On Switching Career Paths Months Before Graduating And Using The Athlete Mindset To Bet On Yourself


You know that moment in a game, where a play breaks down? In basketball that could be a turnover that leads to fastbreak points for the other team. In football it could be an interception that the other team returns for a touchdown. In softball, it could be missing a ground ball that lets up a few runs. In sports, what happens after these situations can determine the outcome of a game.

What happens when your career plan breaks down just before you graduate? How do you respond then? Our interview with Amanda Roosa, Content Marketing Associate at Zendesk and former Wesleyan University softball player, answers these questions.


How did you initially get into softball?

I started playing when I was five years old. There weren’t a lot of sports available where I grew up. At that time, my parents were trialing me through a few sports. Softball and volleyball were my main interests because my dad played baseball in college and I grew up watching volleyball.

Why did you choose Wesleyan and what were your initial goals as a student-athlete?

I went to Wesleyan because it was Division III and afforded me more focus on things outside athletics. I considered playing for the Taiwan National Team, but in terms of playing beyond Wesleyan, there isn’t a career for women in softball unless you try out for the Olympics. Overall, I was hoping for a combination of community and athletics and for athletics to be a supplement to my academics.

Athletically, I wanted to win the Little Three against Amherst and Williams, which we did my freshman year. Winning a NESCAC Championship was also something I wanted. We went to the NESCAC tournament my freshman year, but did not win. I also wanted to earn the right to be captain.

As a two-time captain, what were the biggest challenges you faced as a leader?

I went abroad my junior year to study in Australia. Coming back from being abroad was challenging because I had to come in after the first semester and figure out how to cultivate camaraderie with the team. It was a lesson in assuming authority without ever having been a presence. I was coming in from being away half the year and I had to be a co-captain with a senior. It was difficult because I wanted to be a leader, but I didn’t want to step on any toes coming in at that point. It was a tough middle ground to find my place in.

Being a captain also taught me how to take more ownership for my actions. For example, being mindful of how I reacted during game play was important. Also, not getting down in tough stretches, but not letting things fly either. Remaining austere, but staying energetic and up for the rest of the team is how I would summarize it. It’s a difficult attribute to learn, but one that’s important in leading a team.  

Can you talk about your academic journey?

Originally, I was working towards pre-med, but I decided not to take the MCATs in the last half of senior year. It created a lot of panic within me. At that point, I used the athlete mindset to figure out what I really wanted to do. I figured if I simply put in the work, I would find work that sparked more joy and curiosity in me. I set aside time to find a job that allowed me to write, in a city I wanted to live in (San Francisco), and I essentially dedicated the same amount of time I would spend in a class to my career. I considered it my fifth class.

Why did you decide against med school at that point in undergrad?

Med school and creative writing came into conflict with each other my senior year. In my last semester, two classes I needed were at the same time. I needed physics as my last pre-med class, but it coincided with an Advanced Creative Writing class I had been trying to get into for two years. I had finally gotten into the class and taking this class would fulfill the requirements of me double majoring in Creative Writing. I had to make a difficult decision. At that point I realized I didn’t want to go to med school, so I spent my last semester chasing jobs in writing.

Where did your interest in writing come from?

I have always written since I could pick up a pen and write letters. I started reading when I was four. It has been a big part of how I’ve bonded with my family. When I went to Wesleyan, I didn’t know I wanted to be involved in writing to the extent that it was going to be my career. I spent my time in college being concerned with stability and a path that was already carved out for me to follow. Writing, that’s less stable of a career, but I allowed myself the opportunity to take creative writing and thankfully, Wesleyan provided me the freedom to do that. I didn’t even put one foot into the idea of entertaining it as a career until my senior year.

How do you handle a last-minute change in career?

I had these planning sessions with myself. I knew I enjoyed writing and I knew I enjoyed having a craft to ground myself in. Based on that, I created spreadsheets on what would make me happy, like where I wanted to live and which cities would allow me to be outside and near an ocean. I was pretty intent on going to California, so from there I created a spreadsheet of companies I liked in California. I wanted a company culture I could see myself in. I saw a lot of people throwing applications around and seeing what stuck without thinking about what culture and what environment they wanted to be in.

What pushed you to bet on yourself?

I remember we were on the bus coming back from a game and Zendesk called to offer me an internship. It was difficult remain calm amidst all the noise on the bus. It was the only opportunity I had to go to California at the time. I was offered a job at CAA in New York but their pay for a full-time job was less than the internship at Zendesk and I had the opportunity to write for Zendesk’s second brand and online magazine. Even though Zendesk only promised me three months, I knew I had to make the move. I moved to San Francisco because I believed in myself to work hard enough for Zendesk to want to keep me on board longer than three months. And I’ve been here since.

What advice would you give to the younger version of yourself that was figuring out what she wanted in school?

Pay attention earlier on to what you like and what you don’t like. It’s hard to know when you’re in school. I would have told myself to explore more within the writing world even if that meant writing for free.

Now that you’re at Zendesk, are there any similarities to your life as an athlete?

Your personality matters in the business world. Having strong convictions, confidence, and a hard work ethic are crucial to being successful. These are skills you just have to practice everyday. I used to be more introverted but I overcome that thanks to being an athlete and what it taught me about social dynamics and putting in hard work.

What advice would you give to student-athletes preparing for the transition?

After being an athlete, the muscle memory of being a hard worker is still there. That’s a very important thing to take with you. What’s harder is knowing how and where to apply it.


Amanda graduated from Wesleyan University in 2016 and now lives in San Francisco, where she works for Zendesk. Check out some of her personal work and writing on how technology and humanity converge.