Secrets of the Self-Employed: Tips for Freelance Writers

I've always admired my father for the way he's designed his life. "I made up my mind at 22-years-old to go into business for myself," says Greg Grinnell, a third-generation building contractor in Eaton, New Hampshire.

(25 Publishing FAQs for Writers.)

For 30 years, Greg has been self-employed in NH's Mount Washington Valley, building decks, roofs, custom additions, and custom homes. He's never had a boss and lives his life on his own terms. In three decades of self-employment, he's earned the distinction "Best Builder in the Valley."

I recently took the plunge into freelance writing and asked him what it takes be self-employed. Over the course of three weeks, my dad gave me the beats to his life as a sole proprietor. I condensed our conversations into a playbook that aspiring freelancers will no doubt find inspirational in realizing their dreams of starting their own freelance businesses.

What's your motivation for freelancing? Do you want flexibility or independence? More opportunity? My dad knows why he's in business for himself. "I just want control of my day," says Greg. Such control gives him the freedom to plan his day as he sees fit.

Circumstances will never be perfect for self-employment, according to my dad. "When I decided to start my business, I had a two-year-old (that's me), a six-month-old, and less than $2,000 in my bank account." Oh, he also didn't have a driver's license, so he rode a bicycle to his first job.

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For years, my dad hustled to get customers. "No one gives you anything; you have to go get it." The same is true for freelancing. Perhaps 30% of freelance writing involves actual writing. The other 70% is the hustle: Researching publications, writing pitches, developing story ideas with editors, finding sources, interviewing, transcribing notes and organizing material. After writing, you're right back to the hustle with revisions, follow-up questions for sources, fact-checks, and then publication and promotion, all while continuing to build strong relationships with editors.

Being in business for yourself often requires you to jump before you see a net. When my dad landed his first construction job he told my mom, "So I got the job, now I just need to figure out how to do it." He knew he'd figure it out. He did. You will, too.

My dad follows up on leads immediately. I once watched him leave his house on a Saturday morning for a motorcycle ride when he got a phone call from a potential customer. He didn't say, "Call me on Monday." He told the person he'd be at their house in an hour and built a meeting into his ride. Freelancers should be just as opportunistic. Last fall, I submitted a 3,500-word article on spec to a consumer magazine. An editor e-mailed me and said the piece wasn't the right fit for the magazine, but he liked my style and asked for more ideas. I sent him 10 ideas, one of which became a paying assignment that led to a published piece.

People hire people, says my dad, so you need to be good with them. He never forgets that he's in sales and even replacing a roof takes interpersonal skills. "I know a lot of guys who want to be self-employed, but they don't know how to interact with people in a professional way."

We live in financially risk-averse times, and money is usually the biggest deterrent to freelancing full-time. My dad lived on the razor's edge for three years and only made a few thousand dollars in his first year in business. Writers have to live modestly as well, usually for years. While your salaried friends will be buying cars, boats and second homes, you'll be killing yourself for $1.12/word. If making below the federal threshold for poverty sounds unpleasant, freelancing might not be for you. In addition, you will almost certainly need savings to support the early days of freelancing. I supported my transition with money that two previous employers had set aside for me each month as a benefit. I let the money grow for several years, as I worked full-time in Corporate America. When I left the workforce, I combined both accounts and cashed out.

(When and how should writers negotiate better terms?)

The fastest way to tighten a budget is to reduce expenses. I call it "account preservation." Make a list of every "insult" to your bank account (e.g., cell phone bill, utilities, etc.) and call each "offender" to negotiate. It is remarkable how many expenses can be lowered just by optimizing or canceling extraneous services. The biggest insult to a budget is accommodation. You don't have to avoid Los Angeles, New York or Boston; just be strategic if you want to live in these expensive cities. I chose to live in Long Beach over LA, and am relying on the generosity of a friend who's charging below-market rent. For many years, my dad went without health insurance, but nowadays there are many low-cost or fully sponsored plans for low-income earners. Finally, if you have student loans, ask your provider about income-based repayment plans. I qualified for a zero-dollar repayment plan, meaning I pay nothing for one year while remaining in repayment status, allowing me to avoid the credit-hurting effect of deferment.

"There were a few years when my phone didn't ring much," says Greg, so he paid the bills with odd jobs like painting houses and sold timeshares as a side-gig. You may want to write articles for The Atlantic, but don't turn your nose up at work from brand clients, agencies and corporations. A content marketing gig that pays $40/hour will support your travel essay that pays $0. Try partnering with a creative staffing agency like Creative Circle; they send daily e-mails with freelance copywriting opportunities.

My dad admits that he isn't an artist. He builds sound homes, not cathedrals. What kind of writer are you? If you're more interested in "creative" or artistic work, such as novels, screenplays, and creative nonfiction (which require writing on speculation and don't pay much at the beginning), it's probably best to keep a day job, so that you have a reliable income stream while you hone the craft. If you have artistic ambitions, you may think you can support yourself with work from journalism and copywriting in the days and write your novels in the evenings, but I've found it difficult to do the more inventive work when my days are commercially focused.

My dad is awake and responding to e-mails by 5 AM. If he's working on an especially complex project, such as the building of a house, he might start his day at 3 AM. Most days, he's on a job site "banging nails" by 6 AM. Throughout the day, he works with a sense of urgency, eager for tangible measures of progress. He usually ends his day around 3:30 PM, which justifies a 15-minute lunch. "Anything longer slows momentum," he says.

"Forget billing per-hour," says my dad. "You can't make any money that way." Freelance writers can do the same, and can find a helpful reference guide for estimating project costs in Writer's Market.

(How much should writers charge per word or per project?)

My dad found a niche in roofing. It's not the sexiest work, he admits, but replacing roofs paid well and he could knock them out in a week. While it's important for writers to diversify and have multiple streams of income, finding a lucrative niche can take the sting out of financial uncertainty.

My dad might finish a roof on Thursday so that he can leave for a mountain biking trip on Friday. Last fall, he had a project that didn’t start for two weeks. In his "downtime" he built a garage for his house. "It's not overwhelming," he says, "because it's my time."

When my dad leaves his house, he's working. "Whether I'm at the supermarket or driving through town, I'm representing my business." This applies to one's online identity as well, so make sure your website, LinkedIn profile, and social media presence leave the impressions you want.

Manual labor is obviously more demanding than writing, but writers are still prone to injury. Repetitive-use injuries are often the culprits. Six months into freelancing, I developed low-back pain, so I bought a laptop riser and began standing at my desk. My dad soaks in his hot tub every morning ("Aqua therapy," he claims). Writers should take ergonomics seriously. Heed author Margaret Atwood's advice, "Do back exercises, pain can be distracting."

My dad has managed large crews, but likes to stay small and work with one "right-hand-man," who has a strong work ethic and is fun to work with. "Once we see progress on a job, I want to be able to laugh it up." As a freelance writer, you will need to build a crew of creative professionals. Over the past five years, I've spent most of my disposable income on Upwork, hiring editors, illustrators, video editors, designers, even writers.

My dad hired an accountant early on to help him reduce his tax burden. I'm not in a position to hire an accountant yet, but I make sure to track my income and expenses in a spreadsheet and scan or save invoices and receipts in organized folders, so that I can make smart deductions at tax time. For more information on tax matters (and self-employment in general), I highly recommended the book, Working Solo, by Terri Lonier.

My dad is in his late 50's and knows he can't climb ladders forever. "This is a transition time." He's thinking about the next stage of his working life and has been experimenting with less backbreaking forms of construction work.

You won't be able to guess the meaning of my dad's vanity license plate, so I'll give you the answer. "GOBOGHO" stands for "Go Big or Go Home." It's a motto by which he runs his business and lives his life. "We're not around for that long," he says. "If you want something, go get it."