Interview: James O’Brien

Very often a situation that looks like it’s bad news can be turned around and made into an opportunity. James O’Brien figured that out and started his freelancing career that way. You’ll learn a lot from his tips and perspective.

Enjoy this interview.


You turned a negative situation into the start of a freelancing career. Tell us more about that day in 2008 when the newspaper you wrote for closed. How did you get your first freelance clients?

You know something’s wrong when the editor at your publication tells you that you don’t have to hand in your deadlines for the day. Soon enough, we were gathered around the main reception area of the newsroom and the folks in charge told us that the overseas financier that was bankrolling our paper had stopped sending the checks. We closed, effective immediately. It was April 14, 2008, and it was my birthday. And I was completely thrilled at the news.

I wasn’t thrilled because I wanted to be out of a job — and, look, there were just too many people at that moment who were deeply impacted by what happened — but I knew that I could make a go of independence — of independent writing. Unemployment insurance would buffer the transition. So, I just went for it. And, yes, I was excited to do so.

I pushed hard to get new clients. There were setbacks and missteps and delays. But I also selected prospects that closely aligned with what my clips showed to be my strong suits. And I worked on two fronts: short-term projects and long-term relationships.

Within days of the newspaper closing, I’d answered a Craigslist advertisement and I was on my way to Nantucket, flown there by a client who needed a writer’s help on a sentencing statement. My most immediate work at the time, the courts and crime beat in Boston, made for a close fit on that one. But I also mailed clips and a cover letter to The Boston Globe. Eventually, while I filled the financial gap with short-term assignments (and unemployment), that mailing opened a door for me into the realm of longer-term freelance correspondence. And that was the real game-changer. It gave me the credentials and the experience to move a lot further in my career.

You’ve got an impressive list of clients (Mashable, Forbes, and more). Have you noticed the “feast or famine” world that people think about when they picture freelancing?

If you mean feast or famine in the sense of lots of work and then no work, then no. I haven’t experienced that. But the feast or famine scenario is real when it comes to cash flow.

Editors tend to be right with you and proactive about making the back-and-forth of the relationship work on the story end of things, but all too often publishers’ accounting departments then slow things down when the turnaround on payment should be a heck of a lot faster and easier. It’s somewhat better with the advent of PayPal, but it the whole process remains, in many cases, antiquated and perhaps willfully slow. Writers should be paid within five business days of completing their work, they should be paid electronically, and this is easy to do in 2013. But it’s still a struggle, for whatever reason.

I can’t wait to read your new book, The Indie Writer’s Survival Guide. Tell us about the book and when it will be available.

The e-book is a step-by-step guide through the first twelve months of making the move to full-time independent writing. It’s targeted right at the traditionally employed writer who’s suddenly navigating the do-it-yourself waters, whether by choice or by circumstance.

The Indie Writer’s Survival Guide takes the reader through the process of recognizing their own independent moment — realizing and acting on the right circumstances for that critical leap. It addresses the start-up money needed — several ways to make that work — and then takes the writer through everything else he or she is going to encounter, early on. From setting up a home office to finding new clients, to the realities of cash flow and taxes (incorporation: yes or no, etc.). There’s a lot of practical information in the guide. No fluff, except maybe that I tell a bit of my own story along the way — along with input and examples from other indie writers who’ve made it work as well. But the goal is that you can apply what you read in my book to your own efforts, just about immediately. If you’ve got what it takes to write full-time for a living, this is the manual for putting all the other ducks in a row during that first year, when you go it on your own.

The e-book comes out on September 10, 2013. It’ll be available at the publisher’s website — that’s — and at Amazon.

Tell us what your day is like. How many hours do you work and do you have the flexibility that many freelancers crave?

My day typically starts at about 8:30 or 9 a.m., and it usually begins with either responding to or sending out the first of the day’s e-mails. I never understand the people who are so against dealing with their electronic correspondence. Doing this first thing every day helps me to prioritize, and it helps me to see where my clients need to be throughout the week. I try to acknowledge the privilege of a career in which people reach out to me. They deserve a timely response.

After that, if possible, I try to clear the day’s professional deadlines by about noon or 1 p.m.. I work to reach a certain dollar figure. Once I’ve filed enough material that I’ve earned a couple hundred for the day, I give myself the afternoon for enterprise stories and creative writing.

All this being said, I switch it around every couple of weeks. I’ll start with all creative or all enterprise in the morning, and reserve the business and professional material for mid-day. The key for me is to never let the schedule get stale.

I’ve also learned that breaking away for about 45 minutes to exercise is crucial. Around 3 or 4 o’clock, I force myself to pause and get in a workout. Some of my best ideas and problem solving happens when I’m not sitting at my desk, but out there jogging along the Hudson. It’s important for the brain to run its own routines in the background during this time. And it doesn’t hurt that it keeps you from turning into a total slob.

What’s the biggest misconception people have about freelance writers?

Professionally: that they have to specialize. Specialists are fine, and often useful, but there is a great deal of value in the generalist’s process, too. We know this when it comes to doctors and plumbers and graphic designers, to name a few careers that include both specialists and generalists. But in the writer’s world, it seems to me that there’s this other expectation. It’s something like: you’re a business writer; you’re a middle grade fictionist; you write about science. Period. Specialize.

Whatever. Look, for some it’s not a choice, it’s a necessity to be a generalist. The creative mind thirsts for new topics that are freshly interesting. And some minds are very good at making complicated systems easy for readers to understand. Why limit that to writing about neurons when you could also do it for traffic systems and crops maintenance? You don’t have to run along a single deeply worn track to be successful. There are all these opportunities for the generalist. It’s a journey.

Still, in personal interactions the number one question people ask me is what do you write about? To be fair, I do know what the question means — it’s a wide open query, not a test — but the language in the question is a symptom: specialization as the operating assumption. The better question would be what did you write about, today?

What’s your best advice for someone who wants to start freelancing today?

Do some quick math: what’s the minimum monthly income you need to sustain your essentials and maintain your quality of life? How are you going to supply yourself with that amount during the time it takes to get your first clients, file first stories, and received first payments? Once you’ve solved these two equations, just about everything else about the work of an independent writer comes down to doing what you do best at the keyboard.

Anything you’d like to add?

I think it’s never been a better time to be an independent writer. There are so many new outlets, so many adventurous publishers pushing the envelope of what we can do and how we can do it — especially online.

Along with that, though, there’s a lot of static. Exploitation. The independent writer has to learn to sift through the bad jobs, the insultingly low pay, the exploitative  networks, and find their home bases. Publishers they can trust. Paychecks that represent reality. We live in interesting times. There’s a lot of money to be made out there.

Bottom line, though: high-end curating and filtering are key services that we need, and they’re the services that publishers need as well. I’d like to see even more startups take on this challenge, and while the ones that are iterating solutions right now are pretty good, I’d like to help the next generation that gets involved in this kind of network-building to do it even better. In any case, I’m excited to be a part of what’s happening. We’re growing toward some new version of the writer’s profession.

Where can we find you online?

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