In elementary school, I could never make it across the monkey bars on the playground. My hands were too small, my arms too weak, and my plump little body was more plump than little. Watching my lithe playmates swing across the horizontal ladders during recess, I’d drop my chin deep into my jacket collar, stuff my hands into my pockets, and go sit on the tire swings instead. But no spinning the swing, please! Because unfortunately I had an unbalanced inner ear and became nauseated quite easily.

Fifteen years later in the middle of winter, women twice my age are standing on their heads in the middle of a room in the Jivamukti Yoga Studio in downtown Toronto. I had just moved to the city and the apartment I lived in was fatefully across the street from said studio. I had practiced Yoga before but never the head-standing kind. As a matter of fact I’d even been certified to teach Hatha yoga during a quick 2-month retreat but this was quite different.

While the head-standing ladies did their thing I faithfully performed my beginner’s level dolphin push-ups, all the while feeling like the seven-year-old on the playground, watching the acrobats from the tire swing.

After class I trudged through the blizzard and up into my apartment. I Googled “How to do a headstand in Yoga” and watched a YouTube video of an old Indian man floating on his head. I placed blankets on the floor near a wall and went into my “you can do this” zone.

It took a few months but I began to stand on my head when the leaves started to bud in spring.

I didn’t think much of it. In fact I was mildly embarrassed that it meant so much for me to be able to stand on my head, almost like proving something to myself. It’s still a difficult posture for me today because my mind begins to wander. Perhaps the difficulty has always all been in my head.

This past Christmas, seven years later, in middle of winter in the desert, after months of deliberation, my husband of four months and I decided to quit our jobs. On my 28th birthday in January we launched www.fairejour.com, a company that celebrates independent designers, meaningful retail and thoughtfulness.

It is one of the hardest things I’ve ever done, and I’m learning to do things that feel very unnatural. Every day I feel like I am trying to do a headstand. Or doing dolphin push-ups while everyone else is doing a headstand.

But I tell myself – at least I am trying to do a headstand. Because in retrospect, I don’t think I ever actually tried to swing across the monkey bars.