When the New York City-based trade magazine I was working on was sold to a company in Florida years ago, I had to make a decision. Should I up and move with the magazine? Or was this the opportunity I’d been waiting for all these years, to set out on my own, listing them as my first customer?
This was a no brainer. What junior editor doesn’t dream of freelance writing?
What followed was challenging, memorable, even lucrative. For five solid years I labored intensively, night and day, 24/7, 365 days a year. If you counted 40 hours as one calendar week, I probably racked up 15 years of solid writing. I do not miss that life. Ten reasons why:
1. No place like home. Working at home isn’t all it’s cracked up to be. Sure, you cut your daily commute, sleep in, leave early and there’s no one to stop you. Plus you can work in your pajamas. What’s not to like?
Plenty. Nowhere to run, nowhere to hide. Without a commute, you’re that much closer to work. And since you can work in your pajamas, no one’s going to think twice about calling you just because, say, it’s 3:30 in the morning (when it’s 9:30 in London and mid-day in Tokyo). Ever try to “call it a day” in your own house? Forget it. Imagine never leaving the office. That’s what it was like for me. Work, work, work.
2. It’s a business. Ah, the days I could sign invoices and slip them into interoffice envelopes to accounting. Those days are over. Not a problem? Hey, if you’re like me, the unnecessary, left side of your brain was deleted years ago; my brain is totally right-sided. Ever try to calculate project expenses using the right side of your brain?
Reimbursements and billing are a critical part of the freelance life — like, half your time will be spent collecting what they owe you. And getting paid? Even after you sign on a bunch of monthly Contributing Editor gigs, you’re still going to have to send out bills for everything. And of course you answer your own phone, you open your own mail, sharpen your own pencils, and stock your own supplies. Computer acting up? Say goodbye to Tech Support. You’re Tech Support now. Although there are services that specialize in freelance writers at tax time, the rest of the year, you’ll do all the math.
3. “The check is in the mail.” Speaking of bills, imagine how it would be if, to get paid at work, you had to bill your boss for every paycheck. Imagine doing that two, or five or 10 times a month, or more just to get paid! Nothing’s free in this life – unless you freelance. Then, you work for free until you bill them and they process it and then six months later, after the article is printed, you finally get paid. If they don’t pay up, you bill them again. All this with the right side of your brain.
Believe it or not, some of these editors act like they’re paying you out of their own pocket. Some feel like they’re not doing their job unless they nickel and dime you to death. Talk about attitude. Oy.
Get used to it. Hey, why do you think they call it freelancing?
4. Solitary confinement. Every freelancer I’ve ever talked with says the same thing: It’s lonely. Yes, writing is a job for introverts. But this? Way too isolating. Within a month of working for myself, I was best buddies with the mail carrier, the post office clerk, the guys at the deli counter, and the Federal Express truck driver. I knew railroad conductors, taxi drivers and all my neighbors by name. And I am an introvert.
Working in an office isn’t all about work. It’s also about the water cooler. How was your weekend? (If you freelance, there is no weekend.) Seen any good movies lately? Learned any stupid pet tricks? Hey, half the fun of buying new pair of shoes is talking about the shoes. You can’t do that with the Fedex man. Freelancing is a desert island with no rescue boat on the horizon. Know what I did? I got a dog. Now, there’s something other people can’t take to work with them.
5. Time is money. There is no such thing as R&R in the freelance life. Sick days, personal days, holidays, lieu days, snow days, hurricane days, death in family days, even jury duty starts to look like a good excuse. Kiss them all goodbye, because you work for you, and if you don’t work, you will not get paid.
Which brings us to the myth of the starving writer. Any freelancer who starves is simply not working at this. From the moment your brain rises out of delta sleep, there’s work to do. When you’re not working on an assignment, you’re writing queries. You can do this all the time. I’m sure there was never a day I washed my hair, poured a cup of coffee, walked the dog, put my shoes on when I was not pondering a subject I writing about.
I once sat down to lunch with a group of freelancers. One was a woman who dabbled, submitting one short article a month. The rest of the time, she was happily married. She told us she did not have the “discipline” it takes to support herself as a writer. She asked us, “What’s your secret?” “Fear,” I replied. All heads at the table nodded.
Fear of failure. Fear of homelessness. Fear they’ll turn the electric off. Fear is all the discipline you need to make it in this business.
That said, freelancing changes your attitude forever. The biggest change for me was my knowledge that if I had to, I could make it on my own. I had a new appreciation for the perqs of working for someone else (like paid holidays and Tech Support). After writing thousands of articles, captions, sidebars and headlines, I no longer needed to prove this was something I could do if I had the chance. I’d been there, done that.
Today, I write for fun, not profit. I commute to Wall Street every day. But some things I really miss. I’m working on the no-dogs-in-the-office policy.