How to coast to a writing career

As the only Valleywagger who writes for the Wall Street Journal, I get lots of email from readers who want to know Sweet, how can I land that gig next time you're busy? Careful what you wish for. Freelance writing is hard work. Unless, that is, you follow my easy guide to slacking your way to the top — well, not really the top, but sort of near the top. Which is the whole idea.

  • Before you read this list, set up a new Gmail account with a name like john.smith.writer@gmail.com. If you don't, you're screwed.
  • OK. You want to get paid. You don't want to work. The way to do that is to write for top-tier national magazines, or at least second-tier mags. But you want to be in the sweet spot near the back of "the book," as magazine people unironically refer to their publications. Cover story? Forget it. They'll never leave you alone. They'll make you rewrite six times. Your editor, dreaming of her first National Magazine Award, will ring your cell phone right out of your pocket during your four-hour "lunch" at the Ritz-Carlton in Half Moon Bay. You want to be back in Programmer's Corner, page 142.
  • No no no, don't write articles on your own and then try to sell them. Pitch editors by sending them one-paragraph emails describing short, say 300-word articles you'd like to write. Aim for the lowest person on the masthead whose title includes the word "editor," except for "contributing editor" which means "freelancer in jammies." A good editor will sharpen your vision before you start: "Agrd Facebook privacy frightening. But let's report this forward. Say 200 words on Zuckerberg's sandals — thots?" Write what they want, not what you think. Do you want to eat or don't you?
  • AVOID: Exclamation points in your email. Newspaper, magazine, and Slate editors are a dry bunch. They're fascinated with loose cannons like Nick Denton, but they'd never assign him 600 words on Facebook's new ad model.
  • At first, when you're new, they'll mostly say no to your pitches. Actually, they won't respond at all. Keep emailing. Chin up!
  • Setting up a blog is optional. It could be a good place to showcase your talent, or a scary place to document your lack thereof. Think before you post.
  • AVOID: Blogger ego. If you do blog, just write and forget about it. Don't reply to your comments with more than "Good point, h8rboi, thanks." Don't troll other bloggers for links, or try to get onto Techmeme by posting about whatever's already there. NEVER try to win a fight with Dave Winer. People in the real media don't care what your Technorati rank is, they'll just Google you to see what you write.
  • After your fifth ignored pitch to any one editor, email again with, "Just checking - are you getting these? Regards, John." This usually results in the editor assigning you a photo caption out of sympathy. You're in!
  • Always, religiously, and without fail file your assignments to your editor the day before they're due. Not two days early, just one. Always. And whatever word count they asked for, hit it within 10 words. 290 is good. 330 is bad. They're not looking for the next Jack Kerouac, they're paying for FedEx-like dependability.
  • Newspapers are good places to freelance, too. They're all broke. You're not union. Everybody wins! Again, aim low in high places. Not the New York Times Technology section — that's grueling work. NYT Circuits supplement is what you want.
  • AVOID: Your idea for a book. You'll devote two years of nights and weekends to it, cause your girlfriend to leave you, and for what? A $10,000 advance and a box of remaindered copies. Instead, review your friends' books. You'll make more cash than them and they'll pick up the check.
  • When you're starting out, stick to publications with a clear political agenda. That way, you never have to worry if your article is going to get published, as long as it concludes with the party line. An essay for Harper's on how the housing bubble is just like Iraq would be a sure win. Except they just ran one.
  • Book reviews are easy. Don't bother evaluating the book. Use the book as a springboard to launch into a discussion of current events. Again, lead your horse to your editor's water: "Dan Lyons's Options is a hilarious sendup of the dishonest lawyers who rob American CEOs of their God-given right to back-dated share prices. Poor Steve Jobs! I really identified with him." Ok, that's the pitch for the Wall Street Journal. Wanna guess the rewrite for Salon?
  • Once you've been published, remember that Gmail account? Login there, not at your real email, and send your writerly Gmail address — now that you're a published writer, not just some blogger — to every publicist at every company or PR agency you can find that's anywhere near stuff you want to write about. Close your browser window fast, because that two-gigabyte inbox quota is about to fill up quick.
  • AVOID: Publicists who want to be your friend. They're just using you to get to your editor, and remember it's your editor who decides if you eat or not. Skip the flacks-and-hacks parties, and turn down their requests for what they call briefings or, worse, pre-briefings. "I'm on deadline" is the abracadabra excuse for anything you don't want to do. Stay home (or at Starbucks) and sift through their press releases and story ideas in your Gmail account. Don't worry — they'll spam you whether or not you show at their events.
  • AVOID: Investigative journalism assignments. If you can't do the reporting from your desk, pass on it. All the President's Men is an inspiring story, but who the hell wants to work that hard? Opt instead for 1,200 words on the Democratic primaries in Second Life.
  • Always quote the CEO for any company you write about. If the publicist tries to push you down onto a product manager because you're writing for Programmer's Corner, explain, "my editor wants to spike the piece because we can't get a quote from Bill." You know what? You're not totally lying. The flack will make up a quote from her boss and email it to you. Again, everybody wins!
  • AVOID: Hardware product reviews. Do you want a house full of boxes and a divorce? Even Walt Mossberg's wife flips out about the boxes. Plus eventually, someone will steal a review loaner camera or laptop on its way back to the manufacturer, who'll then invoice you for it. Great: A $2,500 bill for a $500 article.
  • Do software reviews. Most companies will give you a reviewer's guide you can just rewrite. Find one bad, reproducible bug. Google's good for that. File.
  • AVOID: Conferences. No one wants to read about them. Anyone important you meet there won't remember you when they get home. Stay home yourself and wait for their publicist to spam you with a story idea around their next product/startup/book/arrest.
  • About money: Don't ever ask an editor what an assignment is going to pay until you've gotten to the point where you can afford to turn it down. Editors get embarrassed when asked about money, because they make a lot more than you but a lot less than the CEOs you interview. If you bring up the topic again, they'll quietly drop you.
  • Did you see the movie Adaptation with that fat guy, Robert McKee, the foulmouthed creative-writing coach? He's real and so is his handbook, Story. It's fantastic advice. Buy a used copy and read it. Any article you can't imagine as a screenplay is an article you shouldn't write. Unless the rent's due.