Transition to Freelance Writing
Those of you who know me know that my life has been characterized by unconventional decisions. There was that choice I made to live with an Italian family in Rimini for six months after missing all of 9th grade at the age of 16, the decision to deny the opportunities given to me for a college education in order to work and travel, the one where I moved full-time to a developing country at the age of 20… To be clear, I am not bragging about my proclivity for making impulsive, risky decisions. I’ve detoured from my projected path through life a bunch of times because I have the support of a loving family and the understanding that they could probably always bail me out if I needed it. Or that I could always duck back into a more traditional lifestyle if need be.
To me, my impulsivity signals that I am searching for something. I wish I knew exactly what and why. My working theory is that my health problems, which have pulled me from the typical flow of life on more than one occasion, have given me the freedom of only a partial connection to my physical body and human life. Because I have a slight separation from this world–almost like one foot in another realm where I don’t have physical suffering–throughout my life I have felt free to pursue what feels right and attempt to find the way I can best contribute to society and be at peace. I don’t think this makes me superior to anyone, and I’m not even always convinced that I am doing the right thing. Probably I would have been happier if I had just stuck to what was secure and easy, but I believe I would also have been a lot less at peace.
The latest in this series of risky decisions was that of leaving my steady restaurant job in April in order to give full-time writing a go. I began working in restaurants after high school at the age of 18, and was quickly promoted from host to host manager, then server, then bartender, until July of 2020, when I stepped into the role of assistant general manager at a fine dining restaurant. Restaurant work always seemed to complement my contemplative life and writing work, as it provided all the stimulation necessary to get me out of my head and into the present moment. There was physical action, mental challenges (such as learning what to prioritize when serving, or how to bartend as quickly as possible, or how to arrange reservations in order to accommodate the most parties in the most convenient way), conversation with all kinds of different people, and a sense that I was in the thick of things.
While most of my former high school classmates went on to prestigious universities and then high-paying professional careers, I was working my ass off in pubs, taverns, and bistros, earning money quickly, with a flexible schedule, fun coworker camaraderie, and a hell of a lot of life lessons. Restaurant work allowed me to hone my people skills, learn that hard work is often rewarded, and see for myself that there are assholes and angels from every walk of life. It also allowed me the financial and schedule freedom to travel. But after five years of on and off restaurant work, after some particularly horrific interactions with entitled wealthy guests, and after a year of worsening health issues, I decided it was time to try and make my most cherished hobby into a career.
This decision was risky because I went from a well-paying job that included monthly bonuses, unemployment checks during off season, four days a week of work with six weeks off twice a year, to me and my computer and a dwindling bank account. Luckily, my husband was generous and supportive enough to insist that I go into writing full-time with the mindset that I should follow what I love and not worry about money. Since May, when we returned from our honeymoon in Hawaii, he has covered the majority of our bills and expenses, worked 8+ restaurant shifts a week, and celebrated my small successes, all without complaint. I cannot pretend that I would have been able to make this transition without him. Or without the guidance and writing advice of my author father.
I must thank my parents and husband for encouraging me, my previous experiences for informing me that I could make a leap and be alright, and the terrible human beings I had to deal with during the past year for prodding me towards this decision. I also am thankful that I have set myself up for success by dedicating time to writing over the years. As a young girl, I would often put together books of poetry or open word documents on my father’s computer and type away with whatever came into my head. At the age of 13 I won my first writing contest. When I studied abroad in Rimini, Italy, I was accepted by CIEE to be a contributing blogger, and jotted down the ins and outs of my experiences for future travelers. After returning from my gap year adventures in Europe, I wrote several essays about different facets of my exploration and submitted them all over the place until one was accepted. In Cambodia, I applied to different writing contributor jobs until I got one for Verge Magazine, then was hired by a friend at Grasshopper Adventures to learn copywriting. Although at the time I was hired I was nothing more than an aspiring writer with some good high school essays under my belt, by the end of my first year working for them (I am still taking on occasional projects for the company three years later), I had learned search engine optimization, how to write damn good website content, and how to mold words into a marketing-friendly format. For years, I have turned to writing for solace and kept it my number one hobby. I’ve written in journals, jotted down ideas, typed up drafts of essays, returned to those essays to edit them during free time, and even wrote and completed a full-length book.
When I think of my relationship to writing, I go back to Rainer Maria Rilke’s Letters to a Young Poet when he says “Go into yourself. Search for the reason that bids you write; find out whether it is spreading out its roots in the deepest places of your heart, acknowledge to yourself whether you would have to die if it were denied you to write. This above all–ask yourself in the stillest hour of the night: must I write? Delve into yourself for a deep answer. And if this should be affirmative, if you may meet this earnest question with a strong and simple “I must,” then build your life according to this necessity; your life even into its most indifferent and slightest hour must be a sign of this urge and a testimony to it.” To me, this means that I do not believe I deserve success as a writer. I desire to make a living from writing because I love to write. And if, even after all my hard work and the hours I dedicate to words, this doesn’t happen, I will find another path and keep on writing anyway, even if it is only for my eyes. Because I must.
How I’ve Gotten Started:
In May, I activated profiles on two freelancer websites: Fiverr and Upwork. For anyone who has a skill they’d like to make some money from, I recommend these two platforms. While both take a hefty commission simply for connecting you with paying clients, they also offer plenty of opportunities to find satisfying work. Fiverr allows you to choose services you’d like to offer and set your own prices. Upwork allows you to apply to thousands of posted jobs with various budgets. I began by bulking up my profiles with photos, work examples, and specific highlighted skill sets, then set my prices low. I thought of this as fishing, a hobby I’ve picked up since meeting my husband. I had to think about who I wanted to attract and put out irresistible bait.
When orders and jobs started rolling in, I made sure I completed each assignment very quickly and to the best of my ability. Once I had a few 5-star reviews, I began to raise my prices and be slightly more selective about the jobs I took on. Now, after three months of putting all my time into these gigs, I have made enough money this month to just about cover my portion of rent and expenses. I have three long-term part-time projects, am in talks for a few more, and get regular orders and requests. I’ve raised my gig prices on Fiverr by $10 each, my hourly fee on Upwork by $10 as well, and feel positive about the future. In my free time, or once a week on a “creative day” such as today, I write and edit essays, scour the internet for calls for pitches, send queries, apply for writing jobs, and sign up for freelance writing newsletters. While I wouldn’t count myself as a successful freelance writer just yet, I’ve taken some big steps on the path to my dreams, and that feels really good.
To give you a sense of the kind of jobs I do, I currently have one gig where I watch documentaries and write summaries of them, one where I write travel advice articles, another where I ghost write a mental health blog, and recently signed onto a job writing marketing emails for a really cool startup. The majority of my work is SEO blog writing for various businesses, which I don’t enjoy too much but is straightforward, quick, and lucrative. I try to think of all these assignments as helping me get better control of words, as I rein them in to fit certain brand tones, marketing styles, Google requirements, and word count limits.
The Joys of Full-Time Writing:
The ability to make my own schedule (I typically have deadlines once a week, but can choose when I fit the work in. Sometimes I take a day off to go kayak and fish with my husband, other days I pack each hour with writing and research and planning. If I have time, I take on more assignments, if I want a few free hours I turn them down.)
The way it works for my health (In the restaurant industry, when I was hit by a bout of fatigue or a sinus infection, I had to push through and show up for my shifts. Now, if I’m feeling shitty I do my work lying down, or take a nap, or have the time to do yoga and take a gentle walk to get myself going.)
The knowledge that I am doing what I want to do (A lot of the writing work can be tedious, and at this point it is not exactly what I want to be doing. But, it’s a step in the right direction, and that feels great.)
The solitude (Yes, sometimes it is hard to spend the whole day by myself, or to miss out on those laughs with coworkers, but I enjoy it. I can seek out people when I feel like it, or can rest in the silence of my own company. Plus, my job success relies on no one but me.)
The mental stimulation (While restaurant work requires a lot of thought and a few brain cells, it isn’t intellectually stimulating the way writing is. Some of my jobs require research into a topic I may never have learned about before. Plus the challenge of putting together webpage copy with a specific target audience in mind, or checking all the boxes for good SEO, or finding new words and sentence structure to rewrite articles and avoid plagiarism–that’s all fun for me. Sometimes it feels like I get paid to do English homework, and I mean that in the very best way.)
The creativity (In the restaurant industry, like with many other jobs, there is little room for creativity. There are certain specific tasks to be accomplished during service in certain ways. Now, I can base my whole day around creativity. Sometimes I take a break and go lie down by the river and find faces in the passing clouds. Or sit at my computer and give myself free rein to write whatever comes to mind. Or go through my journal and sketch out a plan for my future, or draw a color-coded goal sheet, or scribble poetry in my planner.)
The Challenges of Full-Time Writing:
The sedentary nature of it (This has probably been my biggest challenge in the last few months. I went from running around a restaurant for hours a day, going up and down stairs, carrying plates and trash bags and wine bottles and moving tables… to sitting in one place and typing. While my finger muscles have probably become more toned, it is way too easy to let the day pass without moving around much. The hardest part is forcing myself to get up in the middle of the work day and go out for a walk or hike, even if my mind is still racing and focused on the job at hand. I’ve had to make a real concerted effort to move.)
The screen time (Another unpleasant factor of this work is the amount of time I spend looking at a computer. I find that it affects my vision, state of mind, and ability to sleep well. At first I would simply sit and focus until the work was done, but I found that afterwards my brain would be fried for hours. Now, I try to break up the work day with regular walks, meditation, reading and writing, and time spent outside.)
The irregular income (Some weeks I have 10+ assignments due, others it’s only one or two. Plus, payments are processed through the freelancing platforms and can take a while to come through. Even though my checks from the restaurant varied from week to week depending on tips, at least I knew that there was money coming. Now, I don’t even know if there will be work. I am constantly on the lookout for new gigs, constantly sending off applications and pitches, and often hearing nothing back.)
It’s draining in a different way (During my years in the restaurant industry, I frequently suffered some kind of burnout. There was the social burnout for sure, but also a kind of physical tiredness that stemmed from hours on my feet and really, really long days of attending to other people’s needs. Now, I get mental burnout. Sometimes by the end of the night I can barely think of words, I have no patience for simple tasks, and my creativity is shot. Sometimes all the marketing writing takes away from my personal writing. I’ve tried to combat this by taking days off here and there, forcing myself to just live in the present moment and fill my mind with other things.)
So, there you have it. A quick update for my handful of followers and anyone else who finds themselves here. As always, I attempt to share these posts with openness and honesty in order to document my journey through life and my ongoing battle with the mind.
If anyone is interested in hearing more about my freelancing strategy, how to use freelancing platforms, how I got started, or what my tips are for people looking to make a similar transition, please reach out or leave a comment, and I’m happy to talk or write a follow-up post.
Wishing you health and peace of mind!