What was the snapping point and motivation that made you decide to leave the cubicle for good?
There was no real moment of truth. No one died, I wasn't facing a life-threatening illness, nothing like that. I was 24, loathe to get up before 10 a.m., and bored silly filing and faxing at my assistant gig. When a newspaper I'd interned for after college offered me more money than I made in a day at my 9-to-5 to write a breezy article about fall sweaters, I leapt at the chance. After writing a couple dozen of these advertorials (advertisement-article hybrids) about department store clothing, I knew I had to work for myself. Within a year, I moved to San Francisco, a plan I'd had in the works since graduating from college. I swore I'd never have a full-time staff job again. The rest is history.

Was working for yourself easier or harder than you thought it would be?
Because I leapt first and looked later, I scarcely stopped to imagine how easy or hard working solo would be. Once I'd landed, I found many things about self-employment difficult, at least initially, most notably making enough money to live on, selling myself to potential clients, sticking to any sort of work schedule - pretty much all the essentials of staying gainfully self-employed. Just because I'd decided to work for myself didn't mean I'd bothered to learn the first thing about what that would entail. I also hadn't bothered to line my savings account, line up any clients, or cultivate any contacts before I fled the cube - all things I would do differently if I could hit rewind. On the up side, I found I was a natural at sleeping in, working through the night if needed, working alone (some people hate the solitude), and working in my underwear.

Were you ever tempted to run back to a safe office job?
All the time. Still am. In fact, when I finished my promo events for The Anti 9-to-5 Guide this spring, a client offered me a four-month, 30-hour-a-week project management contract. Even though I could do the gig from home (save for the occasional on-site meeting), this was a huge commitment for me. But I was facing a hefty pile of travel bills, and in a moment of weakness, said yes. The pay was that good. This is actually the last week of my contract and I already feel as though a grand piano is being lifted off my chest.

This isn't the first time I've taken a longer-term contract either; I've done four or five on them in the past decade. The first time I did a contract like this (for a year) I bailed myself out of some beefy credit card debt, and three years back I took a contract gig so I could quickly save for a down payment for a home. Still, I think I need to cut the cord on this type of work. I've gotten to the point this autumn where I can't even imagine what it will be like to go for a leisurely stroll without thinking, "Remember to email Vendor X about the status report they never sent," which is kind of sad.

What has been the most important thing you have learnt through your experience?
Wow, good question. When I first began freelancing I never imagined I'd be giving talks, teaching classes, and writing articles and books on the topic. In fact, if you'd have asked me when I was 24 to stand up in front of 100 people and talk about anything at all, I would have sprinted to the nearest exit. I was actually pretty shy back then. So to learn how to negotiate contracts, market myself, talk in public, and help people with their own career questions has been a wonderful ride, not to mention a wonderful set of skills to acquire. But that's what I think separates self-employed people from nine-to-fivers: we're endlessly flexible, always acquiring skills we never thought in a million years we'd one day be honing, constantly moving in new directions, and damn good at advocating for ourselves. As a result, I think many of us are better prepared to navigate the employment market than our wage-slave counterparts who haven't changed jobs in 10 years and have no idea how to ace an interview.

Do you have any handy tips for staying on top and keeping organized?
Do the pesky little tasks as you go, don't save it all for one big burst. I used to be a One Big Burst gal, putting off filing project paperwork and sorting tax receipts to the point where I'm forced to spend the better part of a day getting caught up, usually when I can't find some important piece of paper or tax time rolls around. It's much more painless, though, to bite off a few minutes of administrative work each week, preferably at the end of the day when you're less than fresh. (Save your freshest hours for your creative work.) It can even be helpful to block off certain hours of the month for your admin chores: invoicing, non-pressing correspondence, marketing, etc.

I have found when I take the time (one hour, one day, one weekend, whatever) to implement a new organizational system, I always (a) wonder why the hell I waited so long, and (b) find it infinitely easier to keep track of whatever it was I was trying to keep track of. For example, I'm really getting into spreadsheets these days. For years I've had one that tracks my invoicing and another that tracks my annual tax expenses. But I recently made a spreadsheet to track my writing assignments so I can easily see what's due when and what story still needs research, photos, and/or invoicing. And a friend just sent me a template she made to track her progress on writing a book, which I plan to use for my next book to keep on top of chapter deadlines and word count. Geek heaven!

After a tough day of work, what are you favorite ways to relax?
Shooting up, picking up unsavory strangers in bars, and knocking off a couple of banks would probably sound more glamorous. In reality, I like to take my mutt to the beach or dog park, go out for steak or sushi or ice cream or something equally delish, read funny books, blog , go to book readings, see the occasional movie or live band, and watch rock documentaries (I'm a sucker for the seventies). I also used to do more yoga and hiking and road trips. And once, earlier this year, I spent an hour on a craft project (a homemade earring rack), which tickled me to no end. I'd like to do more of all these things in 2008, and maybe even cook a nice stew.

Who are your working class heroes?
I love the same funny writers everyone else does: David Sedaris, Sarah Vowell, Anne Lamott, Steve Almond... But I'd have to say my real heroes are the freelancers on the rise whose work I've come to know and love in the past few years, several of whom I've come to know personally: writer Judy McGuire, who's as snarky and funny as they come; writer/illustrator Ellen Forney, whose performances of her work impress the hell out of me; writer Diane Mapes, whose ongoing news of book deals, newspaper columns, and assignments from enviable publications keeps me reaching for more too; writer/instructor Angela Fountas, who got a couple of kickass grants this year and does a tremendous job of giving back to emerging writers; writer/blogger Ariel Meadow Stallings, who's got the online social media thing down; illustrator Nina Frenkel, who's one of the most talented and prolific thirty-somethings I've ever met; erotica writer/editor Rachel Kramer Bussel, who besides being mind-bogglingly prolific is pretty dang fearless - I mean, if writing erotica isn't literally putting your ass on the line, I don't know what is.

I don't think someone has to be a stranger who's been pulling in six figures for the last decade to be a hero. The successes all these women have achieved feel accessible and within reach to me, which I find all the more inspiring. It's not as daunting as comparing yourself to, say, Michael Chabon or J.K. Rowling and thinking, "Will I ever be that brilliant or rich, will I, will I?"

Finally, what projects are you currently working on and what's next for you?
Since this is my last week of that fat client contract I mentioned earlier, I plan to sleep and pet my dog a lot and maybe even buy a new pair of shoes next week. I have a new book to write, so I'll be starting that in November. With the exception of keeping up with my blog and writing an article here and there, I'll be working on the book full time until spring. I also plan to paint my office a nice bright shade of light green and figure out some nifty stencil design to use for accents. I think I'm looking forward to that the most.

Make sure to check out Michelle's blog and if you'd like to learn more about going anti 9-to-5, then check out the book.