The writer’s week: tears, mild panic and the IRS (possibly related)

By Caitlin Kelly

For those of you new to Broadside — welcome! — this is an occasional series in which I share the gory details of life as a full-time freelance writer in New York. Some of you hope to work in journalism or publishing, so this is a glimpse behind the curtain, as it were.



Back to the work world in earnest — I’m losing my Nicaragua tan. I need to find some elusive sources, people so broke they can’t pay any of the taxes they owe the Internal Revenue Service, people who wouldn’t normally want to speak to a reporter. That’s my favorite kind of story. I like difficult-to-impossible!

I Google the words “long term unemployed” and find an organization that might help. Its director calls me back and I learn more, including the fact no one in print has yet covered their fantastic work. I pitch the idea within the hour to an editor I know.

The challenge is deciding who to pitch — the biggest names don’t necessarily pay well or are easy to sell to, while a smaller outlet can pay more and make a faster decision.

I pitch ideas to Marie Claire, MORE magazine and a new website. I check in with my editor at Cosmopolitan — looks like the story I reported last summer is scheduled for the July issue. That will be cool; it’s a profile of a terrific young couple with a highly unusual love story.

MC and MORE pass on my ideas. At least I hear back quickly, usually within hours. I’d rather have a super-quick rejection and move on.

This is what we do.
This is what we do.


I write the profile of the Nicaragua country director, which isn’t due until April 11, but I have so many competing assignments right now that I’m having a mini-panic. Unlike many writers I know, I don’t work nights or weekends. I want a life! This month I have seven assignments in hand, another one possible and a short re-write due; until it’s in, the piece won’t get published and I won’t get paid.

I try to keep a steady workflow of a story or two each week, but it’s not always that tidy. A writer friend has agreed to contribute to a post here, but she’s got four assignments and a teaching job. It’s like that when you’re freelance.

That’s not even addressing the request for a long personal essay — the third version of it, none of it paid for yet, of course — from a large women’s magazine. Part of me just wants the kill fee in hand, and to move on to something simpler and quicker.

Still chasing down an overpayment of $2,600 that a client insists I never repaid them; I don’t want to pay one penny more income tax than necessary! Tax day here is April 15. Running out of time.


I take the train into Manhattan for a noon meeting at WaterAid, with whom I recently worked for a week in rural Nicaragua. I work alone at home, so getting out is always a treat. I drop off my battered four-year-old sandals at the shoemaker at Grand Central Terminal for repair — he wants $72 (!) for everything. I agree to $57 worth of repairs and wonder, once more, why everything here is so damn expensive.

I browse in Posman Books, one of my favorite indie bookstores, also in the station, and buy an Indian cookbook and thank-you card for the country director in Nicaragua who made our trip there fun and comfortable, even in intense heat and 12-hour days.

The view from the village house where we stayed; no electricity or running water. Heaven!
The view from the village house where we stayed; no electricity or running water. Heaven!

The meeting is with the entire office staff, only one of whom I’ve met before, plus three people Skyped in — from Maine, London and Nicaragua. We’re there to de-brief about the trip. When it’s my turn to speak, to my horror and embarrassment, I tear up and can’t say a word for a long, long minute before gaining my composure; the journey was a deeply emotional one for me on many levels.

It was great to meet everyone and to talk to people who are smart, passionate and worldly. I enjoy my work, but after eight years alone at home, it’s lonely!



I have to choose the dates for my fall classes teaching at my alma mater, The New York School of Interior Design, on the Upper East Side of New York City. I’ve suggested a two-hour session on creativity and an eight-hour series on writing. It will feel very odd to be back there as a teacher and not a terrified student; design is much tougher than it looks! I studied there in the 1990s, hoping to become a designer myself, but changed my mind. I absolutely loved my training and don’t regret a minute of it.

But I realized my vocation is telling stories in words, not color or space. We do have a great-looking home though!

I finally score three excellent sources for my tax story and set up three interviews for Friday.

I write a 1,300 word story for WaterAid, the second of three they have hired me to produce. I send several questions to the country director for fact-checking; he’ll be totally out of reach all next week as he heads back into the countryside.


I skipped my usual 9:30 a.m. jazz dance class — too tired from last night’s hip-hop class, my first. So fun!

Out to a local diner for lunch with a fellow writer who lives in town. I met him through his wife, another writer, who takes dance class with me. One of the pleasures of working for myself is managing my own schedule. I normally work a seven to eight-hour day, but can control when those hours are.

I do my interviews for a story about tax season for, a smart new website run by the same publishers as The Atlantic; the pay is decent enough for web work and I like my editor a lot.

I now know a lot about the IRS and have the makings of a very cool story I’ve never seen reported.

I check in with a few editors about possible assignments for May onward and finally tell one that I’m not going to keep working on a personal essay she assigned to me back in January. My heart is really not in it, and I’ve already done two revisions. I just want a kill fee and to move on. I hope this won’t hurt our working relationship, but I know when I’m not into a story and it’s a waste of time and energy to keep going.

Mailed off a cookbook, Indian spices and a thank-you note to the country director in Nicaragua, who admitted he loves Indian food and there are no Indian restaurants there; Jennifer and I want to express our gratitude for such a fantastic experience.

Sent Jose’s 20-year-old duffel bag back to its manufacturer in Colorado for repair, ($12 in postage!), which I shredded while dragging it on the ground in Nicaragua; excess baggage weight was such an issue, I preferred to bring three books instead of the weight of a wheeled suitcase. I ended up reading only one book, Claire Messud’s latest, The Woman Upstairs. I enjoyed it, but gave it to Jen when I was done.

How was your week?




15 thoughts on “The writer’s week: tears, mild panic and the IRS (possibly related)

  1. Pretty good. Made progress on some of my projects, including my current novel. I sat on a panel for OSU’s Office of Disability Services telling potential students with disabilities what it’s like at OSU and giving them advice about school. And I discovered a new band that I fell in love with in a matter of minutes (they sort of remind me of that band you posted about a while back, the two kids who were into metal when all their friends were into rap).

  2. How inspiring to read about your week, Caitlin, and great to read about your digging to bring the IRS story to light. This week I passed my First Aid Certificate and came home reeling off fascinating info (including re-enactments) to my not-so-fascinated family. What really fascinated me were the people in attendance! Amazing anecdotes.

  3. Your work days are so varied – it sounds like you had an eventful week! I work at a local monthly newspaper, so it’s really interesting to see another side to the journalism industry. One thing I love about my job is that every day is different, and it sounds like yours is the same 🙂

    This week in our office we had two deadlines (one for our regular monthly newspaper, and the other for our annual magazine about the Hebrides and the Isle of Skye that goes on sale just in time for the start of the tourist season) so this meant lots of proof-reading and last-minute corrections. There’s always a nice sense of satisfaction when the finished pages get sent off to the printers!

    1. Thanks…every week is crazy…:-)

      One of the elements I do enjoy, as you say, is variety. I would go mad with any sort of fixed routine.

      I am dying to come visit where you live! And good for you for making corrections. My weakest skill is that sort of editing.

  4. i love it when you offer us these real world glimpses into your life, caitlin. i love your story idea too, isn’t that interesting how no one has ever looked deeper into this and explained the other side of the issue? you are amazing in all you do, and even though there are many frustrating moments/days/months, it is nice to have the flexibility you have in life, and i always see these situations as opportunities. you are able to decide to participate or not participate in anything that comes your way. it is rife with possibility.

    1. Thanks! It’s kind of you to take such an interest. My goal is really to prep would-be journo’s for what this life is really like, as well.

      I was going to return my unused mosquito net today to EMS, but decided to keep it as a good-luck talisman and a sign of my determination to get the next story — soon — that requires its use!

  5. Kaitlin, the run-down of your week reminds me that I have been wanting to ask you when you’re planning to run your on-line workshops again. I have ideas, I write but I am totally at a loss when it comes to getting in touch with editors; – read: scared shitless 😦 – rejection or even worse–what do I do next if the story idea gets OK’d!
    Any plans for the workshops again?
    Kathryn Eszeki

    1. Thanks!

      Probably in May or June. Not sure yet, but happy to work with you. I’ll def. announce them well ahead of time. I also do one-on-one coaching, which is a little more costly, but we can sked that anytime workable for you.

      Better to be pitching than scared, although I get it…:-)

  6. I admire your ability to make a living as a freelancer. It can be a challenge, whether design or writing, not only to find work but to just keep at it. For me, the hardest part about writing is coming up with a topic to write about. I’ve found assigned topics easier than thinking up a topic. But (of course there’s always a but) when I do think of a topic that inspires, the words just flow. Fortunately for me, writing is only a small portion of my job. Kudos to you!

  7. Pingback: [BLOG] Some Saturday links | A Bit More Detail

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