From 2X Olympian to Inspiring College Students – an Interview with Cindy Overland

Anderson College scored gold in the serendipitous unfolding of the life events of Cindy Overland, a national and world speed skating champion and two-time Olympic athlete turned admissions advisor for students.

We had the extraordinary opportunity to sit down with Cindy and have her share the history of her childhood ambitions, exceptional athletic career and the turn of events that had her shifting focus from high-level sports to empowering students as they take career and life to new levels.

Backyard Beginnings

“I was an elite athlete, essentially, my entire life. At about three or four years of age, I started skating in the backyard. We had two huge vegetable gardens that my parents would freeze so we could skate all winter. This progressed into a love for the ice, I guess. I don’t know if I knew at the time whether that love would translate into figure skating or speed skating, but, of course, speed skating won out. “

Cindy’s career started out innocently enough, “I think for our parents it was just about keeping we three kids busy.” But as fate, and determination, would have it, for her brother Kevin, sister Amanda and Cindy, it blossomed into a thriving profession, taking them all around the world, competing at the highest levels and experiencing a charmed life that few ever know.

Born and raised in Kitchener, they joined the Cambridge Speed Skating Club where there was coaching support. At an early age she and her brother Kevin (15 and 16 years old respectively), were headhunted by the National Training Centre in Calgary and invited to join a youth program for a short trial period to test the ‘ice’, so to speak. Successful, this led to the relocation of she and Kevin to Alberta and the scholarships they earned for the program paved the way for their 16-year stint on the Canadian National Team.

“This took me to several Ontario championships. I was a seven-time Canadian champion, a seven-time World Championship team member, and then two-time Olympian, from 1990 until my retirement in 2006. Those were super formative years of my life for sure; never in my wildest dreams did I ever think that I would eventually become an admissions advisor at a private career college.”

An Unexpected Career Shift

Cindy had always envisioned her life in sport, but with some health issues and heart surgery required in her last year of skating, she felt it time to retire from professional competition. At 26 she had achieved more than most in an entire lifetime.

“I was definitely pretty bummed [about a perceived-to-be premature retirement] and really sad about it, but I was also satisfied, proud of my accomplishments and, ultimately, felt I’d fulfilled that part of my dream.”

After a 4-year stint living in the US, as her then husband took a job with the United States Olympic Committee in Colorado, and Cindy got a college degree in business, she made her way back to Canada. Lucky for Anderson, she settled in Ontario back with her family. And while this has meant she’s not in a hub for national-athlete training work, it has meant that for 15 years as an admissions advisor she’s helped private education, and over 1500 students, improve their game.

How Did We Land Such a Fabulous Team Member?

“It just so happened that my best friend was teaching the Dental Assisting program here, when it was still Medix, and she said, ‘Hey, there’s a position in admissions. I know it’s not really what you had thought you’d do, because it’s not sport related, but it’s still dealing with people. Why don’t you look at it?’ I thought, ‘Why not?’”

And fortunate for our Anderson College team, Cindy is applying those invaluable skills gleaned from being a high-performance, speed skating athlete to her job every day. A keen balance between a solo sport, racing against the clock, and the team dynamics developed in training and travelling with fellow Olympic hopefuls, Cindy brings myriad transferrable skills to the Anderson College mission.

This isn’t what she imagined for her career after competing in professional sport, but where life leads can often surprise and delight us.

“At first, I thought, ‘What am I doing here?’ I didn’t know how this fit into my life. But the more and the longer I did it, the more I realized, ‘Wow, I really love dealing with people, whether it’s on the phone, in person, or on graduation day.’ Whatever form my connection takes with these students, it’s super rewarding and fulfilling. From a selfish standpoint, it’s like a competition, right? I mean, I’m competitive with myself. I don’t worry about what other people do, but I still have that ability to set a goal, to push myself, to challenge myself to new things. It is certainly strange how many similarities there are between my position with Anderson and the athletic career I loved. There’s no doubt this is what has kept me here for this long.”

Challenges Overcome and an Inspiring Stories

Cindy shared with us that it took her a while to wrap her mind around the fact that the admissions role isn’t one of sales, but relationship development. There are quotas to meet to propel the school forward but ultimately it is, above all else, about aligning students with programs and training that empower them to achieve their career, and life, goals.

“The biggest challenge for me was learning ways to guide people, to assist them and to help them understand that whatever obstacles may present themselves, they can often be overcome with the right mentorship and support. I had to find my comfort level and determine the best way to approach, respond to and communicate with prospective students.”

Adept at overcoming challenge and achieving personal goals throughout her career, tackling this position has been no different. Cindy has helped a myriad of students over her 15 years, even amid her own personal trials. She shared with us this incredible, heartwarming, story that moved her immeasurably.

“Back in 2009, I had an inquiry from someone who was interested in the medical lab program. I talked with her, just briefly, and shortly thereafter my mom was diagnosed with cancer. It was an extreme and sudden diagnosis and a very rapid passing for her, a matter of just a few months. So, I took a leave of absence immediately. As soon as I knew I was taking my 12-week leave, I sent out a mass email to the students I’d already connected with, letting them know the circumstances. I expressed how much I’d enjoyed meeting with them; I told them I’d be out of the office for some time but promised to be in touch when I was back. I directed them to a colleague to support them while I was away.

“Well, as it turned out, I had a student who saved that email from 2009. Ten years later, she came back into my office with the email on her phone and showed it to me. I remembered exactly who this student was and had felt an instant connection when we met. She shared that back then the timing hadn’t been right for her to enroll, but ten years later here she was. Then she said, ‘I never forgot you. You made that much of an impact on me.’

“I tried to keep my stuff together and not shed a tear, but I was struck by how amazing this was. She ended up registering for the program and graduated, despite the challenges COVID presented. I felt so touched by this experience. We don’t always think we have an impact on people, but we do, our words do, our actions do, the way we make them feel – it’s all so important. I always say we really do change people’s lives in this work, and it is absolutely what I love about this job!”

Cindy’s Advice for Those Needing Encouragement

“You literally never know what life can bring unless you take that leap of faith.”

Cindy feels, and it is obvious, that she is meant to encourage, even “pump students up,” so they can recognize for themselves their ability to achieve their dreams.

“Students come from different countries, some from war-torn countries, others from broken families, terrible situations. So, I always try to remind them that one of the most important ways in which we ever learn is by failing. We don’t achieve greatness by always winning. When we lose is when we learn the most. I’m not a two-time Olympian because my coach told me every day that I was the best. I wasn’t always the best, right? No matter what, we’re learning and growing, always.

“I tell my Anderson students (and the speed skating students I coach too), ‘Don’t be afraid of failure. Don’t try to shy away from that. Give yourself a chance. Take a leap of faith. No matter what, you’ll surely have learned something from the experience and be better for it.’”

As we wrapped up the interview, we asked Cindy if there was anything else she’d like to add. In lieu of the February purchase of Westervelt by Anderson College, the coming together of two incredible teams to serve even more students, Cindy shared, “I’m just super pumped to be a part of Anderson and think it’s a thrilling time for all of us. I’m so happy with the transition that’s taking place and can’t wait to see how far Anderson can go. Being in this role, with this team, is an opportunity that makes me genuinely excited for the future, for all of us.”

We are too Cindy and we’re thrilled to have your expertise and passion backing our vision and our students!
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