A week in my life as a freelance writer

By Caitlin Kelly


IMG_20160617_102113083 (2)

Ohhhh, so glamorous!


At the moment, which is blessedly almost unheard of, I actually have no assignments at all. That means, no income for this month. That means, (thank heaven we have one) dipping into our emergency fund. At least my husband, a freelance photo editor, does have steady work.

For those new to Broadside (welcome!), here’s my website.

I’ve been fighting a cold, sleeping 3.5 hours one afternoon to give my weary body a rest — but also heading 25 miles into Manhattan to meet with friends visiting from far away: a retail expert I’m Twitter friends with and hadn’t met before, from D.C.; a former New York Times story source, who then lived in the Middle East and now lives in London and who I last saw at my birthday party in Paris in June, and a bilingual young friend I met at a writing conference in New York who’s from Montreal and is (yay!) moving to Paris.

I’m excited for her — ditching a well-paid corporate career, selling her condo and most of her belongings — and, single and bold, heading into a great new adventure. I had a life-changing year in Paris when I was 25 on a journalism fellowship so I hold tremendous affection for that city and what spending some focused time there can produce.

Next Monday I’ll meet a talented writer who lives in Mexico City and with whom I’ve only, so far, traded notes with in an on-line writers’ group. Then have coffee with another younger writer, a New Yorker back home after years living in Berlin.

So many writers’ relationships now, working alone at home or in a co-working space or library or cafe, are virtual that I’m eager to meet face to face whenever possible.


malled cover LOW

My second book


I also sent a book idea recently to an agent — whose name and phone number a writer I’ve never even met shared with me. This is, at is best, what a successful career in this business will produce — sufficient affection and respect for one another that we boost those whose work and ethics we admire.

People often wonder: How do you find an agent? Once you’re established, often by a referral like this.

To my delight, the agent called me back that same day saying: “I know your work.” Whew!


Because, honestly, there are days, weeks and years it’s too easy to feel invisible and hopeless, watching the Big Name Writers win awards and grants and fellowships and adulation, especially here in New York where people are, ahem, quite vocal about their success.


Being modest can feel weird and self-defeating.

So I burbled out my idea to this agent and he listened and said: “Tell me more.” I sent a bare-bones outline.

He didn’t like it, but said, “Let’s keep talking.” So I thought hard and brainstormed with five smart women friends, several fellow writers and a few who aren’t, to help me refine my thinking and expand it.

One of them thought the idea not useful at all, which was worth hearing — and offered an insight I hadn’t considered that was valuable and which I incorporated into the second iteration.

It worked!


Simple Giving_mech_v4 flaps.indd

This book is by one of the friends whose wisdom I consulted…


I’m meeting my new agent, the sixth I’ve worked with, next week.

But, now comes even more unpaid hard work, a larger gamble for both of us, as I produce a full book proposal, which is much less literary than a hard-sell document filled with promises — our goal to win an offer from a major publisher and one big enough I can actually afford to stop most other work for a year or more. Book advances are now paid out in quarters, (thirds if you’ve got some clout), which means a long, long time between payments, from which your agent first deducts 15 percent.

So, if you’re really lucky and get, say, a $100,000 advance (rare!), you’ll net about $28,000 (pre-tax) per instalment — which, in a place like New York, really won’t even sustain a year’s living costs. I know Big Name Writers with full-time well-paid jobs who turn down a book deal because they can’t afford the drop in income.


My first book, published in 2004. As someone who grew up with no exposure to guns, I was deeply intrigued by this most American of obsessions


I’m eager to write more books, though, as basic story-telling already pays poorly and, isn’t sufficiently challenging. I’ve been doing this work for decades, and want to produce deep, smart work — which very few places now have the space or budget for.

I also applied last week for a cool staff job at the Washington Post, because, what the hell? Why not? I asked a friend who’s a writer there who encouraged me, and then (deep breath) took what for me is a huge risk and asked someone for their help. She’s a Big Name Writer at the Post who I deeply admire and met in person in June 2016. We follow one another on Twitter, but that’s the depth of the relationship.

She said she would mention me to the hiring editor and say good things.

I was grateful as hell, stunned at my good fortune. It’s very difficult for me to ask others for help.

I also, being ill and exhausted, sent out some LOIs (letters of introduction) to editors, spoke to one by phone about possible assignments and emailed back and forth with several others.

Still waiting for payment for work already published.


So much of this business isn’t writing, but finding and nurturing relationships with the people — agents, editors, fellow writers, grant and foundation judges — who need to place their trust in you: to be accurate, to be ethical, to be a decent person to work with, to not miss deadline.


I listened to three interviews with writers and editors from the Longform podcast, one of them the editor of a Big Fancy Magazine which emboldened me to send him a pitch.

If you’re interested in journalism, writing, publishing, media, this series offers 277 podcasts and you will learn a lot, and gain some useful insights into who wins the Big Fancy Jobs, when, how and why.

So, even though I haven’t earned a penny this month (!) it’s actually been great.


As we say in New York, go figure!



25 thoughts on “A week in my life as a freelance writer

  1. Hey Caitlin, I enjoyed this rundown of the variety of tasks, relationships, and opportunities that come and go as a freelancer. I’m experiencing a little of this myself right now–and while I have a niche in education journalism, I’m finding it really difficult to successfully pitch into new areas…I wish you the best with your new endeavors!

    1. I figure a little truth-telling is a good thing. πŸ™‚

      I see so many bloggers saying how easy this gig is and how lucrative it can be. Hah! It depends on your niche(s) — if you do highly specific, in-demand writing (technical, medical, legal), sure. I have a friend making $75K a year doing mostly legal-focused writing. Just not my thing!

      As a generalist, I have a lot more fun but earn less than I could if I narrowed my focus.

    1. Thanks!

      One thing you’ll notice (!) is how privileged many of the people interviewed are. That struck me at once, even after only four interviews. There is good stuff in there, for sure, but that’s an issue for me.

    1. Hey, David…it’s New York! You should see the people I am up against — who all went to the right American colleges and all know one another and…I didn’t and I don’t. I lack the crucial social capital they all bring to the party, so without some measure of self-confidence I could never ever compete effectively. It’s still very difficult, even with self-confidence and determination.

      Frankly, many people would have given up by now. But I have no wish to slink back to Canada, defeated. πŸ™‚

      1. Thanks.

        I KNOW I have the skills but I don’t sell myself very well on paper — so the real challenge is getting into a room with people so they can see and hear my energy and enthusiasm. I hate flattery and bullshit, so I don’t write that down…and I suspect it hurts me competing with those who do it well.

        I also get beaten down by so much rejection that i just don’t even try for a lot of stuff now that I’m absolutely qualified for.

  2. Good luck with the book proposal and the Post application! I’ll keep my fingers crossed and send positive thoughts your way. πŸ™‚

    “So many writers’ relationships now, working alone at home or in a co-working space or library or cafe, are virtual that I’m eager to meet face to face whenever possible” — it’s hard to make connections in the digital age, isn’t it? Personally, I’m finding it difficult to meet new people (potential dates) without resorting to online dating, which seems so…artificial.

    1. Thanks! I’m meeting my new agent tomorrow. Super excited. What I’ve seen and heard so far has been really encouraging. We have to move FAST on this one as it’s very timely.

      I met my husband on-line! πŸ™‚ I was writing a magazine story about online dating (wayyyyy back in 1999-2000) and he popped up! We’ve been together since then.

      I have no issue with online dating, per se. You have to quickly get to a phone and in person date, though, as anyone can seem cool on-line and then…UGH….in person.

      1. Yay! It sounds positive.

        Oh, that’s a nice story. I always like hearing how people meet. Online dating worked out well for you then! πŸ™‚

        Exactly. I’m not interested in having a penpal! The only thing that puts me off meeting people online is the potential safety issue, but I’m probably overly cautious.

    1. That’s the plan! πŸ™‚

      I see far too much rahrahrah writing about writing that is, frankly, self-serving bullshit. I’d say 90% of my work is finding and preserving relationships — and 10% actually writing! Without good/great peer relationships, you’re toast. I found my new agent by asking in a writers’ group online — and he works with another Canadian writer I’ve known for years, even if we’re not friends, per se. Without those connections (and they are do-able) you just can’t move very far ahead.

      People really underestimate the need for social capital and over-estimate the need for talent.

  3. i hope you’re feeling better soon, and i love that you never give up. connections with people are by far the greatest lead in to finding a path in, if there is one to be had. i love your diverse group of people that you meet and stay in touch with.

    1. Thanks. My poor body is worn out from being ill…now into week 3.

      I never give up, but frankly, am ready to. Other than writing books, I’m not very interested in hustling for my living. I’ve been doing it since I was 19. πŸ™‚

  4. Pingback: [BLOG] Some Sunday links | A Bit More Detail

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