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.”
Read profiles of the retirees here: https://wisconsinwatch.org/2026/06/wisconsin-door-county-retirement-destination-older-adults-retirees-still-working/
This story was produced and originally published by Wisconsin Watch, a nonprofit, nonpartisan newsroom.
