Ten Not-At-All Easy Steps to a Successful Writing Career

As one of the unbelievably rare and lucky writers who actually gets to write full-time for a living, I sometimes get asked how I got here and how I keep it going. I have books that sell pretty well, I have regular paying gigs for magazines, I do paid public speaking, I blog with a blogging network that brings in a little cash and helps me promote my other paying gigs. I quit my last day job in 2012, and I haven’t yet had to take another one. All of which makes me ridiculously lucky, luckier than 99% of people who want to be professional writers. So I thought I’d take a moment to offer a few of my thoughts for others on how to get here, based entirely on my own experience.

1: Have talent. I don’t know how to make this happen. But if you do have even a little talent, I know that one good way to get more is:

computer keyboard with hands
2: Write a lot. A lot, a lot, a lot. And then write more. And more. And then write some more.

I’m far from the only writer to say this, but it’s important, so I’ll echo all those other writers: The way to become a good writer is to just freaking write. The way to become a good writer is to let yourself be a bad one, again and again and again, until you get better.

Having a blog changed my writing career in more ways than one. It obviously introduced me to new readers who never would have heard of me otherwise, and it connected me with a network of other writers who support one another. But one of the most important ways that my blog changed my writing career was simply that it got me writing, several times a week. So write a blog. Keep a journal. Join a writers’ group. Find an editor who’s a hardass about deadlines. Put a bunch of money in escrow that will go to the Republican Party if you don’t write 20,000 words in a month. Do whatever you have to do to just make yourself write.

3: Get lucky. I don’t know how to do this. I don’t think anyone knows how to do this. If I did know, I’d sure as hell be doing it more: it is vitally important to a successful writing career. But — well, that’s sort of the definition of luck, right? It’s the stuff you don’t know how to make happen. It’s the stuff that happens regardless of what you do or don’t do.

When it comes to luck, though, here’s what I do know:

4: Take advantage of opportunities. When luck shows up, don’t ignore it. When opportunities arise, do not let them slide. The greatest regrets I have in my writing career — indeed, some of the greatest regrets I have in my life — are the times when I had a once-in-a-lifetime shot at something, and I didn’t go for it.

Often, luck is privilege. Sometimes, luck is just luck. But I think that at least sometimes, lucky people are people who are able to recognize when they have a shot at something — and take it. They don’t make all those shots, they don’t even make most of them — but they make more than the people who don’t take any of their shots, or don’t even recognize when they have them.

Which leads me to:

5: Be open to unusual opportunities. When I was starting as a freelance writer, it never occurred to me that public speaking might be a thing. I now do public speaking almost every month, usually more than once a month — and it’s a non-trivial part of both my income and my publicity for my other work.

So be willing to consider work opportunities that aren’t what you originally set out to do. Some gigs, paying and not, that helped get me where I am today, and that I never considered when I first started out as a writer: Reading at the Perverts Put Out! reading series. Writing for the by-lesbians-for-lesbians sex magazine On Our Backs. Writing catalog copy. Blogging. Soliciting donations from blog readers. Self-publishing my first ebook. If I’d kept my focus entirely on my original plan — writing articles for magazines, newspapers, and anthologies, and writing and editing books for conventional publishers — I’d be pretty much nowhere.

6: Cultivate collegial relationships. Cultivate relationships with other writers, with editors, with publishers, with designers, with organization leaders, with other people who can help promote your work and/or make it better. Help them out when you can. Ask for help when it seems reasonable to do so. Make mutually productive connections. Make genuine friendships, not based purely on tit-for-tat mutually productive connections, but on sincere caring and empathy and shared ways of seeing the world. You’ll get more lucky shots at more gigs if other people help you spot them.

Which leads to:

7: Have help. Becoming a full-time writer is bloody well hard enough as it is. Without an assload of help, it will be damn near impossible. (This is the place where I express my deepest gratitude to everyone who has ever helped me with my writing, and everyone who continues to help me.)

8: Do not fear self-promotion. Remember what Hillel said: If I am not for myself, then who will be for me? (Of course, don’t forget the other half of that: If I am only for myself, then who am I?) The shitty reality of the current publishing world is that, unless you’re Stephen King, nobody is going to sink any sort of significant budget into promoting you. You will have to do all the heavy lifting yourself. Which is horribly ironic, since the personality that makes for a good writer is not even remotely the personality that makes for a good publicist. It sucks. It sucks giant donkey dicks. Deal with it. Learn to self-promote.

Publishers Weekly cover
9: Learn the business. This means a lot of different things: from learning what editors and publishers want, to learning the pros and cons of self-publishing, to learning about marketing and promotion, to learning about cover design and working with designers, to learning how to be persistent, to learning how to do your self-employment taxes, to learning how to deal with rejection. (That could be an item all on its own — Get Used to Rejection, You’re Going To Get A Lot Of It. In fact, pretty much any of these could be an item on their own.) Learn all of it. Learn as much of it as you can.

And finally:

10: Make writing, and your writing career, pretty damn near your number one priority — for years. Being a professional writer is one of the hardest ways to make a living there is. Becoming a professional writer is even harder. It took me a huge amount of time, every day, every week, for years, to get to the place I am now — a place where I make a reasonably decent living as a writer, as long as I keep busting my ass.

There’s a joke I heard once: Being self-employed gives you so much freedom — you can work any hundred hours a week you want. Be prepared for that. Be prepared to give up a whole lot of parties, television, video games, dating, going out for drinks. Be prepared to give up a whole lot of fun things that take time, or money, and especially things that take both. If you have a day job that’s sucking a huge amount of your time and energy, quit it if you possibly can. Find a day job that lets you have a little something left at the end of the day. If you possibly can, get a day job that gives you flexible hours, and that will let you gradually phase out from full-time to part-time. If that job doesn’t pay as well — suck it up. Cut out your luxury spending, cut out your non-essential spending, get a roommate. Do what you have to do. But make this work pretty damn near your number one priority. After your basic survival and your closest relationships, make your writing and your writing career the single most important thing in your life. And be prepared to do it for years.

I love this work. I feel ridiculously lucky that I get to do this work. I want other people who want to do this work to be able to do it. If you follow Greta’s Simple Ten-Step Plan, you might possibly have an outside shot at maybe making it happen. Best of luck!

Ten Not-At-All Easy Steps to a Successful Writing Career

5 thoughts on “Ten Not-At-All Easy Steps to a Successful Writing Career

  1. 1

    11. Nonfiction writing pays way steadier than fiction writing. I’ve made my living as a writer for 35+ years; haven’t published a word of fiction. You might get lucky and write the next “50 Shades of Gray” — but probably not.

    And now, I have a deadline.

  2. 3

    11 – Learn to say “NO” and “HELL NO!” in a variety of ways to the people who want you to write for free:

    To the people who say “it’s great exposure for your career”, tell them if you want exposure, you will moon the mayor in the town square.

    To the people who say “it’s for a great cause”, ask for a % of the hourly equivalent of their charity’s director’s salary. If Nancy Brinker, founder and chief executive of Susan G. Komen for the Cure, took home $417,000 in salary in 2010 ($208/hr is you assume she worked the usual 2,000 hours a year) and paid 50 top executives more than $100,000 each … paying me $50 an hour for that promotional material or the office policy, process and procedures manual should not be a problem. Capice?

    memorize this

  3. 5

    #3 and #8 have a sort of synergy; unless you’re Lana Turner (and I don’t really believe it of her), you make your own luck, to a certain extent, in no small part through self-promotion.

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