The life of a freelance writer can seem pretty glamorous to an outsider, but the truth is that it is an often bizarre career with as many pitfalls as peaks. When we went looking for a freelancer who could share hard-won wisdom and sage advice about becoming a writer-for-hire, the obvious choice was successful Web/print columnist Spike Gillespie. The following interview is funny and illuminating — even though we suspect the interviewer wasn't completely objective...

Published October 20, 1997

My whole life, I've been crap with money. Sort of. The thing is, even when I didn't have it, I always had a job, so I knew more — if only a little — was coming. This was even truer, in a sense, when I waited on tables, which I did off and on (mostly on) for fourteen years, through high school summers, year-round in college, and then for a good seven years after that. So no matter if I blew my wad nightly, there would always be more tip money the following day. When I hit the age of 29, I grew quite weary of the whole hand-to-mouth lifestyle. I was also completely bored with slinging hash into the mouths of tie-dyed trust-funders who seemed to live to order me around. So I decided to ditch waitressing for writing, which I'd always done on the side. That is, my priorities were screwed up. I was too afraid to pursue something which seemed tainted with the possibility of failure. Granted, I hung onto a few shifts for a while, and I bartended weekends, too. Now — it seems suddenly, though it was actually a gradual process — I find myself, four years later, with too much writing work. I am constantly busy, constantly stimulated by work I love. And you know what else? I'm raking it in. Big time. In four years, I've gone from begging for work to begging for respite from all my duties: major online work, a book deal, a weekly column. I'm not complaining, In fact, I highly recommend the good life of hard work that you love. Still, the whole transition has left my head spinning. I mean, for the first couple of years as a writer, I still told people who asked, "What do you do?" that I was a waitress. I recently took time from my busy schedule to sit down and quiz me on how some of this happened. SPIKE GILLESPIE: Who are you and what do you do? SG: I'm Spike Gillespie, diva feminista. I write a weekly column on women's issues for Prodigy, and I also moderate a BB, a newsgroup, and run a women's Web site for them. And my book comes out next year with Simon & Schuster. SPIKE GILLESPIE: That's a lot. How did you manage to scrounge up all that work? SG: Cocktail parties. That's my real secret. I can schmooze and bond like no one else and I make no excuses for it. These days, any woman I run into, I say, "What's your e-ddress? I want to interview you." That's not idle flattery, either. I want to interview every woman in America (and beyond) before I die. Anyway, I was at a party in NYC a few years ago — running my mouth as I often do — and I struck up a conversation with a book editor. She later switched to online work, needed a women's issues writer, remembered me thanks to my big yap and BAM, I was suddenly employed, on a regular basis, as a writer. SPIKE GILLESPIE: How much money do you make? SG: I can't tell. I mean, not "I'm not allowed to tell." I mean, I never can tell. It changes every year — every month, even — because I do a lot of freelance. SPIKE GILLESPIE: What's the secret of making money? SG: I read a Roseanne quote in Bust magazine where she said something like, do what you love — the money will always come. Not sure I would've believed that when I first quit my waitressing job — which paid shit but, hey, at least it was steady. But I read it recently, when I'd already got to the place she was describing, so I understood completely what she meant. And I think, hidden in that quote, is the biggest secret of all: You HAVE to have self-esteem. You must. You cannot self-deprecate. Well, okay, you can — but you have to really, truly be joking when you do. My mind is racing here — money excites me. In particular, I'm thinking two thoughts besides that Roseanne quote. One is, a couple of years ago, on another visit to NYC, I was whining to my friend Jonathan (who is a very, very successful writer who makes excellent money). I said, "Jonny, I need to make more money, I need more work." He stopped me, stared in my eyes, and said, "No, Spike, you need to ask for what you're worth." This stunned me. Wasn't merely getting paid anything at all "enough." NO! Jonathan was right. I probably did three times as many (at least) gigs a year as him — and he was running financial circles around me. So I started asking for more. It doesn't always work, but nor does it lead to editors laughing and saying, screw you, I'll find someone else. That was my big fear, that if I got assertive, they'd blow me off. They didn't. Some said sure, have more money. Some said they didn't have more money so, if I liked the gig anyway, I took it. I will definitely trade perks (like wide audience exposure) for low pay. But there has to be SOMETHING else, if money isn't tops. The other thing I'm thinking about is this article I read in the RICH issue of the New York Times Magazine last year. (I know, I know, I should just move to NYC the way I always refer to it...). In this one piece, they asked successful women what the deal was. How did they compete in a man's world and still come out on top when so many women seemed to settle for making less money for the same work, or worse, settling for lower-level jobs? And one of the best answers came from a woman who said she learned in college to BRAG. To really talk about how good she was at the things she was good at. I'm not saying you need to be an obnoxious asshole and stop people in the supermarket and say, "Hey, do you know who I AM? Do you know what I DO?" But really, start with bragging to yourself. Me? I've always been a good writer and I've been a feminist for .... well, for a long time... and you know I still have a hard time sometimes shaking that "I must be cute and humble and glad for any scraps that come my way" crap. I have to practice saying out loud, "I am a good writer." Because I am. It's not bragging. It's me listing my skills. No, really, assert yourself. Ask for what you're worth. And, look out, here comes the cliché part: Believe in yourself. SPIKE GILLESPIE: What if you aren't in a high-paying field? SG: Well, that's fine. If it's really a job you absolutely love and thrive on — I mean, what did Mother Teresa make? Squat, right? If you can find happiness at your job and you don't mind eating ramen noodles, well, good for you. Me? I want both. I want to love my job and make money. SPIKE GILLESPIE: What's the hardest thing to learn about working as a freelancer? SG: For me, these days, UNBELIEVABLY, the hardest part is saying "No." I had the fear of shut-down utilities and hunger put in me in the early days of freelancing. I depended a lot on friends feeding me and loaning me money, my kid's daycare center being lax about when they got paid, stuff like that. I took EVERY job I could get writing, even if I hated it. Now I don't have to, but, getting back to that "girls must be humble" stuff, part of me is superstitious. Instead of remembering that I have talent and can always feed myself, sometimes I think, if I say no, I'll "never work in this town again." That's bad. That can be exhausting and take a toll on your mental and physical health, not to mention your work quality. So I'm practicing saying, thanks but no thanks. SPIKE GILLESPIE: What's the hardest part about freelance finances? SG: For me? Definitely management. I have no money management skills at all. Well, okay, no self-deprecating allowed. I mean, most of my bills are caught up as far as monthly balances. And I did pretty much live on credit cards for several years. So I have this big debt at which I'm chipping away. So it's not totally "bad" that I'm not sitting on a big nest egg. Still, when I consider how much I make now, compared to how much I made a couple of years ago — when I think what I used to live on... What I mean is, I should be doing a whole lot better. But right now, I don't even have a savings account. Part of this is taxes and my new expensive apartment and all that credit card interest. Part of it, though, is that — and I hate to admit it — I sometimes get this wild hair and do with my cash what I used to do with credit. I shop to cheer myself up. Not, like, all day at the mall. Like, gee, I really need a new $500 appliance or a $3,000 computer. Some of this, like the computer, I really do need. But I also need to get a grip and start dumping my money in the bank. Repeat after me, I will NOT go on more than three trips this year. That's my biggest vice: plane tickets. SPIKE GILLESPIE: It's been a pleasure chatting with you. Do you have any parting words for aspiring writers among the Tripod readership? SG: Much as I am loathe to talk about myself, I have done so in the hopes of inspiring you, too, to go for it. Good luck! RETURN TO CAREER PROFILES MAIN PAGE For more on the working life and financial times of a freelance writer, read Harry Goldstein's The Writing Life. Spike Gillespie writes a weekly online column for Prodigy Services. (You can subscribe by dropping a note to [email protected]. It's free). To view her other writing and pictures of her much-more-exciting-than-yours life, tune to http://www.marystreet.com/SPIKE. Spike is currently working on a memoir for Simon and Schuster. © 1997 Tripod, Inc. All Rights Reserved.