Caitlin Kelly Dishes on the Reality of the Life of a Full Time Writer

Caitlin Kelly is a freelance writer who has written for The New York Times, The New York Post, The Wall Street Journal, Washington Post, Glamour, Business Week, Town & Country, Family Circle and Penthouse to name a few. She is also the author of two non-fiction books: Blown Away: American Women and Gunsand her latest Malled: My Unintentional Career in Retail.

In this, the second part of our two-part series, I asked Caitlin to expose the reality of the writer’s life as I know many of us would like to make a livelihood from our writing passions and quit our day jobs.

Here’s her thoughtful response to my query:

Describe the “writer’s life.”

Now there’s an impossible assignment!

The simple truth is this: we’re all on a ladder. Some of us feel like we’re (perpetually) at the bottom, some stuck in the middle, all of us driven types – yes, that would be me – gazing at the top and wondering if or when we’ll ever get there.

What’s the top?

Best-sellerdom, rave reviews, prizes, fellowships, grants, movies with Julia Roberts or Anne Hathaway playing you. Very few of us will achieve those elusive, lucrative, Olympian heights, so the “writer’s life” is often wherever we are right now, and how much we’re able to enjoy it.

I started writing for a living while a college sophomore, was a reporter for three major newspapers and an editor for three national magazines. I’ve written two non-fiction books, “Blown Away: American Women and Guns” (Pocket Books, 2004) and “Malled: My Unintentional Career in Retail” (Portfolio, 2011.)

I hope to write many more.

Here’s some of what being a writer means to me:

Being a writer means:

never feeling satisfied

being part of a large and honored nation – but one with hostile tribes

worrying about money almost all the time, no matter how many Big Name Publications are on my resume

knowing your work has made strangers laugh and cry, ditch their boyfriends and quit lousy jobs

never knowing how your work is going to be received, whether by your editor, agent, publisher or readers

feeling the fear — of rejection, of being asked to revise the manuscript again, of lousy reviews, of disappointing sales, of not winning the grant or the fellowship – and doing it anyway

finding out that two of your favorite fellow writers have all applied for the same fellowship as you – and then, when none of you win, feeling a little relieved

watching work you find execrable crap dominate the best-seller list for months

seeing people like Jon-Jon Gulian win a $750,000 advance and three mentions in The New York Times. No, I’ve never heard of him either.

shrugging it off and getting on with your own work anyway

speaking on NPR in front of a huge national audience and having a caller sneer: “Why should I read your book? It’s just….entertainment.

spending more than the mortgage payment to buy liability insurance in case someone you write about decides to sue you

having your non-writer neighbors think you’re a celebrity

wondering who’s actually buying your books – and wanting to meet a few of them face to face and say “Thanks!”

bursting into tears of joy and relief when your very first copy of the finished book arrives

suddenly having people ask you to speak and lecture and give webinars – all without payment or even travel expenses — because they’re offering you “exposure”

learning to tell these people hoping to take unpaid advantage of your time, skill and energy — to piss off

getting extraordinarily moving emails from total strangers telling you that your work has changed, even saved, their life

that total strangers who have no idea how to write pull you, and your work, to bloody shreds on because…they can

that libraries worldwide are acquiring your books

going into Barnes & Noble and seeing a pile of your books on the front tables – and taking a photo just to prove it really happened

spending thousands of dollars of your own money to keep your book visible, audible and in demand

putting your faith, trust and career in your agent’s hands – who may or may not deserve it

cheering for your friends who get on the “Today” show when you don’t

driving hours to give a bookstore reading and only one person shows up – and giving it your best anyway

finding people who understand and can explain the words “modified gross” in your Hollywood contract

reading other writers’ work and feeling, gnawed with awe and envy and admiration, you’ll never, ever, ever be that good

reading other writers’ work and wondering how on earth they ever got a book deal, let alone huge advances and their own imprint

your writer friends sometimes have more faith in you than you do yourself

everything, everywhere is material

having the guts and skill to actually use it in your work

having stacks of your own books on the bookshelf beside your bed

needing friends whose own creative work – whether dance, art, photography or writing – means they truly understand the financial, intellectual and emotional rollercoaster of this sort of life

means taking chances month after month, year after year: choosing your agent(s), selecting your ideas, deciding with whom and when you choose to share them (be careful!)

The writer’s life is filled with rejection, joy, panic, fatigue. It’s not easy or simple. Success is rarely quick or lucrative.

Only you can decide if it’s worth it. For me, still, it is.

Read Caitlin Kelly’s take on disclosure in Part One of this series.

Author Caitlin Kelly Talks Disclosure: How Much is Enough?

Caitlin Kelly is a freelance writer who has written for The New York Times, The New York Post, The Wall Street Journal, Washington Post, Glamour, Business Week, Town & Country, Family Circle and Penthouse to name a few. She is also the author of two non-fiction books: Blown Away: American Women and Gunsand her latest Malled: My Unintentional Career in Retail.

Today and next Friday, July 1, Kelly shares some writing insight with us. Having been in the business since 1990 and worked as a freelance writer in addition to salaried writing jobs since 1996, she has plenty of hard-earned wisdom to share. As a bonus, if enough people ask questions (you can comment or email me directly at oc2seattle dot gmail dot com), Kelly has generously offered to do a Q and A to answer those questions, so don’t be shy, give us your questions!

Without further ado, please welcome Caitlin Kelly.

Thoughts on Disclosure
By Caitlin Kelly

Writing about yourself is a dangerous business.

You know how you think and what you feel. You’ve got strong opinions and powerful memories. Why not use them as material for essays, articles or books? 

What if you’re wrong? Does it matter? To whom?

And, once you start your emotional striptease, when do you stop? When is a coy flirtation insufficient – or a raw flood of confession the cringe-making equivalent of a lap-dance?

Welcome to the minefield of disclosure. The only way to know you’ve overstepped is when you’ve lost your legs. Which is where a tough agent, editor and first readers are essential.

I’ve written a great deal for publication about my own life: my marriage, my divorce, my desire not to have kids, putting my dog to sleep, a noisy hospital stay.

For Malled: My Unintentional Career in Retail, my second non-fiction book, I had to dig much deeper than ever before. I found it difficult, painful and frightening — what would the people I was also describing have to say about it? I did not tell them they were about to be in a book, that our private conversations were now scenes and dialogue, shaped by my memory and the exigencies of the book’s narrative arc.

There’s no rulebook on how much to disclose. Every writer, and editor, has their own notion of too much or not enough.

In my first draft of Malled, two close friends and first readers – one of them my sister-in-law – both cautioned me to purge the manuscript of a specific family member and our ongoing conflict. “It’s too much,” said Salley. “We don’t need to know that much. It makes me uncomfortable.”

“You don’t want the fallout,” warned Sheena. “Do you really think it’s worth the family drama to leave it in?” 

Now that Malled is out and widely reviewed – with 34 amazon reviews as I write this, plus some terrific professional assessments from USA Today, The Globe and Mail, Forbes. com and others – I’m also facing the cost of my own candor, of disclosing facts about myself and my worldview that people are now using to attack me, not as a writer but as a person.

For daring to feel them, and daring to include them.

I’ve been called a princess, a racist and an elitist, partly because I chose to disclose that – before working $11/hr in retail – I’d traveled the world, worked for three major daily papers, speak two languages. These are deemed problematic because….?

I could have said nothing. 

Should I?

I think not, and I’ll tell you why. Context.        

I recently read a memoir by a young woman, whose quixotic life choices seemed silly and misguided to me. (She found then charming and compelling, and so did her agent and publisher.) When I dug a little deeper, it was clear she came from significant privilege and had graduated from one of the nation’s most costly and exclusive colleges. Did her background shape her narrative? Of course it did.

Maybe it’s because I’ve worked as a journalist since college, but I want to know the facts! I want the larger contextual framework of who is talking to me, demanding my full and undivided attention for the length of their book. Not for fiction, obviously, but for non-fiction – for me – this is an essential element. Writers who try to disguise their filters cheat us, their readers, of the truth.

Whether we like it or not, we all see, think and write through multiple filters: race, age, education, ethnicity, class, religion, politics.

With no signposts at all to my narrator, a silence where I need context, I lose interest fast.

Who are you?

Why should I listen to you? Or believe you?

So, while some Malled readers continue to beat me up for candidly and honestly admitting in print who I am, where I come from and how I think, I’ll take the hit. I’d rather be that than James Frey or any one of the many “memoirists” whose work — it turns out later – is more deceptively artful fiction than accurate disclosure.

If you’re not willing to share your truth, don’t write.

You don’t have to share everything, nor can your readers listen to it all. It’s up to you, your agent and your editors to determine how much is too much, or too little.

And, no matter what you all decide, someone is bound to hate it.

And love it.

Welcome to the writer’s world!

Part 2: On July 1, Caitlin Kelly gives us her take on the writer’s life.

Writing Tips from Malled Author Caitlin Kelly, A Two-Part Series

Life works in mysterious ways. Really, I can prove it.

One day I was listening to an NPR interview with Caitlin Kelly about her new book, Malled: My Unintentional Career in Retail. The next I was reading about it in Marie Claire. And then I found myself in the midst of an email conversation with the author herself asking if she would give the rest of us some words of writing wisdom. And you know what? She said yes.

Writing Chops

Caitlin Kelly is a freelance writer who has written for The New York Times, The New York Post, The Wall Street Journal, Washington Post, Glamour, Business Week, Town & Country, Family Circle and Penthouse (yes, Penthouse) to name a few. She is also the author of two non-fiction books, Blown Away: American Women and Guns and her latest, Malled. 

Malled is an expose of the plight of the retail worker told from a memoir perspective.  It details Kelly’s two-years working in retail at The North Face after she lost her salaried job at The New York Daily News and wanted some steady income to supplement her freelance career and allow some breathing room in the never-ending story-pitching cycle.  For USA Today’s review of Malled click here.

Guest Blog Writing Series

For the next two Fridays (June 24 and July 1), Kelly will share some writing insight with us. Having been in the business since 1990 and worked as a freelance writer in addition to salaried writing jobs since 1996, she has plenty of hard-earned wisdom to share.  As a bonus, if enough people ask questions (you can comment or email me directly at oc2seattle dot gmail dot com), Kelly has generously offered to do a Q and A to answer those questions.

June 24: Disclosure

Because Malled is a memoir, Kelly had some interesting discussions regarding disclosure with her publishers. How much disclosure is enough? How much does an investigative journalist have to bare her soul in her memoir? 

The issue of disclosure is one us bloggers face all the time.  Do we talk about our families? Our friends? Our day jobs? List our last names? How much information is too much information? Where is the line between voice and privacy? 

On Friday, Kelly’s first guest post will wrangle with the unruly issue of disclosure and share the decision making process she used when writing Malled.

July 1: The Writer’s Life

Many of us dream of ditching our day jobs and writing full time.  On July 1, Kelly will give us a humorous and poignant look at the reality of the life of the full-time writer.

Can’t wait til Friday to start asking questions? Comment now.

The Power of Words

Writers routinely play with words but wordplay is a skill anyone who writes so much as an email should consider. Skillful wordplay can transform a sentence from ordinary to extraordinary and take a sentiment from trite to moving. The following short video illustrates how the same thing written in two different ways yields drastically different results. Enjoy and then start making wordplay a part of your life.

Why Read Food Blogs?

Last night, while hanging out with friends, one of them commented on how much she liked my post Alektorophobia. I was basking in her praise – “your writing has really developed . . . your posts are much funnier…” – when she did a 180. “I didn’t like your post on apricot bread.”

She said something about recipes being boring while I – never one to take constructive criticism or any other kind well – childishly thought “I don’t recall asking for your opinion.” As my mind wandered, she said “I don’t read your blog to read about food, I read your blog to read about your life.” Huh?

Naturally, her comment sent my mind wandering down one of its Romanesque winding alleyways. Why exactly do we read food blogs?

Sites like foodgawker and TasteSpotting imply that we like to look at arty pictures of food – food we want to eat, but can’t find, can’t afford, or can’t live with on our hips.

The popularity of healthy living blogs paints a picture of people looking for advice on how to eat, exercise and become or stay healthy and/or thin. Hundreds of thousands of such people apparently really enjoy looking at daily photos of oatmeal, unappealing green smoothie “Monsters” or mushy SIAMs (“Smoothies in a Bowl”). Don’t even get me started on the freaks making crackers out of pulp a.k.a. waste from their juicers or the constant comments from readers bemoaning the fact that money is always so tight while exclaiming that they just can’t live without their $20 nut butters.

I don’t know why others read these blogs, but I know why I do. Like my friend, it’s not for the recipes. While I often find great recipes, print them out and sometimes even make them, if I’m looking for something in particular, I head over to Cooking Light or Food Network; places where I can type in “chicken” and find 350 ways to disguise it. And if a blog is recipes, recipes, recipes, I don’t read it – unless there’s something more.


I don’t care how amazing the photos or recipes are, the thing that brings me back to a blog week after week is the blogger’s voice. It’s that glimpse of the blogger that shines through. Salty Seattle is the sassy girlfriend you can rely on getting into a bit of trouble with. Anecdotes and Apple Cores is the genuinely sweet, nice, caring sister or friend you wish you could be – if only your cynicism and smart-ass tendencies would go on vacation. David Lebovitz helps you dream of what your life in Paris could be like – if you could speak French, quit your job and move there.

I’ll read posts about restaurants in states I have no intention of visiting, at least not in the forseeable future. I’ll read about recipes I’ll never make. I’ll even look at your daily photos of oatmeal, if in the midst, you seem like someone I might like if we met in real life. To me, it’s not what you write about, it’s how you write it.

But that’s just me.

Why do you read food blogs? And, why in the hell are you reading mine?

Alektorophobia (Fear of Chickens)

Photo by Ian Britton

I have a confession to make, I’m a recovering alektorophobic. Well, that’s not entirely true as I was never actually afraid of chickens. But for fifteen years, chicken did not cross my lips. Steak, veal, pork – especially bacon – fish, shellfish, I ate it all. But not chicken. Never chicken. My mother had murdered chicken.

My mother was many things, but a chef she was not. She could grill a steak to medium-rare perfection, brown and grilled on the outside, rosy pink on the inside with just the right amount of juice bursting to the surface as the knife slid through the meat for the first time. She also put together a tasty, mostly from-scratch Thanksgiving dinner – until she discovered instant mashed potatoes. She toyed with cooking classes briefly – there was a microwave cooking class the results of which I’ve effectively blocked from memory – but for the most part she was an indifferent cook.

Growing up, breakfast consisted of milk and the cereal of my choice – Cinnamon Toast Crunch, Coco Pebbles, Smurfberry Crunch, nothing was forbidden. If you questioned the nutritional value of such breakfast choices Mom would remind you that cereal was fortified and we were eating it with milk. She had a point.

Mom, who never met a processed food she didn’t like, used them all in my school lunches. Beef jerky – the flat, rectangular kind that came by the hundreds in a big plastic jar with a red lid – Goldfish crackers, a mini-candy bar or cookies, Capri Sun and a box of Sun Maid raisins, because although raisins are mostly dried nuggets of sugary sweetness, they are fruit after all. I had the most envied lunch on my elementary school campus. The trouble was dinner.

There was no easy solution to dinner. Trips to McDonald’s and frozen Swanson dinners or pot pies were a once-a week or twice-a week solution but even Mom didn’t feel ok with serving those up on a nightly basis. So Mom mostly made spaghetti – with “Oh, Boy!” garlic bread found in the freezer aisle – and chicken.

Not just any chicken, either. Mom made “drummettes.” Four nights a week we feasted on rice and some version of drummettes, little tiny chicken legs that came from tiny chickens or baby chickens or a smaller bird masquerading as a chicken. tells me they are actually the part of the wing that looks like a little chicken leg, but I have my doubts.

There was barbeque chicken night – drummettes covered with barbeque sauce. “Italian chicken night” – drummettes covered with Italian dressing. “Lemon chicken” – drummettes basted with . . . lemon juice. The drummettes rarely came in the company of a vegetable. But I can guarantee there was dessert, probably ice cream, which was pretty much the only part of dinner Mom ever ate. After years of this drummette regimen, I escaped for college and began boycotting chicken.

The boycott wasn’t intentional, it just evolved. I refrained from ordering and eating chicken; not a hard thing to do in college when sustenance consisted of pizza and beer when you were feeling flush, veggie burritos when the budget became tighter, and Saltines at the end of the month.

After college, my disdain for chicken became more entrenched and obvious. Some of my friends developed disturbingly difficult food tendencies. While there were a vegetarian or two, they weren’t the problem; it was the people who wanted to “be healthy.” They constantly wanted to share the “healthier” chicken dishes forcing me to head off their chicken foisting by proclaiming “I don’t eat chicken.” This answer was never sufficient. Neither was “I don’t like chicken,” which led to my friends’ employment of unpersuasive persuasion tactics – “But this chicken is sauced really well” or “This is free range chicken, it tastes totally different than regular chicken.” No, it doesn’t.

I read a snippet in some magazine that 99% of chicken is diseased. I didn’t read the actual article – which had something to do with the need to properly cook chicken – but I stashed this tidbit in my arsenal and pulled it out on a regular basis. “Healthier? Did you know 99% of chicken is diseased? I’ll stick with the steak.”

Over the years, the chicken lovers – and I mean that to refer only to those fond of eating dead chickens – wore me down. I started consenting to eating chicken if it was “heavily disguised” – so sweet and sour and panang chicken insinuated themselves into my dining repertoire.

Finally, my milkshake-melting metabolism revolted. Faced with the need for lowfat protein and a husband who’s more meat-and-potatoes than vegan, I crumbled like the topping of a Dutch Apple pie. I learned to cook, and eat, chicken. After a fifteen-year hiatus chicken is bland but not half-bad, especially when spices other than Italian and barbeque are added. I now cook or eat chicken once a week, but I still boycott drummettes.

What was in Your School Lunch?

I’m currently reading Anne Lamott’s Bird by Bird: Some Instructions on Writing and Life In one chapter she talks about – in essence – breaking writer’s block by writing about school lunches.

Now while this is an interesting exercise for her, for food-obsessed people like us, the topic of school lunches is a bit more fascinating. Lamott talks about the three kinds of acceptable sandwiches – bologna, salami with “unaggressive cheese” and PB&J – the required uniformity of carrot sticks, the all important wrapping of the sandwich and what your lunch said about how your family was doing.

I’ve never once thought about what my school lunch said about my family, but now that the question has been posed I’m fascinated and a bit frightened. You see, while I know that PB&J must have been in my lunch at some time, the lunch my Mom packed for me most often in elementary school was this:

  • 1 stick of beef jerky (the flat rectangular kind that came in a huge plastic jar);
  • 1 box of Sunmaid Raisins;
  • Goldfish crackers (in a plastic sandwich bag);
  • A Halloween Size candy bar or package of not-homemade cookies; and
  • A Capri Sun.

    That’s right, the type of lunch thrown together in 5 mins by your older teenage brother. I’m not sure this says positive things about my family but I did have the most envied lunch in school.

    So, I’m curious – what was in your school lunch? Did you brown bag it or buy hot lunch? Were there unwritten rules among your classmates about what could or could not be in your lunch? What food was considered too eccentric for school?