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About that time I moved to Hawaii

It's day two of my 7-day writing course with Cole Schafer. Each day we receive a prompt and then have 55 minutes to write, edit, and post to a platform of our choosing. Today's prompt is: Write about a time you chose a non-traditional path and if it led you to where you were hoping to go.



It was a cold, grey day in Norton, MA., which was actually a pretty depressing place even on a sunny day. It was March of my senior year and I remember looking outside my college dorm room window.


I was on the phone with my best friend who had graduated the year before and moved to Kailua, Oahu. I could feel the sunshine in her voice, "Booooook it. Book a flight to Hawaii! I already have a job lined up for you, you can crash on my couch, just do it. It will all work out."


I later discovered this job she had for was the day shift at a local dive bar, Bob's Bar & Grill (I never saw one edible item in that place nor the alleged grill and if I did I would never in a million years consume it). And the couch was a hammock located outside on the porch.


When we hung up, I purchased a $300 one-way ticket departing the day after my graduation. I was hesitant to tell my parents of this new post-college "plan". I knew they'd be skeptical, and they had every right to be. The summer previous I had convinced them to let me live in NYC while I interned at a fashion magazine. This evolved into a shared five-person two-bedroom living situation in NYU housing with a job folding jeans at Levi's on 14th street after being rejected from every interview. There wasn't one magazine in NYC in need of a fresh History student with zero literary, fashion, or formal work background?


I learned very quickly that the kind of writing I wanted to do was going to be highly competitive and not very lucrative. And, I was already very, very behind on my resume.


Up to that point, I spent all of my time focused on things I showed promise in, which was lacrosse, and well, lacrosse. All of my choices were to support one thing that brought me a lot of confidence but I quickly realized that beyond this tiny microcosm of the world, my athletic accolades didn't matter all that much. I felt lost.


So, I moved to Hawaii. Much to my parents and grandparents confusion and concern. There was something in me that knew I should trust whatever it was that was telling me to do it. Not only was it the first time in my life I'd made a big decision that no one really agreed with, or even understood, but it was the first time I went out and tried a bunch of shit I was pretty terrible at and by man standards the trip was a failure. I worked a bunch of jobs many of which were kind of depressing like cleaning toilets in beach rentals, toasting toast at a coffee kiosk, waiting tables, nannying. I even got fired and eventually went broke.


So what's the moral here? I guess after 10 years of being able to do what I love, which is storytelling, whether that's through copywriting, branding, or blogging, I attribute a lot of my passion to that year of travel after college.


It gave me a stomach for doing things I didn't like nor was good at, I endured failure, felt misuderstood, and learned how to throw myself into things without getting too tied up in the outcome. I learned how to fumble through shit I had no idea how to do and get a little more familiar with the uncomfortable. I know it's super annoying to hear about how failure is valuable because who wants to continually endure that? But it's funny that when I think back on the times that I really learned the most about myself I think about that year in Hawaii.

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