filled with toy cars. Hundreds of them flood each room, some in every color, stacked on top of each other on shelves, in old paper boxes or standing alone. Model boats and airplanes squeeze between shelves and shelves of tiny cars; a glow-in-the-dark pirate ship perches in a corner; one-of-a-kind paintings of model planes crowd the ceiling.
Mattei, 74, closed Cycle Smithy, the bicycle store and repair shop he owned for 49 years, in 2022 — to Gottlieb’s dismay. Mattei had worked seven days a week for the better part of half a century, reached the age of 71, and could afford to retire — so he did. He took everything down, swept the floors and left the large storefront exactly the way he had found it years before. To his surprise, Mattei was calm.
“I was worried about retiring because I thought I would have some sort of existential crisis,” he said, three years into retirement. “That wasn’t a problem at all.”
Though he liked Cycle Smithy, Mattei found himself far less stressed once the shop was closed. These days, he sometimes has dreams about horrible customers at work and wakes up relieved that he doesn’t have to face his job anymore.
“I find happiness in the freedom to do whatever I want, even if I don’t really do anything,” Mattei said.
Mattei doesn’t feel aimless as he climbs into his mid-70s; he still has goals, even if they’ve changed. He’s focused on preparing for the end of his life. In January, he started selling from his vintage collection. In the next three years, he would like to have sold almost all of it, at market prices to genuinely interested buyers. He doesn’t want to die and leave his wife with a floor’s worth of stuff to clear out, but it’s important to Mattei that the items he holds dear end up in the right hands.
Through the selling process, he’s met other dedicated collectors of vintage toys. Some will fly in from California or Florida to see his collection and spend several hours with Mattei. That, and the other friendships he maintains — often with old employees at Cycle Smithy — keeps Mattei feeling fulfilled.
George Mannes, executive editor of AARP The Magazine, is surrounded by people like Mattei, who have redefined what purpose looks like after ending their careers. At 62, Mannes is on the tail end of the baby boomer generation, with many of his friends and colleagues in the early stages of retirement.
Mannes has found that people his age are much better at handling retirement than their parents. Retirees in their 60s, Mannes said, have built identities less associated with their careers. Many of them find fulfillment in volunteer work or artistic outlets: Mannes has a friend who organizes a trash clean up club and another who is learning the art of ceramics. The latter isn’t quite retired, but identifying her passion ahead of time — like Wolf recommended — has made her feel optimistic about leaving work soon.
“I am finding, among the people I know right now, that they’re very happy to walk away from (work), and try new things and live new lives,” Mannes said.
He thinks his generation’s more positive attitude toward retirement might stem from the wealth with which so many baby boomers grew up. Many of them learned how to enjoy themselves and prioritize a work-life balance long ago, before retirement was really on their minds. Their parents, however, often “fiercely identified with their occupations,” according to Mannes.
“I see a desire to find a balance between giving to the community and connecting with friends, but also just having the free time to goof off in the way that you want to goof off,” Mannes said.
The art of letting go
Nancy Gottlieb, 73, retired from the world of banks and trading firms at 64 and successfully struck Mannes’ balance. Leaving work hasn’t been an issue for her.
“I think it’s usually more of a problem for men than women,” she said.
While Jon Gottlieb pores over statistics-based baseball simulations — alone — his wife goes out to eat. She plays cards or mahjong five times a week and regularly calls friends on the phone. Jon has friends, too, but his social calendar is not nearly as robust as his wife’s.
Nancy Gottlieb thinks women are more likely to maintain friendships and ask each other out for lunch or coffee. Mannes hasn’t seen many men of his age struggle with retirement, but Wolf agrees with Nancy. Social isolation is more common among men than women, he said, and men participate in activities less than women.
“The running joke has always been that women are gathering friends as they get older, while men are shedding them,” Wolf said.
He explained that socialization is a “major” determinant of health. Members of older generations who tend to isolate, or are generally disconnected from society, are often at a greater risk of mortality. Boredom, too, has a serious effect on health.
But Tai Chin, 75, is wary of needing a goal to sustain him. He just moved into Gottlieb’s building after 40 years in Arlington, Texas, so he could be closer to his sons and grandchildren. He’s divorced and not interested in changing that.
“I’m alone, but I’m not lonely,” he said.
Chin hasn’t fully retired yet from his job helping people sign up for health care coverage; he doesn’t see the point. He works on his own time, entirely remote. These days, he only does about five hours a week plus the time he has to spend renewing his license before September. The rest of the day is his, spent mostly on yoga, messing around on his computer, taking walks and reading.
Chin reads a lot of mystical literature. He’s learning how to exist in the moment and accept the phase of life that he’s in now, when his responsibilities are dwindling and he has, essentially, total freedom.
“My goal would be to not have any goals,” he said.
Gottlieb ultimately wants the same thing, even if he won’t take Chin’s meditative approach. At this late stage in his life, he faces what, for him, might be akin to a Herculean task. His best friend, Bob Burger, isn’t sure Gottlieb can really give up cycling. In his eyes, Gottlieb is unusually motivated, the type of man who needs something to reach for.
“Sometimes retirement creates a void for people,” said Burger, 74, who lives in Wilmette.
For his part, Burger has had no trouble with retirement. He gave up a job he didn’t enjoy very much when he was 49 and took to traveling the world with his wife. In September, he’s leaving for Croatia, Ireland and the Alps.
“I’m much happier being a nobody without work,” Burger said. He’s not so sure, though, that Gottlieb — who not only never sits down but also rarely stops talking — can be a nobody.
Gottlieb is an intense guy; he said so himself. He wakes up at 6 a.m. every day and wears some variation of the same shirt every time he rides his bike. The only time Gottlieb “goofs off” is during his daily gossip session with a group of old ladies. They float on pool noodles and discuss the geriatric drama of their high-rise.
Maybe fulfillment, for Gottlieb, will always be tied to bicycles. He has failed, so far, at cycling retirement: A week after he reached mile 115,000, he was still riding almost every morning. He’s been trying to find an adult tricycle to ride, so that he can stay active in a safer manner, but it’s not the kind of contraption widely available in Chicago. For now, Gottlieb is still a two-wheel guy. Who knows if he’ll ever master the art of giving up.
