How to Be a Six-Figure Freelancer: An Interview with Matt Villano

Matt Villano is the kind of professional freelance travel writer we’d all love to be: not only has he cleared six figures annually since 2008, but his income stream was the best and busiest it’s ever been this September. Here’s a success story that you don’t want to miss reading!

I’m always preaching to writers about the need to be known as an expert in some area. You’re one of the success stories that flies in the face of that, writing about a wide range of topics like poker, personal finance, family travel, social responsibility, whales, wine, and many more. Do you pitch yourself as a guy who can research and write virtually anything or is it just a series of one editor at a time asking for more?

I agree that we writers need to be known as knowledgeable in some area; in my case, after doing this for 15 years, I guess I’ve just established a certain comfort level with a few biggies. You mentioned a few: gambling, family travel, social responsibility, whales. Some others: business, technology, parenting and education.

I definitely wouldn’t consider myself an “expert” in any of these areas, though. I know enough about the subjects to go out and get an assignment, find the right sources and get what I need to inform a story that’s informative, balanced and tough. Specifically, when I pitch editors, I sell myself as a generalist who has covered the particular subject matter previously. Then I provide clips and/or URLs to back up my claim.

You also probably make a better living than most freelancers out there because you always have a series of corporate projects and newsletters going. How did you get into that and how do you go after new business?

Let me start this answer by reciting what has become my professional motto: Writing is a craft, freelancing is a business. I make a good living at this because I don’t see myself as an “artist.” Instead, I see myself as a small business owner—someone who does what he must do to minimize overhead and maximize profit. This is why I do corporate work at all—across my “line” of “products,” it is the cash cow. (In case you’re wondering, travel writing is, by far, the loss-leader.)

I learned in college—journalism school, mind you—that corporate work would pay the bills; some friends and I had a Web development company and I was the copy guy. Since then, I’ve always made sure to have some form of corporate stuff going on—copywriting, marketing collateral, white papers, speeches, and so on. Writing and editing newsletters also are a big part of my corporate business. I pitch this work the same way I pitch more traditional journalism stuff. I research prospective clients. I see the kind of content they are creating. I get a sense of how I might be able to contribute. Then I track down the marketing and/or communications teams. The first volleys usually are innocuous—I ask for a informational interview-type meeting to discuss ways in which we might collaborate. During that meeting, if the prospective client is open to hearing what I’ve got to say (sometimes they have very specific needs), I break out my ideas and go from there.

Your portfolio site has so many writing credits on it that it makes my head spin. How many projects are you typically working on at one time?

It varies. September 2012 [was] my busiest month ever, and at the peak, I believe I counted 45 projects on the spreadsheet. Remember, because of my corporate clients, not all of those projects are “articles” in the traditional sense of the word. Depending on how many telephone interviews I can schedule, I might touch four or five different projects in a given day. During an average (6-day) week (I never work Saturdays), I’ll file anywhere from 10 to 12 projects (including three or four blog posts for my family travel blog at Parenting.com).

It’s worth noting here that because I’m a work-at-home father to our two daughters, I keep an interesting (read: insane) schedule. Mondays and Wednesdays are basically off-days (though in a pinch I can book emergency interviews after my wife gets home around 3 p.m.). Tuesdays and Thursdays, I bring in a nanny for five hours a day so I can do interviews and moderate corporate Webinars. Generally speaking, unless I’m traveling on assignment, I use nights (from 10 p.m. to 2 a.m.) and Fridays to write.

You seem to have a healthy split of print and digital media paying the bills. Where do you see your career headed in three years, five years? How will things change?

Thanks for the kind comment about my portfolio. Print and digital media currently comprise about 55 percent of my workload; corporate work represents the other 45 percent. Interestingly, however, the corporate work represents about 70 percent of my revenue. This means that’s paying most of my bills. I’m not sure this will change too much over the next three years; I plot out 1-, 3-, and 5-year plans every January, and my current 1- and 3-year strategies follow existing breakdowns pretty closely.

Long-term, I do see the mix changing a bit. I’m working on some long-form projects and hopefully one or two of them will assume a 15- to 20-percent chunk of the revenue stream. I’m also in the process of expanding my corporate business a bit. I’m going to sound like a total MBA nerd saying this, but our family’s economic realities necessitate that I pursue work with a greater ROI. (Translation: If we’re gonna have another kid, I need to make more money.)

Two-part question: What advice would you give to a beginner who wants to get into travel writing tomorrow? What advice would you give to a part-time freelancer who wants to make this a real job?

I give workshops and talks about freelancing pretty regularly, and the advice I give aspiring travel writers is this: Unless you are famous 80s actor with gobs of money in the bank or you’re one of those people who has no problem amassing incredible amounts of credit-card debt, NEVER plan a freelancing career around travel writing exclusively. In fact, I’d say that if you plan a freelancing career around any one type of writing, you are destined to go broke or go crazy trying not to go broke. The keys to the business (there’s that word again) of freelancing are to diversify and to stay flexible. I’ve written about this for Writer’s Digest and can’t stress it strongly enough. When times get tough, when the certain industries nosedive, this is the only strategy that enables you to survive over time.

For those who want to make freelancing a “real” job—whether they’re part-time freelancers or people who currently work in full-time staff jobs—I reiterate the mantra: Writing is a craft, freelancing is a business. If you choose this career path, you need to figure out a way to minimize overhead and maximize profit. That means you have to teach yourself how to write quickly. It means that sometimes you have to settle for a piece being great instead of exceptional. It means you shouldn’t be haggling with editors over edits unless the edits make a story a) erroneous or b) something you would never in a million years think of writing. IMHO, if you want to get all artsy-fartsy and pour your heart and soul into every single word of every single article you write, full-time freelancing is not for you. What’s more, if you’re really keen on doing dozens of press trips and/or spending night after night “networking” and reading your own work at industry events, you are destined to fail. Full-time freelancing requires constant and consistent ass-busting. If, at any point, you think it’s easy, you’re not working hard enough.

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In more than 15 years as a full-time freelancer, Matt Villano has penned pieces for publications including The New York Times, The Wall Street Journal, USA Today, TIME, Sunset, Backpacker and Entrepreneur, to name a few. He blogs about family travel for Parenting.com, contributes to a weekly gambling column in the San Francisco Chronicle, and has blogged about adventure travel for the U.S. Travel Association. Learn more about him at Whalehead.com.

Interview conducted in October, 2012 by Tim Leffel and edited by Kristin Mock.

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