Beyond Career Monogamy

A Mosaic of Small Wins

“You’ve been successful at everything you’ve ever done,” my coach stated with such declaration my brain needed a few beats to process it. 

Yet all I could see was failure. “But I've had 7 careers. I’ve failed at all of them.”

“Yes, but you moved forward every single time.”

This moment changed everything for me. For fifteen years, I was my harshest critic, constantly surfacing my supposed failures. But I couldn’t unsee what I now saw. 

It reminds me of when I first put on glasses as a child. Up until fourth grade, I thought the world was made up of globs of colour. Trees had organic shapes of muted green. When I put my glasses on for the first time and stepped outside, the tree above me looked as if someone took a cloth and polished it to a high sheen. Each individual leaf glistened, distinct and saturated with its own hue. 

I wasn’t a failure because I didn’t build a career as a financial advisor. I was adventurous, stepping into an unknown field with just a history degree. I dared to jump.

I wasn’t a failure because I didn’t run my insurance brokerage for the rest of my working days. I helped hundreds of people protect their families. I made a difference.

I wasn’t a failure because I couldn’t even keep a job at a bank — thanks for the dig grandma. I learned how to communicate with business executives and developers to bring new products into the market. I connected dots.

Every career shift wasn’t a fall; it was a collection of small wins that when viewed through the right lens was a step forward, positioning me at the threshold of a new adventure: owning my time and carving out a niche on the internet.

Acknowledging even our smallest victories becomes essential as the blurry transition from the Industrial Age to the Information Age gives way to opportunities at a rapid pace. Success can no longer be confined to a lifelong linear pursuit, to the narrow path of career monogamy, but to a mosaic of varied, vibrant quests, a culmination of small wins.

---