Kaitlin Calogera traipses around Washington, DC, for a living. Her company, A Tour of Her Own, offers tours of historical sites and events that highlight women and their achievements.

So how does Title IX figure into Kaitlin’s story? The law was well in the rearview mirror when she was born in the late 1980s.

“We were the first generation of women to benefit from Title IX,” she says. “As an athlete, I was always in female spaces and I thrived on female energy.”*

I connected with Kaitlin after she saw my post about Olympic softball player Dot Richardson. “Dr. Dot” was an early inspiration for Kaitlin.**

“Her book was the first autobiography I’d ever read by a woman,” she says. “Not only is she an athlete, but she’s a doctor. She’s such an inspiration!”

Heads up!

Growing up in Old Bridge, New Jersey, Kaitlin was an athlete through and through. She faced off against two older brothers and played on Little League, basketball and hockey teams, often with the boys. One of the only girls in her neighborhood, she had to keep up.

“It was either hit the ball or get hit with it!” she recalls.

She admits she wasn’t much of a student,  although she kept up. “I needed good grades in order to play sports. That was my incentive,” she says.

For two years, she played softball at Iona College in New Rochelle, New York, but she took a gap year and coached softball in Germany, traveling to other countries for tournaments. Back in the States, she coached softball at the Jenny Finch Academy at Diamond Nation in New Jersey and then at Fairleigh Dickinson University, where she got a history degree.

Despite Title IX, discrimination didn’t magically disappear. While at Diamond Nation, she learned that a male coach was making twice her salary, despite their identical qualifications.

 “Even then, we were still subconsciously being taught just to be grateful for what we had. We weren’t sure when to make a fuss,” she says.

Is that all there is?

Kaitlin didn’t make a fuss. She left for Washington, DC, where she volunteered as an assistant coach at Georgetown University. But she realized it would take years to make a life as a college coach — years that she didn’t want slipping by.

She took a corporate job arranging travel, hotels and restaurants for visiting groups. But she envied the guides who took people around the city.

“I wanted to know — Who were these people who got to go to the Lincoln Memorial every day?” she says.

Kaitlin’s envy led to certification as a tour guide and her own rounds of the city. It was eye-opening.

“It was all about presidents and wars,” she says. “I started to wonder, Is that all there is? Is this really me?”

It wasn’t her. She was curious about women’s lives and appreciated the female role models in her life. But start a tour company centered around women? She wasn’t sure.

“Is it a thing?” she asked a friend. “I think this needs to be a thing.”

On the road again

So was born A Tour of Her Own. Kaitlin and her guides love sharing the hidden lives of women. And she sees a natural connection between Kaitlin the athlete and Kaitlin the entrepreneur.

“The skills I learned as an athlete serve me well now,” she says. “I was used to always being on the road. My mother would be driving and I’d be navigating with the map. I know how to be loud and take up space. I gained discipline, commitment and a tough skin.”

All good skills for her, but she also loves what she’s created for others.

 “I love having a team of women who are as close knit as my sports teams were,” she says. “As an athlete, I always wanted to be with my teammates, and that’s how my business is. It’s like going to the World Series every day!”

If you aren’t lucky enough to catch a TOHO tour, you can read Kaitlin’s book. In 2021, she co-authored with Rebecca Grawl 111 Places in Women’s History in Washington, DC, That You Must Not Miss.*** But I’m close to DC, so I think I’ll book a tour soon!  

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* Kaitlin’s quotes come from my interview with her on May 31, 2022.

** Find Dot Richardson’s story at https://www.nancybkennedy.com/cut-my-hair-and-call-me-bob/ . She is an orthopedic surgeon and currently is head coach of Liberty University’s softball program. Her book is Living the Dream (Kensington, 1998). https://amzn.to/3NKlEEA

*** 111 Places in Women’s History in Washington, DC, That You Must Not Miss (Emons Publishers, 2021). https://amzn.to/3x61bU2