Dolehide shares personal journey, offers inspiration at Chicago Sports Summit

In the summer of 2023, Caroline Dolehide was playing for a spot in the Wimbledon doubles final for a second time.

She had lost with Storm Hunter in the semis two years prior, but this time Hunter was across the net, teaming with Elise Mertens. Dolehide, now partnering with Zhang Shuai, fell short in the match, but as she walked to the net for the obligatory handshake and congratulations, her disappointment was overshadowed by a different feeling: gratitude. 

Dolehide put her arm around Hunter and, as they looked up into the crowd and took in the magnitude of the setting on Court 1, said, "Look where we are."

The Hindsale, Illinois native was appreciating how far she'd come, and the journey she took to get there, after practicing and grinding and sacrificing for so many years.

That was her focus at the Chicago Sports Summit, where the 27-year-old sat on a panel about the realities of playing collegiate and pro sports, what it takes to get to that level, balancing school with practice and fostering a supportive environment where young athletes can thrive.

Sitting alongside Chicago Fire defender Andrew Gutman -- who also grew up in Hinsdale -- Dolehide shared her humble tennis beginnings, which included biking to public courts in her hometown as a kid, and then developing alongside her siblings, all of whom were state champions. They all pushed each other, she said, but her parents never put additional pressure on her, something she believes would have been a detriment to her development.

"I already put enough pressure on myself," Dolehide said, thinking back to her childhood. "If I had extra pressure around me and more demand from my parents, I don't think I would be where I am today. My parents taught me to work hard, play hard. That was an every-single-day life lesson for our family, and we would compete against ourselves. 

"Having that pressure off my shoulders helped me become who I am today."

The six-time Grand Slam semifinalist also said she found pleasure and enjoyment in the struggles and difficult times, because it meant she was improving and growing.

Dolehide didn't downplay the sacrifices she had to make to become a professional. She missed her prom and her younger sister's graduation from West Point, among many other moments, but that's just the price of committing yourself, and it was well worth it.

"As long as you accept that from the beginning, you'll be able to make those sacrifices," she said. "I'm not saying it won't be tough. But to me, the accomplishments that I've had, and my future accomplishments, are worth it because I have big goals and I pour everything into them.

"You cannot leave any stone unturned if you're going towards something big, and that should excite you, not put pressure on you."

Dolehide also stressed the importance of having great people around you -- people you can trust, confide in and be fully supported by. She had that growing up -- her parents and siblings leading the charge -- and it made all the difference. It kept her coming back to the sport and, perhaps most importantly, made the work fun, not a chore.

She still has that support system to this day, eight years into her professional career, and it's still perhaps her greatest asset.

"Especially in an individual sport," she said, "the most difficult thing is finding the right team around you. I've surrounded myself with such an incredible team, and that's a huge part of my success. It's what excites me every single day to try to get better. Fostering that environment around you is the biggest thing."

Dolehide gives back with the Serving Chicago Style Foundation

Dolehide doesn't just talk about youth sports, and how it builds character and creates lifelong opportunities. She's putting in the work and making a real difference in the lives of children.

Last year she founded the Serving Chicago Style Foundation, a nonprofit organization committed to inspiring children and elevating communities through the positive power of sports, from collaboration to confidence to leadership. The money raised supports youth programming, provides resources to underserved communities and helps put on events like December's Rally for a Clause, which is supporting the Play Like a Champion Today movement.

It's a fitting initiative for Dolehide, who's always had a passion for giving back. She recalls bringing her old tennis shoes, and other equipment, to downtown Chicago as a child and donating it to the homeless. She remembers volunteering at soup kitchens with her dad. And when she turned pro, she contributed greatly to the Hologic WTA Tour's many charitable initiatives across the globe.

Back in 2023, a young boy named Sean Richards was tragically killed in Hinsdale. His family created a foundation, Love Like Sean, in his honor, and when Dolehide heard about it she was compelled to support the cause. She created a fundraiser to raise money for that organization, as well as Chicago Youth Centers, and from there the Serving Chicago Style Foundation was born.

"My mom was like, 'We should create your foundation, because this is something you've always wanted to do,'" Dolehide said. "She's my advisor, and all my siblings are part of my team. That's the board of my foundation, and the mission is about nurturing strong habits and routines. We're creating opportunities that start locally and extend globally, empowering individuals and communities to thrive."

To learn more about the foundation, and to donate, click here.

Dolehide's on-court goal for 2026

Dolehide is enjoying her offseason, but she's eagerly anticipating 2026, and has a clear goal in mind: get back into the Top 50 in the singles rankings (and hopefully climb even higher).

Dolehide is currently No. 43 in the world in doubles and No. 112 in singles. She first broke into the Top 50 in 2023, peaking at No. 41 after reaching the final at the WTA 1000 tournament in Guadalajara.

To get back there, she's committed to taking more time this offseason to properly prepare for next year's grind -- both physically and mentally -- rather than rushing to play as many tournaments as possible. 

"As long as that takes, we'll see," she said. "But my coach and I decided when I'm ready, I'm ready. And then we'll kick off 2026."