The Question that Changes Everything

“So I heard there’s this test…” Nine times out of ten, that’s where the conversation veers when I start discussing calling and career. Generally, we know what we like. We know what we’re good at. However, we often look for a neutral third party, an expert, a formula, or something more statistically reliable than inclination and hunches. While assessments and counseling can reveal new insights, more often than not, these tools simply unearth what’s been there all along.


Yet we want to find something surprising. We want a hidden talent to burst into our seemingly mundane realities. However, reflection, assessments, and expert opinions often reveal what we knew all along. When did the self become so unsavory? Why do we push ourselves aside when we’re trying to figure out who we want to be?

Whether counseling a friend or coaching a college student, I find one question to be extremely powerful (Questions, in general get at the root of the issue must more swiftly than poetic lectures.):

What would you do if you knew you couldn’t fail? 

Forget practical for a moment. We’ll get back to it. Life will force us back to it.

When I consider my most confident, assured self, I think of a spunky, loud-mouthed little girl who ran around in a tutu singing, “Would you like to hear a secret?” At the ripe age of four, I thought I could sing melodiously. I thought I could dance incredibly. I simply wanted to entertain and to help people find joy. But I lost the spunk somewhere. I lost it because the eye rolls came. I lost it because no one had time to listen. I lost it because someone else was a better singer.

Beyond the “what” we would do if we couldn’t fail, lies the “why.” There is motivation behind singing on Broadway, starting a pizza chain, or becoming an adventure guide. You may love the creative process or have a knack for managing people or love to work in the great outdoors. While there are many ways to match up vocation and motivation, it takes time and patience to look inside first. Although the “what” may change during the course of our lives, we can always carry the “why” with us. We just have to stop and ask the question.

Instead of looking outward and onward, what if we first looked inward? After considering our natural motivations, we can better jump ahead, to a place where failure fails to scare us.

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