A week in my life as a freelance writer

By Caitlin Kelly

 

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Ohhhh, so glamorous!

Not.

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.

 

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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!

 

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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.

 

BLOWN AWAY COVER
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!

 

 

You gotta have a posse!

By Caitlin Kelly

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THE BREAKFAST CLUB, Judd Nelson, Emilio Estevez, Ally Sheedy, Molly Ringwald, Anthony Michael Hall, 1985. ©Universal Pictures/Courtesy Everett Collection

It started — of course — as a term in medieval Latin; posse meaning power.

Today, it’s a group of people, more commonly, you can turn to for help and aid, people who literally have your back.

In the military, there’s a great expression — “I’ve got your six” — from fighter pilots who had a fellow flyer behind them.

I’ve been working alone from home since 2006, and have done it many times in my career. It can be lonely! It can feel isolating!

There are days when the millions of us working independently think — HELP!

Which is why, more than ever, you gotta have a posse!

They’re not fighter pilots, nor do they wear spurs and Stetsons, but they’re people I like, trust and admire, people I turn to for all sorts of advice — how to find a mortgage broker, what to charge for a seminar, how to wrangle a testy editor two years out of college.

They call me, too. I had a long phone conversation yesterday with a younger colleague as she drove from Alabama to Tennessee. We met earlier this year at a writers’ conference and immediately liked one another, sitting in the bar for hours.

Today I’ll be Skyping with another posse member who lives an ocean away.

I find it, literally, heartening and encouraging to hear how others are doing, helping one another through our inevitable ups and downs. Those of us who work without any safety net, (unemployment insurance, paid sick days or paid vacation days, a company-matched retirement plan), really need one another’s wisdom and insights.

 

My posse — and I as one of theirs — is global, thanks to social media.

 

But the essential elements remain timeless. You only want people you trust absolutely, who are discreet and smart. They can be decades younger or older. They can, (and often should), be someone from a very different background or industry.

Fresh eyes. Fresh insights.

When you don’t work in an office or belong to an organization, with coworkers, managers, HR and set policies, (no matter how frustrating they can be sometimes), figuring it out is all up to you.

 

When you work independently, you’re the cook, janitor, CIO, CFO, CMO and CEO, switching roles constantly.

 

When you work alone, it’s even more essential to know what’s going on in your industry — how to read (and alter!) a lousy contract, how to negotiate rates, what others are being paid, which deadbeat clients to avoid.

Much is being written about the “gig economy” (a phrase that makes me crazy every time I read it) — but very little about how difficult it is to do everything by yourself.

Sometimes you just need a smart, tough brain to bang up against, to test out a theory or see if you’re really brilliant this time, or heading off a potential cliff.

I enjoy my autonomy but there’s still a lot I don’t know and a lot I can help my peers with.

Do you have a posse?

Does it help?

C-C-C-C-Confidence!

Skyhammer & Airlift Mini-Con  Power Core Combi...
That's what I'm talking about!!Image by Rodimuspower via Flickr

Can we get anything done without it?

Yet, and yet and yet, I have entire days I think I just can’t: make that call, send that email, ask that favor, knock on that door or send that resume.

People have told me for decades how confident I appear, and the operative word might be appear, for there are too many days I feel like some medieval warrior girding her loins before even picking up the phone or sending out an email.

As someone with no steady income, salary or pension down the line, I’m in lioness mode: I eat only what I catch and kill. That means having to hustle for clients every day, whether reaching out to former or current ones or finding and cultivating new ones.

Either way, it means a lot of people contact and no guarantee of the outcome.

Which, if I fail, means — I’m broke!

No pressure.

I can blame my reticence on a few things:

— I’ve been canned from a few jobs, which has permanently dented my sense of likability, no matter how businesslike a layoff can be

— I was badly bullied in high school for three years by a small gang of boys

— I spent ages 5 to 30 in Canada, a country that has no tolerance for self-promotion or boasting then moved to the U.S., a place with a population 10 times larger, competing with some mighty sharp elbows. Time to man up!

— I faced a tough crowd in my own family, people who often found much to criticize and little to praise

But without a cheery demeanor and the conviction you have something worthwhile to offer, it’s tough to get out there and ask for what you want, whether a job referral, grant recommendation or help with a new project.

I had recently reached out to two people, one an old friend who didn’t call back for weeks and one a new contact whose initial voicemail sounded fairly frosty. So it was with a heavy heart I called both of them back.

Both were delighted to hear from me. Both had lost my phone number and wanted to hear my ideas.

If I hadn’t had the confidence to reach out again, I would have lost out on some cool opportunities.

Do you ever feel lily-livered?

How do you get past it?

How (not) to network: Smile, listen, less small talk!

Name Tags!
Image by freakapotimus via Flickr

I’ve just registered for the annual conference of the American Society of Journalists and Authors, April 24-25, on whose board I serve; if you’re an ambitious writer, it’s well worth the effort and cost to get to Manhattan for it.

I’m looking forward to catching up with dear friends: Greg from Minnesota, Lisa from Maryland and Randy from San Diego, who found me the best researcher to help me with my book. I’ll also meet many new-to-me people.

They’re great places to make a ton of new and incredibly useful contacts, but a conference can make your stomach hurt with social anxiety: all those people you don’t know, some of them terrible blowhards, some at a totally different level professionally, some vampires.

How to sort them all out?

From Bnet.com, a British business-focused website:

  • Question 1: “What do you do?” This is a neutral start. It allows people to talk about their favourite subject: themselves. The pompous types tend to give the game away immediately. They do not tell me what they do: they tell me how important they are by saying that they are a Senior/Executive Vice President or Director at MegaBucks. Interesting people tell me what they actually do. Whatever people actually do, be it cleaning toilets, pawn broking or exploring the Antarctic, they have interesting stories to tell.  The more they talk, the more I learn.
  • Question 2 — For the pompous types who failed Question 1: “So what is it you actually do in that role?” Some people make a miraculous recovery and become interesting again. Many others tell me more about how important they are. They meet important people (name drop), travel (place drop) and have big budgets and, by implication, big d***ks. For these people, I have to resort to the killer question.
  • Question 3: “So do you enjoy your job?” Anyone who has answered question 1 well, will already be exuding enthusiasm and passion for what they do. There is no need to ask them this question. The pompous types have never even thought of this question. They are so focused on being important, that nothing else matters. If question 2 makes them stop and think, question 3 creates total mental meltdown. It is a joy to watch.
  • From The New York Times:

    It may sound counterintuitive, but people who spend more of their day having deep discussions and less time engaging in small talk seem to be happier, said Matthias Mehl, a psychologist at the University of Arizona who published a study on the subject.

    “We found this so interesting, because it could have gone the other way — it could have been, ‘Don’t worry, be happy’ — as long as you surf on the shallow level of life you’re happy, and if you go into the existential depths you’ll be unhappy,” Dr. Mehl said.

    But, he proposed, substantive conversation seemed to hold the key to happiness for two main reasons: both because human beings are driven to find and create meaning in their lives, and because we are social animals who want and need to connect with other people.

    I recently attended an event in Manhattan for writers held by mediabistro.com, and met three people I found fun, interesting and potentially helpful future contacts: a fellow memoirist, someone writing a lot for on-line sites and an author with a book whose subject I found fascinating. I was surprised the author didn’t bother to follow up — I offered to write about her here (hello, free publicity!) — but it happens.

    If you do meet someone you enjoy, don’t lose touch. My trick is writing down, right away, when and where I met that person on the business card they give me. I used to wear myself out saying hello to so many people. Now I try to have a few, deeper conversations. I enjoy it much more and come away less exhausted.

    The worst, exemplified in this funny video, also British, (who love to skewer the pompous), from YouTube:

    S/he looks constantly over your shoulder looking for next, better blood supply; can’t be bothered remembering your name; talks only about himself and peels away at the first opportunity to the Much More Important contact across the room. Don’t be that person!

    Do conferences work well for you? Any tips on how to make the best use of our time there?

    When Is Help Worth Paying For? The Creatives' Dilemma

    A chimpanzee brain at the Science Museum London
    Pick it, but for a price...Image via Wikipedia

    Correct me, please, if I am wrong, but I suspect that engineers or dentists or plumbers or dry-cleaners, when meeting someone socially, don’t get: “Oh, can I ask your advice?” Do you actually show a DDS your molars or point to a stubborn spot on your sleeve? I doubt it. It would be weird and rude and intrusive.

    Writers do get this question. All the time. Maybe because, y’know, it’s just writing.

    People email me, and perhaps also to many others, out of the blue to “pick my brain” as though that were an activity I might enjoy and find satisfying. Yes, it’s flattering that people think you have something useful to offer them. Sure, one works hard to acquire some level of visibility and credibility. But I’m not emailing random Big Name Person to ask them for their help, free. I know it took them years of hard work and experience, perhaps costly travel and education and internships and apprenticeships, to acquire the very knowledge I wish I had. Why should they just hand it over to me gratis?

    I also studied interior design for a few years, planning to leave journalism for that field. One of our classes was  focused on the legal issues designers face. Like being sued. We were warned, in all seriousness, not to hand out advice on anything too substantive lest the suggested curtains catch on fire or someone slips on that sisal or their kid got caught their thumb caught in the Knole sofa and they’d come after us for it. I also liked the basic message — we were experts and would bill for that time and expertise. Clients will ask for anything they think can get away with.

    I’ve spent many years mentoring, helping, advising dozens of strangers, free. Not so much any more. I plan to retire and in order to do so need to retain control of my time, which, in addition to my skills, is all I have to offer in the intellectual marketplace.

    Here’s the challenge. I’ve already committed to serve on two volunteer boards, for several years, that take up a fair bit of unpaid time and attention. I enjoy giving back.

    If you’re someone who really likes to help others succeed, as I genuinely do, and you like to be liked, as many of us do, yet you must carve out a decent freelance income from your well-developed, otherwise uncompensated skills, when and where do you draw that line?

    Do you think, or find, that women have a harder time saying “no” to such requests? Do you feel any hesitation asking such questions?

    Life In A Virtual Newsroom

    Newsroom panorama
    Image by victoriapeckham via Flickr

    Losing a journalism job can also mean losing easy access to a pool of smart, talented, helpful colleagues whose work you know and whose judgment you trust. That’s a serious loss. While every newsroom and office has its share of divas, it’s a rare one that doesn’t also offer a few helpful veterans. Wandering across the room, even into another department, to get a phone number, brainstorm a feature or just share a joke is something I miss terribly. Freelancers are typically helpful to one another, but times right now are very tough and many people are keeping their cards much closer to their vest.

    TrueSlant has become my virtual newsroom. Yesterday morning I got an email from PJ Tobia in Kabul pointing me (thanks!) to a fun story — and I alerted another T/Ser to a Manhattan event that might help promote his new book. I haven’t met either of them face to face, nor did I know them before arriving here, but I’ve read and enjoyed their work here. I’ve been chatting via email with a dozen T/S fellow contributors who range in age from 20s to 70s, all across the U.S. Thanks to T/S, I’ve talked via email to new colleagues in Hong Kong and Kabul, two places I’ve yet to visit and am deeply curious about.

    I also get a kick out of the exchanges, however tart, that happen within an intergenerational community that (dinosaur alert) even includes the niece of one of my former Globe and Mail colleagues. My sweetie works at a newspaper where daily newsroom tensions can run very high between the 20 or 30-year veterans and the young ‘uns who are sometimes shockingly arrogant, dismissive of the Pulitzer-winning work some of their bosses produced before they were born. It’s easier to listen to someone 20 years younger — or older — when they’re not shouting at you on deadline or sneering at how you perceive and produce content.

    T/S is a virtual newsroom like no physical workplace I’ve yet seen: culturally and racially diverse, undergrads to senior citizens, physicians, policy wonks, techno-geeks. No newsroom anywhere would, or could, hire all of us. It should be one hell of a holiday party!