Fueling the Competitive Fire in All Aspects of Life

Today, in this double feature I speak with 2 men who had to answer that question themselves. Both ended up as Country Financial Representatives, but each took different paths to get there. Let’s start by taking a look at Perry May.

Perry May is a business leader who is going into his 26th year with Country Financial. He specializes in insurance and investment planning. A former collegiate golfer, Perry graduated from Illinois State with a degree in economics in 1993. He talks more about jumping into the real world below.

*This interview has been lightly edited for clarity

You graduated from college and started in the golf world.  Tell me more about that experience and why you left the industry.

I started in the golf industry out of college as it was a dream of mine to become a PGA professional. I realized a couple of years in that the demand of the job and the desire to start a family, was too much to have both. The financial industry was an opportunity presented to me and it allowed me to create my own work schedule.

Was Country Financial a lateral or vertical move for your career?  What lessons from the golf course did you take with you?

I left my position in golf because of the desire to raise a family. At the time, I felt it was a vertical move on the career ladder – I just didn’t know if it was up or down yet. I felt confident I could succeed due to my work ethic, integrity, and ability to network with people. This doesn’t mean I lost my love of the game of golf. I still give lessons to this day as a way to keep contacts for my business and because I truly enjoy the teaching aspect of being a golf pro.

You’ve trained former student-athletes to be talented agents.  What traits do they all have that make them successful?

I’ve had several student-athletes come through my door. They are all self-motivated to learn, work hard, and take advantage of their opportunities – something that has clearly transferred over from their days as an athlete. Even today, I still have that competitive edge to be the best I can be at my office every day like I am back out on the golf course playing 18.

You bet on yourself and made a huge career change.  Any advice to current student-athletes that are afraid of what comes next after college?

I worked on the construction of the golf course (Senica’s Oak Ridge) for 2 years and then ran the golf course and finished my PGA program to be certified. It gave me the opportunity to try other adventures in the working world and helped me realize that I had more aspirations to better myself and allow me to earn a greater income while also giving me flexibility for family and life. My advice to them is this – I found a successful career by trying new things and recognizing what worked and what didn’t. I work in a completely different industry than golf and still give lessons and give back to younger golfers. Never lose your passion for whatever sport you play. It will keep the fire burning and the desire to better yourself every day will always be there.


Alec Schwab is another Country Financial Representative and one of Perry May’s understudies who was able to find success outside of athletics. Alec attended Illinois Valley Community College and then William Penn University. He played collegiate basketball all 4 years and graduated with a degree in Business Administration in 2015. He spoke to me about his journey.

*This interview has been lightly edited for clarity

Were you ever nervous about your post-basketball life?

Yes, I was nervous. My life pretty much revolved around sports, specifically basketball, so when that was over with, I had that feeling of “What Now?” I graduated with a business management degree, but asked myself what was I going to do with it? As a competitive person, I needed to find something that gave me the excitement and competition that basketball gave me. I also needed to find work that allowed me to have some financial freedom to do what I want to do.

Did you always know you wanted to end up in the business field?  Did anyone influence you?

I did not start on the path of being in the business field. In my first year at IVCC, I took a curriculum aiming towards the athletic training of the physical therapist field. I thought those fields would keep me close to the game of basketball. Turns out, I wasn’t the greatest at those classes and after some conversations with the guidance counselors and my parents, I decided to start studies in business and economics. Fortunately, I did well with those classes and enjoyed them through graduation at IVCC and William Penn.

Originally, you worked in the business development field.  Talk about getting that job and what that field entailed.

After basketball was over, I needed something to replace the enjoyment I got out of playing. So, I decided to take a dive into the business development field as a sales rep for an HR Communications company in Chicago. In my head, what better place to go to than the fast-paced life of the city. I worked for a company called Jellyvision for 2.5 years as a sales rep, pitching products and solutions to companies all over the country.  We had commissions built into our contracts for how well we did and had quotas to hit every month, so that filled the competitiveness of basketball not being part of my life anymore. I wanted to strive to be the best I could be at this job and to have my peers see that I can be great at this job too.

You made a move from business development to Country Financial.  Was it a lateral move or a vertical move?

In 2018, I decided to move back to the area I grew up in and pursue a job as a Country Financial agent. This was a vertical move and into a somewhat different field.  Part of the move was to come back home and to find something that I could make a career out of. As a financial representative, I am a business owner. I must make decisions every day about how I’m going to grow my practice and retain the clients that I have.

I’m sure you questioned yourself about moving jobs and the uncertainty that comes with that.  What lessons from the playing court carried over to calm you down during that time?

Team building, relationships, and accountability in sports make you check yourself on who you are as a person.  This translates right over to the working world. In sports, you learn how to control your emotions in stressful situations.  You learn how to build relationships with people who you’ve never met before and build trust with them as the season goes on.  This isn’t too different from running a business. You’re going to have days where everything seems to go wrong, and how you react to those situations is how well your business is going to succeed, just like in a basketball game.

Any advice to current student-athletes who have no ideas what they want to do after college?

Don’t be afraid to step out of your comfort zone and try something that’s going to challenge you.  As an athlete, that’s what coaches try to get out of us. Find a hobby or passion that can replace what you got out of playing your specific sport. Ask questions, and talk with people that are in a field you may be interested in.  You’ll never get a ‘no’ from someone if you show interest in what they do. Surround yourself with people that believe in you, no matter what you may be doing or going through. Leaning on people for support and help is not a bad thing. Most importantly, believe in yourself. If you believe you can do it, you will.

*Editor’s Note – Alec continues to give back to his sport as a varsity assistant at his alma matter – Saint Bede Academy in Peru, Illinois.


About the Author

Kane Clendenen is a student intern for Game Plan.  Currently, he is a junior at Purdue University Northwest majoring in Business Analytics and Finance while also balancing time as a member of the PNW Baseball team.  His future plans include attending Law School and pursuing a J.D./M.B.A. dual degree.

About Game PlanGame Plan’s comprehensive software platform integrates mobile-first eLearning as well as virtual mentorship and career services, uniquely designed for athletic organizations. Game Plan works with 350+ athletic departments and organizations with over 240,000 courses completed yearly. Our eLearning courses provide student-athletes ultimate access and flexibility while equipping both athletics departments and the conference office management tools and insight to ensure outstanding experiences and outcomes. To learn more about Game Plan, please visit wearegameplan.com.