About a year ago, I made a scary but a conscious decision to quit my full-time job which I was desperately unhappy with to take a job as a contractor in my field for 6 months. This meant that I would have a 1099 tax status and wouldn’t be eligible for any benefits. Most importantly, it also meant that my contact could be terminated or extended at any time.
I’d been working professionally building my career for the past 7 years but always with benefits as a W2 employee at large tech companies and universities. I was on a roll and moving further up in an industry I was excited about and was increasing my salary with every job change. The contract gig would be a chance to pad my portfolio with work with no other obligations required of me, which often happened in my full-time roles. It was the most money (and taxes due!) that I had ever made, but it was temporary and that was intentional.
See, I’d paid off my debt 2 years prior and had the goal of saving back much of what I had paid off. I wanted to have one year’s salary saved so that I could spend a year writing and traveling. During that year, I intended to discipline my writing habits and teach myself the skills I was most passionate about refining. In my day-to-day life, I typically only had 4 hours after work between my 9-5 schedule and a 4 hour commute in bumper-to-bumper traffic to devote to personal study and maintain my social life while keeping up with household chores and survival so I constantly felt time-starved.
To get through the incessant daily grind I promised myself: Someday, when I had a year’s salary saved, I would spend a year traveling, studying and embracing extra time in my life.
It was a dare. A challenge to myself to set a limited time to mentally and financially prepare for this Gap Year, Sabbatical, Mini-Retirement, whatever you want to call a year away from the grind, the rat race, the hustle and bustle of the East Coast capitalist money-making machine I had been conditioned to subscribe to as the best way to be a responsible adult.
Well it worked. July 1st, 2019 my contract ended while I was on an approved vacation working remotely so since, I was already out and packed for 2 weeks or more, I decided my Gap Year would begin then. One pack and a week’s worth of clothes would have to last me because I wasn’t going back. I made phone calls to friends and family that I don’t always get to see every year to find out if I could visit them for a few days and many were available and welcomed me with open arms.
I bought one-way plane and train tickets as I made my way from the Southeast to Hawaii and the West Coast of the United States, revisiting places I’d first seen exactly 10 years ago when I started traveling on one-way tickets when I graduated college. It wasn’t lost on me that I was celebrating a very special and personal 10-year Anniversary. I was commemorating the time that, against all my workaholic conditioning, I’d mustered to step out into the unknown with just my savings to buy me time to enjoy the unscheduled life for awhile.
Similarly to now, 10 years ago I was overscheduled, overworked, cooped up in my hometown and becoming bitter about the monotony of this sick dance we perform between affordable living outside of the city and making a good living inside the city just to keep up with the Smiths down the road, forget the Joneses, who were barely cobbling a life together outside of commuting under these circumstances. I needed a break then to hear myself think without the clatter of daily stress and anxiety about schedules, bills, debt and making plans with others also worrying about the same, and I needed it again.
I started to tell people when they ask me what I do for a living, that I’m currently taking a Sabbatical unpaid from my career. Really, let’s be honest, I’m unemployed but rather intentionally unemployed. What I mean is, was planning for this for 3 years and took steps to bring it about without actually quitting my job because as a stubborn and hard-working goal-oriented person if it was up to me to quit, I never was going to do it while I was being paid handsomely.
The responses have been very interesting.
My boss’s finance said that the idea of taking a year off to live in perpetual uncertainty gave him anxiety just thinking about it. “I could never do what you’re doing. Not knowing where you’d be sleeping next or where your next paycheck was coming from would scare the bejesus out of me even as someone who works in theatre on shows that are constantly changing.”
Others say I inspire them. They’ll introduce me as “the girl who saved up a year’s salary so she could travel the world.” They ask how I did it and I tell them that I spent 3 years getting out of debt, then 3 years saving back that money to equal 1 year’s salary. What I don’t mention is that I chose to live 50 miles outside of the city where the good-paying jobs were so that my rent was under $800 which meant that in the course of 6 years, I spent roughly 25,960 hours sitting in my car angrily daydreaming about taking a year off to do anything but commute 4 hours a day.
My dad who hasn’t had a job in years said that my plan “Sounds fun but future employers don’t like a year or more gap in work history. Keep that in mind.” I did. I thought about it a lot leading up to making this decision. The fear kept me from taking the leap myself, that’s why after I’d gotten more than halfway to my salary, I took a job that would FORCE me to take action when it concluded. With all respect to my dad, I refuse to accept that I am only valuable as a worker for consecutive work done for huge companies. Why would the work I do for myself and for my own business not be valuable to employers? It would demonstrate courage and an entrepreneurial spirit, as well as experience building and maintaining a business. Most importantly, it would demonstrate my committment to lifelong learning and skills enhancement, since this is my main goal for my year off.
Dad didn’t buy this. Instead, texted back, “Ya, sounds good until the North Koreans, Chinese and the RUSKIES hit the button and take down our financial system and you and I can’t pay for a cup of coffee! Stick your money under your mattress or in a money belt. this all seems like fun and games until somebody, probably everybody, gets hurt. Invest in a fatta wallet and buy a shovel to maintain your standard of living.”
“A shovel?” I asked.
“As in, people used to bury their money in the backyard when shit hit the fan.”
I can’t help but think that fear mongering like this is what kept him in New England his entire life, no more than 3 vacations ever to other states and once to Canada. In my opinion, life is too short to stay in one place your whole life where you’re never challenged to see that there are other ways of living than the way you’ve been raised to live. If he was happy where he was born and raised that’d be one thing to choose to stay. However, I know many more like him who are unhappy there but are too afraid of discomfort and change to try to find something more agreeable to their inner needs.
I’ve had people reach out expressing a mix of admiration and jealousy. That used to be me when I’d see Instagram posts of people living on the road full time. However, I’ve done this before out of college and I have no illusions about the psychological challenges of wandering, intentional or not. As I told a girlfriend who reached out, “It’s not glamorous. It takes practice. I have 10 years of this kind of long form traveling under my belt now but it’s certainly not for everyone. You’re constantly in new social situations and sleeping arrangements. your routines go out the window and you get homesick even if you can’t stand where you live. When you do get home, you are depressed after the initial relief wears off cuz you realize you’re caught between your previous life and the idealized version of one that only lives in your head as a daydream. It’s living in constant uncertainty and trusting and hoping that things will work out when you’re tired and ready for consistency.”
My Instagram feed won’t show you what the self-doubt looks like, wondering if I made a mistake while I’m watching the sun set on another coast or unrolling my pajamas from my pack wondering when I’ll be able to sleep naked in my own bed upstairs in my sunny apartment again. It won’t capture the feeling that any moment I might get a phone call that will break my heart and cut short my trip. That smile on my face won’t show the anxiety that I feel when my mouth returns to its resting position and I hope that my dad isn’t right about future employers and gaps in my resume.
All of those emotions mix with the feeling of pure joy in the freedom to take my time to literally bend to smell the lavender growing in the Northwest or the roses growing in Sonoma County, CA or to take Amtrak along the coast to visit a friend instead of flying because I have time to stare out the window and scribble in my journal.
I have chosen this path mostly because I trust myself. I know that I am capable of providing for my needs wherever I am. Those needs however have shifted. I am no longer willing to procrastinate making creative writing a daily part of my life. I am no longer willing to spend 4 hours commuting to my job where I sit in an office chair for 8 hours using some else’s internet and electricity to do my work just to make money. I am no longer willing to dream about building a business and writing life that I’m proud to tell people about. I’d rather be doing the work to build it each day as intensely as I work at my day job.
I know that I am risking everything I built in my career thus far of course I’m scared, but I’m more afraid of getting any older without having told my story and produced work that helped others that I can always be proud of. I can’t let any more time pass without honoring my time and energy by producing good writing. It’s worth the discomfort, change, and fear that I have to live with everyday to make my dreams my day-to-day reality that I might have the privilege of taking for granted when I forget to be grateful
The alternative: ceaseless regret, is all the motivation I need to make this work.
The Type A Bohemian 
It’s always good to see the perspective of someone walking the talk. The amount of hours you spent commuting make me cringe just thinking about it. Of all things, I resonated most with the last piece. There are some things we do for ourselves in spite of all other possible alternatives. That’s the beauty in it. Glad you’re chasing fulfillment how you see it!
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