Successful Freelancer Spotlight: Michelle Goodman

Good Monday morning readers!

Today, I’m shining the spotlight on Michelle Goodman, author of My So-Called Freelance Life: How to Survive and Thrive as a Creative Professional for Hire, and The Anti 9-to-5 Guide: Practical Career Advice for Women Who Think Outside the Cube.

Michelle also writes a weekly career column for ABCNews.com and blogs at Nine to Thrive for The Seattle Times. Her articles and essays about alternative careers, personal finance, and human mating rituals have been published by CNN.com, Salon, BUST, Bitch, The Bark, Yahoo! HotJobs, AOL.com, and other media outlets. Michelle also writes a blog about the freelance life at Anti9to5Guide.com.

Given the fact that so many people are leaving the 9-to-5 grind, either by choice or necessity these days, I thought Michelle would be the perfect person to talk to about how to make this transition and build a successful freelancing career.

How long have you been freelancing, and how did you get your start?

I started freelancing sixteen years ago. A newspaper I had interned for after college offered me some freelance work writing advertorials about clothing trends—basically ad copy disguised as journalism.

Some of the pieces paid more than I made in a week at my day job (in book publishing), so who was I to say no? I researched and wrote these articles evenings and lunch hours, loving every minute of it. I was pretty much ruined for 9-to-5 work after that.

Did you work a 9-to-5 job before you started freelancing? What prompted you to take the leap into full-time freelancing?

I did, first as a newspaper reporter in Los Angeles, then as a publicist at a book publishing company in Manhattan. When I was 24, I quit my book publishing job and moved to San Francisco.

On the cross-country drive west (somewhere in Colorado, I think), I decided I would do everything in my power to avoid getting a full-time office job again, mainly because I considered 9 a.m. the middle of the night and hated schlepping to work every day. After a couple years of doing odd part-time jobs to offset my initially paltry freelance pay, I was off and running as a full-time independent professional.

What advice would you have for someone who wants to escape a cube farm to freelance full time?

Start freelancing on the side and rack up as many writing clips as you can before you quit. It can take several months to a year or more to work up to having a full-time freelance workload and client base. And unless you have six to 12 months’ living expenses saved, you need a paycheck of some sort while you get your freelance business off the ground.

Also, if you haven’t already, get yourself a Web site (nothing fancy—one to four pages does the trick). Not only does this show editors you mean business, it saves you loads of time doing that “So tell me about your experience…” dance.

With so many people in the media and publishing industries facing buyouts and layoffs these days, what advice would you offer to people who need to or are considering making the transition from a 9-to-5 staff job to full-time freelancing?

Screw up your confidence and start networking your buns off. Meet as many people in your field as you can, both online (via LinkedIn, Twitter, etc.) and off (via your regional writing organization of choice). Learn from them. Trade ideas with them. Charm them. These may be future editors or clients—or people who will refer you to them.

Diversify. If you’re a technology writer, don’t just rely on magazines like Wired and sites like ZDnet. Worm your way into the tech sections of in-flight magazines and general-interest sites like Yahoo! Look for paid blogging opportunities. Write for trade and alumni publications. And don’t turn you nose up at writing newsletters for the software industry or writing marketing copy for companies selling consumer electronics, mobile phones, or any other products in your area of expertise.

When you transitioned into freelancing from a 9-to-5 job, what were some of the biggest adjustments that you had to make? Based on your experience, how would you advise other people to deal with those adjustments?

Cracking my own whip was not something that came easily to me right away. My first year as a freelancer, I slept till noon, pissed away the afternoon drinking coffee with friends, and wound up scrambling to finish my work well into the evening.

Establishing routines and putting yourself on daily work schedule is a quick fix for this. So is sharing your weekly list of deadlines with a friend. Nothing beats your inner procrastinator into submission like having to admit to another human being that you watched daytime TV instead of making your deadlines.

Also, handling all the infrastructure of working solo was initially overwhelming—not to mention frustrating. It’s important to line up a computer repair guru (even if it’s just a friend you ply with free meals) asap so you don’t have to scramble for one when your laptop dies the day before a big deadline.

Ditto for finding an accountant who regularly works with freelance writers. The time to ask for CPA recommendations is not April 1st. It’s now.

Finally, while I’ve never minded working solo, many new freelancers do. Befriending other freelancers and ensuring you get out of the house at least once a day can remedy this. If you have the funds, you might want to try a coworking space, even just once a week.

As you know, it takes much more than good writing and editing skills to be a successful freelancer. In your opinion, what are some of the other traits and skills that people need to build a successful freelancing career?

Customer service, negotiation prowess, and diplomacy are key. You need to strike a balance between giving editors and clients what they’ve asked for (sticking to word counts and so on) and speaking up when you see a problem with an assignment (say, if your research proves that the article’s premise is dead wrong).

You need to be flexible, too. Project teams, deadlines, and parameters change all the time. At the same time, you can’t be shy about putting your foot down if someone’s making outrageous requests that reach beyond the terms you agreed to in your contract. (“I know we said you’d write me 1,000 words by tomorrow, but can we make it 2,500?”)

You also can’t be afraid to market yourself. Freelancing means that you’re constantly “interviewing” for the job. Fortunately, e-mail takes greatly simplifies this process.

What are the three most important things that you’ve learned as a freelancer that you wish you would have known when you first started out?

One, you don’t need to say yes to everything. Doing so has led me down some paths that took me far, far off course from where I wanted to be as a writer, in pay and in subject matter.

Two, you can never be too specific in a contract (oh, how I learned this the hard way). If you’re handed a contract that’s missing some critical details on when you’ll be paid, how much revising you’ll do, what copyrights you own, etc., by all means speak up. And if you don’t like the kill fee, non-compete clause, or anything else about the contract, negotiate your heart out.

Three, freelancing is a business. Don’t let your desire to be liked by your clients get in the way of asking for the rate you know you deserve (that is, as long as the market will bear it).

Four (can I add a fourth?), you don’t necessarily need 10 years of experience to approach the biggest market on your wish list if you’ve got the right clips and expertise.

Have you ever struggled in your freelance career? What are some mistakes you have made as a full-time freelancer, and how would you advise others to avoid those?

Hell, yes, and I list many of them (and what I’d do differently if I could rewind) in My So-Called Freelance Life.

For starters, I once made the grand mistake of getting 90 percent of my workload from one client for 18 months straight. When the company folded without warning, I was left scrambling for work. Moral of the story: Don’t let one publication or client account for more than 25 to 30 percent of your income, especially in this economy.

Many freelancers are nervous about the current economic conditions and what it means for business. How are you doing in your business, and do you have any advice on how to keep the dollars flowing in the right direction despite this current economic downturn?

I have to admit, I’m slammed. This is the case for most seasoned freelancers I know. I did have one journalism gig recently dry up, but it was just 10 percent of my income, and two new, better-paying writing gigs immediately appeared in its place.

That said, I’m a bit more on my toes than I might have been six months ago. One newspaper I write for just went through an ugly round of layoffs, so I’m well aware that my gig with them could disappear if the paper continues to falter. To compensate, I’m networking a bit more than usual and keeping my ear to the ground for new opportunities should I suddenly have to fill a hole in my schedule.

One thing freelancers can do is capitalize on (or beef up) any writing-related skills they have. If you can edit, project manage, broadcast, podcast, design, code, market, or teach, you’ve just greatly expanded your marketability and income-earning potential. I don’t just do books, articles, and blogs. I occasionally teach, copywrite, and edit too. Besides helping my bank account, I enjoy the variety.

With all the media layoffs these days, do you think that there are more people trying to make a go of freelancing? Does this mean more competition for existing freelancers?

Freelancing certainly pays better than those unemployment checks. So any time there’s a recession, you’ll see more people starting to freelance, whether it’s something they’ve always wanted to do or just something they’re doing to survive right now. Thing is, half of freelancing is knowing how to run your own business, and many new freelancers haven’t the foggiest. So the sooner you learn your way around pitching editors, negotiating rates, and deciphering contracts, the sooner you’ll have the advantage over the other folks diving (or being thrown) into the freelance pool.

Another way to stand out from the freelance pack is to cultivate two or three beats or specialties: business reporting, product reviews, technical editing, service-y health pieces, and so on. Editors want to work with someone with relevant experience and clips, so it’s in your best interest to become an expert in a couple areas. As a bonus, you won’t have to work quite so hard to find story ideas and get up to speed on the pieces you’re writing, which means you can work less and/or make more money.

In this competitive marketplace, how can freelancers increase their odds of landing new assignments, clients, and gigs?

Again, it’s all about the networking. See mediabistro or your local writing center of choice. Join a subscription service like Freelance Success. Find out what email discussion lists your writer pals subscribe to and join them.

But don’t limit yourself to mingling with other freelance writers. Designers, photographers, programmers, and project managers can also be fantastic sources of job leads. Attend a happy hour hosted by a local graphic artists’ association, and you’ll face far less competition for any writing leads in the room.

Where is the future of freelancing headed? What should people be focusing on, and is there work that they should avoid or shift away from?

The Web has made it a snap for just about anyone to hang their shingle as a freelancer. For the most part, this is a blessing. As a result, more and more people are freelancing and/or telecommuting with each passing year. And since working with freelancers and telecommuters saves companies major overhead dollars, this trend promises to continue.

The downside of the Web making freelancing so accessible is that there are a lot more bogus freelance jobs listings out there. As a rule, I’d stay away from any Google ads, e-mails, and sites that say “Make $$$ from home!” Almost all of these are scams. Also, skip the craigslist ads for freelance jobs that don’t mention a company name or Web site. Why waste your time shooting in the dark when so many ads for freelance writers on craigslist are posted by people “who have an idea for a book and just need someone to write it for them” or new blogs/websites/magazines with no freelance budget to speak of?

I’m also not a fan of freelance bidding sites like Elance, though I know some new freelancers with empty portfolios find these sites helpful for landing those first few samples, despite the lower pay many of those jobs offer.

Call me old school, but I prefer to cultivate contacts the old fashioned way, using online and offline social networks to target the publications and companies I’m interested in working for. So much of freelancing is who you know, so why wouldn’t you first want to see what contacts you might have sitting right under your nose?

You recently wrote an article in The New York Times called “When to Work for Nothing.” Could you talk a little bit about that and what you hope freelancers and media professionals took away from that piece?

A freelance pal and I were joking a while back about how cheapskates with no freelance budget are always offering even the most seasoned of freelancers writing gigs that “pay in exposure” (what I call “PIE”) and nothing more. But unless you’re Paris Hilton, you wouldn’t walk into a department store and expect them to fork over a dress you like in exchange for the “exposure” of you wearing it out in public on New Year’s Eve.

That said, there are some instances in which working for free is valid. If you have no writing samples to speak of, doing a couple of short freebies is a quick way to line your portfolio. And seasoned freelancers will do PIE gigs from time to time if the exposure’s truly worthwhile. For example, The Huffington Post doesn’t pay, but if offers insanely high visibility, so many writers and authors will write for it to boost their credit list, attract other editors, and/or boost book sales.

I also don’t dismiss charitable work or volunteering. In fact, if you want to get some great exposure for your freelance business and make some killer contacts, lending your talents to a high-profile fundraiser in your community often does the trick.

In this current economy, many freelancers may be tempted to work for lower pay or take on assignments that they might not otherwise. Is this a good strategy?

If you’re trying to break into a new freelance niche, you might have to endure lower pay to get your foot in the door (because you might have to start with smaller publications). This is true in any economy. But I would not agree to a significant pay cut for those freelance gigs you’re more than qualified to do, especially not for editors or clients you’ve worked with before, unless you’ve exhausted every other income option you have.

To me, a better option is to secure some higher-paying work that may not be your first choice (trade magazines, service pieces, more formulaic articles, and the like). I’ve had struggling clients try to drop the rate on me in the past, and I’ve always chosen to move on and find something that pays better instead. The more lower-paying gigs you take, the more hours you have to work just to survive each week.

Many companies and clients are taking longer to pay these days—any advice for freelancers with slow-paying or no-paying clients?

Believe it or not, some clients will take a week off or leave the company without letting their freelancers know. For that reason, it’s imperative you have more than one contact at the company. Your contact’s assistant or manager makes a great backup. You also should try your hardest to get the name of the person in accounting who cuts your checks.

Mention that the check is late right away (a week to ten days after it was due); don’t wait a month or more. Resend the invoices if you have to. Some freelancers add a late fee, though I’ve never done this. Hound your contacts if that’s what it takes. If you have more assignments lined up for the editor or if it’s a steady gig, you have the perfect leverage: no more articles turned in until you get your money.

If a check is obscenely late and your repeated (and increasingly stern) reminders get you nowhere, you have a few options: collection agency, small claims court, or threatening letter from a lawyer. You might also want to tell your editor that you’ll be warning the freelance writing community about their crappy payment practices.