Photo by mark sebastian

A self-described cubicle expat, Michelle Goodman previously authored The Anti 9-to-5 Guide: Practical Career Advice for Women Who Think Outside the Cube for Seal Press, and has recently followed it up with My So-Called Freelance Life: How to Survive and Thrive as a Creative Professional for Hire.

Here are the highlights from a conversation with Michelle Goodman that was probably more fun than we were allowed to have. There’s also a special bonus round for reader participation:

How and when did you make your escape from the cubicle? Was it a long evaluative/meditative process or did you just take the plunge?

No, it was not well planned at all. I was 24 and I decided to move from the East Coast to the West Coast. And I decided “Well, I’m never gonna have a day job again.” I was stubborn enough to kick my day-job to the curb… a little too soon.

I would have stuck out the 9 to 5 a little longer, not necessarily because I felt like I needed three more years of it …, but had I taken the time to cultivate some stuff that really would have helped me work on my own.

Photo by mark sebastian

I didn’t know the first thing about running a business, I could have taken a one-day workshop on that, which you could take at Score for $100, and it would have helped.

I didn’t have any money, I didn’t have any clients, no contacts on the West Coast, some work samples…but there was no plan. I just did it.

So if you could go back to your younger self or talk to a roomful of travel writers/travelers who want to be cubicle expats, what would you say?

Work on getting clips now. Don’t wait until you’re leaving the job. It’s actually such a great opportunity, while you have the cushion of a regular paycheck, to be saving a little—I don’t know, “saving” seems like such a funny word to say right now in this economy…

Everybody’s different, but I feel like my 20s were so much about exploring. I did a lot of exploring and traveling on the West Coast, mainly in my car or on foot.

Was this before you moved to the West Coast?

When I had moved to the West Coast from the East Coast. I originally moved to LA when I was 21, then I moved back to the East Coast and then back to the San Francisco Bay area, then up to Seattle when I was 30.

Every time I went to a bed and breakfast or a new backpacking trip or hike, I wish I’d been more savvy about either doing the article in advance or [making] pitches and getting an assignment.

I would say to start looking at everything as an opportunity for a story, whether it’s non-fiction or a creative essay… that may not be so much of a how-to travel thing. Take the camera, the notebook, and the tape recorder (or the laptop) and travel everywhere.

Practice documenting your trips; practice your craft.

Photo by ~MVI~

One of the best parts of both your books is the idea that you don’t need to be a trustafarian or have a rich partner to explore your options or explore your world.

I think some of us who are attached to the unconventional career realm are better equipped in some ways for an economy like this where people are terrified that they might not have a job next week.

If you’re used to contracting and you know how to get contract jobs and you’re skilled at moving around and being flexible, you’re gonna fare better. Even if you’re not someone who relies on freelancing as your sole income, you know how to moonlight and… supplement in tough times.

You mention building client and contact bases. How would you recommend travel writers choose their clients or publications?

…On the one hand, you should absolutely approach the publications that are publishing on topics that you’re really knowledgeable about or interested in. It’s helpful to become an expert in a couple of little niches.

[Editors] would rather have someone who knows what they’re talking about, like the person who knows all the small restaurants in Spain.

Another part of developing some niches is that you have the potential to make more money because you don’t have to re-learn the topic every single time. The downside of that is that you can get a little bit bored or burned out writing about the same thing. That’s why I think it’s nice to have maybe two or three [niches] that are unrelated.

You also have to look at what the markets you’re interested in pay. I am all for writing on the topics that you’re most passionate about, but if you happen to be getting paid ten cents a word for those and there’s something you know you can do that you’re a little bit less [passionate about] but you can make some more money off it, then go for it.

Maybe it’s a trade travel publication. There actually are trade publications like “Retail Store Displays for Stores Like REI.” Or maybe you’re writing catalogue copy. These can help balance out the fact that the travel publications you want to write for aren’t paying as much.

Photo by Shayan (USA)

Do you think there’s a corporate ladder in the writing world, or is it possible to jump in with a killer book and rave reviews?

There’s so many different ways people do it; there’s no formula for the bestselling book and how you get there. Some people go from “I started a blog for kicks and it’s the first time I’ve really written” to having the book because of that blog.

Some people start with the articles in newspapers and magazines, go to columns, and then to books. Some people go right to books. There’s no real “you have to do it this way, you have to do it that way” thing. You don’t have to get your master’s in journalism or creative writing.

Especially if you keep writing books about the technical aspects of freelancing. All people need then is a copy of Bird by Bird: Some Instructions on Writing and Life
and Ariel Gore’s How to Be a Famous Writer Before You’re Dead and they’re good to go.

One argument I do not buy into for writers is (and I know all of the MFA people will hate me now) the people who got their degree 30 years ago and say “it’s the only way I network. It’s the only way to make connections.”

I think it’s the most ridiculous thing in this day and age. We have the Internet. And we have people barely able to afford college yet you’re encouraging people to stay and get two more years of higher education on top of that? I’m not against it at all; I still weigh the options of doing a low-residency program myself.

But travel writing—you have to go and travel. A classroom’s not going to help that much. You can take a couple of classes online or workshops to help you with the craft and work on your pieces, but you have to go live and experience and all of that.

School of life!

Yeah, man!

So for those writers who are starting with unpaid blogging gigs and places to showcase their work, how can they make that jump into jobs that at least help to pay the rent?

Somebody asked me recently “What should I put in my blog and what should I pitch?” and I think the value in having a blog is if you have no other samples and you’re actually doing posts that are beyond journal entries—posts that might be tips for travelers of some kind or a review of a restaurant or place you stayed at or something.

But don’t fall into the trap of spending so much time on your blog that you could spend pitching publications.

I think the only way to make the jump is to basically get out there and pitch. I know it’s hard; it’s hard when you don’t know an editor, it’s hard for them to take a chance sometimes with someone they don’t know, but so many publications are still using freelancers. I would go to websites like MediaBistro.com or Masthead.org, the newsstand even, and continue to send queries.

But it’s not enough to just pitch in the dark; you really have to know people so you have to go to local events in the community.

If you’re in a major metropolitan area—or even if you’re not– maybe it’s worth making the trek for an hour to get to the writing center or arts center that has those once-a-month talks.

…[G]o meet those people or go to parties through your local writing organization and meet other writers who are often the best source of referrals and the best way in not only to a publication but to an editor.

I know a lot of people probably think “Ooh the competition, I shouldn’t tell anyone what I know,” and you have to be careful about not giving too much away when you don’t know somebody because there are some unscrupulous people out there.

But they are few and far between, and one of the best ways to get introductions is through other freelancers who either don’t have the time to do the work or have maybe outgrown a certain editor or happen to be very busy that month and are happy to take you under their wing.

Keep pushing it. Set up little goals for yourself—”I’m going to attempt to get in the door with one publication a month” or whatever you have time for. Attitude counts as well.

I think a lot of us think, “I have to have ten years under my belt before I can approach my local newspaper or The New York Times,” and that’s really not true. There are lots of people I know who have been working as a freelance writer far less than me and they’re all “I pitched [the New York Times] this thing and now I’m writing for them.”

At the same time, if you have few clips, you would do yourself justice to work your way up a bit.

Photo by moonjazz

What would you say is the biggest mistake that freelancers—especially beginning freelancers—make?

Thinking that you can tell the editor what they need. …[P]eople do not necessarily look at the publications and see what the different sections are, what the word count is in the sections, and what kind of material is being fit into each section. And they’ll go to a publication that’s not an outdoor publication and say, “I want to profile this guy who’s climbed K2.”

Then there’s people who say, “Well, I know I was assigned this, but it turned into a first-person essay that was kind of like a short story on a completely different topic; do you think she would go for this?” And I say, “No, because that’s not the assignment!”

Make it as easy as possible… to say yes, because if it’s not the right length or tone or style, you’re just giving them more reasons to not respond.

It’s a mistake that I think a lot of freelancers make. And what goes hand-in-hand with that are the people who say “I don’t want to be edited.” There are people out there and you won’t like their edits and you’ll be pissed that they cut your best paragraph or flattened all of your jokes, but I can tell you from being on the other side that you actually learn a lot from a good editor.

You learn how to write a better story, learn these tricks of transition and ways to attribute things, ways to better structure a paragraph…. Publications pay so low as it is, that’s an added benefit, working with a good editor.

Editors will take an okay writer who does everything they ask over a kick-ass writer who’s unreliable. Any day.

Finally, can you give the folks at home an exercise to get their freelance juices flowing?

I think this will be cool; I recycle my article ideas for more than one publication a lot, and that seems to be a good way to go financially because you’ve already done the research.

Pick an idea that you’ve either been nursing or wrote about in your blog or think of a trip you’re taking and then think of three different places you could pitch it to—that would not be competing.

Say, one of your local newspapers, a small piece for a magazine you’d like to break into, and maybe a Q&A, or whatever it is. Find three different ways you can spin it.