When Michelle Goodman kissed 9-to-5 life goodbye, she never turned back. Now at 40, this Seattle-based author shares some of her wisdom on kissing the cubicle goodbye, publishing books and making time to blog.

Kristen Fischer (KF): You’ve written this fabulous book, The Anti 9-to-5 Guide. How’d you get the inspiration to come up with the book? Tell us a little about your career history.

Michelle Goodman (MG): I studied journalism in college, briefly worked as a newspaper reporter and then a book publicist, then started working as a freelance writer and editor. That was in 1992, three years after I graduated college.

Ever since I went solo people have been asking me how I find clients, swing health insurance, survive the lean times, work from home without going insane—all the usual questions. So besides crafting copy on video games, marital aids, and home colonics, I started writing about the freelance life, first for sites like Guru.com, then—after the dotcom bubble burst—for magazines and newspapers.

The Anti 9-to-5 Guide actually stemmed from a story I wrote in 2005 for BUST magazine, called “Wage Slave: A Day-Job Survival Guide for Arty Girls.” I thought there was a book about alt careers in there, and luckily, my publisher did too.

KF: What exactly are you doing now?

MG: I started writing a new book in November, and that’s pretty much all I’m working on now, as it’s due in about five minutes. (More on this below.) In the past three months, I’ve also taught a couple classes and written a bunch of articles on everything from doggie daycare to dietarily divergent couples. But now that I’m in the home stretch of the book writing, the only other things on my plate are my blog and this fun column I do for the Seattle Times called “How’d you land that great job?”

KF: Compared to the many readers on this site just starting out, you’re a veteran. What wisdom do you have to share about leaving your job in a practical way?

MG: Like I talk about in The Anti 9-to-5 Guide, milk your day job for all it’s worth while you still have it:

• Volunteer for projects that are going to yield you the best possible samples for your portfolio.
• Stay on your manager’s good side so you have excellent references (and stand a better chance of turning her into a future client).
• Take the company up on free business and software training.
• Save all the money you can so you have some cushion when you strike out on your own, at least three months, though six is even better.
• Pay down credit card debt and resist the urge to splurge on shoes, software, and anything else you don’t absolutely need.
• Start freelancing before you give up your day job to (a) see if you have the stomach for it; and (b) build up your portfolio/client base.

KF: You also talk a lot on your website about the common mistakes you made in leaving your 9-to-5 job. What were some of the mistakes?

MG: Quitting without any contacts or freelance leads. Not having a cent saved. Barely having any samples in my portfolio. Having the business sense of a fruit fly. Waiting two years before I took a business class. Not realizing I had to continually market myself. I could go on and on.

Basically I was 24 and working in book publishing in New York one month, and the next month I was driving to California, where I planned to live. Somewhere around Kansas, I vowed I’d never be someone’s employee again. I kept that promise, but I could have made things a lot easier on myself if I’d gotten a bit more writing/editing experience and business know-how under my belt before I gave up the day job.

Michelle’s book, The Anti 9-to-5 Guide.

KF: What do you love most about what you’re doing now as a writer and a teacher?

MG: With the writing, I love that I’m getting away from the corporate work I spent so many years doing and that I’m dedicating more time to the paid writing projects I most enjoy: magazine and Web features, humor pieces, first-person essays, books, and the like. It feels really good to be finally putting that journalism degree to use on a full-time basis.

I don’t teach that much, maybe an online or live class once every quarter or so. Teaching isn’t my main focus. But I do it every once in a while because it’s a lot of fun. It’s easy to get jaded when you’ve been doing something for years on end. But the students’ enthusiasm is contagious. And when you realize how much knowledge you’ve amassed over the years, and how helpful it can be to others, you start to feel warm and fuzzy about working for yourself all over again.

KF: Tell us a little about your typical workday.

MG: How about my ideal day, because there isn’t really a typical one: Wake at 7 or 8, walk the dog for an hour, then hit the computer and write till lunch. Eat. Play catch with the dog. Return to the computer and write for three more hours. Answer email and phone messages before walking the dog once more and having dinner.

Unfortunately it never quite works this way. Often an editor will email at 9 a.m. to say she needs a slight tweak on an article I turned in last week, ASAP. A source I’ve been trying to reach for days will call at 10 a.m. and I’ll have to take the call and do the interview then and there, even though I’d so much rather do interviews late in the day, once I’ve shot my writing wad. An editor from a dream publication will write me at 11:30 a.m. and ask for my clips and bio by end of day (which, if she’s in New York, is 2 p.m. my time). And on and on.

As the deadline for my book draws nearer, though, I’ve gotten pretty good about ignoring email and the phone till lunchtime and/or the end of the day. Otherwise, I’d never finish.

KF: What do you enjoy when you’re not working?

MG: Oh man, I have become so boring. My idea of a wild time is taking my dog swimming at the dog park, watching the Democratic debates while downing a row of Girl Scout cookies, or—if I really want to cut loose—catching a movie at the nearby second-run theater or a book reading at my favorite indie bookstore.

In the summer, I’ll try to do a little hiking, kayaking, car camping, beach combing, and/or road tripping. However, I recently bought a 60-year-old shoebox of a house that needs a serious cosmetic makeover, so my favorite new pastime is hanging out at the hardware store.

KF: How can freelancers advance their careers? Many who have been at it for years are burned out, looking for new opportunities. You’ve branched out into teaching and setting up events. What can burned out freelancers do to rev up their motivation?

MG: This is such a great question. I’ve been charred beyond recognition many times, where I’m wishing I could just dig trenches or clean toilets for a living, anything to not have to string together any more words. Besides teaching, which I talked about earlier, I’ve done the following to mix things up:

• Accept an on-site permalance contract at some big-ass corporation. Seriously. I know a lot of people in the high-tech sector, and I’m frequently offered a 3- to 12-month contract at some software giant or other, complete with cubicles and commuting. Every couple years or so, I actually say yes. I’ve done about 4 or 5 of these short-term contracts in the past decade. Each time, I pick up some kick-ass new job skill (Web community editor, project manager, book editor), I make a ton of money, and I remember exactly why I love freelancing so much.
• Cultivate a new niche. Maybe you’ve been building websites or blogging exclusively for the telecom sector and if you have to look at one more mobile phone review, you’re going to hurl. Instead of grabbing a bucket, try expanding into a new industry or subject matter, be it gaming, genealogy, or green technology. I don’t just write about alt careers and workplace etiquette. To mix things up a little, I also write about dogs, dating, and health.

KF: Tell us about publishing the book. Did you get an agent first? What was the process and timeline like? Any new books you’re working on?

MG: I had a direct relationship with Seal Press, my publisher, because I’d submitted and contributed essays to their anthologies. Seal is a 30-year-old indie press originally from Seattle (they’ve since relocated to San Francisco and been bought by a larger publishing house), and I’ve wanted to do a book for them for as long as I can remember.

A friend who did a book with Seal put me in touch with her editor, and the rest is history; they liked my proposal and gave me a contract. Since I was talking directly to the publisher, I didn’t use an agent. I think I had about nine months to write the book, but I did in six, maybe less. The book was out in stores and online six months after I turned it in.

I’m currently finishing up book number two, My So-Called Freelance Life, which Seal Press will publish in late in 2008. While The Anti 9-to-5 Guide covers everything from temping and flex time to landing an overseas contract and starting your own business, the new book focuses exclusively on the self-employed life. When I get the final cover art, you know I’ll be broadcasting it all over my blog.

Because doing books for women is Seal’s thing, the new book will be pretty women-centric too, though I suspect guys will probably steal their girlfriends’ copies, as I hear happens a lot with The Anti 9-to-5 Guide.

KF: You update your blog regularly with really useful stuff. How do you keep the content fresh and how do you make time for blogging?

MG: I make time for blogging by not sleeping. Kidding. Sort of. I’m a blog of one, so it can be tough to keep up when the client deadlines pile up. Lately, though, I’ve been all about the short-and-sweet posts that take under an hour to write and still serve up some useful freelance tip or other. I’m a big fan of profiling other anti-nine-to-fivers, doing Q&As with other authors/experts, and answering people’s burning questions about self-employment in “Dear Abby” style posts. It’s taken me a year and a half to get to the blog down to a science, but I guess that’s why they call it a work in progress.

Michelle’s new book, My So-Called Freelance Life: How to Survive and Thrive as a Creative Professional For Hire, is now available for pre-order at Amazon.com.