When workers aren’t free

By Caitlin Kelly

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The level of poverty in the U.S. is deeply shocking — given the astonishing wealth here

This recent column in The New York Times hit home for me:

After all, America is an open society, in which everyone is free to make his or her own choices about where to work and how to live.

Everyone, that is, except the 30 million workers now covered by noncompete agreements, who may find themselves all but unemployable if they quit their current jobs; the 52 million Americans with pre-existing conditions who will be effectively unable to buy individual health insurance, and hence stuck with their current employers, if the Freedom Caucus gets its way; and the millions of Americans burdened down by heavy student and other debt.

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My greatest freedom — to take on amazing assignments, like working with WaterAid in Nicaragua in March 2014

Pushpushushpush = success! Maybe not…

By Caitlin Kelly

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It’s a deeply American belief that if you never ever ever give up you’ll eventually get what you want.

It’s charming in its meritocratic faith — but it’s also often bullshit.

Some doors, for all sorts of reasons, stay shut, locked and barred to us, whether social or professional.

Maybe not forever, though.

Patience, it turns out, really can be a virtue. (Oh yeah, and tenacity, in it for the long haul.)

I recently broke through to a market I’ve been wanting to write for for, literally, a decade or more. I wanted it soooooo badly, and wrote to the editor in chief several times, even as every new one arrived.

I had all the right experience and credentials.

Crickets.

Then (yay!) someone who works on staff there followed me on Twitter and I asked, nicely, for an introduction to someone higher up the ladder. She did it. Now I have an assignment I’d finally given up ever attaining.

Sometimes it’s best to just lay down your tools and walk away.

We’re taught from childhood that winners never quit and quitters never win.

But sometimes it’s wisest to retreat and re-think strategy, to ask ourselves why we even want this thing we think we need so desperately.

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Patience — such a Victorian ideal in this era of instant everything —  can produce results.

I won a New York Times national exclusive, a story about Google, (and I don’t cover tech nor live anywhere near Silicon Valley), by waiting six months after learning about it. During those months, my contact and I exchanged more than 100 emails, as the negotiations were so delicate and protracted.

Here’s the story.

Sometimes you just have to wait:

— For the right person to get the hiring/budgetary authority to appreciate you and your skills. That might take months, even years.

— To develop the emotional intelligence to handle a situation you’re sure is yours right now. Maybe you’re really not quite ready for it.

— To nurture social capital, and its referrals to the players who can help you achieve your goals. Trust takes time!

— To polish the social skills required to network well with senior people in your field or industry. Not everyone will respond to your texts or emails just because you’re in an unholy rush. Buy and use high-quality personal stationery. (It works, I know.)

— To acquire the requisite technical skills to add real value to whomever you’re approaching. Just because you want it rightnow! doesn’t mean you’re offering what they need. Your urgency is not theirs.

— To realize, by thinking about it calmly for a while, that a golden opportunity is…not so much.

— To accumulate the savings you need to be able to ditch a crappy marriage or live-in relationship, a nasty job, abusive internship or freelance gig. Once you have a financial cushion, (or, as we call it in journalism, a fuck you fund), your choices become true options. You don’t have to rush into a decision, or stay miserably stuck in a bad situation.

— If you’re mired in endless conflict and confrontation with someone, withdrawing for a while, (maybe even years, if social/family),  might be the best option while you decide what’s best for you, not just for them. It takes time to reflect deeply and to process difficult or painful emotions.

What success(es) have you gained by waiting and being patient —  even when you didn’t want to?

 

Caitlin Kelly, an award-winning non-fiction author and frequent contributor to The New York Times, is a New York-based journalist. Her one-on-one webinars and individual coaching, by Skype, phone or in person, have helped writers and bloggers worldwide; details here. Contact: learntowritebetter@gmail.com.

The joys of a small(er) life

By Caitlin Kelly

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I found this essay intriguing, originally published on the blog, A Life in Progress (and which garnered a stunning 499 comments):

The world is such a noisy place. Loud, haranguing voices lecturing me to hustle, to improve, build, strive, yearn, acquire, compete, and grasp for more. For bigger and better. Sacrifice sleep for productivity. Strive for excellence. Go big or go home. Have a huge impact in the world. Make your life count.

But what if I just don’t have it in me. What if all the striving for excellence leaves me sad, worn out, depleted? Drained of joy. Am I simply not enough?

What if I never really amount to anything when I grow up—beyond mom and sister and wife? But these people in my primary circle of impact know they are loved and I would choose them again, given the choice. Can this be enough?

What if I never build an orphanage in Africa but send bags of groceries to people here and there and support a couple of kids through sponsorship? What if I just offer the small gifts I have to the world and let that be enough?

It was a friend of mine, someone I met in freshman English class at University of Toronto decades ago, who posted it on her Facebook page.

She is often wearied by the insane pace others have set for themselves and keep setting.

It can feel like a race.

This always felt like our theme song, from Michelle Shocked:

Leroy got a better job so we moved
Kevin lost a tooth now he’s started school
I got a brand new eight month old baby girl
I sound like a housewife
Hey Shell, I think I’m a housewife

Hey Girl, what’s it like to be in New York?
New York City – imagine that!
Tell me, what’s it like to be a skateboard punk rocker?

I wasn’t exactly a skateboard punk rocker, but I did leave Canada — dear friends, family, thriving career — for New York.

When two paths diverge sharply, one to crazy, restless ambition (mine), one to settled domesticity (hers), raising three daughters, and a steady job in a smaller city, it often breaks a friendship.

One life looks too sharp-elbowed, the other ordinary and mundane (M’s word choice — I showed her this post beforehand.)

Social media can make these comparisons somewhat excruciating, with all the dark/messy bits of either choice edited out.

Life is more complicated than that.

I chose to leave Canada for New York when I was 30.

When people ask why, I answer with one truthful word: ambition.

It hasn’t all turned out as I hoped. The man I moved to be with, my first husband, proved unfaithful and soon walked out on our marriage.

Three recessions severely slowed my career progress.

Jobs came and went.

Friendships I hope would last for decades imploded.

Shit happens!

But I’ll never forget the heart-bursting joy when I exited the Sixth Avenue headquarters of Simon & Shuster clutching the galleys of my first book.

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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

Or how cool it was to compete for four years in nationals in saber fencing.

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I now have a happy second marriage and a home in a town I love.

I have an agent, and work, and ideas and friends.

No kids. No grand-kids. No family homestead.

Do I regret my ambition, and its costs? No.

Choosing a quieter life limned by one’s own family, town or community is a choice.

Choosing a life of ambition-fueled drive, another.

Each brings its own satisfactions and joys.

Which sort of life have you chosen?

Are you happy with your choice?

Stand down

By Caitlin Kelly

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Much wisdom in this (too-long) blog post, on Medium:

True growth and success is always sustainable. It’s not a short sprint with an inevitable physical, mental, and emotional crash. All goals are means, not ends. Each succeeding stage of your progression should clearly build one-upon-another, leaving you stronger and more able, not weaker and permanently damaged.

In order to do this, you must properly “recover” from the following things on a daily basis:

  1. Work

  2. Technology

  3. People

  4. Food

  5. Fitness

  6. Being awake

This is so damn smart!

This is so utterly counter-cultural.

I make it a point to recover from all six of these, as a matter of course and of self-care and self-preservation.

For numbers 1 through 3, I’m fortunate enough to be self-employed, so setting boundaries, and keeping them, doesn’t mean potentially threatening my livelihood.

For Number four, I eat 750 calories two days a week.

For fitness, I work out/exercise 3-4 days a week, sometimes (sigh) only twice.

Working from home, I nap as needed, sometimes as little as 15 to 20 minutes, sometimes 90 minutes; without dependents, not difficult.

Living in the United States these days, and I live/work near New York City in a thrashing/disrupted industry (journalism), means waking up every single morning in something of a panic.

Not helped by the daily chaos of Trump.

Whose civil rights will disappear tomorrow?

Which new executive order will require more calls and emails to elected representatives or another street protest?

Should we move back to Canada? When? Where?

If I stay — or if we go — would we be able to find work?

 

This is also brilliant, from a writing-focused website called Catapult:

Call it self-care, sure, or call it life, but a soul is a thing that requires tending. The soul is not quite interchangeable with “heart” or “mind,” or any other word we mean to denote only the “spiritual” part of a person. In the words of the philosopher Dallas Willard, the soul is the entire inner person, not detached from bodily life but inclusive of it, as well as heart and mind, thought and motivation, feeling and judgment. An untended soul drifts toward inertia.

But what does my soul benefit from being “productive”? Am I any number of inches closer to God because I wrote an essay that was praised by someone I desperately wanted to impress? What is the moral imperative to produce?

These questions are all tricks to say that I have no idea what the answer is. I know that when I am anxious, I often think I can produce my way out of it. I have an uneasy relationship with productivity, thinking my anxiety will be placated if I just do enough big things.

 

Every day, I see talented, experienced friends losing well-paid jobs in our field, with no certainty of being able to replace them. One pal needed almost an entire year to find his new job, yet another insecure contract position.

We also live in a time and age relentlessly demanding increased productivity.

We’re exhorted constantly to domorebetterfaster!

 

Not to think.

Not to reflect.

Not to sit still, alone, in silence.

 

Not to take good, slow, thoughtful care of our most valuable resource, our health.

And yet, and yet, we’re each of us simply human, de facto limited in some way, whether by lack of time, impaired physical stamina, weakened emotional energy or by restricted access to social capital or financing.

We’re not robots.

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We’re not robots. We need to rest and recharge.

We’re not machines, no matter what laissez-faire capitalism (and stagnant wages) relentlessly demand.

We’re all running too hard, too fast.

As a result, many of us vibrate with anxiety, shoving sweets and fats and pills and liquor down our throats in an attempt to satiate much deeper, more painful sadness and anxiety, whether personal, political or professional.

Sometimes (sigh) all three.

It’s a very wise choice to pay attention, to read the signals, to try our best to stay safe and to protect the rights and needs of others.

But not 24/7.

Here’s a 14-minute story (from one of the best shows I listen to on NPR, the Brian Lehrer Show on WNYC), about how stressed many Americans are feeling since the election of Trump.

Chronic anxiety will kill you.

Even soldiers need sleep, food, companionship.

Stand down!

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A barstool conversation

By Caitlin Kelly

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Grand Central Terminal; the view from Cipriani. What’s not to love?

Sitting at the bar is where I’ve had some of my best conversations — in Corsica, in Atlanta, in San Francisco and last Friday evening in New York City.

It was about 6:30.

Commuters were rushing to their trains north, to Connecticut and to Westchester, tourists, as always, posing on the steps and slowing rushed New Yorkers down as they raced for the 6:47 or whichever train was next.

Never get in the way of a New Yorker in a hurry!

I settled in at Cipriani , an elegant Italian restaurant in a balcony overlooking the station. I had a magazine and a Mr. C, a citrus-based cocktail. The bartender kindly plugged in my cellphone to charge it.

A handsome young man in a navy suit and white shirt, no tie, slid onto the stool to my left; a slightly older man with a head of wild black hair and oversized sunglasses sat to my right.

“How’s your week been?” I asked the man to my left.

He told me he’d just gotten a new job, and we toasted, clinking our cocktail glasses.

He seemed surprised I was happy to toast a stranger’s success. Why not? Who would be too churlish to deny him that pleasure?

It’s a big deal to flee a job that’s a poor fit for one you hope will be a much better one. Been there, done that.

That’s the beauty, I suppose, of being near the tail end of a long career. For someone only a decade in, every decision can still feel problematic because you’ve yet to make that many of them.

An investment banker, he admitted he didn’t much like the field, but — probably like many people, especially those unhappy at work — he had pretty much fallen into it. If you know anything about I-banking, the income is certainly seductive, but golden handcuffs are still handcuffs.

I urged him to start creating an exit strategy. Life is far too short to stay in a field or industry you really don’t enjoy, I said.

He looked surprised by my vehemence, and my insistence one could actually enjoy one’s work life.

We ended up talking for about an hour, sharing stories of family and work, of dating woes and East Coast snobberies, and the classic diss we’d both experienced: “Where’d you go to school?”, a tedious sorting mechanism. (The only correct answer being the coy, “In New Haven” (Yale) or “Providence” (Brown University) or another of the Ivy League.)

“I’m strapping, right?” he asked me, at one point. He was, actually.

It was a bit awkward to be asked, even though the answer was affirmative.

He was a little drunk.

It made me a little sad.

He was single, and just under half my age, a fact he finally realized but managed to handle with grace.

We had a good conversation with lots of laughter, a few of of life’s more painful challenges and a few high fives.

I like how the right bar and a drink or two can connect two strangers companionably for a while.

(Just in case, though:

  1. Make sure you don’t get drunk; stay safe!
  2. Make sure no one has access to your drink except you (beware someone dumping rohypnol; i.e. getting roofied.)
  3. Make sure you feel 100 percent comfortable with the tone and content of any conversation. If not, move or leave.
  4. Make sure you can leave quickly and safely, if necessary; trust your instincts.)

 

Do you ever sit at the bar?

Do you ever talk to strangers there?

Do you enjoy your work?

By Caitlin Kelly

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Most people don’t.

It’s shocking, and sad, that so few Americans enjoy what they do for a living; every new Gallup poll finds a majority of them, two-thirds, “disengaged” — a state of affairs that leads to endless, tedious screeds on LinkedIn and Twitter about how to “engage” your staff.

If you hate what you do all day, you’re unlikely to do it well.

That photo above is of one of Jose’s credentials; he’s been working freelance with the United States Golf Association for a few years now.

He got the job thanks to a few introductions, (and his excellent skills!) The man loves golf. Now they fly him across the U.S. to photo edit their major tournaments.

I lost my fancy newspaper job in 2006 and freelancing was going poorly. So, in September 2007 I took a part-time job as a sales associate, for $11/hr and no commission, at a local mall.

Long past my teenage years, I was the oldest member of our 15-person team, including our manager and assistant manager.

Initially, I really liked the job.

And yet it’s a job everyone knows is nasty — crappy pay, no challenge, tedious and repetitive.

Any job, if you enjoy elements of it, can make you happy

My fancy newspaper job had actually been a year of misery, (details tedious), the most difficult experience of my career.

So being once more liked, accepted, even welcomed — albeit into a low-wage, low-status part-time job, healed me. No one was trying to force me out. No one refused to speak to me if I said “hello” to them.

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My second book, published in 2011

I was good at selling, able to relate easily to a wide range of customers, from the emissary for an Arabian prince to Finnish bankers to a Boy Scout. I loved the variety of people who shopped in our store, (The North Face), and being able to help them.

When you emerge from a job, no matter how prestigious or well paid, where nothing you ever do is deemed good enough, simply being able to please someone is a real solace.

It was for me.

Working retail also allowed me to use my French and Spanish skills occasionally, sharing travel tips with shoppers who were buying a backpack to train across Europe or a suitcase to go to Peru, places I’d been to and could discuss helpfully.

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One of my first national magazine stories, examining what happens in an animal testing lab.

Every job, even the most putatively glamorous you can think of, has elements you will probably never love — highly-paid actors often loathe the press junkets and conferences and interviews they have to do to promote their films. They just want to act!

So I appreciated this recent essay:

First, make sure you choose a career or project that you enjoy pursuing, one that offers present benefits for you. Keep in mind that unless you find small pleasures in your daily routine, you will not stick to it.

Second, add present benefits to your working hours. Listen to music, make friends and break the routine with social activities. Do whatever makes you happy at work; you can stick to your career goals longer if your work is enjoyable in the moment.

Third, bring to mind those present benefits that do exist at your work. Maybe you just have not been paying attention to them…You can similarly motivate yourself to engage in your work by directing attention to the positive aspects of your tasks.

As I write this, I’m wearing a sweatshirt and leggings, no make-up, hair unbrushed, listening to classical music on the radio aloud, (no need for headphones.)

I don’t have to get dressed or waste hours commuting, crammed into a crowded train or traffic or subway, leaping pools of icy water and slush.

I don’t have to pretend to like mean co-workers or a bullying boss.

I’ll go to the gym when it suits me, or go for a walk, or (rarely) even go to an afternoon movie. The freedom to set my schedule matters enormously to me.

I usually eat all three meals at home, saving time, money and calories. My husband is home today as well, sorting through a mountain of 2016 receipts to make sure we get every possible tax deduction from our combined freelance incomes.

Do I enjoy my work?

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Yes, I do. But I also clearly enjoy the conditions in which I perform it.

What do I still love about writing, editing and teaching?

— Meeting and speaking with an amazing array of people, from Queen Elizabeth to convicted felons to Olympic athletes.

— At best, working with smart, tough editors and clients who expect high levels of skill and emotional intelligence.

— Finding and sharing complex stories with millions of readers.

— Learning something new with every story I write, whether pension reform, utility deregulation, air turbulence, Broadway stagehand work or apotropaic traditions in house construction.

— Connecting worldwide with fellow writers, some of whom are generous enough to share referrals and clients with me (and vice versa.)

— Meeting smart younger writers through my blog and Twitter.

— Helping others think more clearly and communicate more effectively. Here’s my website, with my classes.

— Intellectual freedom.

That’s not even a complete list!

How about you?

Do you love your work?

If not, what’s your exit strategy?

The writer’s life, these days

By Caitlin Kelly

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As some of you know, I write for a living, and have done so since my undergrad years at U of Toronto.

As some of you know, the industry of journalism is in deep, widespread and massive disruption; The New York Times is about to get rid of 200 more of its staff and is making other significant internal changes to cut costs and boost revenue. I write freelance for the Times, producing three stories in 2016 for them, one on turbulence, one on a Broadway stagehand and one on real estate, which I’m researching this week.

But the life of a freelance writer is now, more than ever, like that of a polar bear on a small, melting ice floe. One of the most successful freelance writers I know sends out 10 to 25 marketing pieces every single week. Out of sight means out of mind — and broke.

Most of my colleagues are either clinging to staff jobs, working now in public relations, teaching or producing “branded content”, i.e. writing copy for corporate clients.

Here’s some of what this year brought:


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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 obsesssions

Working on two book ideas, both non-fiction

People think. “How hard can it be? Look at all the books in bookstores.” Yeah, well…It really depends on a variety of issues. How much money do you want or need to earn from researching, writing and revising a book? (It can take years.) How large a potential audience can you offer a publisher? How timely is your idea? How well-covered is the subject? What credentials have you already established?


Realizing how essential a strong network is

Two of my very best gigs came from people I know through an blogging project we all worked in in 2009. I haven’t even met one of them, although we’ve also both freelanced for the Times as business writers. Both contacted me with lucrative, ongoing work, and I’m so glad they did! Both know the quality of my work and chose to offer opportunities to me, not to any one of the 100’s, let alone 1000’s, of my competitors.

Some very slow and frightening months 

That’s unusual for me, and was crazy stressful, as our monthly health insurance costs are now an insane $1,800. Our fixed costs don’t suddenly shrink or disappear if I or Jose are having a slow month, or few months. Thankfully, my husband, also now full-time freelance after 31 years at the Times, has three steady anchor clients.

A stiffer spine

As I mentioned here in an earlier post on fleeing toxicity, I finally dropped an ongoing project that was making me really unhappy. I usually find it difficult to quit working on something I’ve committed to but this one, from the very start, was far too much work for far too little income. The way I was spoken to, consistently, felt rude and dismissive, on top of that. And (of course!), days after I finally said “enough!”, several much better-paid projects showed up to replace that lost income.

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The New York Times newsroom…since 1990, I’ve written more than 100 stories for them

Loving being a generalist

I’m really proud of writing for the Times, (100+ stories since 1990), but also for three different sections this year on three utterly different topics, all of which I pitched. Most freelancers (and, yes, this costs me lost income), specialize narrowly on medicine or parenting or personal finance. I have so many interests and experiences, I’m much happier roaming around intellectually. As long as I can find a decent price for my idea, I’m cool with that.

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Part of The library of Congress — spectacular!


Tossing my hat into competitive rings

I won a fellowship in June in D.C. to study retirement and its various challenges. That gave me three intense days listening to 19 speakers, introduced me to more smart writers in the group, (one of whom became a very good friend) and allowed me a brief vacation. I later applied for another fellowship, on the same subject, that would allow me the income and time to do a deep dive into a specific aspect of the issue.

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Meeting a few editors face to face.

They’re sort of like unicorns now, out there somewhere but elusive. I met with several, including one at National Geographic Traveler and one from Elle. Neither has resulted in an assignment, but it was a thrill anyway.

Coaching and teaching


I love it! Clients included a tech PR writer from San Francisco and a local film theatre. Happy to help you as well; here’s a list of my one-on-one webinars.

Today being “a writer” means a lot more than writing, at least if you hope to earn a living doing it. It means being flexible, learning new skills, constantly marketing yourself, paying attention to industry shifts, happening daily.

Knowing, more than ever, how much real journalism — fact-based, deeply reported on firsthand knowledge — matters now

Stop consuming fake news! It is a disgusting disaster, enriching liars and cheats.

Read this great piece about why copy editing matters so much, still. It’s true. When “the desk” has a question, your heart stops.

 

Here’s to a great writing year for those of you who do it as well!

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.

Done.

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.

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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.

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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.

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Open the lock.

Go.

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

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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?

Those #firstsevenjobs — yours?

By Caitlin Kelly

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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.

 

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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.

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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?