Book Spotlight: The Indie Writer's Survival Guide by James O'Brien

We're pleased to spotlight a new book today: The Indie Writer's Survival Guide: Dos and Don'ts of Full-Time Freelancing, Year One by James O'Brien, just out from SlimBooks. It's a terrific overview of the freelance writing world, and a guide to transitioning from full-time writing to independent writing as a full-time career.

GG talked to James about cultivating clients, building networks, and anecdotal puffery.

What prompted you to write this book?

I found the publisher before the book was even an idea. SlimBooks is on to something when it comes to how business books work best, and how they don't work to the reader's benefit a lot of the time. They were looking for authors who could strip out the fluff and leave aside the repetitive anecdotal puffery that all too often pads business writing. I mean, anecdotes can be illustrative, and they can contextualize, but business-book readers have told me that they're annoyed by endless iterations of "Here's what Bob experienced one Monday in a meeting!" I like to think that we read business books to take away practical information, to receive a template or strategy that we can apply to what we're doing (or what we want to do). 

What do you think is the biggest challenge to being an independent writer?

After cash flow, it's cultivating the client list: building and maintaining one that will sustain you week after week, one that can survive, and allow you to survive, for months and years at the job. Getting clients is often a giant problem when you're starting out, but even after you've earned your way into outlets that will take your work, it's equally nerve-wracking to be in this reactive space all the time. Editors change, publishers' business models shift, networks bloom and then dry up . . . you're never not in entrepreneurial mode, really. And that can wear a writer down if the projects aren't fine-tuned to emphasize elements that keep you engaged—passions, interests, challenges. You have to stay in love with the stories, or the vicissitudes of the environment are going to burn you out. 

What do you find most rewarding about being an independent writer?

Freedom. And I don't mean the freedom to go sit in a coffee shop with your laptop all day; I mean the freedom to take on projects that you wouldn't be able to tackle if you were woking in a traditional full-time writing job. As an independent, you can write your way to a financial place that creates whole weeks without a deadline, and then you can start to explore. This kind of exploration, as a writer, takes you to places, literally, that you might never otherwise go. One morning you're answering an e-mail or pitching a piece to an editor, and then two weeks later you're on a plane, following a source or an idea that keeps you at the edge of your own skills and knowledge. This is the deeper kind of payoff that I think the happiest independent writers end up realizing and pursuing. 

The publishing landscape is changing dramatically. How do you see this affecting independent writers?

Mostly I see it as beneficial. There are so many outlets and so many developing spaces online that an entrepreneurial mind can find its way into multiple revenue streams. I know that this is often not the ideal scenario for traditional full-timers—there's a lot to be said for security and benefits and the comfort of a team that you grow to know and trust. But once I made the transition to independence, a whole world opened up. There's a real frontier in the digital publishing milieu. Don't listen to the voices that only say "No pay! No pay!" They're wrong: there is a lot of money on the table, but you have to be aggressively open to the way mastheads and editorial work now, and it's not what J-school taught back in 1985, 1995, or even 2005. What we mean when we say "news" or "article" or even "journalism" is subject to a number of new and interesting pressures that just weren't there ten years ago. This is not all bad, or even mostly bad, but it takes some flexibility and time and effort to sort out what works about this for the individual writer, and what does not.  

What other resources would you recommend for those who are transitioning into an independent writing career?

Avail yourselves of well-connected high-end networks such as Contently and Gotham Ghostwriters. That may sound like an advertisement, and I'm aware of where this interview is being published, but it's authentic advice, on my part, coming from what I know to be effective. Networks, especially online networks with well-funded projects, are more powerful than individuals, or at least they can save the individual a ton of time in the search for good work. There are lots of smart, young, successful people—writers, publishers, and network builders—who know this already. Be like them, and work with them, and with time and some humility, they'll change the way you work.

James O’Brien writes about business, technology, social media, film, wine, and travel. The Nieman Journalism Lab has called his work in the custom-content space "sponsored content done right." From 2008 to 2012 he reported and wrote extensively as a news correspondent for The Boston Globe. In 2012, he joined the caption-research team for photo-essayist Rick Smolan's The Human Face of Big Data. His fiction and poetry appear most recently in The Newer York and in Commas and Colons. New fiction is forthcoming in Space and Time and Footnote. O'Brien holds a PhD from the Editorial Institute at Boston University, where he researched Bob Dylan's other-than-song writings. 

Around the Word

Freelancing, Contently. We all know the freelancing paradigm is shifting in a big way, leaving the field wide open for evolution, and our friends over at Contently are trying their hand at building a new model. Contently has positioned itself as an all-digital "project management platform" that provides a place for freelancers to brand and market their services, facilitates client-writer relationships, and provides easy access for clients to post projects, audition writers, and provide input. One of the features that separates Contently from the myriad other freelancing sites is the quality of its writers, who are required to apply and submit to a rigorous vetting process in order to get on the roster. Another great feature is Contently's blog "The Freelance Strategist"—which, in case you missed it, recently posted an article featuring thoughts from GG's fearless leader Dan Gerstein.

Editor and Writer: The Special Relationship. The writing process can be highly personal, and the ideal relationship between editor and writer is like a sacred bond. Last week's New Yorker featured an illuminating piece by John McPhee, which gave a glimpse into his relationships with the the three very different personalities that shape the magazine during his tenure: William Shawn, Robert Gottlieb, and Roger W. Straus. McPhee describes Gotlleib's ability to digest entire manuscripts in a single sitting and steadfast unwillingness to allow the f-word to grace the magazine's pages, Shawn's careful deliberation and insistence that "the subject shall not be the title," and Straus' effusive commentary and loyalty as a publisher who kept authors' works in print.


Food Puns Gone Stale. Here's a cautionary tale about the fine line between pun use and abuse. Someone in Mayor Bloomberg's communications office is in hot water for a speech written for his appearance at the 2012 Nathan's Famous Fourth of July International Hotdog Eating Contest, which featured no less than a dozen hotdog-related puns. One cringe-worthy example: "This is one of my favorite traditions; I relish it so much." The mayor had a hard time, er, digesting the remarks, and in classic Bloomberg fashion asked an aide "Who writes this sh-t?" Remember, "too much of a good thing" not only applies to our favorite foods, but to puns about them as well.

Farewell to Arms: 39 Flavors (And Then Some). One of the greatest legends in literary lore is that of the myriad alternate endings to Hemingway's classic Farewell to Arms, which the author rewrote "thirty-nine times before I was satisfied.” It turns out that there are actually forty-seven endings, which have been locked away—until now. A recent agreement between Hemingway's estate and Scribner has paved the way for the publisher to release a new edition of the beloved novel that includes all the alternate endings as well as early drafts of the work. One of the most notable alternates, excerpted in the Times, is "No. 34, the 'Fitzgerald ending,' suggested by Hemingway’s friend F. Scott Fitzgerald. Hemingway wrote that the world 'breaks everyone,' and those 'it does not break it kills.'"

Gotham Featured on Contently's "Freelance Strategist"

Gotham was recently featured on publishing and media site Contently, in an article entitled "Diversify and Increase Your Income with Ghostwriting." Reinforcing a point we often like to make, the article, which was written for their "Freelance Strategist" blog, illuminates the idea that ghostwriting is no longer the domain of celebrity vanity, but has evolved into an increasingly key piece of many corporate communications and thought-leadership strategies—making it a great opportunity for freelancer writers. From speechwriting to white papers, from big-think pieces to smart blog posts, many businesses are realizing that hiring freelancers is a time-saving and cost-effective way to improve brand positioning and awareness. Says GG President Dan Gerstein in the piece, "On one hand, there are shrinking opportunities in the journalism field, but the flip side is that there are growing opportunities to get paid for what are increasingly in-demand skills... Ghostwriting collectives are a way to diversify your business and get access to opportunities you wouldn’t have otherwise."