Here’s how to sell your writing (and stay sane in the process)

Here’s an interesting post, recently featured on Freshly Pressed, about the importance of luck to a writer’s success:

I don’t mean to sound defeatist or to say it’s all about chance. This isn’t sour grapes (I don’t have a bestseller because I never got lucky, etc.). No, talent and marketing and skill and savvy all help put the writer in a position where the odds are better. But it really does seem to me that, at least in some cases, luck is as much a factor as talent.

And in some cases, more.

No one seems to talk about it, though. Maybe because it’s something that can’t be taught–or sold–on a website.

I’ve been writing for a living — my sole income — since my second year of university. I was an undergrad studying English literature at the University of Toronto and all I wanted to do was become a journalist. I decided not to study journalism because I knew I needed a broader education and wanted that instead. (I’ve never formally studied journalism or writing.)

Victoria University at University of Toronto
Victoria University at University of Toronto (Photo credit: MKImagery (Toronto))

Here are some of the ways, since 1978, that I have found editors and agents to whom I’ve sold my work, and/or gotten staff writing jobs:

— While at college I worked at the weekly college newspaper. I wrote long, complex features so I would have clips (samples) to show to paying editors of what I could produce. Moral: What’s your goal? Start accumulating the skills you need and the visible proof you have them.

— I cold-called editors at every major magazine and asked for meetings. I got them. Moral: Be bold! No one is going to hand you your success.

— When I had the meeting, I went in with a multi-page list of story ideas and would not leave the office until I had sold one of them and had a firm, paid assignment. Moral: Be prepared. Be way over-prepared.

— After I had amassed a larger pile of clips, I began aiming higher, for more prestigious or better-paying markets. Moral: Never stop moving. What’s your next step and what will get you there?

— I talked myself into a meeting with the editor of a local weekly section of our national newspaper, The Globe and Mail. I got a column to write about shopping, for anything, that paid me, then, $125 a week, $600 a month. (My annual tuition was $660. No, that’s not missing a zero.) Moral: Try for a regular gig.

Paris Exposition: Eiffel Tower, Paris, France,...
Paris Exposition: Eiffel Tower, Paris, France, 1900 (Photo credit: Brooklyn Museum)

— I won a journalism fellowship, at 25, for eight months in Europe, based in Paris, traveling on four 10-day reporting trips alone. It changed me, and my work, forever. Moral: Aim high. Start applying for rocket-boosting opportunities once you have the skills and resume to compete for them.

English: Globe and Mail newspaper staff wait f...
English: Globe and Mail newspaper staff wait for news of the D-Day invasion. Toronto, Canada. It looked a little different by the time I worked there! (Photo credit: Wikipedia)

— I got my job at the Globe and Mail six months after returning from the fellowship. Moral: strike while the iron is hot and you have a significant point of difference from your many competitors.

— I got my job there after hearing that the sports editor was soon to become the managing editor; i.e. he was the one to impress, now. I knew nothing about sports! He sent me to cover several huge, high-profile sports stories, knowing that. I rocked it. Moral: Follow your targets closely to know when an opportunity exists. Then impress the hell out of the person with the budget and authority to hire you.

— I got my job at the Montreal Gazette when a Globe colleague who once worked there tipped them off I might be looking for a new opportunity. Moral: Find and make allies.

— I fell in love with an American who was moving to (!) a small, remote town in New Hampshire for the next four years. Because I had been stringing for Time for a few years already, while working in full-time jobs, I asked my Time editor if he knew of any jobs there. I got a well-paid contract job there — which is insanely improbable — through one of his former New York magazine colleagues. Moral: If you don’t ask for help, you never know what might happen.

— I found every agent I’ve had through personal contacts. The first came to me through one of my NYU journalism students, who knew someone at William Morris who knew three new agents hungry for clients. Moral: Put the word out and take the chance.

— I started writing for The New York Times in 1990 after I called someone from my Paris fellowship (eight years earlier), living in New Orleans. I called an editor at the Times Book Review who began giving me 300-word reviews to produce on topics that were really difficult and often boring. I did them, gratefully. It gave me a Times byline. Moral: Start wherever you have to. But be strategic.

The New York Times Book Review
The New York Times Book Review (Photo credit: Wikipedia)

I won a National Magazine Award in Canada, for humor, for an essay about surviving my divorce. It’s a topic many would avoid writing about: painful, private, cliched. Instead, I turned it into something (darkly) funny. I tried to sell it to an American women’s magazine who quickly rejected it. I sold it to a Canadian women’s magazine, who submitted it for the award. Moral: Rejection is normal. Get over it! Move on. Find another market. Or ten.

— Once you find an editor who likes your work, hang on tight! Repeat business will save you a ton of wasted time and energy. Moral: Remember the 80/20 rule of business; 80 percent of your business likely comes from 20 percent of your clients.

— But, think like Caesar and keep on conquering. Never rest on your laurels, as editors can lose a job with scary speed and you can very quickly lose a nice little sinecure. Moral: ABC, Always Be Closing (i.e. making sales.)

— Last week I got an email from someone I have never met, a man who lives in Beirut, who is married to an NPR correspondent. He and I were both bloggers for True/Slant, in 2009. He asked me for a valuable editorial contact — while offering me one of his. Win-win! Moral: If you’re going to ask for help, offer something of value upfront in return. No one likes a taker.

— Remember that publishing remains a team sport. If you’re selling to print publications, think about the art or photos to go with your story. If you’re working on books, be polite and kind to everyone as no one is likely getting rich and most of them love this work as much as you do. Moral: If you plan to stay in this game, keep your nose clean.

Selling your writing is hard!

It’s tiring.

It can take a much longer time to “succeed” than you thought possible.

You may have to re-define what “success” looks like: Tons of money? Huge readership? A TV show or movie based on your work? Or…some appreciative readers and some people who will pay for your skills?

Sell, Sell, Sell
Sell, Sell, Sell (Photo credit: Wikipedia)

35 thoughts on “Here’s how to sell your writing (and stay sane in the process)

  1. Hard work is ultimately the best kind of luck. And some of it is what kind of risks you are willing to take and what you are willing to give up. If you aren’t up for it, admit and find a line of work you are happier in, even if it isn’t your dream job. Contentment lasts longer.

    1. I disagree that hard work is enough — if you’re rude or charmless or unwilling to work well with people. It takes a lot of skills that have nothing to with talent or writing ability or desire. People really forget that and focus too much on Being Famous. Which is nuts.

      But I do agree you have to ready to take risks (financial, emotional, intellectual) and love what you do. It’s so full of BS you have to love the rest of it. I like being a member of a large, global tribe of creative people. I would find that very hard to leave behind.

      1. I don’t mean that hard work is enough, but it does seem to me that you have worked very hard to be where you are–not just at writing, but at building relationships and taking hold of opportunities when they presented themselves. And it also seems to me that you have achieved the degree of success you have in part because of that hard work. Many people complain that they’ve fallen short of where they wanted to be, but they simply haven’t been willing to do what the job required.

      2. I wonder if that’s true….and it may well be, that people just don’t really understand that you never (unless you’re a HUGE name) get to just chill out and let people call your agent. Hah! I don’t find hard work demeaning (which I think some people, bizarrely, do) or especially annoying. Every job has hard work in it, and when you work for yourself, you have no one to blame if it fails to work out! Unlike an office or organization job where others can sabotage you with laziness or politics.

        I never stop seeking opportunities, no matter when or where they appear…we just came home from an evening in NYC and sat on the commuter train with a colleague of my husband (at the NYT) who’s a friend of mine as well. She works in a section of the paper I have never written for and she tells me they are hungry for new writers. So…tomorrow morning first thing, I’m on it! (When people fail to follow through, I don’t get that bit either.) I think there are many opp’s out there that people just ignore or forget to follow through on…or they just don’t want it badly enough.

      3. I think perhaps they understand that the writing will be hard work, but not how often they will need to pick up the phone or talk to people at publication parties. Writers are not always the best talkers, and grappling with the fear and losing may be behind those missed opportunities. My background is art, and I realized fairly early on that I just didn’t want to do anything other than create work: I didn’t want to talk about my work or try to convince gallery owners to show it. I also wanted security and a regular paycheck. Not knowing if I can pay the rent drives me as close to mad as I want to get. And so I am not a working artist. Not everyone realizes they don’t want the business end of a creative career–and the two go together.

      4. Do they ever!

        I was just this evening at a bar for a friend’s birthday party…as I was leaving, I ran into a woman I had hoped would become my next agent before Malled. She had a competing book so could not. I could have just said “Hey!” and left, but I like her very much and it was really comforting to just stop and talk shop a bit. It isn’t always SELLSELLSELL but also the reality check of how hard it is (or fun) for others whose work I like and respect — a shared conversation about the challenges we all face.

        She said something so profound it made me really glad I stopped to talk. She said authors get so disappointed when a book fails to sell well (no matter how good or what the editor or agent hoped for). “I’m not a therapist,” she said. “or trained as one. But I end up being one to my authors. Then I need one for myself!”

        That gave me a lot of insight I had never heard about her side of the table.

      5. That kind of conversation is so important. So much of writing is just the habit of listening to what other people have to say about what it’s like to be them.

  2. I’ve had some lucky breaks as well in my writing, and some days I think I’m getting more than others (at least I like to think so). Hopefully someday I’ll be lucky enough that I can at least make a living off of my writing.

    1. And then define “living.” Some people would look at my current annual income and walk away to something far more lucrative — there are days I consider it as well. This life of writing is filled with trade-offs and compromises.

  3. As it was recently explained in a web series I enjoy, “Success is mostly luck. Luck, hard work,and more luck.” Sounds defeatist to some, but I found it refreshingly honest. Few people talk about the role serendipity or just good timing play into positive personal and career moves. Although I think half of good timing is just paying attention and keeping an eye out for potential ins – something I’m trying to get back into practice doing. Speaking of it, good luck with the new NYT section tomorrow (saw your earlier comment)!

    1. There is this fantasy that if we just WORK HARD, everything will fall into place. As if. I admit, for sure, that some of the very best things in my life have happened through insane serendipity….like (true)…bumping into my landlord’s ex-girlfriend in the grocery store (chance); saying hello (being friendly); chatting (ditto) and learning she had just applied for a fellowship in France. I was desperate to flee my life in Toronto, applied for it (had never heard of it before) — won it. (And she — ouch — did not.)

      That is sheer damn luck — plus chasing it hard and fast when I fell into an amazing opportunity (oh, and having acquired the credentials to be able to compete for it and win.)

  4. I’ve said it once, I’ll say it again, I love your attitude – your courage, your belief in yourself and your strength to get back up after you’ve been knocked down. Rejection is a part of life, but so many people are more afraid of rejection than they are desirous of success. The qualities you possess are qualities I strive for – and like to think I possess them too – but they are not qualities that come easy. They are qualities you must work to maintain. It’s always great to read an inspiring article like this to get a re-boost of confidence. Thanks for all your invaluable advice and for yet another well-written article filled with tons of useful information!

    1. Thanks!

      If you’d had my earlier life (gah), you’d understand it better. I was lucky/confident enough to start having successes in my teens (sold three of my photos for Toronto magazine covers) that I figured I did have something to offer the world, so when people ignore or reject me I just think “Your loss!” and go find some more people who will use my work.

      I also have a totally bizarre and rejecting family so had to learn very early to get along well with adults/strangers/clients and meet their needs to survive both financially and socially. I get a lot more love and appreciation from them than I ever have from some people to whom I am related. That has also kept me going…to realize that when your own parents or siblings reject you (painful indeed) but entire piles of talented, picky clients do not….it’s not about me.

      I simply do not understand the fear of rejection (so I think that’s now tomorrow’s post!)

      FYI, I’ll be in touch by email about the story we discussed. I’d like you to be a source for it.

      1. Wow! I am so honored and over-the-moon that you would ask me to be a source for one of your stories! I cannot express my appreciation enough! I very much look forward to your email.

        Your fearless attitude – in the face of rejection or otherwise – is probably the most valuable quality a person can possess. And conquering an individual fear is probably one of the most rewarding of life’s experiences. It’s unfortunate that you had to develop your fearlessness of rejection in the way that you did, but the fact that you became a stronger person because of it – rather than letting it break you down – and that you used it to create your own successes in life shows what type of person you are: strong, courageous, a fighter, and driven to succeed. I’ve seen so many people use their setbacks in life as a perpetual excuse of why they can’t and don’t succeed at something – or anything. I have one friend who is constantly blaming her mom for her unwillingness to go after her goals in life: “my mom never believed in me so I don’t know how to believe in myself…” blah blah blah. I have endured many setbacks in life from my childhood to my adult years, but I share your attitude in that I don’t let them knock me down. I learn from them instead.

        I know from my own experiences – especially in law school where, for the first time in my life, I found myself surrounded by people who were born with a silver spoon in their mouth (many of whom had never done a load of laundry or washed a plate before entering college) – that those who have had more challenging upbringings but have carried on in spite of their setbacks are the most likely to succeed. They generally tend to think outside the box, they don’t take “no” for an answer where they see the answer as “yes”, and they often take a non-conventional road to success that is filled with more diverse and rewarding experiences along the way.

        I am very interested to hear more about your upbringing/family, although I know it’s a very personal topic. I am also really looking forward to your post today! I’m interested to hear more from you on your view of the oh-so-prevalent fear of rejection!

      2. Thanks.

        I have zero patience with the entitled. My husband grew up with no money, no connections, attended state school on full scholarship — and went on to spend eight years in the White House Press Corps (photographing 3 Presidents), shot several Olympics, Superbowls — and won a Pulitzer for his photo editing on 9/11. He is my hero for his ability to climb to the highest ranks of his profession through talent, grit and determination.

        I’ll email you in the next few days.

  5. Highly highlights;
    ‘Moral: Start wherever you have to. But be strategic.’
    ‘Moral: Rejection is normal. Get over it! Move on. Find another market. Or ten.’

    1. Thanks!

      I think being strategic is really, really important and people forget that. You can be deeply creative or bohemian (i.e. work at home in your PJs) and still be deeply thoughtful about how to use your talents and resources.

  6. I absolutely love this. It’s so nice to have some concrete examaples.When asked about how to succeed at almost anything, far too many people talk in general terms about the need luck and skill and hard work (all of which is clearly true) but never explain what they mean in practice.

    It’s a bit like the way everyone knows that if you want to lose weight, you ought to be eating less and exercising more, but it’s much less useful to be told that than it is to be given some suggestions of good exercises and healthy recipes.

    So, thanks for the ‘recipes’. While clearly not all of that is exactly replicable, I definitely feel that I’ve got some real ideas for things to try

    1. Thanks.

      I agree. I am getting REALLY bored by all the generalities I read everywhere about this stuff. I realized that my successes have been very much the result of a whole pile of attitudes and behaviors, but put into ACTION.

  7. Hard work, effort, networking and direction are all vital to the business – and writing IS a business. But I do think chance opportunity, or chance combination of fortunes also plays a part along the way, certainly in the earliest stages of trying to break into an industry where the people who get published are the ones who can show they have been published – realistically, where those of known quantity are preferred over those of unknown.

    For myself, I probably wouldn’t be where I am today, writing-wise, if I hadn’t been picked up and given a semi-regular column by a newspaper editor back at the start. And while on the one hand he wouldn;t have done that if he didn’t think I could do it, at the same time, it gave me a foot in the door which became a device for getting more work. None, of course, handed out on a plate – but I could use the growing publications list to add cred to my pitches. And, looking back, in many ways it was chance that things came together that way; call it luck, perhaps.

    1. It’s very true that you need a few breaks — luck? — to get started and gain the access to more people who will use you. I can’t remember how I got into the Globe newsroom to sell my first piece at 19 or so (about cycling in the city) but if you can get in and impress a few of the right people (and don’t screw up!), off you go.

  8. Thank you for this kick in the pants. It’s so easy to blame luck when things don’t go your way, but the reality is that you need to work hard, as well as have the talent necessary to succeed. Now I just need the courage (which I believe is another important element).

  9. Nice post (and I’m looking forward to the one on rejection). Luck and timing are certainly factors, but without basic skills, perseverance, and flexibility, they aren’t enough. I also agree with the poster above who mentioned courage–very necessary when writing. 🙂

  10. This post is plain awesome. Something I really liked reading every word of. I feel the same and would definitely try to follow the invaluable advice you’ve included. But in my case, I have as slightly different story.

    I don’t remember if I wrote about it on this blog before, I’m not a native English speaker nor do I have any top-notch English learning course here in my country. I’ve been writing for newspaper (first class, national ones) and magazines (again, top of the line here in Bangladesh) since a couple of years. I’ve known a number of editors and there is really a huge opportunity for me to stick around and make my career out of it.

    But the problem is, my field of writing (when it comes to non-fiction, at least) is technology. You might know that not really much happens in Bangladesh when it comes to technology. Most of the time all we need to do is translate articles from int’l magazines, add our thoughts and insights into it. As it’s more like a translation job, the payment is very poor. No one ever dreams of becoming a sub-editor (that’s the highest you can get) in technology desk of any newspaper. Everyone that is a sub-editor also has a side job like photography or something alike.

    This is the reason I opted for writing in English.

    Based in Bangladesh, it’s nearly impossible to write for int’l news media like The Next Web or TechCrunch for example. Some of them often do hire global writers. But I’m afraid I’ll never get there. I’m still writing tech articles on various blogs I own (more like building my portfolio and improving it so that I can add to my resume). I pitched editors but never received a response possibly because of my location.

    Now I’m wondering if I’m just wasting my time trying to write in English.

    1. “I pitched editors but never received a response possibly because of my location.”

      I’m not the best person to ask about tech writing — which I never do — but unless (?) you were offering some amazing news/profiles/trend stories, you might not get a response. I don’t follow tech, or write about it, but have you also tried pitching English-language print publications like Wired or various newspapers (Britain, Canada)? Again, I doubt most editors immediately assume that there are terrific tech stories to be reported/written from Bangladesh — but if there are, why not try?

      Most everyone in print now also has an online component (which pays less) but which doubles your chances of finding an editor there to pitch.

      If what you want (?) is to cover tech *from* Bangladesh about other places, I think that’s a fairly lost cause.

      1. The journalism programme is fantastic. I’m learning a lot on every level: news writing, feature writing, photography, blogging. And 3 of my stories got published in local papers already 🙂

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