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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 amazon.com 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.