Years ago, when I was applying to universities, Western University sent me a letter indicating I was on their waiting list to get into their teaching program. I had already received acceptances from the other universities I applied for, so I didn’t check the box to indicate I’d like to be kept on their waiting list and send the letter back.

What would have cost me five seconds of my time and a postage stamp was probably the biggest mistake in my life. And yes, if you read my blog from last week, this is one of my biggest regrets.

I would have loved to be a teacher. I once had a psychic tell me they saw me teaching small groups of people and to this day, when I get to run training sessions at work, I absolutely love it. Before I started my career, I seriously thought of going to China or Japan to teach English. Regret #2.

Instead, I wound up in insurance.

On career days at school, when they ask little Jimmy or Susie what they want to be when they grow up, nobody ever says “I want to work in insurance”. All of my friends in our industry say the same thing, we never planned to work for an insurance company.

But life has its own plans, and sometimes following fate’s footsteps isn’t such a bad thing.  

This has hit home for me several times over the years and especially this year during COVID.

I went to school for journalism, and even before COVID, most of my friends who went into mainstream media were forced to make career shifts as the industry became decimated and reporters and journalists were being laid off.

This year, I have been able to continue to work, and safely from my own home, while others in industries and professions that would have been thought imaginable are struggling.

Did I sell out? Maybe. Do I wish I had checked that box? Most definitely.

But I’ve been grateful to have a rewarding career and work with amazing, talented people who care about each other and the work.

Who knows, I may still teach some day. I believe it’s never too late to take on new challenges.

One thing I promise you, next time I’ll check all the boxes.