When James Carson, 72, retired to Washington Island a decade ago, he envisioned the next stage of his life as many do: leaving the workforce, volunteering, traveling, caring for his family.
Instead, unexpected medical expenses and the rising cost of living soon forced him to pick up two service industry jobs to make ends meet. Today, he regularly clocks in seven days a week, logging 45 to 50 hours.
Door County is home to one of Wisconsin’s oldest populations, largely thanks to its status as a serene retirement destination. But like Carson, more of those older adults and retirees are returning to work. Unwilling or unable to quit for good, they’re picking up jobs to afford the rising cost of living, to stay social and to become involved in the community.
The trend is reshaping what retirement in Door County looks like today as people live longer and life becomes more expensive.
Carson wishes he would have saved more aggressively – he “was kind of naive” about retirement. He also thinks people have false ideas about what it looks like.
“You cannot live on Social Security, and unless people have a very good retirement plan, they’re going to be hurting,” Carson said.
Given Door County’s booming tourism industry, many retirees like Carson seek out hospitality and customer service jobs. Even for those not driven by finances, these gigs offer the chance to interact with others. But others simply continue their careers past retirement age or pivot fields.
To meet the demand from job-seeking older adults, local employment services nonprofit We Are Hope runs a program to match them with employers. Executive Director Kim Carley said the organization served more people in the first half of 2026 than it expected for the whole year.
“The need is definitely, definitely there. The majority of it is that social connection, but you do have that small population that financially they need to work still,” Carley said. “Not everybody in Door County is rich. The cost of living has really affected things right now, too.”
Wisconsin Watch and Door County Knock spoke with several workers over the age of 65. Together, their stories create a changing image of what retirement and aging look like today. Keep reading to learn more about their jobs.
James Carson
Age: 72
Job: Bartender
Former career: Amtrak conductor
Town: Washington Island
Why: Money
“Everyone wants to talk to the bartender,” Carson said. “I’m well-suited for the job.”
Carson was not always a confident speaker. When he was younger, he stuttered badly. A fifth grade teacher helped correct it, he said, “and I haven’t shut up since.”
Being well-suited for his job may be a good thing, but Carson did not think he’d still be working at 72 years old, especially not in Washington Island’s demanding summer service industry.
Carson and his wife, Stacey, bought a house there about 10 years ago, after he retired from a 20-year career with Amtrak. Stacey spent summers on the island growing up, and her parents live there now.
He envisioned volunteering and traveling, and the couple would care for Stacey’s aging in-laws, he said. For the first year or so, that was what he did. Jim served on their church council, worked with a developmentally disabled young adult, volunteered for the island’s nonprofit Art & Nature Center, and gave back to a community he said welcomed them with open arms.
“Until reality kicked in,” he said. The cost of living, including utilities, groceries and ferry travel, ate away at the couple’s savings faster than they anticipated. Jim needed eye surgery, then knee surgery.
He quit volunteering and returned to the workforce, where he has remained for the last eight years. Between shifts as a prep and line cook at Nelsen’s Hall & Bitters Club and as a bartender at the Albatross Drive-In tiki bar, he works seven days a week during the busy tourist season.
“I’m working more aggressively this summer to bank against having to continue to work this much next year,” Carson said. But with the fluctuating economy, higher grocery bills and gas prices, that might change. Ideally, he would like to only work for another two years, he said.
Mentally, Carson enjoys talking to people and has formed good relationships with the island’s youth — the Albatross is a popular hangout spot — but physically, the work takes its toll. The knee surgery made it harder to be on his feet all day and he falls into bed exhausted every night, he said.
“I’m doing better than most. I hear about folks splitting or foregoing their medications and going to food pantries,” Carson said. “I’m not there yet.”
Cindy Good
Age: 71
Job: Retailer
Former career: Software and business consulting
Town: Sturgeon Bay
Why: Keeps her busy
Cindy Good plopped down on the chartreuse furniture clustered at the front of her store, The Naked Sheep Yarn Shop & Gift Boutique. At 2 p.m., it was her first time sitting that day.
Good, nearly 72, is exhausted. But she said she’ll continue working “as long as my body will hold out.”
She retired at 70 after a career in software and business consulting. She once thought that she’d work part time at most at her age and take advantage of having more time to read books or catch up on knitting. But before she could do that, she and her sister opened a second venture: a yarn store on the west side of Sturgeon Bay.
The store sells yarn, knitting tools and other tchotchkes. They also host classes, social knitting groups and crafting events. Good regularly bounces between handling orders for inventory, checking what’s in stock and helping customers with their knitting projects.
“There are days when I wake up and I think, ‘Oh God, why didn’t I just fully retire?’” she joked.
But in reality, she knows why: She feels the need to keep busy.
If she quit working, her Social Security payments would provide enough money for her to live on. But she recognizes the rising cost of living that influences other working retirees in the area. For instance, no houses in the area are for sale at the price she and her sister bought theirs for.
“We have friends that have money and they travel and do all that kind of stuff,” Good said. “That was sort of my goal, but I don’t have that kind of money. I was thinking I would do a trip a year or something, but now I’m here.”
Good loves Sturgeon Bay’s tight-knit feel and the downtown location of her business. In mid-June, business had just started picking up as tourism season began. By July, the street will bustle for their busiest month.
Maybe, she considered, once business is where she wants it to be, she might take those yearly trips.
Charlene Keith
Age: 68
Job: Door County Maritime Museum associate
Former career: Grocery distribution
Town: Sturgeon Bay
Why: Social interaction
Charlene Keith never envisioned herself retiring.
Five years ago, she technically did. But she went right back to work. After two and a half years, she decided to finally slow down — but not fully.
“If I sat home, I would just drive myself crazy,” Keith said. “I have to be doing something.”
She reached out to We Are Hope, where MatchUp program leaders recommended a part-time opening at Door County Maritime Museum in Sturgeon Bay.
Here, she works the front desk, welcomes visitors, sells tickets, stocks the gift shop, keeps tours running on schedule and closes the museum at night.
It’s a far cry from her grocery distribution career, where she navigated difficult roles and recalled everyone around her being unhappy. Nowadays at work, “everybody’s happy to be where they’re at,” she said. Most of Keith’s co-workers are retirees, too.
“It’s just fun. It makes me believe that it can be done. I thought everybody was unhappy in (their job),” Keith said. “You hear people say if you have a job you love, then it’s not really working, and I thought, ‘Yeah, that doesn’t happen.’”
Keeping busy brings her joy. She enjoys seeing guests’ excitement over the museum’s exhibits.
Keith lives and shares expenses with her sister, so she doesn’t necessarily need the part-time wages to get by. But she sees why finances motivate other people her age.
“It’s expensive to live, but people are living so much longer,” Keith said. “Unless you’re a millionaire and can travel, what would you do with yourself? I mean, I guess there’s people that sit around and fish for hours every day, but I’m not that kind of person.”
Lee Engstrom
Age: 87
Job: First responder
Former career: Factory quality control
Town: Washington Island
Why: Keeps him busy
At 87 years old, Lee Engstrom is almost certainly among the oldest in Door County, according to county Emergency Services Director Aaron LeClair. He may be the oldest first responder in Wisconsin.
Engstrom is a fourth-generation member of the family that owns and operates Sunset Resort on Washington Island. He grew up in Michigan and spent summers helping his grandparents at the resort. He always dreamed he would end up there full time.
That dream came true when he and his wife, Janet, moved to the island in the late 1980s after he retired from a 30-year career in a factory’s quality control department.
Engstrom was not ready to stop working completely. He got a job with the local hardware store and did some plumbing work on the island. When he turned 62, he started getting Social Security and quit those jobs, but still needed something to keep busy.
He became an emergency medical responder, then got certified as an emergency medical technician and joined the island’s volunteer fire department. Today, he spends 80 to 100 hours every two weeks on call as a first responder because he enjoys it. He also does maintenance and odd jobs around the resort.
At 87, he did not think he would still be working, he said.
“I didn’t think I’d be alive,” Engstrom said. “When is it going to stop? As long as I feel good like this, I’ll just keep going. I have slowed down some, though … I’ve got fake ears, fake eyes and fake teeth. Everything else is original.”
Unless there’s a rescue call, being on standby doesn’t take much time. Engstrom just needs to be dressed near the emergency services facilities in case a call comes in — easy enough on an island. He’s happy to be one of the responders on call during the day because many of the younger volunteers are working their regular jobs during that time.
Engstrom focuses on patient care when he goes on calls. His primary objective is to make them feel comfortable and cared for once their medical condition is stable, he said.
When there is a fire, Engstrom’s primary job is to fill the tender truck — a mobile reservoir that supplies water to hose trucks when fire hydrants aren’t available. Rural departments often use them.
“I’m too old, and not as agile, to be going around dragging hoses and that kind of stuff,” he said.
For a while, fewer and fewer new recruits became island first responders as agencies statewide saw dire staffing shortages. But a recent influx of younger people has changed that, he said.
Financially, he and Janet are doing fine, and they have family who support and help them. But he enjoys his work — especially interaction with patients and knowing he provides a valuable service to his beloved island community.
When he does stop for good, Engstrom said he might golf more, keep working in his shop and do what he can to help at the resort. He would also continue his daily cruise around the island with Janet, he added.
“Whatever I’m doing, I enjoy taking the ride with my wife for a cup of coffee,” he said.
Jeff Gildersleeves
Age: 65
Job: Door County Parks Department maintenance staff
Former career: Manufacturing plant management
Town: Gardner
Why: Money
Jeff Gildersleeves is no stranger to physical labor. The 65-year-old works for the Door County Parks Department’s “mow crew.” The part-time gig lasts from May to October, and he spends his days hauling equipment, mowing, trimming trees, planting grass seed, picking up trash and tackling other tasks to maintain the county’s parks.
Gildersleeves’ first job as a teenager growing up in Door County was picking cherries and strawberries during summer. He loves the outdoors, and the work suited him well, he said. He went on to obtain a degree in biology and wildlife management, which he used to work for the Department of Natural Resources.
When Gildersleeves and his wife were expecting their first child, he switched careers and took a job at a chemical production and manufacturing plant in Milwaukee. He retired in 2021 and returned to Door County with his retirement benefits and a plan.
According to Gildersleeves, a local company was offering an Employee Stock Ownership Plan. If he worked there for at least three years, he would receive his full investment and returns, enough to supplement his retirement savings from the Milwaukee job.
Three months before his three-year anniversary, Gildersleeves got injured on the job. He needed surgery to repair a torn left rotator cuff, and that was it, he said. “I only got 20% of my investment back.”
Today, the mowing job is replacing that lost income.
“We thought at 66, 67 we’d be able to sit back and enjoy life, but with the economy the way it is, and health insurance costs?” Gildersleeves said. “My wife has some hefty prescriptions. Social Security is not enough to live on.”
The physical part of the job can be hard, he said. “You think you are physically fit until you’re out there doing it.”
Beyond the manual labor, Gildersleeves guides younger employees. His supervisors value his experience, and he has a good rapport with the teenagers on his crew, who listen to him, he said.
Doing something valued and worthwhile is good for his mental health, he said, but he is not sure how long he’ll continue.
“Until I’m unable to work anymore,” he said.
He has a small IRA put away and a pending lawsuit against the Door County company where he was injured, but he said he doubts he will see any settlement money. He knows one thing for certain: He would like to remain in his own home for as long as possible.
“I don’t want to sell off and go to a nursing home,” he said. “I watched my in-laws do that, and it’s not a good way to live.”
Kathy Bandstra
Age: 76
Job: Therapist
Town: Sturgeon Bay
Why: Is fulfilled by her career.
Kathy Bandstra returned to school in her 40s to become a licensed clinical social worker. Her sixth decade began before she paid off her student loans. At 68, she started considering retirement.
“I retired in June of 2018 because my financial person said, ‘Don’t ever retire in the winter, because that’s too depressing,’” she said. “I followed his advice.”
By the next month, though, she already returned to work part time for a private practice. A year later, she shifted to volunteer as a hospice worker during the COVID-19 pandemic. Then she moved from Racine to Door County and began volunteering at the area’s Aging and Disability Resource Center.
“I still felt like something was missing … It just felt like I could do more with the skills I had,” Bandstra said. “And I still had the energy to do it. And volunteering doesn’t pay you anything. I like making some money.”
People had told her that it was hard to find affordable mental health services in her new home county. She rented an office in Sturgeon Bay, opened her own business and offered services on a sliding scale to help people afford care. She couldn’t offer her services for so cheap if she wasn’t retired and receiving Social Security, she said.
Now, at 76, Bandstra regularly sees several clients a day in person and through telehealth. She helps people through distress and trauma with cognitive behavioral therapy and eye movement desensitization and reprocessing therapy.
Continuing to work gives her the freedom to go out to eat, get a new car if needed and cover expenses that pop up outside of bills. If she stopped working, she might have more time for her hobbies — making clay pots, writing her memoir, doing open mic readings. But she would miss feeling helpful to others. She also feels her physical and mental health has improved because she keeps going.
Bandstra believes people largely have false ideas about what retirement looks like. She thinks “it’s unrealistic to look to retire,” period. If clients continue to see her, she’d like to work into her 80s.
“I don’t know if some people would want someone that’s old enough to be their great-grandma,” Bandstra said. “But the people that stopped coming to me didn’t say that they thought I was too old or anything.”
Miranda Dunlap reports on pathways to success in northeast Wisconsin, working in partnership with Open Campus. Find her on Instagram and Twitter, or send her an email at mdunlap@wisconsinwatch.org.
Emily Small is a reporter for Door County Knock and a Report for America corps member. Contact her at esmall@doorcountyknock.org.
