Coping with rejection

By Caitlin Kelly

What will you do if that door stays closed?


It happens.

It stinks.

It hurts.


You want(ed): a job, a friendship, a sweetie, a fellowship, a grant, a book or film or music deal.

When you or your idea face (repeated) rejection, it can feel annihilating.

It shouldn’t.

I grew up in a family of freelance creatives, who wrote television shows and directed films and series and wrote and shot magazine articles. I saw, firsthand, what it’s like — emotionally, intellectually and financially — to put in a lot of hard work and hope only to discover that your ideas won’t receive funding.

Rejection is a powerful sorting process, quickly winnowing out those who really want it — and may still not get it! — from those who don’t. Maybe they’re ambivalent or don’t work hard or missed the deadline, again.

When you “fail”, (which to me is only temporary; if chronic, that’s not good), what’s your back-up plan?

Aircraft manufacturers plan for failure, creating planes that can still fly and land safely if an engine malfunctions.

Football coaches have a playbook, and everyone, everyone, needs a Plan B, C and D.


If we’re not thinking ahead to the next step, and the one after that, defeat can feel permanent.


How badly do you want it?


Here’s a wise blog post on what to do next…


I spent the past six weeks working on a book proposal.

Thanks to referrals from generous colleagues, I found top New York agents who replied to my email within hours. I worked with one for several weeks, but we quickly saw — to our mutual regret — this wasn’t a project he felt invested in, and I did. With the best humor and grace we could each muster, we parted ways.

The next agent replied to my email within half an hour — with tart, tough analysis of my idea’s weaknesses (yes, plural) and the intense competition it would face.

To say that — in British terms — these two men were  chalk and cheese, is an understatement. Whew. One was lovely, kind and gentle and encouraging, even if I could tell this wasn’t probably going to work out.

The second was brash, abrasive and cutting.

But neither was a fit.

So, for now, I’m putting that goal on hold; both taught me about the current marketplace (useful) and, essentially, reminded me of the kind of person I want to do business with.


None of this, sorry to say, is unusual within the cruelly competitive world of journalism and publishing.

Pretty much every creative field I know — art, music, dance, design, film, theater — is equally filled with smart, talented, well-trained, determined thousands who want the same things we do: money, attention, a job, a gig, a contract.


In my decades in this business, I’ve been rejected so much it just feels normal — I tried for eight years before I was hired as a reporter at the Globe & Mail, Canada’s best newspaper.

I tried multiple times, never successfully, for the Alicia Patterson fellowship, (one of 14 finalists among 387 applicants that year.) The latest winners of the McGraw Prize, awarded to seasoned business writers  — all three of them — beat out the 77 others who sent in their ideas.

Both of my previous books were rejected 25 times before finding a major publisher.


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



malled cover HIGH
My second book, published in 2011



Whether we welcome it or not, rejection offers us information we have to process.

Simply stamping your foot, shouting”It’s not fair!” or pouting in a corner won’t get it done:

What did you fail to include?

What skills do you need to strengthen?

Could you have prepared more thoroughly?

Would additional training or education help you succeed?

Is your network powerful enough to guide, mentor and promote you?


I would never dissuade anyone from following their dreams.


I would strongly suggest having a thick, strong coat of armor — for your bank balance and ego — if you do.

The reality of the creative life

By Caitlin Kelly

montreal 4


This essay, from LitHub, is brilliant and spot-on:

The writerly apartment in this fantasy is bare and minimal; the walls are unpainted plaster, or the wallpaper is peeling; the heat is faulty or not there; there are books stacked on the floor. It looks this way because it’s Paris struggling out of the deprivation and destruction of a world war, or New York soldiering on through the Depression, living in the wreckage of 1920s glamor. The writer spends hours in cafes, working and drinking, because the cafes are heated and the apartment is not. The aesthetic of this fantasy is permanently frozen in the first half of the 20th century, in the cities (and occasionally the beach resorts near cities) of Europe and the United States. The reason the fantasy writer lifestyle is set in such a particular time and place is that the interwar and postwar American writers who went to Europe for cheap rents have exerted a massive influence on the American idea of what literature is. Who casts a longer shadow across American fiction and curricula than Hemingway, Fitzgerald, and Baldwin?

While considering the specificity of these images, recently, something came to me: It’s an Anthropologie catalog.

(For those unfamiliar with it, Anthro is a major American retailer, with stores that change their look every few weeks and who sell a costly-but-gauzy kind of clothing and accessories to women who typically work in a corporate environment.)

Everyone wants to be a writer!

Or make films or art or music because…freedom from typical work constraints is so deeply appealing.

The catch?



Life costs money.

I grew up in a household of creatives, and we did live in a house my father owned, and drove decent used cars. Some years were better than others financially, but we also lived in Toronto, where the CBC and NFB had appetites and budgets for my father’s work as a film diector, long before there were dozens of cable channels seeking content.

Living in Canada also meant we never paid a penny for healthcare — which has cost me and my husband, living in New York as self-employed workers, $1,700 a month for the past two years.

Yes, really.

Thanks to a new plan, I’ll “only” pay $700 a month starting today, saving us $700 a month.

But our monthly “nut” is still more than $5,000 and we have no children.

Living a life creating things is one many people dream of. But it still has to be supported by someone, usually multiple someones, actually paying for food, fuel, medication and housing — let alone haircuts, dental work, new eyeglasses, etc.

The solo creative life is affordable only to those who can stand to live frugally, and for long periods, because so little creative work actually pays well enough to live a life that allows for sick days, a vacation, owning a home.

As one childhood friend, who, as a single mother helped to create animated films you might have watched, told me recently: “I lived on air.”

I know artists and illustrators and film-makers and writers and playwrights and poets. They love their creative work but rarely enjoy the payment and insecurity that comes with it.


So, to pursue this life often also means having a side hustle, a day job, a trust fund, a hard-working, well-paid spouse or partner.


It’s extremely rare for me to have a month in which I’ve generated no income from my writing, because I don’t have a side job. It is my job! That means, without my husband’s hard work at his two freelance positions, (and our emergency savings), we’d be in deep shit, unable to pay our bills in full and on time.

It shames me to admit that this is the case for me right now — but the reason I do so here is because it’s true.

This can be a financially precarious life, and often is.

Here’s a post I wrote in 2011 about this dilemma — would you rather be creative or (the great American fetish) productive?

Whenever I’ve taught or lectured on journalism, I crush a few young dreams when I make clear that traditional news journalism more resembles an industrial assembly line than an artist’s studio.

Editors aren’t terribly interested in whether you’re feeling creative — they want accurate copy/content/visuals and they want it now!

The worst of its managers rely on the crude tool of by-line counts, i.e. how many stories have made it into the paper with your name on it (your byline.) So re-writing press releases or dumping puff pieces all add up to more bylines, if total garbage. So you’re visibly and undeniably producing and are therefore (whew! job saved!) productive.

Now….how to be creative?

What does that look like to you?

It might mean inventing a recipe, choosing a new color for your living room, or starting a poem or sketching your cat or simply staring into the sky for an hour to let your weary brain lie fallow, like an overworked farmer’s field that needs time to re-generate.




Inertia…or action?

By Caitlin Kelly


Sidewalk closed, use other sidewalk…


From The New York Times:

Habits are powerful. We persist with many of them because we tend to give undue emphasis to the present. Trying something new can be painful: I might not like what I get and must forgo something I already enjoy. That cost is immediate, while any benefits — even if they are large — will be enjoyed in a future that feels abstract and distant. Yes, I want to know what else my favorite restaurant does well, but today I just want my favorite dish.

Overconfidence also holds us back. I am unduly certain in my guesses of what the alternatives will be like, even though I haven’t tried them.

Finally, many so-called choices are not really choices at all.

I finally hit bottom on two issues this week, and finally acted to try and deal with them, instead of just stewing and whining.

I live in a town north of New York City, whose main street is increasingly jammed with traffic, including 18-wheel trucks. Pedestrians have been struck and injured while in the crosswalks, which is illegal.

It’s getting worse and worse and worse.

The other day, I watched, enraged, as two drivers, in broad daylight, once more drove right through the crosswalk as I was crossing — and saw me looking right at them.

I gave them both the middle finger and went directly to the police station where I filed an official request for how many summons they issued in 2017 for this violation. (My guess? Fewer than a dozen.)

To my delighted surprise, the chief of police called me the next day and we discussed the 60 (!) summons they’d issued and how to potentially reduce the problem. I was so glad I’d done something.

I also called a friend in Canada to ask his advice and help potentially finding me and my husband full-time staff jobs there — because Canadian residents don’t have to pay for healthcare.

That alone would save us $2,000 every month.

I left Canada in 1988 and have no burning desire to re-patriate; we don’t want to sell our New York apartment and can’t rent it under co-op rules, which is a huge deterrent.

We love our town and region and would miss our life here.

I can return to Canada as a citizen, and we have yet to discover whether Jose has the right to live there with me, let alone work.

But we’re now so burdened with health insurance costs that are rising and rising and rising, and despite all our hard work, we feel increasingly frustrated and angry with our financial struggle.

We’re both full-time freelancers, living in a one bedroom apartment.

There’s no fat to cut.


Even if we choose to stay in New York, and we might, (and might have to), I already feel better for:

1) admitting these issues are driving me to my wits’ end rather than just bottling it up, as usual;

2) asking for help, which I’m always reluctant to do;

3) talking frankly with my husband about how badly this stress is affecting us individually and our marriage.


I was inspired by a New York Times column with the wise words:


Fury isn’t strategy


For me, 2018 is going to be a year of strategy and action.


How about you?

Kim Wall, talented young journalist, found dead in Copenhagen waters

By Caitlin Kelly

Columbia Journalism School

It’s every writer’s worst nightmare — to head off reporting what appears to be a cool, fun story  —- and end up dead.

From The New York Times:

The Copenhagen police announced on Wednesday that a torso found this week in local waters was that of Kim Wall, a Swedish freelance journalist who disappeared after boarding a Danish inventor’s submarine.

The announcement, which followed DNA tests of samples from the torso, turned what had started as a missing-persons case into what Christian Jensen, editor in chief of Politiken, Denmark’s largest daily, called “the most spectacular murder case in Danish history.”

The inventor, Peter Madsen, 46, has been held on preliminary charges of involuntary manslaughter. It is not yet known how Ms. Wall, 30, died, nor how or why her body was dismembered.

Her torso — missing its arms, legs and head — was found by a cyclist on the edge of Amager Island on Monday afternoon,

Kim Wall, a talented 30-year-old freelancer, educated at prestigious and demanding schools like Columbia University’s School of International and Public Affairs, Columbia Journalism School and the London School of Economics, headed out aboard a submarine with Danish inventor Peter Madsen.

Like many ambitious journalists, she decided to do the reporting first — and sell the story (one always hopes!) later, i.e. “on spec.”

Full-time freelancers like Kim, (and me), work with no institutional protection, often with no danger training or back-up.

We hope to, and must, quickly sell our stories — as she did to The New York Times and other publications.

I didn’t know Kim, nor had I read her work, but her death — her appalling, terrifying end while at work — is hitting my tribe, journalists, and especially bold women like her who venture alone into funky places alone around the world, very hard.

Freelance work, de facto, can require a sort of bravery, initiative and decisiveness that’s unique to our industry:

No one sits around waiting for the day’s assignment from a boss.

No one revises a press release and hits “send” and calls it journalism.

No one has a paycheck, nor even a guaranteed sale, let alone a well-paid one.

We work alone, often without the witness or putative aid and protection of a fixer, translator or photographer.

Those who, like Kim often did, work overseas, must cover their own expenses and arrange all their own travel and accommodations.

And, as this story did, it demands that we trust others, often with our safety and our lives.

You gin up a great idea, and, sometimes without a definite assignment, (i.e. a sale, income, let alone your travel costs repaid, and an editor invested intellectually and financially in what we produce) — and go.

Like Kim, I’ve gone to a few places to report a story that others told me not to. Nothing as truly scary as a war zone or natural disaster, but — like her — working alone with or around men I had never met before.

At 25, I jumped into a truck with a French driver I’d never met, 10 years my senior, and traveled with him, sleeping in the truck cab every night, for eight days, from Perpignan to Istanbul.

There were no cellphone then, no GPS to track our location, no Internet.

It was — as Kim’s decision to board that damned submarine — a decision I made, eagerly, on a common and basic calculation in our field:


adventure + exclusivity + access + firsthand reporting = terrific  (saleable) story


And, for many women I know, like one who ventures repeatedly into a nation riddled with vicious crime, I made a bet.

Like female freelancers who cover war and conflict zones, places where women are often raped and slaughtered.

The same bet I made when I traveled alone, also at 25, into a small Sicilian town to report on a complex topic, not speaking a word of Italian, relying on men I had never met for translation and lodging and transportation.

The same bet I made when I walked, at dusk, into Brixton, then a no-go area of London, to interview a male squatter.

In every case, thank God, I got my story, and came home.

Safe — and alive.

We bet, each of us, every time, that we will return unharmed.


Tonight at 7pm there is a candlelight vigil being held at Columbia Journalism School, in upper Manhattan, in Kim’s honor.


A freelance journalist’s week

By Caitlin Kelly

carr service01
The New York Times newsroom

If you’ve never tried working freelance — i.e. no job, no salary, no paid sick or vacation days — it can look cool.


I’ve been doing it since 2006 (and for periods before then as well), and enjoy it.

It’s rarely dull.


Here’s some of what this week has been like:


I pitched a story to The New York Times, realizing, two weeks after returning from an overheated, often non air conditioned Europe, that it’s an uncomfortable, even dangerous, situation for travelers and hotel owners.

And one only likely to worsen with climate change.

I’ve been writing for the Times since 1990, and had previously written for that specific editor, so he quickly replied to my emailed pitch — but I had barely four days in which to find all my sources, interview them and write the story.

Thanks to my active life on social media, including Facebook and Twitter, I soon found what I needed.

Here’s the story.

I’m working on a big (3,000 words) story for a local university about their school. Have been doing interviews for weeks, some by phone, some in person. It’s a challenging assignment and one I’m enjoying, but it has a lot of moving parts. Did seven interviews, in person, in one day on campus — pooped! Slept 10 hours and took the next day off entirely to recover.

During one of the interviews, heard a deeply distressing story of murder in someone’s life. I didn’t react much, which — to those who don’t know any journalists personally — can make us look cold and unfeeling. Not so! One of the keys to success as a journalist is being able to manage and control the most powerful of emotions, even in the moment, and stay focused on your goal — reporting the story. It can, and does, lead to some trauma later as you process it eventually, or don’t.




I speak fluent French,  so I was asked to interpret between an editor in Alabama and a French-speaking farmer in Quebec to determine if there was enough to produce a story. There is, so I’ll be heading north to Quebec soon to report and write it.

A former client in Chicago sent me an assignment they needed done right away —- and had to turn it down because they needed it fast and, for once, I’m too busy at the moment.

I emailed editors in New York City and London to follow up on personal meetings to see if there’s work I can produce for them — no answer, so far. It’s normal for even people who know me and my work to take a while to respond. You can’t freak out or take it personally.

Pitched another idea to a new client who loved it — have to constantly be pitching ideas or the income stream dries up fast! Bills never stop arriving, funny thing.

Jose and I took a day off to explore the North Shore of Long Island, about a 2.5 hour drive from our home. In our years together, we’ve been to Paris together a few times — but never there.

Found this astonishing Spanish chest — 17th century? — in a local antique shop.




This area is gorgeous and we loved it, including this amazing general store, built in 1857, now on the National Register of Historic Places.






Fleeing toxicity

By Caitlin Kelly

I took on a freelance project in August that, while hardly ideal, sounded like it might be worth doing.

I was willing to try.

It was a lot of hard work for not-enough money.

It was also, though, a lot of hard work with editors whose skills proved deeply disappointing.

Last week I ditched it.

I rarely walk away from regular paid work; like every full-time freelancer (or anyone running a business), I know how difficult it can be replace one client with another or, more realistically, with three or four.

But I finally hit breaking point when I spoke up for myself (not a quick decision) — and in reply was smacked down like a puppy who’d peed the rug.

By someone barely one-third my age and with two years’ experience.


Anyone who grew up in a family where their feelings were routinely ignored, let alone one with some seriously nasty behavior patterns, knows that it can a lifelong challenge to parse what’s “normal”, (especially indifference to respecting you), and what isn’t.

To determine if it’s “just you” feeling shitty about that relationship all the time, or maybe, just maybe, there’s a reason for that, and you need to get away now.

To know when to stand up for yourself — sick to death of cringing and genuflecting to people whose treatment of you is miserable, but whose payments cover stuff like your groceries and health insurance.

And to know when to simply say, enough toxic bullshit.

Throughout my life, I’ve marked these pivotal moments with a piece of jewelry, a talisman to signify, with beauty and grace and a tangible memory of taking the best possible care of myself, the important transition away from a soul-sucking situation and a movement towards freedom, re-definition and independence.

It’s scary.

It’s not easy.

I don’t bolt quickly, easily or without much deliberation and self-doubt.

The first was the decision to end my first marriage, at least in its then-iteration, (deeply lonely, adulterous on his part), while I was 100 percent reliant on his income.


I was alone in Thailand, on  Ko Phi Phi, a remote island when I decided. I bought a coral and turquoise and silver ring for about $20 and brought it home to remind me of my resolution. My husband, of course, didn’t like its style. Within six months, the marriage was over.

The second was putting my alcoholic mother into a nursing home. Our relationship had been tumultuous for decades. The experience was emotionally brutal for reasons too tedious to detail here.

I found, in a craft shop on Granville Island in Vancouver, a small sterling silver heart that looked like a stone that had washed up on some beach or river shore, pitted and rutted, battered — but intact.


It symbolized exactly how I felt; I wear it on a long piece of cord.

The third was this one, to shed a client I’d had doubts about from start.

So I found this gorgeous small lock at a Christmas market in New York’s Bryant Park, a Turkish design. It consumed almost exactly the paltry sum I’ll earn from my last piece of work for them.


Open the lock.


Freedom feels good.

Talismans remind me to chase it, cherish it and never relinquish it so easily again.

You gotta have a posse!

By Caitlin Kelly

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?

Do you prefer journalism or “content”?

By Caitlin Kelly


Ooooooh, content! Aka books.


Good old English.

Content, with the emphasis on the second syllable, is what I used to be to work in journalism.

See also: happy, pleased, satisfied.

Today it’s about content — i.e. kawhn-tent — with the emphasis on the first syllable.

This is where I thump my cane and start shouting “Kids, get off my lawn!”

Or some similar shriek of frustration.

Truth is, of course I’m a “content provider”, in that I write words on demand to specific lengths that I sell to others for their use.

I guess it’s a nice little catch-all. Sadly, though, there’s nothing in that phrase to connote, oh you know, history, ethics, values, quality.

It’s like calling the sun a “light provider” or the ocean a “fish (and many other creatures) provider,” reducing what journalists once offered to a pile ‘o words, delivered as fast and cheaply as humanly possible.

My story in July 2014 Cosmopolitan (U.S. edition)

I can, after decades in this field, legitimately call myself a journalist, author, writer – having worked as a staff reporter and feature writer for three major daily newspapers and on staff for several national magazines as an editor.

That, plus hundreds of freelance pieces.

But the irony of an industry in disruption is that there are now many more people working in public relations — trying to sell stuff — than there are journalists. I get pitches every single day for things I couldn’t care less about from people who clearly couldn’t care less that they’re wasting my time deleting them.

Here’s a post about the rise of “content marketing”:

Content marketing is currently “in,” and brands are finding it’s surprisingly difficult to create compelling content that actually draws in readers. So they’re opening their pocketbooks and are willing to pay for content creation, and if you’re well-positioned with some decent writing credits, you’ll find that there’s plenty of work to go around. There are several freelancer job sites popping up where brands can advertise for these positions.

Unless you’ve been living under a rock, you’ve likely noticed the news industry has struggled in recent years. Newspapers and magazines have endured thousands of layoffs and freelancers have found, in addition to facing shrinking budgets, news organizations are paying significantly less for digital stories compared to what they paid for print.

And a cheerful piece about why journalism students don’t even want to consider a job doing what the job used to mean — actual reporting.

I have several friends who teach journalism, both undergrad and graduate level, and find a scary trend — students who sit at their desks, Google and think that’s journalism. My friends have to shove them out of the building to actually look at stuff and talk to strangers, some of whom are intimidating as hell and two to three times their age.

Yes, really!

It could be funny, perhaps, if all those PR people weren’t being paid to make everything look and sound shiny.

It could be funny if the people being hired to pump this stuff out weren’t really young and utterly inexperienced, like the editor who sent me an email I literally could not understand.

This is the person being paid to edit me, two years after leaving college.


Did you read my coverage of the Paris Unity March? I blogged it here. That’s journalism

Which is why places like ProPublica, (where another friend is still doing dangerous and complex international reporting work), and The Washington Post are needed more than ever — if you haven’t been reading David Farenthold’s reporting on Donald Trump’s many misuses of his charity, you need to do so before the Presidential election.

Journalists get paid, (less and less and less), to tell real stories about real people — about crime and poverty and graft and corruption and politics and the environment. The stories are often dark and depressing and often crazy-complicated and have multiple furious gatekeepers insisting: “There’s no story here!”

Which always means there’s a hell of a story to be told — if there’s a place to publish it and someone to pay us to do that.


Are you content being offered a steady diet of content?





My NYC writing life — update

By Caitlin Kelly

IMG_20160617_102113083 (2)

As many of you know, I earn my living writing journalism for places like The New York Times, Quartz, Reuters Money and many others. My most recent quick hit was about a new luxury hotel in Mexico for a design trade magazine.

In June, I participated in a National Press Foundation fellowship on retirement, and its many challenges: physical, financial, emotional. We had 19 (!) speakers in three days, so I’m still processing it all.

I’m a generalist, and write about almost everything, (not science, tech, parenting, beauty.)

If you need help with a writing or editing project or can refer me to someone who does, let me know!

I’ve also worked with the Consulate General of Canada, the New York School of Interior Design and WaterAid America to craft their messages.

This week has been crazy; for a story, I spent a day in Manhattan visiting the new Westfield mall next to the 9/11 memorial, interviewing a few shoppers — including, in French, a couple visiting from Brittany.

I hadn’t been down there since 9/11 and I deliberately avoided even looking at the memorial. I know some tourists love it, but the memories are, even, 15 years later, too painful and weird to re-live.

Using  a cane right now for balance, (my right knee has bad arthritis), slowed me way down but I hopped a city bus and headed back uptown to 48th Street to meet and interview a young woman for a Times piece.

The range of shawls, sweaters, caps — in the most gorgeous colors! These are shawls in Avoca, a Dublin shop

My latest venture is a retail/shopping blog at Forbes, which pays a small monthly stipend (welcome to digital journalism) — plus payment for each view.

I hope some of you will make the trip over to check it out and, if you like it, Facebook and tweet it.

I’ll be writing five posts a month.

A reminder that I also teach and coach fellow bloggers and writers, and have done so with people worldwide, from Singapore to New Zealand to Germany to Maryland, often via Skype.

I charge $225/hour, (payable though PayPal), with a one-hour minimum and my time and skills are yours; you can ask me for whatever help you need: reading a pitch, reading a story draft, advice on blogging, how to sell a non-fiction book…been there, done that!

I also offer specific, highly-focused webinars, $150 for 90 minutes. scheduled at your convenience and done one-on-one via Skype, phone or in person.

I’m the winner of a National Magazine Award for a personal essay about my divorce and have written two books of national reporting and analysis published by major New York houses.

A former reporter for three major dailies, I can also help you figure out where and how to dig up information or conduct a useful, incisive interview. Let alone how to write more, better and faster!

I know this writing game inside out, from negotiating fees to wrangling (whew!) PR people determined to control every single word.


Thanks for reading, commenting — and returning to Broadside!

Those #firstsevenjobs — yours?

By Caitlin Kelly


Off on the train, hi-ho…


A little late to this party, but those of you on Twitter might have seen this popular hashtag, where people share their first seven jobs.

It’s been really interesting to see all the odd and unlikely things people do to earn money…tank driver, fishmonger, clown, pipeline surveyor, funeral musician.

It was also interesting to see how many of the jobs were fairly low-level/low-wage until people hit a well-paid professional career, and it seemed like a longer, slower trajectory for the Americans who tweeted, maybe because so many go on to graduate school, maybe because some just didn’t need — or couldn’t get — a better position sooner.


Here are the first seven ways I tried to make money, (and you’ll quickly see a pattern!):


  • Made and sold home-made bead necklaces on a street corner in a chi-chi shopping area of Toronto. I was 12.
  • Made and sold home-made envelopes (magazine pages, with an address label). I was 15.
  • Lifeguard at various Toronto swimming pools, public and private. Ages 15 to 18.
  • Waitress (very briefly!)
  • Busgirl (even worse)
  • Sold my photos on the street. Age 19
  • Sold my articles to national magazines and newspaper. Age 19.


One of my first national magazine stories…I entered an animal testing lab. Grim and gruesome. But it was part of my job as a reporter


I soon learned that:


  • I like to sell
  • I like to talking to strangers
  • I’m not scared of selling or of speaking to strangers
  • I like seeing how people respond to my creativity
  • I like it even more when they pay me for it!
  • Lifeguarding is really, really, really, boring — until or unless (which never happened) someone is in serious trouble
  • Waitressing and bussing tables demands huge physical stamina, patience and a shit-ton of emotional labor
  • I prefer being paid to challenge and question authority (journalism) than kow-towing to bosses and customers (service work)


The world of work can appear terrifying, impenetrable, overwhelming. No matter how hard you work or whatever degree(s) you earn or your stellar marks/GPA, you can still hit a wall, or many.

There are many people out there insisting you follow your passion, without regard to — you know, money.

Just because you like making cupcakes/walking your dog/playing the banjo doesn’t mean you can earn a decent living from it.

The challenge for everyone, from first job to last, is finding steady work we enjoy, (at least much of the time), and that uses our skills and emotional intelligence.

Working for income is such a potent blend of drive, determination, talent, sheer get-this-shit-done-now, emotional labor, (i.e. sucking up, being nice to people even when — especially when — you’re being badly paid and treated like crap, as in retail and foodservice), management draaaaaaamas, finding smart/kind (if you’re lucky) co-workers, bosses and clients…

A job can look perfect on paper and then you start and….ohhhhh, shit…It’s not.

Or, yay! It really is.

I’ve spent much of my career as a journalist working freelance, i.e. without any paid sick days or paid vacation, without a boss or co-workers or raises or promotions or bonuses or commission. Whatever I earn has to come through my efforts and skills, and, when it works, the generosity of my networks who refer me on to their contacts.

Some years have been terrific, others much less so.

I do enjoy working in/with/on a team, as one does in a newsroom or magazine. I enjoy, and I miss, the camaraderie and the mix of smarts and energy.

But I also treasure autonomy, being able to plan and manage my own time, (and time off — Americans with staff jobs are terrified to ask for or use their skimpy vacation days) –and to pick and choose work that makes sense to me, intellectually if not always financially.

malled cover HIGH
My second book, published in 2011

I’ve had three well-paid staff jobs at major daily newspapers, in Toronto at the Globe and Mail, (Canada’s best), the Montreal Gazette and the New York Daily News.

I loved the first, enjoyed aspects of the second and barely survived the third; daily American newspapers, now struggling mightily and shedding staff like autumn leaves, are highly specific cultures, some welcoming, some less so.

I’ve also worked as a senior editor and editor in chief of a few magazines, work I enjoyed less, as it was totally desk-bound.


What were some of your first jobs — and what did they teach you?