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Common Cents: A Review of ‘101 Tips for Becoming a $100,000-a-Year Freelance Writer’

By Charlie Kasov September 24th, 2014

Go to any bookstore and you’ll see plenty of weighty hardcovers and paperbacks promising to help you make your first million dollars. But what about books one-tenth as long that promise one-tenth the money? If that grabs your attention, look no further than writing coach and veteran freelancer Dawn Josephson’s 101 Tips for Becoming a $100,000-a-Year Freelance Writer. At 32 pages, the only thing weighty about it is the title.

That title may be long, but Josephson knows that every word of it speaks directly to her intended readership. We freelancers aren’t easily duped by get-rich-quick schemes; we want realistic advice. And $100,000 is often seen as the top benchmark for very successful freelancers. We all want to know how to get there.

In e-book form, the text reads like part manifesto, part listicle (manifesticle?). In published form, it reads like a pamphlet. If the e-book is free on Amazon with Kindle Unlimited, and the published version goes for $5.99, why would anyone pay for a pamphlet? Actually, Josephson may be onto something. The pamphlet is a fresh, low-risk idea—the production costs are cheap, and the unique size is inviting, as is the page length.

As I read through the first few pages, I was reminded of another pamphlet: Thomas Paine’s Common Sense. Sure, Paine’s pamphleteering was intended to galvanize support for the revolution against Britain, and his comma usage makes him more accessible to fellow gasbag orators rather than to freelancers. However, Paine and Josephson have something in common: Their pamphlets share a sense of urgency—a call to action for those who wish to prosper without an oppressive authority figure in their lives, be it the British crown or an office manager.

Josephson has written something for freelancers who want more than a fledgling sense of independence. Her thesis? A successful freelancer is a self-governing freelancer. Tips number 3 and 4, which she expands on throughout the book, put it plainly: “Think of writing as a business” and “Do the things businesses do.” The implication is if you’re a one-person operation, you’re both the CEO and the secretary, the bean counter and the janitor, the slick marketing exec and the workaholic sales force. Everything you do should benefit your business.

While the tips are helpful, about halfway through the book, I found myself longing for an Adderall prescription—not to help me finish the book, but rather to get me to follow through on any of the wisdom I’d already gleaned from it. Thankfully, Josephson understands not all freelancers are as über-Type A as she is, so she threw in tips like number 60: “Treat yourself as number one,” followed by a few more tips about finding time for breaks and relaxation.

As I read on, several of the tips elicited my inner snarky Valley girl, who repeatedly said, “Uhhh, yeaahhh? Obvs…” out loud. But Josephson didn’t intend to write 101 completely original ideas for successful freelancing. If she did, she’d be both a fraud and a failure. There aren’t 101 new ideas to be had. Instead, she intended to give freelancers an organized set of affirmations that wouldn’t take too long to complete.

“I didn’t want to write a long book because freelancers shouldn’t waste their time reading,” she said to me during our Q&A. “They should be spending their time writing.”

Buying the print version of 101 Tips has an unintended upside: Many freelancers feel like they’re not taken seriously by friends and family who fail to appreciate the work that goes into successful self-employment. The amount of effort Josephson insists freelancers must put in to make a low six-figure income should persuade the skeptics. Leaving Josephson’s book out on a coffee table or on top of the toilet is an effective way to change some minds.

Image by GLORF
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