From Broken to Better than Ever: 5 Inspiring Stories of Divorced Women

As part of our “Love Essentially” series, Jackie Pilossoph helps us navigate the complex world of relationships. Have a question that you would like her to answer? Contact her here, and it may be featured in an upcoming article!

It’s been almost 10 years since Kathleen McCarthy got divorced, but she can still recall the raw emotions she was feeling back then.

“I was completely devastated. Scared to death,” said McCarthy, a Glenview personal trainer and fitness instructor, who had been married for 29 years. “I was frightened about my future and I felt broken.”

McCarthy, a mom of three and now a grandmother of three, isn’t alone when it comes to the difficulty and pain of divorce. According to Ashley Wood, a divorce attorney with Katz & Stefani, there have been more than 8,500 new divorce cases filed in Cook County in 2020, and some experts say divorce rates could drastically increase in the months ahead because of Covid-19.

But as depressing as getting divorced might seem, believe it or not, the long and painful journey from being newly separated to officially divorced can lead to an unexpected, happier and better life. 

I sat down with five divorced women, including McCarthy, who went through heartbreaking divorces, but as a result are now doing extraordinary things—things they say they would never have done if they were still married.

Kathleen McCarthy: World Traveler

In the summer of 2012 with one of her closest girlfriends, then newly divorced McCarthy headed to Camino De Santiago, the historic walking trail in France and Spain. They spent 12 days walking a total of 380 miles and sleeping in cabins and other camping-type accommodations. 

“I wanted to do something out of the ordinary and challenging and empowering,” she said. “As I was walking, I would think about my future. It was a religious pilgrimage with a lot of opportunity for soul searching and quiet time.”

Kathleen McCarthy poses for a photo with her host family in India in 2017. Photo courtesy of Kathleen McCarthy.

McCarthy caught the travel bug after that, and over the next decade visited places that included Israel, China, Peru, India, Paris, St. Lucia, Puerto Rico and Costa Rica, most often traveling solo.

“It made me stand up and say, ‘I got this.’ Every time I’ve been on a trip, I’ve grown. It’s never the same experience,” McCarthy said. “I took some nice trips when I was married, but I had someone taking care of me. I felt like, ‘If I’m going to be independent and not married, I have to act like it and step out of my comfort zone.’ Not just for the trips, but for the rest of my life.”

McCarthy said she’s looking forward to traveling to Vietnam and Cambodia after COVID ends.

Sheila Jacobson: Life Coach

Several years ago, when Sheila Jacobson’s mom was diagnosed with Alzheimer’s, she knew she needed to make a life change.

“I realized how short life was and I wanted to be happy,” said the Highland Park mom of three. “I realized I’d forgotten who I was. I was miserable and exhausted from pretending my life was great. I had no strength left.”

Jacobson, who was working in her family business at the time, hired a life coach, who she said paved the way for clarity. 

“I cried the whole time for the first four sessions,” said Jacobson. “My fear was change. I was comfortable with what I knew regardless of how miserable I was. I was terrified to get divorced. I didn’t think I could do it.”

But Jacobson did do it. She got divorced in 2016, and then found a calling: becoming a life coach herself.

“Coaching is all about action,” she said. “After my divorce, I started seeing the world in a different light. Instead of seeing myself as a victim, I started seeing opportunity. My divorce gave me a mission: to make as many people as possible feel empowered and find an opportunity during a very difficult situation.” 

Sheryl Weiss: Dog owner and Aerial Arts Performer

If she was still married, Sheryl Weiss said she wouldn’t have four things: her house, her dogs, her involvement in aerial arts, and self-confidence.

Divorced in 2017 after a 20 year-marriage, the North Carolina based mom practices and performs aerial arts—climbing and holding poses while hanging from the ceiling, supported by aerial silks.

Sheryl Weiss practicing aerial dance last month. Photo courtesy of Sheryl Weiss.

“It’s like doing gymnastics combined with yoga. It’s hard and it’s exercise, but it’s fun,” said 53 year-old Weiss. “I don’t have a dancer body, so for me it was a big challenge. After I got divorced, I didn’t feel self-conscious about my body anymore. I wasn’t seeing my body through his eyes. He called me “clunky,” and wondered why I was doing it. He judged me. Other women don’t judge.”

Weiss also bought a home and adopted two dogs after her divorce, stating that her ex-husband never permitted the family to have a pet.  

“It’s debilitating to be in a relationship where your needs aren’t regarded,” she said. “You start to feel bad about yourself, you doubt your decisions, you second-guess yourself, and you think, ‘I can’t handle this’ but you can. I’m doing it. I’m doing all these things I held back on that I wanted for myself and I don’t have to explain myself to anyone.”

Heather Harmon: Vintage Market Owner

Heather Harmon has had a lifelong passion for decorating and repurposing furniture. Opening an antique furniture store has been her dream for years. The dream just came true. Two weeks ago, Hazel Reese Vintage Market in Athens, Ohio opened.

“It’s a vendor mall where people who make handmade items can sell their things, and I sell my furniture, too,” said Harmon, who also works as an associate professor of public health at Ohio University.

Harmon, who split up with her husband three years ago, said she doesn’t think she’d have opened her own business if she was still married.

“I would have doubted it. I doubted everything back then,” said Harmon, whose market is named after her two daughters. “I now have a lot of strength that I didn’t know existed in me. The divorce made me realize that I do everything on my own now, so why can’t I do this? I feel like I’ve blossomed.”

Jackie Pilossoph, Journalist 

Jackie Pilossoph and son
Jackie and her son

Several years ago, I lived the devastation and the suffering of divorce, traveling the tough road of getting through it. A single mom of two toddlers with no family living in my town, I felt very alone, like I was on an island, in fact. I didn’t know anyone who was divorced, and it seemed like no one understood how I was feeling. 

Because I never wanted anyone else to feel that way, I took my journalism experience and my passion for writing and created Divorced Girl Smiling, a website aimed to connect, inspire and give hope to men and women going through a divorce. Divorced Girl smiling turned into a large divorce support community, with its popularity leading to financial success, and to the launch of Love Essentially. But more importantly than a career, I feel like I’m giving back, which gives my life meaning. 

In closing, I think that divorce at one point or another, forces self-reflection and a reevaluation of one’s life. Looking in the mirror in that regard can feel painful, scary, confusing, and sad. 

But the beauty is, divorce, although an ugly word, does come bearing gifts. It fosters courage, empowerment and wisdom. Divorce enables you to custom design the life you want moving forward. Remember that it’s never too late to reinvent yourself, or to make changes and do things you think will bring you happiness. These divorced women did it, I did it, so why can’t you?


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Jackie Pilossoph is a former television journalist and newspaper features reporter. The author of four novels and the writer of her weekly relationship column, Love Essentially, Pilossoph is also the creator of the divorce support website, Divorced Girl Smiling. Pilossoph holds a Masters degree in journalism and lives in Chicago with her two teenagers.

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