Why Athletes Should Become Entrepreneurs When They Retire

Photo by Fernando Hernandez on Unsplash

Professional athletics is a weird industry in that the moment your career begins, the clock is ticking — there is only so much time your body can hold up before it starts to break down. Record books are filled with the Tom Bradys, LeBron Jameses, and Patrick Marleaus of the world who continue to defy Father Time, but eventually even their careers will come to an end, and it will happen far before people with “normal” jobs need to retire.

Every athlete knows this. Throughout our careers we are constantly reminded to prepare for life after pro sports, but the reality is that when you are in the midst of a career as competitive as athletics, you need to direct all of your energy to the task at hand and making it one more day. I believe athletes should not focus on anything but their sport during their time playing.

The highest paid stars in each sport will have a team of people around them that are paid to invest their money and make smart financial decisions. However, there are still a lot of players who are making good money that don’t have a “team” of advisors setting up their next SPAC or VC fund, and who are not making enough to carry them through their entire lives. Athletes who make it to the professional level of sports are the 1% of the 1%, and to be one of the top pro athletes you have to be 1% of the 1% of the 1%. Almost every pro athlete who has played at the highest level but was not one of the ‘stars’, will eventually be looking at life after sports in the form of some sort of new career. My advice to all of those athletes is to focus entirely on their athletic career while it is happening and when the last buzzer sounds, re-focus on their second career using all their “soft skills” that got them where they are in the first place.

I played 4 years of Major Junior hockey plus another 11 as a pro. After graduating high school, I never attended any post secondary classes as my pro career started at 20 and became my entire focus. I was fortunate to travel the world and make a good living playing hockey, but when I retired I knew I only had a short window of time before I had to start my next career. I was fearful during this transition — I had no idea what the next chapter of my life would be because all I knew was hockey.

A few months into retirement, I started reaching out to friends, ex-teammates, mentors and family members to ask for guidance on what my next career path should be. One piece of great advice that has stayed with me to this day was from a mentor who told me “if you are going to be wrong, be wrong quick”. This hit home as I knew a lot of ex-teammates who spent years in inaction because they were unsure of what to do. Uncertainty can be paralyzing and it is easy to waste time on indecision, which ironically is a decision unto itself. I decided it was better to be wrong quick so I dove headfirst into what I knew — ice hockey.

I started volunteering at the local rink and getting to know a life that wasn’t as a professional athlete. I worked long hours for no pay and loved every minute of it as I started to learn what I wanted for my future, and more importantly, what I didn’t want. In my experience, too many people wonder what they want to do instead of just trying it out. With how connected we are these days it doesn’t take much effort to reach out to individuals or businesses and ask to volunteer or intern. The best part is you cannot lose. Either you are going to come away with a newfound passion to pursue or you are going to learn quickly that you aren’t interested in pursuing that type of career.

Once I got more clarity on what I wanted to pursue, the next practical step was writing a resume. As an athlete we always just had stats — if a team wanted to sign you they checked your stats and called your agent. From there, you might meet with the coach to understand your potential role further and if the financials worked out, you had a new employer. I never needed to type up a resume or interview before this moment. I had never worked a job that wasn’t as a hockey player.

I used a standard resume template from Microsoft Word and searched the internet for examples and advice on how to prepare a resume. I had no traditional business experience in accounting, product development, KPI’s, corporate structure, UI/UX, marketing, design, or anything in that vein. I started panicking as my resume only consisted of a bunch of hockey stats and achievements on teams I played for. Who was going to hire someone that basically just hands them a larger version of their hockey card as a resume? A solutions-oriented person, that was when I started reflecting on the value of intangibles or as Jack Ma calls them “soft skills” that I brought to the table from my experience as a hockey player.

Years of playing athletics had taught me some of the most valuable skills that employers are looking for in the business world. Strengths I had started developing at as young as 5 years old playing sports emerged as being most sought-after qualities the more I interviewed and understood about the hiring process. No matter your education level, most businesses require unique skills that you can only learn on the job. Every company does things a little different and it will take some time for most people to assimilate and understand the nuances. Employers these days know that people can learn almost anything on the internet and basic business skills such as typing, computer literacy, spreadsheets, cloud computing, file sharing and collaborating are easily teachable. What is harder to find are people who possess certain foundational skills that all great teams require.

These are the top soft skills I learned playing sports that have helped me as an entrepreneur:


Very early on in sports you start to understand that there isn’t one player who is bigger than the team, and in order to have sustained success each teammate needs to pull his or her own weight. This applies to both individual and team sports because even though individuals compete by themselves, it takes the team of people around them to help them reach the pinnacle of success. Jocko Winnik uses the term “extreme ownership” — if you take pride in being accountable then people will want to work with you. Simple examples of accountability are punctuality, preparedness, ability to take and apply criticism, and willingness to ask questions if your role or task is unclear to you.


No one can do the work for you. As a human you are not going to feel great every day. Some days will be cold, windy, damp, dark and the work will feel tedious and draining. Getting yourself out of bed and following through on accomplishing tasks is up to you, and you alone. If achieving greatness was easy than everyone would do it, and the reason it is so rewarding to reach difficult goals is because of the passion and effort required. One trick I have found effective to manage my motivation levels is to do a normal level of work on days I feel less than 100% and go as above and beyond as possible on the days I feel great. To apply this in a practical business scenario, on a day you don’t feel great I suggest you work the normal 8 hours but don’t be too hard on yourself beyond that. Then on the days you feel great, you might try to get to work early and stay late so you can push yourself to accomplish 30-40% more. Over the course of the year your productivity levels will increase and it will manifest in you feeling great day-to-day!


Everyone needs teammates. There isn’t a person in the world who has achieved true greatness without a team of supportive people around them. Your level of success will be largely determined by the people you choose to surround yourself with as you build your career. In order to attract the right teammates you have to understand the nuances of working with others and hold up your side of things by being someone people want to work with. It’s okay to keep high standards and hold people accountable — just make sure you also have the self-awareness to check in with your demands so you don’t push too hard and drive good teammates away. Some qualities I have valued most in a good teammate are humility, receptiveness, thoughtfulness, dedication, accountability (see above) and kindness.


Every team, business or organization you will walk into has a hiearchy, but as the saying goes in sports, “no one is bigger than the team”. This all has to do with respect. The moment an individual thinks they are more important than the team the respect is gone. Any new person joining a new team or business should take the time to learn the hierarchy and do so with humility and respect for the people who have been there longer and built the existing foundation. This is not to say the culture or foundation should always stay the same as some businesses and teams need a culture change, but you can always do that with respect. There are so many people involved with running a successful business and everyone should get the same respect as everyone else. Do not ever look down on new employees, interns, or support staff that keep things clean, orderly, and running smoothly. Sometimes people forget what it was like when they were starting out and a simple way to always be grateful is to treat everyone you work with and encounter with respect.



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