Michelle Goodman is like the impossibly cool, “been there, done that” older sister to thousands of non-traditional workers. Or as Michelle calls them, “cubicle expats.” Her first book, The Anti-9-to-5 Guide: Practical Career Advice for Women Who Think Outside the Cube, was published in 2007 by Seal Press and inspired many a reader (including this one) to leave the 9-5 grind and strike out on her own.

Now, she’s at it again. Michelle’s second book, aptly titled, My So-Called Freelance Life: How to Survive and Thrive as a Creative Professional for Hire, is due out this fall. Her writing has also appeared in numerous publications including Salon, Bust, Seattle Times, and San Francisco Bay Guardian.

WOW! was thrilled to get Michelle’s insights into dealing with rejection, breaking into dream markets, and handling all the other ups and downs of freelance writing.

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I felt pretty badass when I sold a piece to Salon on speed dating back in 2000. I don’t think I had any national clips at the time, unless you count writing catalog copy about vacuum cleaners. The way I got the assignment was somewhat stealth. I was writing a weekly web column on freelance markets for a now-defunct site called Content Exchange. I decided to profile Salon for the column, so I’d have a legitimate excuse to call one of the editors and have an actual conversation about breaking into Salon with him. Because my story idea was time sensitive (once upon a time speed dating was news), I pitched the editor at the end of our phone call. Shameless. But effective.

Everything. Seriously. I didn’t save money, contacts, or clips before leaving my day job. I had only one client lined up, with no backup income in sight. And I knew nothing about running a business, which is essentially what freelancing is. In other words, I didn’t know the first thing about pricing, contracts, negotiation, or marketing myself without being pathetic or annoying.

What I did have, however, was the fantasy that clients would somehow magically find their way to me (and this was before there were websites), and my bills would all magically get paid. If only I’d spent a little time educating myself about what self-employment entailed and padding my checking account before I took that running leap, I could have saved myself a lot of fumbling in the dark—not to mention credit card interest rates.

I knew some of them from my extended freelance and personal networks. Others were sources I’d interviewed for articles in publications like the Seattle Times and BUST magazine. Others were just people starting cool-sounding businesses and nonprofits that I discovered through web searches. Also, the gals at TheRealHot100.org graciously gave me the contact info for some of the inspiring women profiled on their site (an astronaut in training, a women-oriented sex shop owner, and a minister, to name a few). Plus, one interview always leads to another. Invariably sources will tell you, “You should really talk to so-and-so. Here’s her contact info.” And then you just add that name to your “to call” list.

I kept all my sources straight through multiple Word documents and Outlook folders. I had folders and files for “career changers,” “entrepreneurs,” “flex timers,” “women in the trades,” “overseas workers,” “craftsters,” “side giggers,” and on and on. For the new book, I actually used an Excel file to keep all my sources straight—not so much who’s who, but who I’d already interviewed and who I was waiting to hear back from—that sort of thing.

I did go straight to Seal. I had always wanted to work with them and had been following their books for years (they were once based in Seattle, where I am). And I’d published an essay in one of their anthologies (The Moment of Truth: Women’s Funniest Romantic Catastrophes), knew some other writers doing books with Seal, and was writing for BUST magazine at the time. Seal seemed like a natural fit. Basically, they were on my “dream client” list.

The best advice I received from other authors (as well as Brooke Warner, my editor at Seal) was to write the book I’d write if this were my one and only chance in life to do so. Stringing together thousands upon thousands of words is as grueling as it is joyous, and you’re going to have to live with your topic—not to mention the sound of your own voice—for many months on end. So, if you don’t love the subject matter to death, there’s absolutely no point in doing it. Put another way, if you’re writing a book “to get rich,” you’re definitely in the wrong line of work.

Yes, definitely easier. Mainly because I’d had the chance to learn what wasn’t an effective use of my time (doing three times as many interviews as I needed or writing three different introductions to each chapter, for example). And while The Anti-9-to-5 Guide required research on some topics I initially knew very little about—such as working on Antarctica or starting a nonprofit. My So-Called Freelance Life was all familiar terrain. I still did a load of research, but there was no learning curve or getting up to speed on the topic needed. Plus, I included some quirky anecdotes about my freelance life, which for me are always a blast to write.

Maybe not surprised me, but while doing interviews with other freelancers, I found it inspiring, even comforting, to hear that some of my freelance writing and illustration idols have the same issues, concerns, and, yes, even money woes that all freelancers do. It’s not that I wish them any amount of aggravation, insecurity, or late payments from clients—not at all. But when you realize that a freelancer you greatly admire shares the same career struggles and frustrations as you, suddenly you don’t feel like there’s any secret key to the solo workers’ kingdom anymore. You realize you’ve already arrived so to speak. And because your heroes are human rather than, say, some Paris Hilton type of pod person with a plastic-perfect life, their successes seem that much more attainable to you.

I’m a huge fan of cherry-picking your clients as best you can, rather than waiting for them all to come to you (unless every last dream client is banging down your door). Even the most seasoned freelancers will tell you that they get stuck in the same old ruts, working for the same old clients they know they’ve outgrown, just because it’s easier than making the time and getting up the nerve to approach the clients they’d most love to write or illustrate or take photos for.

Other than that, four to six months’ savings, a decent health insurance plan, an accountant, a website, and a thick skin are essential ingredients.

Admittedly, I did not have much of a life while writing My So-Called Freelance Life. I did it in four to five months, and most of the time, it was all that I was working on. My dog and boyfriend are very happy to have me back, and I am elated to be getting a full eight hours of sleep again.

“Licking procrastination is all about playing mind games with yourself.”

As you’ll probably glean from the book, I still fall prey to the dreaded P-word from time to time. (Damn you, YouTube!) When a deadline is dire, I’ll have to shut off the phone and unplug the modem. Otherwise, finishing the project just doesn’t happen, or at least, it doesn’t happen without involving an additional six hours of emailing and IM’ing friends about nothing of consequence.

This probably goes without saying, but if you don’t work, you don’t eat, so there’s always that motivation. I’m single and bootstrapping it all the way, so it’s not like I have anyone to pay my bills for me. Besides, the more deadlines you have on the calendar, the more you learn to just motor through the pile of articles or projects on your plate. When you’re mistress of your own schedule, it doesn’t take long to realize that if you have three 1,000-word articles due in a week—articles that require locating and interviewing sources—you need to start now, not the day before they’re due.

Licking procrastination is all about playing mind games with yourself. These days, I’m loving the piecemeal approach to writing articles (write the intro one day, the middle the next, and the ending the day after that) while I research and edit other articles on my plate. So, instead of having to write 1,000 words in one four- to eight-hour sitting, I may only have to write 300 words over the course of an hour or two. Much easier to face.

Write about what interests you because you’re going to have to continually read up on and talk about the topic. I’ve always been a champion of flex work and the freelance life, so this topic was a natural fit for me. Of course, some niches (like business) pay better than others (like book reviews), so you may want to cultivate a couple areas of expertise. Truth be told, I’d recommend doing that anyway so you don’t get fried on one topic. Besides careers and self-employment, I’ve also written articles and essays about dogs, sex, relationships, and home ownership.

It’s pretty much a must these days because even if you’re making that almighty $2/word or $3/word for your articles, there are still rewrites to drive your rate down. And no matter how efficient an interviewer you are, you always get more information than you need. So, you might as well put it to good use and start thinking about where you can resell the story from the get-go.

For example, say you were assigned an article about punk rock yoga for a national women’s magazine but you learn that there are a number of quirky types of yoga out there catering to certain demographics (doggie yoga comes to mind). So, you pitch a round-up of the five hottest types of alt-yoga classes to a national mind/body magazine. And to your local weekly newspaper. And maybe you profile the woman who’s built the dog yoga empire in your town for a local business journal.

The possibilities are endless, as long as you’re not violating any contracts you’ve signed (something I talk about in the book at length that I can’t possibly do justice here). And the beauty of recycling story ideas is that you boost your income by reducing the hours you have to spend researching the topic each time you cover it.

“...the beauty of recycling story ideas is that you boost your income by reducing the hours you have to spend researching the topic...”

I think it’s been both. There’s that tendency to think, “If I was in New York, I’d probably bump into at least three major magazine editors just on my way to the post office today.” It’s true that Seattleites do have to work harder at schmoozing online—and get up a little earlier—if we want to get in bed with New York editors. But, I’ve found that the web has really, really helped reduce that sense of “But they’re soooo far awayyyyyy!” Both past clients and writers I’ve connected with in various online forums have referred me to editors in New York. And the website mediabistro.com keeps you so dang connected to the heart of the publishing industry it’s scary.

I occasionally have had the chance to meet out-of-town editors when they’ve swung through the Northwest on business. And I just consider meeting with editors and other writers in New York a really great way to write off visits with the friends and family I have there. (I’m originally from New Jersey.)

One advantage of working from Seattle is that I might get a lead on a local trend that I can spin into a national story long before anyone in New York knows about it. So in that regard, I have a leg up on the 9 million writers who live in Brooklyn.

It’s more of a struggle to find the time to use all the story ideas I have. When you focus on one subject area, you develop relationships with industry leaders, publicists, and other key sources, and they’re constantly feeding you new story ideas. Plus, one story can often beget a couple more story ideas. So, I’m happy to report that I have a story list a mile long.

What’s that saying? If you’re not falling flat on your ass from time to time, you’re not trying. Or something…. The thing about rejection is it happens to everyone, even the biggest and best. And the more you put your pitches and written pieces out there, the more you’re going to get rejected. But, the more sales you’re going to make too. And the more you’re going to learn—about what you could have done better, what a particular editor or organization likes to see in a submission, and so on. My strategy has always been to have several pans in the fire at once (pitches out to editors, applications for residencies, et cetera) so that if one opportunity blows up in my face, I still have the others to look forward to.

I haven’t noticed a change. Companies still need to get their copy written and edited. Magazines, newspaper, and websites still need content. And freelancers are cheaper than staffers, so you do the math.

Some organizations are tightening their freelance budgets or consolidating staff positions (witness newspapers). And many freelancers far more seasoned than I will lament that publishing outfits are still paying the rates they paid in 1985. But, that doesn’t mean it’s a lost cause. It just means that you need to work for a variety of publications or companies. That way, if one market dries up or one editor or manager leaves (invariably, they will) and doesn’t “take you with them” to their new employer (sometimes they will, sometimes they won’t), you’re not left twisting in the self-employed wind. It also means staying on top of technology changes in the publishing industry and writing for a variety of media (broadcast, print, glossy, web) so that you’re not left SOL and scratching your head if one morphs beyond recognition.

“Talk shop with like-minded freelancers. Swap ideas and suggestions. Collaborate.”

This happens to me at least once a year. Especially if I’ve hit a financial snag (client dries up, car needs $500 of repairs). In fact, I’m starting to think there’s some “financially down and out” freelance pheromone that gets released into the marketplace because clients never fail to call and offer me financially tempting long-range, full-time contracts when I’m at my neediest.

I’d prefer to not go back to a day job, but I won’t say never. If the freelance economy collapses (doubtful) and working in an office suddenly becomes the only way I can pay my bills (sigh), I’m there. That said, I’d be negotiating like mad for telecommuting and flex time privileges.

In fact, just last year, I took a 30-hour-a-week, four-month-long contract with one company, though I did telecommute 90 percent of the time. After writing and promoting my first book, I needed to replenish my checking account—and fast—and biting the corporate bullet for a few weeks seemed like the best way to do it. Plus, I still got to work in my pajamas.

To survive the financial ups and downs, do everything in your power to avoid living check to check, even if it means keeping your day job a tad longer, taking some freelance work you’re not wild about, or working a bit of overtime to line your checking account.

To survive the emotional rollercoaster, get yourself some freelance friends, like now. (Start with your friendly neighborhood writing organization.) Talk shop with like-minded freelancers. Swap ideas and suggestions. Collaborate. And if you need a shoulder to lean on or someone to vent to, call your fellow freelancers, not your clients. Not feeling like you’re an island will do wonders for your morale.

I’m enjoying writing articles at the moment. I plan to keep doing that for a few months and hopefully expand into some new publications and finish a few first-person essays I have clogging up my hard drive. I have a couple of ideas for future books, but right now, it’s glorious to not have a huge book deadline hanging over my head. I’d love to savor this newfound time for at least a few weeks longer before I dive into a new book proposal.

Thanks, Susan, and WOW!. It’s been fun! To find out more, visit https://www.anti9to5guide.com/.

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BIO:

Susan Johnston is a Boston-based freelance writer who covers careers, entrepreneurship, and lifestyle topics for a variety of print and online publications. Her writing has appeared in The Boston Globe, DailyCandy.com, MediaBistro.com, Self, and WomenEntreprener.com. Read more on her website (www.susan-johnston.com) and blog (www.UrbanMuseWriter.com).