The 5-Minute Freelancer Q&A #24 — Caitlin Kelly

In this regular feature, Story Board asks Canadian writers to share a few details about their work habits and their strategies for navigating the ups and downs of freelance life.



Caitlin Kelly is a Canadian writer based in New York City. She has been writing for clients such as The New York Times, SmithsonianMore, and Marie Claire for over 20 years. She is a prolific blogger with more than 15,000 blog followers worldwide. She also works as a writing teacher and a private writing coach. Caitlin took the time to speak with Story Board recently about writing rates, building your online presence and the importance of having a posse. The conversation was fascinating and wide-ranging. Here are some highlights:

On tweeting:

When I wake up, the very first thing I do is I flip open the laptop and I tweet. I don’t tweet automatically, I see what people are doing. And the reason I do that is that I’m really interested in what’s going on in the world. The minute I wake up, even if it’s 6 in the morning, it’s already 11 in England, France, or beyond. So that helps me see what’s going on globally and it helps me jump into conversations that are already ongoing. And there’s a reason that I do this. I don’t tweet because it’s a fun thing to do. I enjoy it, but it’s strategic. I want to be out there. There’s a motto that I came up with and it’s three things: “be visible, be audible, and be credible.”

On blogging:

I blog much less than I used to. I used to blog every other day for four years. The reason that I blogged so much is, again, strategic. It kept my Google rank high. If you Google “Caitlin Kelly” I’m in the top three, always, just because I’m really consistent on social media.

And the blog is a really wonderful place to just write. The reality of freelancing is that we make-to-order. We do intellectual piecework. The blog gives me a place to explore, to noodle things over. I get a global conversation. I just want to talk to smart people around the world. And my blog followers are those people.

To me a blog is an artist’s proof. It’s a place to test out an idea, a different language, a different approach. It’s my little magazine. I think it’s great practice. You write your hed, you write your dek, you write your captions. I think it really keeps you sharp in thinking how an editor thinks.

So the blog helps me remember to a) be creative, play and b) think visually and c) try stuff out, see what your readers think of it.

On #MissingAZero, a hashtag she recently created to draw attention to the problem of low writers’ rates:

I don’t know how people in journalism now can actually make a full time living without teaching, coaching… I do other things as well. I think the low rates are a really big problem because look at the math. How many hours a week do you want to work? How many hours a day do you want to work? You have to take vacations, you have to have weekends, you have to see your kids, pat your dog, say hello to your sweetheart.

Hence #MissingAZero. If you’re making $150 a story, how can you make a living? You’d have to write about 20 pieces a week. I don’t know how you’re going to do that, but let’s say you do. Can you sustain that pace? And then the next question, which, to me, is really important, is do you want to? And the next question is “what’s the quality of the work you’re producing?” And the question after that is “And what it is leading to?”  Because at that point you’re a hamster on a wheel. You’re not producing work that’s going to get the agent to sell the book that’s going to help make your reputation.

On why writing for low rates is a bad idea:

Number one, you can’t make the money. Number two, it’s really demoralizing. Number three, you’re really tired because you have to crank out so much. And number four – and this, to me, is an essential point – you’re reifying that this is a valid decision on the part of the publisher.

On the importance of having a financial cushion:

If you don’t have at least three months’ full expenses in the bank, you’re going to go crazy. You have to have a cushion. Desperation is just not a selling tool. Skill is, talent is, great reporting is, accuracy is. But the underlying piece of it is you run a business. You have to be able to keep pulling away from the toxic clients, the toxic situations. Because they’ll sap your energy, they’ll sap your strength. They’ll make you feel so demoralized.

On working part time jobs on the side:malled cover LOW

Nobody wants to take a low wage job. I did one for two years from ’07 to ’09, which became a book. And I didn’t do it to write a book, I did it because I needed cash.

I think there’s a lot of discomfort if you’re working as a waitress or barista or whatever. “What if my editor sees me? What if a friend sees me? What if my journalism professor sees me?” You know what? Give them a big smile and ask them to leave a tip. Do what you’ve got to do to get the bills paid. Because at the end of the day, you want to produce good work.

I just read a review of a biography of T.S. Eliot, apparently the guy worked at a bank. There was a beautiful photograph of T.S. Eliot, who was a legendary writer, in his banking clothes. People forget this.

There’s this bizarre notion, like we should all be able to support ourselves on being an artist. Well some of the best writers in the whole world never did that. They had patrons. There’s no Medici paying my mortgage. We don’t have that sort of model. Very few of us win the fellowships, win the grants. It’s really, really hard. So do what you have to do to get the money in.

On getting into a business mindset:

I hate the word “freelance.” You are not a freelancer, you are a small businessperson. Small businesspeople have business plans, they have lines of credit, they have accountants, they have financial planners. You run a business and your business is ideas. Your business is words.

My job working retail, I folded t-shirts, I swept the floor, it was a tough job. Two and a half years I did that job for The North Face. It was the best thing I ever did because I would come home and I would say to myself “you just sold a $600 ski jacket to a hedge fund guy from Greenwich. Why can’t you sell a story to fill-in-the-blank?” Now I know how to close a sale. Your writing is just another product. Go sell your product.

On asking for more money:

Think it through. You know what your costs are. You need to know to the penny what do you need to make an hour. And then you have to really drill down and say “what do I need to be making every hour that I am working?” And once that number’s very clear in your head it’s very easy to say “I’m sorry, I can’t work at that rate. Can you do better?”

You can be passionate about your work and still say “can you pay me more?” And this is a conceptual leap people have to make. You have to say “can you do better” or “I’ve done three pieces at this rate, can we bump up the rate?” And I think it’s very legitimate if you live in Vancouver or Toronto, the two worst. If somebody is going to be really cheap with you, you may just recuse yourself and say, really nicely, “we’re probably not a good fit for each other.”

On thinking long term:

I think smart, ambitious writers – I don’t care if you’re 20 or 40 or 60 – you really look and say “what do I want to do?” When I was in my early 20s when I was at the Globe and Mail, my single greatest dream was to write a book. I wanted more than anything to write a non-fiction book. I didn’t publish a non-fiction book until 2004. I left Toronto in ’86. Long time. And you know what, that’s fine. I had to develop my skills, I had to develop my confidence. I had to develop my network. I had to find a good agent. I had to have the credentials.

Stuff takes time. You have to say “do I really want it?” “what’s it worth to me?” “what sacrifices am I willing to make?” There are going to be sacrifices. There were years all I could do was pay bills. There are years that just aren’t a lot of fun. But those are years that you’re building your portfolio, you’re building your contacts, you’re spending money going to conferences. You’re taking some classes. Whatever it is that’s going to build your skill set so that suddenly you’re not the 20th person competing for a $50 story. Just get out of that pool.

I think you have to be very clear “who do I want to write for,” or “where do I want to be published.” “How do I meet those people? Where are they?”

On building a professional network:

We’re all shy. We’re all introverts because we’re all writers. And you think “oh I can’t talk to that person.” The person sitting beside you could be the agent who makes your career if you have the social skills to smile and shake their hand and give them a nice business card. It can’t all be virtual. You can’t tweet your way to a career.

You have to be a nice person. You have to be a fun, interesting, alive person who reads, who travels, who looks you in the eye, who shakes your hand, who writes a thank you note (maybe on paper!), who picks up the phone. That’s part of the piece right now. Our industry’s really hard. We’re going through a really challenging time. There are a lot of places to write, this is not a dead industry. But you have got to jump around.

Two words I want to give younger writers: be flexible. Not “work free,” “be flexible.”

On dealing with late invoices and deadbeat clients:

I’ve sent lawyers’ letters and they work. This is how you get money out of a deadbeat. It’s a three-step process. You find the biggest, baddest law firm in the city. They’re probably $800 an hour, so if your invoice isn’t big enough, it’s not going to work. But let’s say your invoice is over $1000. Then you ask “how much does your firm charge to write a letter?” Have them write a letter that says “my client.” You’ll get paid. Because what you’re really doing as a businessperson is signalling “I have power. And I have knowledge.”

People will really play rough with younger writers. The people you’re dealing with are businesspeople. And guess what businesses need to do: they need to make a profit. And guess where they’re going to make a profit: off of your labour.

On building a network of writers:

Find a posse. Create a posse in the best sense. If you have a posse of five, six, seven, eight people that you can trust, you run a pitch by them, they don’t steal it. You need an agent, they refer you to their agent because they like you and they trust your work. Once you have people that you trust and that know they can trust you, you’re not going to be writing for pennies.


Caitlin Kelly has won the National Magazine Award for her writing. Check out her blog for information about two upcoming writing workshops that she’s teaching in Tarrytown, NY. You can find links to her work on her website and follow her on Twitter at @CaitlinKellyNYC.


Posted on October 2, 2015 at 8:00 am by editor · · Tagged with: , , ,

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