My Year of Relentless Risk-Taking: An Experiment


I’ve always taken the easy way out. I set my sights high and inevitably chicken out at the last second, always opting for the path of least resistance. When things feel like they exist in the distant future, I hedge my bets on the idea that I’ll be a different person by the time that far-off future finally arrives. But I never am. I’m the same person I was at sixteen and the same person I’ll be at thirty-five. 

At fourteen, I visited New York for the first time. Back then, I still felt far enough removed from adult life that becoming an author seemed possible. Like all of the steps to becoming published could still fit inside the dark, mysterious future that stretched vastly between 14 and adulthood. I fell in love with the city. I fell in love with the idea of being a writer in New York. 

I held tightly to this dream throughout my teenage years. At sixteen, I returned to New York for college tours and decided that I would go to the New School, an artistic university in the heart of the city, home to Parsons School of Design and Eugene Lang College of Liberal Arts. I could live in the middle of the city. I could graduate with a master’s in writing in just five years! The expanse between sixteen and adulthood felt smaller than it had at fourteen, but there still seemed enough time to transform completely before starting my new life as a starving artist living in a shoebox apartment in the biggest city in the country. 

And then I was seventeen and applying to colleges. I still had my heart set on the New School, but I wanted to give myself options. A backup plan, I told myself. Just in case. I applied to twelve schools. Only two of them were in New York. As Decision Day crept closer, the distance between who I was and who I would be by the time I left for college began to feel like it was shrinking, smaller and smaller, until I could step easily from one to the other. It was no longer the wide expanse filled with possibility. No longer some futuristic version of myself with easy confidence who would be going to New York. It was me, exactly as I was: seventeen, insecure, and afraid of leaving home. Suddenly and brutally aware of just how unrealistic a career in writing actually was. 

I panicked. After some last-minute college tours of schools closer to home, I made my decision down to the wire. I would go to the University of Portland (UP). Driving distance from my hometown of Seattle (and driving distance to my high school boyfriend’s school in Eugene, Oregon). As much as I struggled at the University of Portland, I didn’t regret not going to New York. At least not then. 

Portrait of a Young Woman in White, c. 1798

When I transferred to the University of Oregon, I felt like I could breathe again. Sure, it was another easy way out (going to the college that my boyfriend at the time already attended), but it felt like a better fit for me than UP had ever been. With that space to breathe, I found my way back to myself again. I changed my major from psychology to journalism, bringing myself one step closer to the creative side that had always longed for a life surrounded by artists and writers. I absolutely loved the School of Journalism and Communication, and I am so grateful that the long and winding path of my own resistance led me somewhere I felt like I belonged, in the end. 

But a small part of me has always wondered, what if? That voice became louder when I started writing again earlier this year. Finding my way back to an old childhood dream opened a Pandora’s Box of alternate universes and unrealized opportunities. Who would I be if I had gone to the New School? Who would I be if I had gone to Reed (another top choice of mine)? Who would I be if I had kept writing all these years that I was too afraid to? Who would I be if I had taken a leap of faith, trusting myself to find the answers in that great expanse of the unknowable future?

I don’t think I was ready back then. I don’t think I’m ready now. But I now know that we don’t just drift aimlessly through the darkness to become different people on the other side. Each step we take leads us closer to (or farther from) the version of ourselves we see on the other side. And sometimes, that person is just a mirage, someone who never existed at all. And sometimes she’s real, but the path to get there is longer and more winding than you thought.

So even though I’m fucking terrified (!), I’m going to do what I was too afraid to do at seventeen, or nineteen, or twenty-one. I’m going to step into the darkness and see who comes out the other side. I’m not going to New York, but I am choosing the risky option, for probably the first time in my life. I’m leaving my stable, well-paying marketing job to do a month-long freelance writing workshop in Tokyo. I don’t know what I’ll do when I get back, but I can feel the window of time to take a chance on myself shrinking smaller and smaller with every opportunity I back out of. 

I have one year left on my parents’ health insurance (for now, though I wouldn’t be surprised if Trump comes for that next). I don’t have pets, a mortgage, or children. If I’m going to make a reckless and financially irresponsible decision for the sake of my own pleasure, I’d better do it now. So, for the next year, I will be taking risks and trying new things, metaphorically throwing spaghetti at the wall to see what sticks. 

Maybe I’ll keep writing freelance articles about food and farming in the Pacific Northwest. Maybe I’ll post more YouTube videos. Maybe I’ll sell T-shirts out of the back of my Subaru (but seriously, I’m working on some fun screen-printed tees, and I will be hawking them like a used car salesman). Maybe I’ll road trip across the country, finding odd jobs wherever I end up. Maybe I’ll work in a bakery (I really think I would love working in a bakery). Maybe I’ll burn through my savings and find myself right back in the marketing world like I never left. 

Regardless of where I end up on the other side, I’ll consider this year a success if I do even one thing that I would’ve been too afraid to try at seventeen. As someone who graduated college, moved back to Seattle, started my new adult job, and turned twenty-one all in the span of one week, I feel like I’ve never given myself a chance to truly fuck around and find out. I’ve seen the dark, vastness of the future and plotted straight ahead with a supercharged headlamp and a topo map of the easiest path forward. 

This year, I want to get lost in the woods.


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