For years, Darrell Pennington thought he would work until his 70s and enjoy his retirement then. Gradually, he says he considered what it would be like to accelerate retirement, uproot from Evansville, and experience worldly cultures.
He realized this would mean selling the beloved Victorian home – and nearly all its contents – where he and his wife, Penelope, have lived for 27 years and raised two children. In January, he gingerly broached the subject.
Penelope’s response surprised him: “Can we leave tomorrow?”
“That put it in a whole different perspective,” says Darrell, who retired May 10 as chief operations officer with Mortgage Masters of Indiana.
It’s been full steam ahead ever since for the Owensboro, Kentucky, natives. They are downsizing their home just outside the Riverside Historic District item by item. Friends and former coworkers have browsed the Penningtons’ collection, which is set up “kind of like a flea market,” Penelope says. An auction likely will be needed for larger pieces.
The home’s uniqueness has caught Evansville Living’s attention in the past – a secret basement-level speakeasy called The Red Polka Dot was profiled in 2021, and in 2023, the magazine returned to check out a terrace space. In earlier years, the Penningtons had rooms dedicated to University of Kentucky sports (which also was profiled in Evansville Living) and legendary rockers KISS.
But Penelope, who retired five years ago from Milestone Investments, says her sentiment for the house is overshadowed by excitement about what’s to come.
“We have 27 years of everything,” Penelope says. “We’re not hoarders, but we have 5,000 square feet that’s full. There are things in the house I wouldn’t get rid of otherwise … but it’s nice for people to take things that I love and give them another life.”
The Penningtons’ immediate plans are to purge their belongings and put their house on the market. In mid-October, they board a vessel on a one-way voyage to Spain. Norway, the United Kingdom, Europe, North Africa, and Central and South Americas are on their wish list.
They do plan annual visits back to Evansville, staying in a camper, completing some U.S. travel, and visiting their daughter, 22, and son, 18.
Indicating their readiness to hit the road, the Penningtons headed to Ireland for 10 days in late May and early June to celebrate their 35th wedding anniversary.
That trip, Penelope says, represented “a big kick-off to our new life.
