What Softball Taught Me About Tackling Debt (and other scary challenges) / by Jennifer Chan


For the past two summers, I've played recreational softball in a slo pitch league. Since my first game ("please just make me catcher"), I have steadily progressed and can now even confidently state my favourite positions ("3rd Base and S.S, please"). My learning curve with softball reminds me a lot of my debt repayment journey. Here are some of the lessons I learned from softball, which I believe is useful for those tackling their financial goals.

You’re Always Embarrassed When You First Start

When I first signed up to play in Summer 2016, I was nervous. I hadn’t played since my last year in high school. I graduated high school in 2007.  Not to mention, I was signing up with some friends from law school, who would be the first to witness my entry-level skills. Also, aside from knowing that the pitcher would be throwing underhand and that I had to hit the ball and run to the various bases, I forgot the rest of the rules of the game. I was embarrassed at how much I didn’t know and I was worried that I was going to let my team down.

It’s Okay, and Encouraged, to Ask Questions

In the beginning, I engaged in some good ol’ self-deprecating humour to make everyone on my team extremely aware that I hadn’t played softball in 9 years. But, I quickly grew tired of using that as an excuse for my lack of skills. I started asking questions. Basic questions. Most notably, “Where do I stand if I’m rover?” and “Why do I have to tag that player even when they’re clearly running towards this base?” I asked a lot of questions. Repeatedly too, because I often forgot the following week. I was blessed with patient teammates.

Consistency Is Key

In the 2016 season, I embarrassingly did not have a great attendance record. This was partly because early games were difficult to make right after work. Admittedly though, there were times where I was just not committed enough to go because I resigned myself to the fact that I just wasn't good.

When I signed up for softball this summer, I was much more committed. I proudly attended all games except when it conflicted with one pre-scheduled vacation (it was my birthday) and a few work commitments (i.e. I had a hearing or mediation the following day). For a season that spans from May - September, that’s pretty good. While it helped that I changed jobs that enabled me to leave work earlier, I also was much more determined to step up my game. I quickly learned that just by showing up consistently is half the battle. Whether I realized it or not, every single week I was slow improving through constant practice.

Seek Advice From Those Who Are More Experienced

This season I ate a lot of humble pie and reached out to my more seasoned teammates. My biggest problem was batting. I didn’t know if I was standing too close or too far from the home plate and if I was following-through on my swing. I asked a teammate if she could pitch to myself and a few other teammates, and arranged an informal practice session one weekend. After seeing my swing, she suggested that my hands remain firmly together when holding the bat. And guess what? That was probably the best piece of advice that changed my batting performance. Unfortunately that practice session was towards the end of the season, so while my batting improved I only had a few games to test it out. Moral of the story though, don’t be afraid to reach out to people who excel in an area you're struggling with. Chances are they won’t hesitate to help you out.

You’ll Start to Discover Your Competitive Side

As the 2017 season progressed, I found myself getting increasingly competitive. Not necessarily against the other team, but against myself. I wanted to be faster in the field and more accurate at bat. Now, progress isn’t linear. I found myself performing well one week, and then perform terribly the week after. But I remember that a fellow teammate told me at the end of the season that she thought I drastically improved since the beginning of the summer, which made me extremely happy to hear. 

I quickly realized that by playing softball in this recreational league, it was not only a healthy outlet for my stress, but challenged me to work on aspects of myself that I once considered to be weaknesses.

You’ll Walk Away With More Confidence

Finishing this season, I not only gained new friends but also gained more confidence. Not necessarily in my softball skills, but in my ability to tackle situations that were initially very intimidating. I never loved organized sports. I was always someone who enjoyed working out alone, usually in the form of running. For the longest time, the idea of strangers watching me perform in any athletic capacity felt like a personal hell. But conquering that fear, while simultaneously enjoying the journey, feels like a personal win for me. I feel more self-assured and willing to take the initiative with other challenges in my life.

Challenge Yourself

Whether it’s with your finances or some other facet of your life, I encourage you to intentionally face an obstacle you’ve been deliberately avoiding. In the beginning of my debt repayment journey, I was so completely overwhelmed when I calculated everything I owed. At the time, I didn't have a permanent job, let alone a game plan. Completely in over my head, I just decided that I was going to figure it out as I went along. As I learned, don't let the fear of sucking hold you back from starting. Feel the fear and do it anyways.

Challenging yourself tests your tenacity and dedication. You'll surprise yourself with just how much grit lies inside you. 

What scares you? What challenges would you like to conquer?