Written by Doug Goodnough
A summer trip up north after her sophomore year at Hillsdale College changed everything for Paige Howell O’Leary, ’93.
While driving to meet her family in Horton Bay, Michigan, O’Leary and her then-boyfriend were involved in a serious car accident.
“The car flipped five times, and I was pulled out with the Jaws of Life,” she recalled.
She sustained a serious head injury that eventually ended her playing career as a member of the Chargers women’s basketball team and threatened her academic standing at Hillsdale. In fact, her doctors recommended that she leave school and live at her South Lyon home during her rehabilitation and recovery. She refused.
“After that [accident], I couldn’t walk and chew gum,” O’Leary said of her slow recovery. “I just lost all my coordination and had memory issues.”
But she was determined to stay in school and stay at Hillsdale—even against her doctors’ advice.
“If I don’t go back, I’m never going to finish,” she recalled of her decision to stay at Hillsdale. “It was super important to finish my degree at Hillsdale.”
Although her basketball career was over, she worked through her memory issues to earn her degree in five years. O’Leary credits Hillsdale’s faculty, staff, and students for helping her make it through.
“I slept a lot. I missed a lot of classes. But the professors worked with me, and I had some really good friends who helped me,” said the business major. “You know, everybody was very accommodating based on the circumstances.”
She said then-Head Women’s Basketball Coach Phyllis Cupp and the Athletic Department allowed her to keep her athletic scholarship. She served as a student coach for the program during her remaining time at Hillsdale.
“It was the people and the relationships with my professors,” O’Leary said of the reasons for being able to complete her degree. “When I was struggling with the academics and when school became very hard and I couldn’t remember a lot, they worked with me and supported me.”
O’Leary continues to use that determination to succeed in both her professional and personal life.
After graduation, she worked for Paine Webber setting up seminars and radio advertising. She next moved into sales, working for various companies in the Detroit area. When she met her eventual husband and married, they decided to build a home on a golf course in Charlevoix, Michigan, where they still reside.
She moved into real estate, where she had success until she and her husband decided to start a family. Wanting to spend more time at home, she opened a small marketing and graphic design company, which she ran for 16 years.
By this time, she had been bitten by the entrepreneurial bug. In 2018, she opened a pottery studio in downtown Charlevoix. When the COVID-19 pandemic hit, she ended up closing the storefront. However, she restarted Cottage Pottery as a “roving” business model, teaching “paint your own pottery” classes around the area by request.
“I just decided to go mobile,” she said of the pottery business. “Now I go to local restaurants and bars. There are a lot of wineries and breweries up here where I teach classes.”
Part of her business model is fundraising for nonprofits and charities.
“We raise money for people in need,” O’Leary said of her efforts. “I put on big programs for groups that are near and dear to my heart.”
Three years ago, she and her husband bought an established restaurant in Charlevoix and are now the owners and operators of the Happy Troll Deli and Pub.
“We’re both 55 now, and even in our 20s, we said we should open up a restaurant and do breakfast and lunch,” she said. “We had always joked around about opening a business, and then this downtown business became available.”
Her husband, Dennis, now retired from a long corporate career, runs the restaurant, with Paige helping where she can.
“We gutted the whole thing and put in a huge bar,” she said of taking over the restaurant. “We put our marketing skills to work, and we’ve increased business by 35 percent. I do all the marketing, social media, and the graphic design on the menus.”
Two of their three daughters also work at the restaurant, which features a “massive” menu of handcrafted sandwiches, hamburgers, and some of the best prime rib around.
“We pride ourselves on serving fresh meat that’s never frozen,” O’Leary said. “We slice all of our vegetables every day.”
She had a chance to visit the Hillsdale campus a couple of years ago and has fond memories, in spite of the adversity she experienced.
“A lot of it had to do with the people I met on my journey there,” said O’Leary, who also was a member of the Alpha Xi Delta sorority at Hillsdale. “The biggest thing I learned at Hillsdale is to be determined. Never give up and keep moving.”
Doug Goodnough, ’90, is Hillsdale’s senior director of Alumni Marketing. He enjoys connecting with fellow alumni in new and wonderful ways.
Published in November 2025
