The Renegade Writer Blog

Michelle Goodman is the author of The Anti 9-to-5 Guide: Practical Career Advice for Women Who Think Outside the Cube (Seal Press, 2006). We talked with her about how to escape the cube and find success as a freelancer. [lf]

In your book, you focused on women who want to pursue their dream careers. Why did you target women? What are the differences between the way men and women go after their freelance dreams in particular?

Men certainly seek out flexible, autonomous work, too, but the stats say women do it more. We start businesses at twice the rate of men, and we fill a majority of the part-time and flextime jobs out there. For women, creating a self-styled career is a great way around the wage gap, mommy track, glass ceiling, and rigid workplaces that aren’t family- or life-outside-the-office friendly.

When it comes to chasing our freelance dreams, women generally have an easier time letting go of the whole 9-to-5, breadwinning thing than men do. But we have a harder time tooting our own horns and talking money—two essentials for freelancers. We worry about bragging and sounding crass, probably because some numbskull told us early on that such topics were taboo. Hopefully sites and books like ours can help the marketing- and money-squeamish get over it.

What stops people (especially women) from going after their dream gigs, whether that’s starting a freelancing career or targeting a national magazine?

Fear of failure. Fear of success. Fear that they’ll wind up living in a cardboard box under the freeway. Outmoded ideas of what A Respectable Career is. The misperception that changing gears mid-career means all previous training and experience was for naught.

Perfectionism is another biggie for women. We’ll sit on a book proposal (been there), business plan (there too), or Big-Time Magazine Pitch (yep) for months on end because it’s just not Pulitzer quality yet. Forget about the dang Pulitzer. Do your homework, write and edit the thing, then show it to a trusted colleague or two. If they say you’ve done good, take a deep breath and hit Send.

Why is it important to pursue your dream career? If the money’s good, why not stay in the cube?

If it ain’t broke, I wouldn’t fix it. If you like your job, your boss, and your salary, more power to you—why change? But survey after survey comes out each year saying that one in two people hate their jobs, think their coworkers are a bunch of monkeys, and just show up each week to collect a paycheck. So obviously something’s not working.

When people get to the point where heartburn, depression, or migraines set in every Sunday around 5 p.m., the idea of that safe, steady paycheck loses its luster real fast. A crappy work situation can quickly take its toll on your mood, attitude, even your health. I wrote the book for anyone who can relate, whether they want to give working from home a whirl, start freelancing on the side, or explore a change in profession altogether.

What are the three most important qualities someone needs to have to find a career “outside the cube”?

I mentioned the ability to toot your own horn without having heart palpitations earlier. Being able to gently hawk your skills or wares week after week is key.

Flexibility and negotiation savvy are the other two biggies. As a contractor, freelancer, or entrepreneur, you have to roll with the changes and learn to anticipate them as best you can. Changes in deadlines, project parameters, and team members can seriously screw with your schedule and income. How well you deal with this—and how well you weed out problem clients—will greatly affect your sanity and livelihood.

This is where negotiation savvy comes in. If you’re not up to speed on delicately haggling over deadlines, rates, and contracts, get there. Read a book, take a class, and brainstorm with other freelancers. Some resources I love (besides The Renegade Writer Empire):

• Laurie Lewis’ book, What to Charge: Pricing Strategies for Freelancers and Consultants
• The rate chart in Writer’s Market
• The contract negotiation services that The Authors Guild and National Writers Union offer members

Many freelance writers become sick of taking whatever assignments editors throw at them just for the money, and want to start writing about topics they care about or that can help others. Do you have any tips for transitioning from “have to write it” to “love to write it” — without going broke?

I hear people say over and over that they want to pitch new topics to their editors or break into new markets but haven’t made the time. I’ve certainly been there too; it’s so easy to get stuck in the steady-money rut.

I find designating a morning a week for a pitch session works well. Yes, this will mean shaving several billable hours off your schedule, but you will need that time free if you land a new assignment anyway. And if you can’t bear to part with a few billable hours to market yourself more, then give up a Saturday morning or an evening every couple of weeks until you’ve landed some bigger and better assignments.

Building pitch sessions into your weekly or monthly schedule is the best long-term strategy. That way you’re constantly reaching for bigger and better assignments, rather than just taking whatever comes your way.

What if you’re not sure what your dream gig is? Can you tell our readers how to figure out what it is you want so that you can formulate a plan to go for it?

Ask yourself what skills you want to learn, what friend’s career you’ve always been jealous of, what you were doing when you felt like you were at the top of your game in life, what you would do if time or money weren’t factors. Daydream and make lists.

Then do your homework and look at the finances of making such a career change, but don’t just rely on books and the web. Talk to people doing the tasks and working in the industries that have piqued your curiosity. Ask to observe them at work for a day (a.k.a. shadowing). Get hands-on experience through classes or volunteer work to see if anything on your list could sustain your interest for 20, 30, or 40 hours a week.

Do you have any tips for negotiating higher rates from magazine editors?

If an editor’s standard rate is much lower than my usual rate but I really want the clip (because I love their publication or I’m pursuing a new niche), I will say, “I normally work for $xx/word—any way you can come up in price a bit?” If they can’t, I probably won’t write for them for long, or I may decide the gig isn’t worth my time. After all, one of the best ways to raise your rates is to stop writing for publications that pay peanuts.

If an editor I’ve worked with at least a year is among my lowest-paying clients, I will say, “I love working with you, I love the assignments, and I love your publication, but I have to put on my business hat here. All my other assignments are paying me xx percent more. Do you think you can sweeten the pot?” Subtext: If you can’t come up in price, my eye’s eventually going to wander toward more lucrative publications.

Is there anything else you’d like to add?

I’m all about transitioning, keeping your day job and maybe reducing your hours while you dabble in a new career or build up your freelance business on the side. That way you don’t have to sweat the bills while trying make a go as a solo artist. Doing it on the side means you get to do it sooner, rather than spending a couple years saving up for it. And if your side project doesn’t pan out or you decide you hate the work, you still get to keep that blessed steady paycheck.

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