Founder’s Diary: Leap

This week, J and I found ourselves in the most unexpected situation.

There we were, in a crowded Moxies. Having dinner and drinks with a guy who, two years ago, we would have had no business knowing. This guy has spent the last 25 years working with the hottest, emerging retail brands, and has the ears of CEOs who manage companies I could only dream of working for.

And somehow we were there with him, swapping stories and talking strategy over potstickers and guacamole.

Surreal, right?

How did we even end up here?

I’ve asked myself this question SO many times in the past two years. Like how did we end up in the Philippines last February, interviewing sex trafficking survivors and displaced peoples? How did we end up in the homes of artisans, people we barely knew, who welcomed us in with open arms? How did we wind up at some exclusive bloggers’ event in Toronto, with the endless flashes from phones and the posed selfies clouding our vision?

The absurdity of it all boggles my mind.

See, I’m a compulsive planner. I love making to-do lists, writing out timelines, figuring out how to get from entry level to senior manager within X years. But even with my obsessive tendencies, there’s NO way I could have foreseen any of this.

Two years ago, I was still working a 9-to-5 job, working in a financial institution (which is as corporate as it gets). I had a so-so salary, good job security, a clear cut path to becoming a manager within the next two years, and a growing sense of dread that my life was not going where I hoped.

So I quit my job and hoped that something better would come my way.

I guess you could call it a leap of faith.

But here’s the crazy thing. Entrepreneurship is one big leap, every day. And as a freak planner, that’s a tough pill to swallow. People like me are not on friendly terms with The Unknown. Not knowing where your next paycheque is coming from, where your business is headed, whether you’ll even have a business in a year, and what you’ll do with yourself if it turns out that’s not the case – all of that gives people like me anxiety.

But on those quiet mornings when I have a chance to slow down and reflect, maybe while I wait for the kettle to boil, or while I stand on the subway platform awaiting my next action, I see the lesson. I see my life then, and my life now, and I see the void inbetween.

Could I have imagined any of this? Probably not. But my reality is far greater than what any figment of my imagination could have drummed up, or planned for.

So, the way I see it, my life right now is about taking leaps forward.

Where will it all lead me? I don’t really know.

And for the first time, I’m tempted not to care.

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