Zen and the Art of the Underachiever

By: Michael Youngblood, Co-founder, Unsettled  

“You meet your destiny on the road that you take to avoid it” — Carl Jung

When you were a kid, what did you want to be when you grew up? I mean, what did you really want to be? Not what did your parents, grandparents, and aunts and uncles expect of you. Throw that doctor or lawyer stuff out the window.

I’m talking about an ice cream scooper that pushes her cart down a beach at sunset. A dog groomer. A playground engineer.  

What’s your underachiever dream job?

I’ll go first. In 7th grade, I used to doodle in class about building the halfpipe, jumps, and jibs at the local ski area’s snowboard park. My science teacher caught me one day and forced me to write a paper about the physics behind my designs. Turns out that some of the same laws that rocket scientists apply in their work — inertia, centrifugal and centripetal force, and motion acceleration (equals hang ten, bro) — drive the work behind my underachiever dream job. And herein lies a major point: There’s no such thing as an underachiever job because every job is defined by you and you only — and by your ability to draw meaning out of a job whether or not society looks down at such a job. That’s precisely the point, to remove society’s judgments and to ask yourself what matters to you.

So, there we have it, when I grow up, I want to be a professional terrain park builder at a ski area.

I’ve been asking this question about your underachieving side for the better part of a year now. I usually ask it to small groups…of you guessed it…overachievers. I like it for many reasons. For starters, it gives them permission to not take themselves or their careers so seriously. Once the tone of the conversation is playful, I find that it’s a good exercise for us all to tap into our inner child and to ask ourselves a series of questions, such as:

“Why are we ambitious in the first place?”

“Is the source of my ambition from within or something external to me?”

“In what ways do I draw happiness from my work? Can I shift my perspective on this?”

Here are a few things that this question has taught me:

    1. Work should be defined by internal rewards, not externalities (the parents, grandparents, etc). When my friend says, with the biggest smile on her face, that she wants to quit her job as a stockbroker and serve drinks on a beach in Costa Rica, everyone else looks stunned, “why wouldn’t you do that?”, until the question comes to them. It’s easy when the externalities are not yours.
    2. The most rewarding work may be what renowned psychologist Mihaly Csikszentmihalyi calls optimal experiences or the state of flow. That is, when we get so focused in our work that time just flows by, that’s when we are truly present. Most importantly, I’ve learned that all work has the opportunity for these optimal experiences, it’s a matter of applying ourselves.
    3. Work is rewarding when it’s challenging. Life is rewarding when we grow. But not all challenges are created equal. I love to be physically and intellectually challenged. My true dream job is probably building that terrain park during the day and writing intellectually stimulating content by night.
    4. Realizing that we each contribute to people in important ways, whether as a garbage man (another dream underachieving job of mine) or as a CEO, is more fulfilling than working for the sake of an external achievement.  
    5. We need to be engaged with our work, yet carefree. When we can take our purpose seriously, but laugh at ourselves on a daily basis, we’ll get through the toughest days.

The goal with this thought exercise is to shift how you see the value, meaning, and growth in any job because every job offers these…if your perspective allows it! At the root of this is the idea of living for the moment. In the West, this thought may be best expressed in the Latin phrase, Carpe Diem. In the East, it may be best expressed in Zen Buddhism. Monks are trained in the Zen Rock Garden technique precisely because it forces their mind to focus on the present and to give little thought to the future.

If you ask me, Forrest Gump is the most successful underachiever from the 20th century. Towards the end of the film, after making his “gazillions” as a decorated war hero, an athlete, and a successful entrepreneur, he retires back home in Alabama to mow the lawn of his local high school. Only someone with a low IQ could do such a job! This scene is remarkably Zen. Throughout all of his success, his mind never wanders too far from the present. He never lets fear, worry, or the analytical mind think too deeply about the consequences of the future. He is always present. He is the Zen Buddhist working his way through the metaphorical Zen Rock Garden of life. Who has the lower IQ? Mr. Gump or the ambitious do-gooder of today dreaming of the future?

The art of the underachiever is a thought exercise. Use it to reflect on your true north. On what makes you happy. How can you manage an ambitious career that pulls you in one direction, while taking care of your true north?

As I write this article, I look out my window at one of the largest ski areas in the world. What may be the world’s best terrain park crew is out there building jumps for what may be the most important snowboard competition this year, the U.S. Open. I’m watching, wondering if those guys know they have my underachiever dream job, and then I catch the reflection of myself working in the window’s glare and I surprise myself by how focused I am. By how content I feel in this moment.

As the great Master Shifu reminds us, “One often meets his destiny on the road he takes to avoid it.”


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