Triathlon Guide Caroline Gaynor knows the value of hard work

Caroline, at right, crossing the finish line of a triathlon as a guide for visually impaired athletes.

Like most people, Caroline Gaynor has a day job, working as a regional director for a large asset manager. Outside of her job, though, Caroline works hard at something that isn't a job but is more than a hobby: guiding visually-impaired triathletes. A triathlete since her college years, Caroline got into guiding by chance in 2008 and was hooked. Throughout several years of professional ups and downs, "guiding was the one constant thing in my life when things weren’t going super well professionally," and in fact, she found her current job with a company she loves through someone she met at a bike race! 

Caroline's day job is in finance as a regional director for a large asset manager.

FAST FACTS ABOUT Caroline

Where she’s from: Evanston, Illinois
Grew up with: mother, father, siblings
Education: Bachelor’s degree in history from Columbia University
Where she lives now: Charlotte, North Carolina
Now she’s: a regional director at a large asset manager and a guide for visually impaired triathletes

Tell us about yourself growing up!
I wasn’t a natural athlete. I played a lot of different sports but I wasn’t really good at very many of them. I really wanted to have a lot of friends but it took me a while to really understand how to relate to people. I definitely wasn’t very cool at least in my elementary and middle school years. I always really liked school and I was pretty good at it. Doing well in school was never really an issue for me. I liked math a lot when I was younger, and I really enjoyed English. I went to a math camp one summer at Northwestern but that was mostly so I could skip a class.
I did always like to volunteer. I remember really enjoying doing 5ks and I loved the fact that the many of the races would support specific charities. I remember always having an interest in that. I also used to tutor people in high school.

Approval and positive reinforcement are great for everyone, but when you get a compliment that you really earned that’s so much more gratifying than just somebody always telling you how great you are.

Were sports a big part of your life growing up?
Athletics were something that were always very highly regarded in my household. My dad won the World Championships in rowing when he was in his 20s, so I grew up watching him continue to compete when we were in Philadelphia. I remember when I was about to enter high school and I planned to join the cross-country team that fall. I told my dad, “Hey I think I’m in shape!” We went for a run together, and he said, “You’re not in shape yet.” I could barely run a half mile! I needed to be more aware of what I was getting into.
His comment wasn’t meant to be negative, but it was very honest. Honest and direct feedback is something I’ve always appreciated. Approval and positive reinforcement are great for everyone, but when you get a compliment that you really earned that’s so much more gratifying than just somebody always telling you how great you are. When my dad ultimately did tell me that I was in shape, I knew he meant it.
I also played water polo in high school. I can be pretty aggressive, so water polo fit my personality well. Water polo is helpful for guiding because [guiding] is a contact sport in a lot of ways, especially when you’re tied to another person. Water polo teaches you how to be very close to people who are swimming aggressively and I don’t think there’s another sport that really does that.

Did you continue training independently?
When it came to running, I learned pretty early on that there were a lot of girls who were just more talented than I was. They could show up on the first day of cross country and run paces that I had to work really hard to hit.  When I was a freshman, I was able to run with the top seven girls in the freshman-sophomore team.
But when I was a sophomore, I was in the middle of the JV pack. It didn’t feel all that fun to me to finish in the middle of the pack. I remember saying after my sophomore year that I was going to get fast enough to be able to train with the varsity team. If I couldn’t at least train with them I was going to quit. I ran every day during the summer between sophomore and junior year of high school. I ended up not only being able to train with the team but making the top seven group of girls racing in all of the varsity meets. Most of the other girls on the team had been on the team since they were freshman and were really talented, and I had to work my butt off to get there.

You went to Columbia University for college. How did you decide to go there?
In high school, I really believed that I had to go to an Ivy League school. I want to be very clear, in case anyone reading this has a similar delusion: you don’t have to go to an Ivy League school to be successful. I, unfortunately, thought that the world would end if I didn’t get into a highly competitive school. Thankfully, through a combination of luck and hard work, I got into my top choice. I wanted to go to Columbia because number one, I wanted to go to an Ivy League school. Number two, my brother was there, and I wanted to be near him. I was sort of recruited to row there, mainly because my brother was already on the team and they knew about my dad’s history.
I had a little bit of experience rowing. I spent one winter with a small club team in Chicago. We didn’t have a team in high school, but I spent a few weeks rowing at a camp in Vermont, so I knew that I could move a boat. Rowing is the only division one sport you can walk onto. I was fixated on becoming a D1 oarswoman. Division 1 sports are your whole life, though, in college, so you have to be committed. I did stop at the end of my junior year, but that was because I didn’t think the coach had her athletes’ best interest at heart. The minute I quit, I signed up for an Ironman so that nobody would ever think that I had quit just so I could go party.

Caroline guiding during the swimming portion of a triathlon. She says that playing high school water polo made her comfortable with swimming close to other people and being aggressive in the water- important skills when she's tethered to another person and keeping her on course.

Caroline guiding during the swimming portion of a triathlon. She says that playing high school water polo made her comfortable with swimming close to other people and being aggressive in the water- important skills when she's tethered to another person and keeping her on course.

Why did you decide to do a triathlon?
I had actually already done a bunch. I did my first triathlon when I was 17. I even wrote my college entrance essay on what it was like to do my first-ever triathlon. I would compete during the summer as cross training. Ironman had always been on my bucket list, but quitting crew gave me the motivation to do it. I ran my first and only marathon when I was a senior in high school, so I figured I’d do my first Ironman when I was a senior in college.
I didn’t break any records, but I raised money for a charity I had been volunteering for. I wrote letters and mailed them to potential donors. I remember hand writing all of the thank you notes for people who had donated. I raised around $5,000, which was a lot of money, at the time. I liked the idea of doing a race for a purpose that was greater than myself. There’s an article from my senior year of college in which I’m quoted as saying that triathlons are a really selfish sport. I stand by that. Training for and competing in triathlons is a worthwhile endeavor, but it definitely takes time away from the people you love. It can be a very solitary sport. Nowadays, there are a lot of training groups and teams, so you can make triathlon a more social sport, but back then I didn’t know anyone that did them.

How did you get into finance after college?
My decision process when it came to choosing a career path wasn’t very well thought out. It was like, “Okay, do I want to work for a nonprofit or do I want to work in a job where I can make enough money to donate to nonprofits?” That was my logic. I went into finance because I was a competitive person. I knew that smart, motivated people went into finance. That’s the main reason I went into it. I was like all right, I should be challenged in finance. That, and I didn’t know what other jobs existed!
I worked for a large asset management firm for a couple of years. Then the financial crisis hit. I basically did that millennial thing where you have way too many jobs over a short period of time. If you look at my resume, sometimes I feel like it looks like I just couldn’t commit to anything. There are periods of time where I’m not working, or years where I worked for a few months at a couple of companies. I never found a “home,” while I was living in New York. Feeling like I couldn’t fit in anywhere had a huge impact on my self-esteem. I began to question myself.

What did you do when you left New York?
In 2013, I went to Austin, Texas to volunteer at a triathlon camp for veterans through an organization called Team Red, White & Blue. I was so enamored with Austin, I decided, “This place is great so I’m just going to move.” After I moved, I still felt really lost. After trying a couple of contract roles, I ended up working at a bike shop, so that I could take some time to figure out what I wanted to do.
I really enjoyed working at the bike shop and I met some wonderful people, but I realized that I wanted something different out of a career. In an interesting turn of events, I met a woman at a bike race who learned about my background in finance. We became friends and she encouraged me to apply for a job at [my current] company. Initially, I was reluctant to re-enter the finance world because my confidence was pretty shattered at that point. I wasn’t sure if I could cut it, and I wasn’t sure that any company in that industry shared my values.  But the more I learned about the firm, the more intrigued I was. I heard the same message from employees at every level of the firm.  The message was this: “We want to create good investment solutions that actually help people.” The idea that this firm really wanted to help people have a good investment experienced resonated with me. I realized that in order for me to be happy at a firm, there had to be a greater purpose. I’m so grateful that I gathered up the courage to apply for that job.

I need to work in a place where everyone’s ideas are heard and respected.

What do you think makes a good work environment for you?
I need to work in a place where everyone’s ideas are heard and respected. I was hired as a 30-year-old in basically an entry-level position. Many of my peers had just graduated from college. I’m very lucky because I have moved up very quickly. Over the course of two and a half years, I went from associate to regional director, which was really exciting and not something I expected. I wouldn’t have done well if I hadn’t been able to come in and say, “It doesn’t matter that I’m nine years older than the other people at my level.” And it really didn’t matter how old I was. The caliber of people at my company is unbelievably high. I felt like I could learn from every one of my colleagues. I was also given a chance to contribute, which helped me feel invested in the role. I work with incredibly smart people at all levels and it’s a very team-oriented environment. It’s still a competitive environment, but it’s more collaborative than anything. We all want to do well for the good of the team and the good of the client. Everyone is shooting for the same thing.
I like that this firm helps me feel that I can be a whole person and be fully supported with what I do in my free time, which is guiding blind athletes in triathlons. In other places, people thought it was cool but I really had to prove that it didn’t detract from my performance. I don’t think it does. When sports are going well, work is going well. My workplace has really embraced it.

As a guide, Caroline takes the front seat during the biking portion of a triathlon. (Photo credit: Scott Flathouse)

As a guide, Caroline takes the front seat during the biking portion of a triathlon. (Photo credit: Scott Flathouse)

How did you start guiding visually impaired triathletes?
When I began guiding in 2008, I didn’t know many people who knew what guiding was, let alone people that had actually guided. I pretty much fell into guiding. I remember getting a call from my friend, Matt Miller, who ran a nonprofit that connected blind athletes and guides. This was the week before the New York City Triathlon in 2008. He said, “I have this girl coming into New York City and she’s going to do this race. She’s visually impaired and this will be her first triathlon. But, she doesn’t have a guide yet. Do you know anyone that can race with her?” And I was like, “Well, I’m already signed up. I’ll try.” And after that first race, I was pretty much hooked.

I like the idea of helping somebody else have the best race that they can have.

What kind of relationships do you have with the athletes you guide?
There’s no faster way to get to know someone than to be tied to them for many hours during an athletic event! The majority of the people I’ve raced with are still good friends of mine. Sometimes, my relationship with an athlete will morph into more of a friendship and less of a guiding relationship, but I often continue to race with athletes for years. I like the idea of helping somebody else have the best race that they can have. It feels natural to put someone else’s needs ahead of my own. It’s really fun and it’s also uniquely challenging. Every person is different and every single race is different so what works for one person doesn’t work for another. I like the challenge of figuring out the best way to work with each person I guide.

How do you match your athletic abilities with the people you guide?
Ideally, if you’re going to guide someone, you should be faster than they are when you’re having your worst athletic performance day and they’re having their best day. That’s what you should shoot for. Of course, not always possible, but if you’re trying to be really competitive that’s what the goal would be. Certainly, the faster an athlete is, the harder that is to find somebody.

How many races do you usually do in a year?
It depends. The long races obviously take more out of you so the most full Ironmans I’ve guided in one year is two. I probably race five to ten times a year as a guide, any distance between sprint and other events for para-athletes when I can. I race on my own a little bit, mostly bike racing.
The events that I guide are rarely local. I always like to emphasize the fact that I have a day job, because this sport is not cheap. I use my vacation days very strategically. Having a partner who is so incredibly supportive iskey. My husband actually guides now, too, so that’s really cool.

There’s no better feeling than somebody saying, “Hey, I have this athletic goal. I’d like to race with you. Can you help me accomplish this?” It’s rewarding in every single way and it’s so much fun.

What keeps you interested in guiding?
Everything, really. First of all, the relationships that I’ve formed through this sport mean the world to me. I’ve met, some of the most amazing people on the planet. I don’t really consider it to be volunteering because I get as much out of guiding as the athletes that I race with do. There’s no better feeling than somebody saying, “Hey, I have this athletic goal. I’d like to race with you. Can you help me accomplish this?” It’s rewarding in every single way and it’s so much fun. This year I’m racing with some people I didn’t know very well and I’m getting to know them better. Sometimes it’ll be people I’ve raced with for a long time and honestly, it’s almost like, “Oh, my friend wants to hang out and go do this race,” so we go do it. You become really close with people when you’re physically tied to them for hours on end.

Guiding helped me feel like I had a purpose. Being part of the universe of people who are using sports to better their own lives and the lives of others really kept me going.

Caroline (left) says that guiding has been a constant through life's ups and downs. (Photo credit: Paparazzi on the Run)

Caroline (left) says that guiding has been a constant through life's ups and downs.

(Photo credit: Paparazzi on the Run)

What advice would you give someone who wants to be a serious athlete as an adult, when that isn’t your job?
It’ll open more doors than it closes. If you have something that you’re passionate about, people will be drawn to that in you. I found the job that I have right now because I met a woman at a bike race. There are many benefits to being athletic. Whatever on Earth that it is that you do, find the community of people that share your passion. You will make connections that you just didn’t even know existed.
Guiding was the one constant thing in my life when things weren’t going super well professionally. When I didn’t know what I was going to do with my career, I knew that I could focus on guiding. Guiding helped me feel like I had a purpose. Being part of the universe of people who are using sports to better their own lives and the lives of others really kept me going.
It’s helpful to have something outside of your job that sort of rounds you out as a person. I think of it like a buffer. You can’t tie your identity to just one thing, because if you have a set back it can be devastating. You really have to make sure that you know what matters about yourself and it’s important to have things that keep you excited and motivated and passionate, in a couple different areas, if you can.

Failures are what help you become a whole person and help you to relate to people better and on a deeper level.

 What advice would you give for weathering professional setbacks?
When I graduated from college assumed, that because I had been successful, I would continue being successful, and that’s just not how my life played out. Failures are what help you become a whole person and help you to relate to people better and on a deeper level. The struggles that you have are maybe more important than the successes that you have, whether it feels like it or not at the time.
It’s great to be super academically oriented but that does not mean that it’s going to be easy for you when you enter the work force. Understanding your strengths, learning about yourself and being willing to accept feedback and constructive criticism and always being humble are things that will serve you better than anything else. It’s good to work on the things that you’re not great at but it’s okay to not be the best at everything.
I do hope somebody will read this and realize that no matter how many obstacles or setbacks you’ve had, if you keep trying, you can end up in a good place.  Take the time to figure out what you need in a work environment in order to be happy and productive I’ve been at the company that I’m with now for three years and I have never been happier, ever. But if you’d asked me this four years ago? I probably would have just broken down crying because I wouldn’t have known what to say. So much can change overnight. Things change really fast in both good and bad ways.  Hard times never last forever. To anyone who is going through a rough patch, I promise, you’re stronger than you think you are!

This interview has been edited and condensed.

Check out books Caroline loves!