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5 Things I Wish I Knew Before Committing to Life as a Freelance Writer

In the early years of my writing career, I spent many hours daydreaming about working for myself. In those days I worked full-time, reluctantly. The rigid shape of a 9 to 5 felt claustrophobic and creatively limiting. What if my most productive hours were before 8 am or after 10 pm, I wondered? What if I thrived working on multiple projects with multiple clients? What if I needed to stand on my head for 10 minutes to kickstart my productivity? What if I didn’t want to make small talk in the elevator?

After a handful of full-time gigs I started to understand that job satisfaction is as much about how you work as it is about what you do. I’d swivel back and forth in my ergonomically correct chair in the open-plan office space, avoiding the questioning looks of my colleagues and sink into the fantasy of being my own boss—a writer on her own terms. I imagined myself tapping productively away on my computer in a sun-drenched home office, meeting deadlines and kicking ass, apologetically turning down new projects because my roster was already full to overflowing with exciting work. I saw myself skipping down the aisles of Target, running errands on a blissfully deserted Tuesday afternoon and chaperoning my son’s filed trips between deadlines, because, hey, I’m the master of my own professional universe.

Eventually, I did manage to eek out a version of the image above, but not without learning some surprisingly tender lessons (sometimes literally). Here, I share the hard-earned nuggets of wisdom that now guide my every day life as a freelance writer.

Learn from my mistakes, my friends.

  • Write these 5 points out on a piece of paper.
  • Tape that piece of paper on or near your computer.
  • Read them at the start of each work day.
  • Practice consistently.
  • Hey, look! You’re thriving as a freelance writer.

1. Connection is key.

Regardless of where you fall on the extroverted scale, clock enough hours spooning your computer and you will inevitably loose your ability to interface with other people. You may be a deft social warrior, slaying both friends and strangers with your scintillating wit on the daily, but spend a few work weeks conversing with only Siri and your dog and it’s likely that you’ll fumble your way through your next interaction with a human creature.

Conversation is a muscle that must be exercised, so whether it’s scheduled lunch dates with a friend, time at a co-working space, or simple exchanges with cashiers and baristas, commit to connecting with one or more people during each workday, dear isolated freelancer. Use it or you’ll lose it.

2. You are not strong enough to resist the magnetic pull of Amazon Prime.

Sure, you may be a type A self-starter with the willpower of a samurai, but you will not be able to resist the hypnotic call of the interwebs unless you invest in an internet-blocking app, also known, fittingly, as an “anti-distraction app”. I’m partial to Freedom ($2.42/month for a year membership). This simple app is the number one reason I am able to call myself a book author.

Surely, some will find me weak for leaning on technology in this capacity, implying that focus and discipline alone should keep me on task. But I ignore their jeers and jabs. I know I’m strong—strong enough to accept the fact that I wouldn’t have written more than one complete sentence without some serious anti-distraction assistance. The app blocks all access to the internet—that means your email, too—for as long as you ask it to and can only be disabled by fully shutting down and restarting your computer. This means no headline scanning, Facebook stalking, or hunting for the perfect hi-top sneaker. No, you won’t be able to confirm that it’s nine hours later in Fiji or 80 degrees in Miami or that pitbull puppies are still outrageously adorable. You’ll have no choice but to work. Go, you!

3. Writing hurts.

It was as recently as my latest ghostwriting project— an 80,000 word treatise on wellbeing by a notable actor’s wife—that I realized that writing can be as draining physically as it is mentally. As my massage therapist pressed into my aching wrists, hands and seizing lower back, I felt it was time to accept that spending the majority of the last five months hunched over my laptop had damaged something. I wasn’t a construction worker or a farmer, occupations that are legitimately taxing on the body, but I couldn’t deny that I was in pain. It would have been embarrassing if it wasn’t true; yes, I hurt myself by sitting.

My team of healers—a hodgepodge posse of massage and cranial sacral therapists, acupuncturists, chiropractors, and ART and NKT specialists (specialized injury treatment practices)—agreed. In addition to repetitive strain injuries like carpal tunnel and the like they said that excessive computer time can lead to eye strain, severe back and shoulder pain, even hemorrhoids (ouch). This isn’t breaking news, of course, but it bears repeating. When embarking on lengthy writing projects it’s not only essential to take the usual ergonomic precautions—lift your screen up to eye height, use a detached mouse, sit on a good chair—but to also take set movement breaks, drink lots of water, and even consider a standing desk.

4. Always have one conversation.

As a book author, ghostwriter and collaborator, I field many requests from people who want to write books (pretty much everyone wants to write a book). And while it would be easy to brush off a perspective author or idea, I have a hard and fast rule that requires me to have at least one conversation with everyone. Even when the topic seems strange and the author stranger I commit to one conversation before passing judgement on the person or project.

These dialogues sometimes make me uncomfortable—I’ve talked to bitter single dads fresh from brutal custody battles, retired prostitutes, cynical executives—but they have also surprised me. A conversation opens the door to possibility and I’ve walked away from many initial discussions with an unexpected project in my pocket. After chatting, a client may realize that she needs help solidifying her idea before she can begin writing a book proposal and hires me as a concept developer, or a copywriting client may discover that his website needs an overhaul more than his press kit needs updating. It never hurts to have a conversation.

5. Hone your hustle.

Freelance life is a delicate balance between finding the work (the hustle) and doing the work (the application). To keep my equilibrium on point and my business thriving I exist in a 60/40 split of hustle to application. It wasn’t always this way. In the early years of my sole proprietorship, fresh out of college with a severe case of know-it-all-ness, this dance between worlds was disheartening. I resented the hustle. I was hesitant to take a job that wasn’t sexy or spend time connecting with folks in my industry if there was no promise of work. I wanted to do what I was here to do—change the world with my masterful wordsmithing, of course—and my sparse client roster and uninspiring project list reflected this poor attitude. But as my self confidence eventually dipped in equal proportion to my income, I was motivated to do what any creative freelancer has to do if she wants to make a living: I got over myself.

I said yes to everything even if it didn’t pay well or was remarkably unglamorous. Along the way I made what would turn out to be lifelong professional contacts and, more importantly, turned the hustle into a natural part of my professional life. Soon looking for work became something I did whenever I wanted to take a breather from doing the actual work. I would sketch out a clear sense of what I wanted to be that month, or year—a landscape that has shifted over the course of my career from journalist, blogger, editorial consultant, book editor, book author, and copywriter to the delightful mishmash of job descriptions and skill sets that I enjoy today—and then I’d network like a beast. Not so much at industry meetups and cocktail parties, which I’ve always found to be awkward and unfruitful, but with my own circles and my circles’ circles. I let my world know what it is I wanted to do and was amazed at how much came back to me.

And I haven’t stopped since. I check in with past clients and managers about every three months and stay in consistent communication with my fellow writers and editors. We often kick each other projects when our plates are too full or when it’s clear that someone else would be notably better at telling a certain story or working with a specific client. It’s a system that seems to work.


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