From Tennis to Tech: One Woman’s Journey to Startups

Phoebe DiLeoIn today’s fast moving society, more and more young professionals are switching between different companies, jobs and even industries multiple times. The assumption that a young professional will stay in one role for less than three years is no longer taboo. In fact, it is expected. However, following this kind of career path is easier for some professionals than others. It is not hard to make the transition from a sales role to a marketing role, or from a job in graphic design to a job in web design. But take, for example, a former-professional tennis player trying to pursue a career in sales. Sounds impossible? Well, Phoebe DiLeo is proof that it is not.

Phoebe spent four years of her life touring the United States and the world as a professional tennis player. Following her tennis career, Phoebe received a degree in Biology before realising it was time to make a change, and she began to look into new career opportunities. These searches lead her to the Startup Institute, where she is currently a student in the Sales and Account Management track. There, she is learning a combination of hard and soft skills, as well as how to leverage her past professional sports experience to succeed in a startup business. I sat down with Phoebe to get her insights on life as a professional athlete turned businesswoman.

Amelia: So tell me a bit about what motivated you to start playing tennis professionally?

Phoebe: Throughout my childhood my mom taught tennis to little kids and I would often go with her to help out with the lessons. Gradually I started to play tennis myself, and half way through high school I realized that I was a pretty decent player, good enough to compete professionally. I always had a dream to become a professional athlete, so that’s really what motivated me; I was pursuing my dream at the time. My parents had always been supportive of my enthusiasm for tennis and they encouraged me to forgo the typical college route in pursuit of my dream. I knew that college would always be an option in the future but education was still very important to me, so while I competed professionally, I enrolled myself in online community college classes to keep my brain active.

Amelia: And for how long were you a professional tennis player?

Phoebe: I played tennis professionally for four years. I started travelling internationally for tennis after my high school graduation. I competed on the international circuit in Australia, Brazil, Canada, Ecuador, England, France, Mexico, South Africa, and South Korea.

Amelia: Wow, a long time! And so many places! What was it that made you stop?

Phoebe: I got injured. It was a back injury, which required surgery. Compounded with that, I realized that my body was deteriorating, having negative impacts on my health. It had just come to a point where I knew I’d given tennis my all and had done everything I possibly could to be successful and with this, I have no regrets. After my injury, I was a bit down and I couldn’t imagine picking up a racquet for a while. But, when it came to choosing a college to attend, my motives for playing took a different direction. A small private school in Florida was prepared to offer me a full scholarship if I was willing to play on their tennis team. It was really too good of an opportunity to pass up. I’ve always been a very goal oriented person, so actually having a goal in tennis again was enough to make me want to give it a second try. The goal now was not to become the number one professional tennis player in the world; it was to excel in collegiate tennis (whilst earning a degree that would allow me to succeed in the professional world).
Amelia: So now you’re a Sales student at the Startup Institute. Professional tennis and sales are very different! How are you finding the transition?

Phoebe: I admit that I was worried at first. There I was, with no tangible business experience and a degree in biology, wanting to start a career in sales. But it has actually been a lot easier than I thought! I never realized how the skills I gained competing and travelling were actually translatable to the business world. Throughout my tennis career, I had actually done a lot of things related to business; I just needed something like the Startup Institute to point it out to me. Essentially, my tennis career was like a business. I had to research locations to which I was travelling, arrange flights, make connections with other players to build up a network, communicate with people from different cultures, build relationships with adversaries who I was competing against – ultimately, I was selling myself. I think the most important skill I learned was how to pick myself up after a failure and persevere to achieve goals. I learned that failure is inevitable, but it is your ability to recover from those failures that makes you successful. As an example, I travelled all the way to Australia to play a tournament – ended up losing in the first round– and had to fly straight back home. I felt like a complete failure; I had spent so much time, energy and money for what felt like nothing. However, over time I realised it wasn’t a waste, it was a learning experience. I still kept playing, and it made me stronger.

Amelia: Such an inspiring recovery. How are you finding ways to apply the skills you’ve gained from playing a competitive sport in order to succeed in sales?

Phoebe: A lot of things really do carry over from the athletic world into the business world. Having a competitive mindset helps with sales as you’ve got to be hitting targets all the time. Additionally, when you’re playing a competitive sport you get used to ambiguity, so I’m pretty comfortable working on things that don’t always have a defined outcome; which is important to realize when working in sales. When I was playing college tennis, I learned the importance of being a team player and then when stepping in a team captain, I learned the importance of being a team leader. I also gained time management skills, juggling tennis, my studies, as well as tutoring for a part time income. Amongst other things, I had learned how to be resourceful and communicate my needs to others to achieve the best outcome and how to persevere in high stress situations – these are just a few examples of the skills that transfer over.

Amelia: It’s no doubt there are many young women in the same position as you- either former professional or collegiate athletes, or even other career changers who are struggling to find how their current skills apply to a new job. What is your advice to them?

Phoebe: Have a clear understanding of your past and really develop and understand your personal story. I honestly believe that no matter what your background, there is a way to relate it to your future business goals. As a professional athlete or career changer, you will undoubtedly have a number of relevant skills in your repertoire. All you have to do is recognise what those skills are and be able to clearly demonstrate them to potential employers. With the right mindset you can achieve any goal.


Photo on 3-10-2014 at 5.29 pm #2 copyAmelia is an adventurous 20-something Australian who wants to share her passion for writing and interpersonal connection with the world. She graduated from Macquarie University (Sydney, Australia) in February 2014 with a Bachelor of Commerce majoring in Marketing and International Business. Since then, she has moved to Boston where she is currently a student at Startup Institute and hopes to begin her career as a content marketer.
Read more about and from the author: Amelia’s WiLab Profile