On Failure

And betting on myself.

Failure feels a lot like grief: deep and enduring and tastes like hot tears.

I hear the shouts of “failure isn’t final” and I wonder when failure turned into something to fear instead of an opportunity to embrace.

For the past few weeks, I’ve wrestled with my own beliefs about failure. My mind can make all kinds of promises about my value, but my body still quakes with doubt:

Am I worthy?

Do I matter?

Will this ever work?

Photo by Michael Dziedzic on Unsplash

Being an entrepreneur is a daily dance with failure. Sometimes I follow the steps with relative ease and other times I’m fumbling around, wishing the spotlight would go dark.

From the outside, people might see my life as safe and comfortable—my choices driven by an aversion to risk. But being a writer and online business owner is far from risk-free. I make bets on myself every time I sit down at my desk, never knowing if the odds are in my favour.

I took a leap of faith when I decided to host the Soul Care Retreat this year. By most measurements, this risk did not pay off.

I don’t have enough people registered to run it.

I could’ve chosen to discreetly share this information with the necessary individuals, but I’m opting to be more transparent about the realities of entrepreneurship because it has the potential to alleviate the sense of isolation we often feel.

Running a business that’s as much about you as a person as it is what you offer feels vulnerable and heart-wrenching when things don’t work out.

It’s only in the last few years that my income has surpassed the number of times I’ve wanted to quit each year. I don’t know why I do it except to say that I can’t not.

No matter how many times I ask myself why I keep going, my heart compels me forward.

I may never achieve success according to society’s standards, but each time I place faith in myself, I affirm my belief in the inner little girl who carries feelings of abandonment and betrayal.

I engage in this work not only for the dozens of people I’ve assisted over the past decade, but also to ensure that the little girl within me and the daughters I have nurtured and raised understand the realm of possibilities that exist for them. They need to know it’s possible to believe in yourself no matter what the world says about you or expects of you.

Fear and failure grip my heart like a vice when I think of not being able to host the retreat this year, but every time I bet on myself—regardless of the outcome—I find a truer sense of belonging and peace.

I’m okay because I’m always on my side. No failure has taken that away from me yet. My confidence doesn’t come from being certain I’ll succeed. It comes from being certain I won’t abandon me.

— T