Define “successful”

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I’ll be back for 2020 as well…

 

By Caitlin Kelly

So there I was last Sunday, wearing my black dress and chartreuse silk scarf, all dressed up to attend an annual holiday party in Manhattan at the home of a man I’d met a few times at conferences. He’s had a career studded with highly visible and well-paid success, including becoming the first digital director of the Metropolitan Museum.

The room was packed with people, some of whom have Big Jobs at places like CNN and The New York Times and many teach at local journalism schools.

At one point, when it was a bit quieter, we were all asked to briefly introduce ourselves — like many, when I said “freelance writer” I heard some laughter, (kind? unkind? sympathetic?) as this is where so many talents now work — nowhere.

 

 

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A legendary writer and war correspondent — much of her life was spent frustrated by overwhelming, unfulfilled ambition. Makes me feel better!

 

Thanks to social media, other people’s BIG and quantifiable successes are in my face every hour: a book deal, a TV series created from their book deal, an award, a grant, a fellowship. It can feel completely overwhelming as I work, alone, more slowly and quietly.

I do have a major piece of work that will appear nationally in late January — that I worked on between August and October.

But for now…crickets.

People are fired daily now in my industry, with even well-funded and highly regarded places like the magazine Pacific Standard disappearing overnight.

So when you’re surrounded by people with visible, credible “success”, it can feel stupidly intimidating.

So I mostly, I’m embarrassed to admit, sat in the corner of that party, eavesdropping. I really enjoyed the great Indian food, but didn’t engage in much conversation. I’ve never been a fan of chitchat — and a NYC journalism party can present a heinous pecking order.

I don’t have children or grand-children, the traditional default place to park your pride when work fails.

I’ve been full-time freelance since 2006, when I was laid off from a well-paid job at the New York Daily News. I’ve applied for staff jobs since, rarely even getting an interview. I’ve stopped applying for fellowships and had two grant applications refused this fall.

 

So “success” is a moving target for me, and maybe for some of you as well.

 

By necessity, if not desire, I look beyond work, visible accolades and high payment to my thriving marriage (20 years together, nine married); deep friendships across oceans and generations, a lovely home, generally decent health instead.

 

 

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This was my most recent New York Times story, about a sailing program for New York students

 

I’m already booked to speak in 2020 at two major conferences (unpaid, but smart, interesting audiences, one in the U.S. and one in Canada, where I do hope to find paying clients) and we’re planning (let’s do it this year, dammit!) a three to four week holiday in England.

Thanks to a link on the blog Small Dog Syndrome, I found this powerful insight, from American comedian Jenny Slate — who was hired into the cast of Saturday Night Live (never one of my favorite TV shows but considered the pinnacle of comedy success)then later fired.

Her take:

First, I just felt really, really embarrassed and terrible. … Hardly anyone gets kicked out of a cult, because I guess they want you to stay…But suddenly I just couldn’t imagine anything worse than getting fired. And then I just thought: I have to keep going. And no one can ever take away the dream.

And nothing will ever dim the lights of that experience, which was like: getting the job, leaving 30 Rock, calling my parents and saying “I am going to be on Saturday Night Live“? That is what it is. It’s such a beautiful achievement. And it’s real and I did it…

But what had also happened at the time, and what always happens, is that: Until I eventually croak, I will not die. I truly will not lie down. And you can be kicked out of a place; I definitely believe that. But I also believe the opportunity to find self-love and creative fulfillment is not a hallway with one door guarded by a super-old man. Actually, it’s spherical, and you just have to hold it between your legs. Just look down, find your opportunity.

 

 

Failure? Let’s discuss

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By Caitlin Kelly

In the shiny, buffed world of social media, how often do you see someone — or do it yourself — admitting to failure?

It’s a parade of perfection, and one that can make any of us feel like a total loser for not being as thin/pretty/well-dressed/groomed/wealthy/well-employed/living on a Greek island…

Loved this New York Times piece about why we need to talk more openly about it:

In a new working paper, co-author Alison Wood Brooks, an assistant professor at Harvard Business School, found that discussing failures can help to humanize the sharer by making them seem more approachable and relatable in the workplace. It also generally increased levels of so-called “benign envy,” which can motivate and drive employees to perform better.

However, the enemy of benign envy, according to the paper, is “malicious envy”: The type of envy others feel when we talk about our achievements much more often than our struggles. Projecting that image of perfection can be especially harmful for those in leadership positions who risk coming across as disingenuous, Ms. Brooks and her colleagues found.

A simple way to understand this is to look at the polished-though-unrealistic lives many of us present on social media.

 

 

One of the most powerful lessons I learned last year — despite their towering reputations lasting centuries — is that Japanese print-making legend Hokusai, Michelangelo and even Leonardo da Vinci all suffered setbacks and penury and failure.

It happens!

I’ve spoken here a few times about the many failures I’ve experienced in my life and career, but let’s review a few.

The only true value of failure is learning something useful.

 

— Moved to Montreal age 30 for a staff newspaper job I had doubts about (not a very good paper.) Was gone within 18 months after some unpleasant interactions with my boss and a union that shrugged and wouldn’t help.

Lesson: trust your gut.

— Moved to a small town in New Hampshire, pre-Internet. Despite efforts, made no friends and, again, left within 18 months to move to New York, just in time for a recession.

Lesson: I’m not a rural girl!

— Took six months, crying every day, to get a magazine editing job after cold-calling hundreds of strangers.

Lesson: Re-starting your career in a highly-competitive industry in a highly-competitive city with zero social connections is really hard.

— Married in 1992, husband walked out 1994. 

Lesson: Don’t marry someone who won’t do the work to go the distance.

— Have applied many times for competitive fellowships like the Knight-Bagehot (to study business at Columbia), the Alicia Patterson (tried three times), a Canada Council grant (worth $20,000 Canadian) multiple times.

Lesson: Thousands of competitors want the same bag of goodies. You can keep trying, even if you feel pissed off and humiliated.

— Spent many hours in 2018 producing two full book proposals, both of which were rejected by five agents. Fun!

Lesson: Intellectual growth — creative growth of any kind — is almost always going to be unpaid, speculative and suck time away from paid work. How much do you want it?

 

I admit, though — I’m much less amused by failure at this point in my life.

I want to stop working within five years, ideally sooner, which places a lot of pressure on me to to do good work and well-paid work and work that I really care about and am proud to have produced.

All of which now run directly counter to current industry trends in journalism.

I’m not someone who spends her days consumed by envy when I see social media brag-fests. Sure, it hurts to see people winning, especially if you feel like you’re losing. But it doesn’t accomplish anything to focus on their success and your (relative) failure.

No one succeeds alone, so I’m also attentive to people’s headwinds and tailwinds — the many invisible forces beyond talent, skill and experience — that can propel some people to massive/quick success while the rest of us struggle.

That might be family money, social capital, alumni connections, anything that offers a leg up.

Some of my younger friends, in their 20s and 30s, end up consumed with envy at their peers’ glittering achievements, which is a terrible distraction. I do think, once you’re past 40 or 50, life should — ideally! — have brought you some of the rewards you once coveted.

A feeling of success, despite the inevitable setbacks and failures we all experience.

I’ve also found that some things we’re completely obsessed with at 25 or 35 or 45 can shift so that not getting it — i.e. what we once would have deemed a failure — is no longer a goal we even want.

It’s too easy to focus solely on one area of accomplishment — work — rather than being proud that you’ve been a great friend or spouse, have managed to regain and maintain good health, have planted a thriving garden.

We’re all diamonds, multi-faceted, and several sides will always catch the light.

We also all have many successes, if we take time to notice and celebrate them.

 

How do you handle failure?

Do you obsess and freak out or just move ahead?

 

The pinball machine of success

By Caitlin Kelly

 

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Remember those?

 

The ball is put into play by use of the plunger, a spring-loaded rod that strikes the ball as it rests in an entry lane, or as in some newer games, by a button that signals the game logic to fire a solenoid that strikes the ball. With both devices the result is the same: The ball is propelled upwards onto the playfield. Once a ball is in play, it tends to move downward towards the player, although the ball can move in any direction, sometimes unpredictably, due to contact with objects on the playfield or by the player’s own actions. To return the ball to the upper part of the playfield, the player makes use of one or more flippers.

 

I think success is a lot like a pinball machine…

 

You put in your money, release a ball and hope like hell to keep that ball moving, and rack up enough points by the end of the game.

But, like pinball’s bumpers and alleys and pits, some of us face multiple obstacles to overcome:

sexism

racism

chauvinism

chronic illness

mental illness

disability

surgeries

illness

unemployment

underemployment

debt

lack of self-confidence

language barriers

death of  a loved one

divorce

lack of education

lack of skills

lack of social capital

poverty

luck

timing

the larger economy

Which means, when you “fail” — and, like many of us, might then wallow in shame and frustration and self-flagellation — be a little kinder to yourself.

I see the people who succeed, at least here in sharp-elbowed New York, and know the incredible advantages some of them bring, and take for granted, whether prep school and Ivy League educations or access to decision-making people in power through their social networks, often both.

They keep winning and think: I did that! All by myself!

It was said of one American President — using a baseball metaphor — he was born on third base, confident he had hit a triple.

As that little metal ball pings and caroms around the pinball machine — as in life — we  react as quickly as we can, flipping flippers and trying our best to guide it and keep it flying.

 

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But, as in life, not every game ends in delight.

So there’s a larger, deeper, more candid conversation we need to be having about who’s winning, who’s losing and why.

In the United States, there’s a firm and fixed belief that every success — and every failure — is due only to each individual’s hard work, determination and intelligence.

Hah!

Talk to a person of color.

Talk to a woman of color.

Talk to an immigrant whose graduate degrees from a foreign/unknown institution mean nothing to American employers.

Talk to someone waylaid by their partner’s terminal illness, death and grieving.

Which is why we all need to lighten up on the fantasy that success is soooo easy to achieve, which — if you look at social media — can drive you mad with envy.

We hide our struggles and defeats: the crushing student loan debt, the chronic pain, the multiple surgeries, the needy relatives or un(der) employed partner…

We also need to lose the conviction that only visible wealth, prestige, power and luxury goods mark us as “successful” while kindness, generosity, frugality, humility and wisdom remain dismissed and perpetually undervalued.

 

We need to be ruthlessly candid about what powerful headwinds some of us face and what tailwinds propel some of us forward with a speed and velocity that look so, so effortless

 

When they’re not.

Your “failure” may have very little to do with your hard work, determination, education or skills.

Same with your success.

 

 

 

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.

Four recent “failures” and what they taught me

By Caitlin Kelly

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We’re not robots. We all need a hand, a hug and some help!

It’s the new black, failure.

Every day I see a new book or article exhorting us all to fail — and enjoy it.

Fail forward!

Like it’s really fun and comforting and the sort of thing you just can’t wait to blog about or tweet about or post an Instagram image of you at the elevator holding your cardboard box with all your shit in it after doing the walk of shame from your desk when they’ve just canned you.

Sorry, right-sized you.

Whatever.

Here’s an interesting blog post about why trying (and failing) is good for us:

Schools, particularly in the U.S., set us up for fixed mindsets, which means there is only one answer or that you believe talent is something you’re born with and it can’t be evolved or changed.

A person with a growth mindset, on the other hand, welcomes a challenge and enjoys doing things they’re not good at because they know they’ll learn.

Perhaps you’re learning how to read analytics and metrics. Or you’re trying to figure out how content and search engine optimization work hand-in-hand. Or you’re moving beyond media relations to do some really hard, but powerful communications work.

Whatever it may be, you have a growth mindset and fear of failure won’t paralyze you.

Talent can be learned. It can evolve and grow.

 

But I’m damn glad it’s 2016, because 2015 really kicked my ass in some new and excruciating ways.

Because four in a year, (and these are only a few of the bigger ones, the ones I’ll even admit to here), is a shit-ton of failure in my world.

Kelly’s don’t fail.

So that’s an issue right there.

I hate the tired phrase “comfort zone” — and yet I wholeheartedly agree with the premise we all need to flee ours, often, to try new things, stretch our wings, learn new skills and behaviors.

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Gone! One of my favorite antiques/vintage clothing shops in NYC. Was their decades of prior success now a “failure” because they closed? Not to me!

Failure Number One

I was hired to teach two classes a day, one day a week, at a schmancy private college, the kind where the rich kids fly home to Asia on long weekends and everyone dyes their hair purple and septum rings are de rigueur.

I had previously taught at several New York City-area colleges, no novice. I read up on millennials and what to expect.

This was different.

Tuition there runs a cool $60,000 a year, to study high-earning fields like…writing.

I loved the first semester, grateful for lively students who were warm and hard-working. What’s not to like? Half of them arrived each week 20 minutes before class began just to hang out. I really enjoyed getting to know them as individuals, not just a pile ‘o papers to grade.

The second semester was…not that. Suffice to say it started badly and ended much worse. I don’t teach there anymore and I wouldn’t if it were the last income source on earth. An MIA dean made it even more difficult.

Lesson learned: Adjunct teachers, especially of writing and especially in New York City, are more disposable than Kleenex. Without solid institutional support — of any kind! — it’s impossible to navigate complex scenarios you’ve never faced before.

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There’s never enough beer when things are shitty

Failure Number Two

I take on a web-writing assignment for a large charity, excited to work on something I believe in for people whose work I respect. The fee is fine and the people seem pleasant.

But they’ve never worked with an outside writer before and it becomes increasingly clear that they have no idea how to manage my time effectively, both being vague and micromanage-y all at once.

It gets worse week by week until finally it’s one Friday at 5:30 p.m. and we politely and cordially enough call it a day.

I lose $4,000 worth of anticipated income by failing to complete that project, and feel like a fool for not realizing how complex it would be.

Lesson learned: Ask a lot more questions before committing to a project, especially one that’s going to be edited by so many people.

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This little monkey is so NOT my role model. Flee, monkey!

Failure Number Three

I congratulate someone I know, vaguely, on Facebook about a great new managerial role he recently assumed.

Within a month, to my great surprise, he’s hired me to manage two complex, multi-part projects. The potential income is excellent and the content challenging. It does look a little hairy, but I’m a quick learner.

So I thought.

His managerial style proves to be a pendulum between charm and bullying. Our communication is both excessive and insufficient to our needs.

And the writers I need to hire and contract for work are fearful — naturally, given the state of our industry now — that they won’t be paid or paid quickly.

I reassure them, but with no sure knowledge of this man’s business ethics, or that of his employer. Which makes me very anxious indeed; he’s only one client, while my wide network of trusted colleagues is what keeps me working year after year thanks to their referrals. I don’t want to inadvertently screw anyone over!

Within weeks, I’m debating how soon to walk away, but hating the idea of letting down a large team — our initial meeting, (hello, warning sign) included 25 people.

I’m fired.

I’m also hugely relieved — and out at least a month’s income because I’ve been 100 percent focused on this thing, not marketing elsewhere.

Lesson learned: If a job or assignment feels this wrong within days, let alone weeks, it probably is. If someone lashes out at me, I don’t care how much they’re paying. I’m done. I won’t tolerate this kind of behavior at this point in my career.

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Our van, 95 degree heat, 12 hour days. My WaterAid gig in Nicaragua — for all its challenges — was a joy and a pleasure. That’s what I seek.

Failure Number Four

I’m asked to chair a 13-member volunteer committee for a registered charity, a board I’ve served on already for six years.

I’m passionate about the mission. I have a ton of ideas and am really excited to see what we can do to advance its goals and make its value much more visible.

I choose a co-chair to help, as I know some heavy lifting lies ahead.

We have no training in how to actually run a board or a meeting.

We do our best, but are soon, at every step, ignored by half the board or undermined and criticized by three women, all former presidents of it, who have very strong opinions. Nothing we say or do is met with enthusiasm, and some of it with serious opposition.

Not a great start.

I’m soon spending more unpaid time turning to others who run or serve on other boards for advice and help. Demoralized and worn out, I end up in tears.

My husband says — just leave.

We spend weeks crafting our letter of resignation, trying to be polite but honest about why we’re quitting our roles, and the board — to be met with “I’m overjoyed” by one of these women who then sends the entire board a vicious laundry list of our personal faults.

Lesson learned: Walking away is often the only choice. No one can “lead” a group of people who have no interest in supporting your ideas.

Admitting I’ve made lousy decisions hurts.

Admitting to my weaknesses hurts.

Admitting I can’t take on, and master, new projects quickly is less difficult — but I now know for sure that opposition, whether aggressive or passive-aggressive, means guaranteed failure.

Admitting I was unable to rally the support I needed is painful and I’ve spent a lot of time trying to determine what went so wrong.

We all like to succeed.

We rarely, if ever, publicly discuss or admit to fucking up.

But we all do it.

 

I’m guilty of sometimes moving ahead too quickly, leaping before I look deeply enough, perhaps. As a full-time freelancer living in a costly part of the world, we need steady income in the four figures every single month. I can’t sit around twiddling my thumbs waiting for the perfect fit on every opportunity.

But I’m also forever eager to try new experiences, face new challenges and grow my skills and my network. If I stick to my knitting, that can’t happen.

 

Onward!

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10 lessons creatives can learn from athletes

By Caitlin Kelly

As some of you know, I was a nationally ranked saber fencer in my 30s, a sport I took up when I moved from Canada to New York. I’ve been athletic since childhood — competing in swimming, diving, sailing and other sports, and recreationally playing squash, softball, badminton and skiing, horseback riding, cycling and skating.

But working with a two-time Olympian as my coach forever changed the way I think, behave and react to stressful situations.

Having just finished a 15-week semester teaching college writing and blogging, it became clearer to me once more what useful lessons any creative person can learn from competitive/serious/elite athletes, like:

Dancers work through pain every day
Dancers work through pain every day

Pain is inevitable, suffering optional

We’re all facing challenges, whether finding clients, paying our bills, drumming up ideas, collecting late or missing payments, seeking inspiration. It’s easy to feel overwhelmed and depressed when it piles up, but much of this is — sadly — quite normal. Knowing that others are facing similar issues, and finding solutions to them, will give you a necessary sense of perspective. We all struggle! Some show it more than others. The most successful, though, are able to pick up and keep going.

Your competitors are fierce, determined and well-prepared — are you?

It’s naive and foolish to think your success is going to happen quickly and smoothly. If it does, cool! Champagne! For most creatives — whether you’re a fine artist, graphic artist, writer, photographer, film-maker — it’s a road filled with people every bit as determined to succeed as you are. Possibly much more so. Find the smartest and toughest mentors possible; take classes and workshops to sharpen your skills; attend conferences to see what everyone else is up to.

A great coach is essential

I would never have considered it possible to compete at a national level were it not for a tough coach who pushed hard and knew exactly what excellence looked like — and what it required to achieve. It’s hard to get up to speed if the only people you turn to for help and advice are all working at the same level as you, or below. Aim high!

Practice, practice, practice

I’m amused by people who say they want to write — but never do. Nor they read. That’s a toughie, really. Athletes spend hours watching footage of themselves and their competitors to analyze what’s working and what’s not. Then they get to work on their weaknesses. It won’t happen if all you do is wish and hope and read blogs about other people succeeding. You have to do it, too. A lot.

Take time to notice -- and smell!
Take time to notice — and smell!

Your mind and body need to rest, recover and recharge

In a gogogogogogogo culture, where everyone is always tweeting and trumpeting their latest success — a grant, a fellowship, a new book, a big fat gig — it’s tempting to compare yourself unfavorably and feel you’re falling behind the pack. No matter how hard you practice, train and compete, you also need downtime to rest your mind and body. Take a hooky day. Sleep in. Play with your kids/dog/cat. Take in a matinee or a museum show. Pleasure refreshes our spirits. Rest recharges our minds and bodies.

Stamina is key!

It’s tiring to stay in the game, week after week, month after month, year after year. It’s also difficult to stay if and when you’re weary, fed up, hurting from rejections. Stamina — which includes mental toughness  — is often what separates champions from also-rans.

What are your competitors doing better — and how can you do so, too?

No matter your creative field, you need to stay abreast of developments. What new skills do you need to be acquiring? Do you need to find a new teacher?

Just keep writing (and re-writing!)
Just keep writing (and re-writing!)

Someone is always going to lose. Sometimes that’s going to be you

Yes, it hurts! No one likes losing and it can feel like the end of the world when you do. Take it as a testament to the strength and dedication of your competitors.

Is this your best sport?

If things are going badly, no matter how hard you try, maybe this isn’t your game. It can be very painful to admit defeat (or what looks like it) but it might be worth considering if your very best efforts keep producing little satisfaction or success.

Working through pain is simply part of the process

We live in a world that focuses all its energy on winning, happiness and success. But we’re all likely to have down times — illness, lost clients, a period of creative frustration. Knowing it’s all part of the game reminds us of that. A pain-free, disappointment-proof life is usually unrealistic…and resilience a key component of creative success.

 

 

Crash, burn, recover

By Caitlin Kelly

When was the last time you failed?

The sort of shit-storm tempting you back into bed for a week, whimpering?

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Crash (Photo credit: Wikipedia)

Some recent challenges include:

— An editor killed my story — which cost me $2,200 in budgeted-for and relied-upon income.

One of the dirty secrets of journalism is that, no matter your skills level, some of your stories get “killed” — i.e. they are commissioned, a contract signed, a fee and deadline agreed upon and the editor can simply flap his or her hand and decide “it doesn’t work.” You don’t get to stiff the airline of its fee if the plane is dirty, crowded or late. You don’t get to pay your plumber, dentist or barber a fraction of their fee because…you feel like it. It’s almost always a surprise and it’s expensive and very few of us can just re-fill a four or five-figure income hole in a flash.

— My book proposal didn’t sell

My agent was upbeat and excited. They always are, at the start. But after the rejections piled up, it became clear to both of us this was a no-go. Editors who loved it, and there were a few, couldn’t sell it to the rest of their staff. I spent a year gathering the information and sources for it, and months writing and polishing it. Tant pis, mes chers, tant pis.

— Another editor decided to turn a 2,000-word story with five sources into…captions

That’s a really crappy first in my career. They’re going to pay the original fee, but there’s another piece to that story — having to explain to my patient and helpful sources I interviewed back in August that all the time they spent being interviewed by me is basically wasted. I was so gobsmacked I didn’t argue the point with the editor. Preserving that relationship has meant sucking up a lot of frustration.

— We got whacked with a surprise income tax bill, a big one

We married in September 2011 and my new husband changed the witholding of his income. To…not enough. Holy shit. Add that pile of debt to the kitchen over-run.

— Journalism’s fees remain stubbornly low, stagnant or falling

Everywhere in journalism today, writing has really become just one more commodity, like gas or orange juice. Cheapest wins. I have to fight harder with every single editor on every assignment for a decent contract and higher fees. I hate feeling embattled. It doesn’t build great client relationships, but feeling taken advantage of doesn’t work either. My costs are rising almost every month, but my income will only rise as much as I position myself and argue effectively for my value.

On the plus side of the ledger:

— My individual coaching and webinars have found favor

This is a new venture and one I’m enjoying. When I lost that $2,200 overnight, I vowed to make it up through my own efforts. The hell with snotty editors. I’ve almost done so, thanks to the enthusiasm of students in Chicago, Connecticut, Brooklyn, upstate New York, New Zealand, Australia, Virginia and San Francisco. Thank you! I’ve missed teaching and the pleasure of helping others. One student told me she was having “aha!” moments. I hope you’ll sign up, too!

– I made a contact with a Very Big Magazine’s top editor, one I’ve wanted to write for for a decade

Some magazines feel like Everest, even to someone with a lot of great experience. They’re career-changers. They pay a lot of money. At a recent lunch with someone I met at a party, I discovered she’s related to a top editor there and I was bold enough to ask for an introduction and she made it.

— Reaching out to new clients in PR has shown me there’s some significant enthusiasm out there for my skills

Of the first three local agencies I contacted, two showed immediate interest.

— I’m trying out new ideas and new markets

Next week, I’m meeting with a younger writer who’s broken into corporate writing and making boatloads of cash from it. It’s an interesting lesson in networking with people much younger, as we’re all working in slightly different says, some more lucrative and less visible, some more prestigious but poorly-paid.

— My agent likes my new book idea

Book ideas are difficult. You have to be able to create a narrative arc with 80,000+ words and be able to persuade a publisher to pony up an advance you can actually live on. But from the embers of the still-cooling rejected proposal came this more focused, more positive iteration of one of the ideas in it. Now I have to go…sigh…write another proposal.

People love to think that writing is a cool, fun easy way to make money. You stay home in your PJs, crank out some copy, then head off to Bali for a few months.

I wish!

The reality is a constant hustle and scramble: for new clients, new markets, negotiating better pay and treatment, finding and wrangling sources for your stories…

Crashing is nasty, (and inevitable.)

But there’s no time to sit and snuffle.

Bills, baby, bills!

Does it ever get (much) easier?

By Caitlin Kelly

I think there’s a comforting fantasy that being “successful” = easy.

As in, life suddenly smooths out into something calm, cool, stress-free.

Awesome! Sign me the hell up!

While in Tucson, I’ve gotten to know some of the Institute students, as well as some of the Times and Boston Globe staffers here working with them. In a long and personal conversation with one local student, a 21-year-old man who is already well-launched in journalism, he wondered why I still struggle.

Aren’t I successful?

Maybe it’s just me, but I don’t see “success” as a specific and final destination, and if it is, I wonder if that’s really the best way to look at it.

He asked me to define success. (No pressure!) My answer was very different from what it would have been in my 20s (career!), 30s (marriage!), 40s (finding a new partner/husband). As readers of this blog well know, I tend to be driven, ambitious and obsessive.

But success for me today looks quite different. It’s the hard-earned blend of a healthy retirement fund, a lovely second husband, good friends, health, a nice home and — oh, yeah — work! That order surprised me even as I wrote it, but the sub-conscious is a powerful little thing, isn’t it?

Maybe it’s being Canadian or being a Baby Boomer or having lived in five countries or being a journalist whose industry is “in disruption” — (fucking total chaos is more like it!) But I never expect life to be easy.

I wish it were easier, certainly. Struggle is wearying and distracting. Struggle without any visible, measurable progress is deeply dispiriting.

But just because something is difficult — your friendships, marriage, school, work, workouts — doesn’t mean it’s not worth pursuing.

It doesn’t mean you’re not succeeding.

I suspect that most of us rarely publicly admit to struggle; it’s not sexy or slick and it can make us appear ill-prepared or incompetent or dis-organized.

I call bullshit.

Life is sometime just really damn hard. The more we’re willing to be, (optimistically, resourcefully), candid about this with one another, the easier it gets, because then people with wisdom can help (some of them) and our struggle diminishes.

Not everyone is kind or compassionate, of course. But the people who sneer at the notion of struggle, glibly insisting that their path to glory has been 100 percent smooth, are usually lying — or their path is short, flat and well-paved, if not well-funded by others.

Ignore them.

One of the editors here said something to me at breakfast I found helpful and comforting. When I told her how many of us in this industry, certainly those over 40, are scrambling to “reinvent” ourselves, she suggested that this struggle, and it really is a struggle, is something attractive, not repellent.

Not if you’re about to lose your home and plunge into destitution, but having to figure stuff out, no matter if you’re 21 or 71, keeps us alive and attentive and connected and paying attention.

I generally enjoy the challenges of my work and life. I’m easily bored. I like to grow and acquire new skills. I like to test myself and see how many new things I can cram into my head.

As soon as I can easily clear one bar — (the high jump kind, not the alcoholic kind!) — I usually raise it by finding something new and tough to learn and potentially get better at. A life spent coasting, happily resting on one’s laurels, is just not very appealing to me.

(This might be something that runs in my family; my Dad turns 84 in a few weeks and plans to go sky-diving to celebrate.)

How about you?

Does struggle invigorate or annoy you?

NOTE: I leave today — computer-free! — for five days travel and into the Grand Canyon. So if your comments go unanswered until Friday, please don’t despair.

Jose may post a pre-written few things in my absence, or offer a guest blog of his own.

Play nice!

Rejection to a writer is like blood to a surgeon

It’s a normal, if messy, part of every working day. Every single person who hopes to earn a living as a writer needs to memorize it.

Courage is a muscle: use it or lose it.

If you never show/try to sell your work, how can you determine its wider appeal?

Yes, you will almost certainly be rejected. Possibly many times. Assume so!

Surely by now you’ve all heard how many times billionaire author J.K. Rowling was rejected when she first sent out “Harry Potter”?

Writer's Stop
Writer’s Stop (Photo credit: Stephh922)

Here’s a list of 11 others who had their butts kicked hard before they became best-sellers.

And here’s a great post of 25 things writers need to know about it from writer Chuck Wendig’s blog on the same subject:

2. Penmonkey Darwinism In Action

Rejection has value. It teaches us when our work or our skillset is not good enough and must be made better…Rejection refines us. Those who fall prey to its enervating soul-sucking tentacles are doomed. Those who persist past it are survivors. Best ask yourself the question: what kind of writer are you? The kind who survives? Or the kind who gets asphyxiated by the tentacles of woe?

3. This, Then, Is The Value Of The Gatekeeper

Hate the autocracy of the kept gates all you like, but the forge of rejection purifies us (provided it doesn’t burn us down to a fluffy pile of cinder). The writer learns so much from rejection about himself, his work, the market, the business. Even authors who choose to self-publish should, from time to time, submit themselves to the scraping talons and biting beaks of the raptors of rejection. Writers who have never experienced rejection are no different than children who get awards for everything they do: they have already found themselves tap-dancing at the top of the “I’m-So-Special” mountain, never having to climb through snow and karate chop leopards to get there.

I’ve added the bold and italics here…

Writer's Block 1
Writer’s Block 1 (Photo credit: OkayCityNate)

So, my question to all of you is why you are so damn scared of being rejected? A few theories.

Because having your work rejected seems, for some of you, to really mean:

I  have no talent

Entirely possible. OMG. Did she just say that! Yes, I did. Because, despite what your friends and sweetie and Mom have told you your whole life, maybe you are really just not very good at the thing you are absolutely determined you must be good at. (Or what? Or what? Then what happens?) Stop being a Special Snowflake, already!

I’m such a loser!

Maybe. Maybe not. If you are ever going to survive being a writer you must do this: find a way to separate you from your work. You are not your work. (Here’s a truly disgusting analogy: we all use the toilet and most of us excrete waste every day. It is a product of our bodies. But we do realize that it is not us.) In other words, being rejected may make you feel like shit. You, however, are not shit!

I just wasted all that $$$$$$$$$ on getting my MFA

Can’t help you with that one. I’ve avoided any formal post-graduate education because I’m too damn cheap. If you want to spend a ton of money developing your skills, great. But if you’re looking for serious financial ROI on an MFA, I’d say you’re a little out of touch with the marketplace.

The competition is way too big/famous/established

Here’s the thing we never say out loud. If you’re a total newbie, you’re not my competition! Nor am I yours. Your ego wants to think we’re equal, but we’re not. You will be paid less than I will. (Probably.) I’ve earned it, over decades of consistently good work. You’re still earning it.

If you write about science or babies or science fiction, you’re not my competitor, nor am I yours! I sometimes think of the writers’ marketplace the way an air traffic controller sees the thousands of planes in the air. They never (thank God!) collide. Because they are all on slightly different trajectories.

Stop freaking out about all the other writers out there. Just go be better than they are. (Maybe that means being better at going to a few select conferences and finding some people to help and advise you. Not just banging away all alone at your keyboard.)

I’m scared my email or phone call will be ignored

Bet on it! Count on it! You are not (just) a writer or artist. You’re are a salesperson, hoping to sell your work to people (agents, editors) who’ve quite possibly never heard of you and couldn’t care less if you ever succeed. Be prepared to be more persistent than you ever thought you might possibly ever have to be to get to the right/powerful people who will get your career going. Then double it. Now triple it.

I hate competing

Waaaaaaah! It’s a crowded marketplace. Go big or go home.

But I’m really scared

Of what? Seriously. Of what? Creative failure does not = terrifying medical diagnosis. CF does not = end of your marriage. CF does not = your dog/cat/guinea pig just died. (A friend of mine in London, a super-successful young photographer, is mourning the loss of her guinea pig.)

It is ultimately both self-defeating and self-indulgent to sit in the corner and be too scared to get into the game. We’re all scared, damn it!

Every freaking time I turn in a story I’m still scared the editor will: hate it, not pay me, never use me again and tell everyone s/he knows that I am an incompetent hack. Hey, it can happen.

Then I hit “send.”

I will never be good enough to sell my work

Maybe not. Or maybe so. Maybe you’re trying to sell to the wrong people, or at the wrong time. (i.e. your skills are not yet good enough to compete with all the other people doing that right now.)

It’s depressing being rejected all the time

Which is why God invented martinis, puppies and very good sex. You need to feel really happy at least 63.6 percent of the time in order to deal with the nasty reality of rejection. It hurts. It really does.

I hate my life and being rejected only makes it worse

This is the real problem. I guarantee it — if you are really happy with other aspects of your life, then the endless frustration of trying to sell your work will be annoying and tiring, but it won’t kill you or make you lie in a corner in the fetal position weeping. If it does, you are placing way too much emphasis on your work. Deal with that instead.

But my blog followers love me!

Of course they do, sweetie. Your work is free. It costs them zero social, political or financial capital to read and adore you. Now go find someone to lay their reputation on the line for you…

No one will ever know my name

Pshaw. Go do some volunteer work for a year or so. Join a faith community and show up. Join a committee. Sit on a board. There’s this narcissistic fantasy that Being A Writer means everyone knows you and cares deeply about you. They don’t! You’ll find much deeper satisfaction and happiness from being a valued member of a community of people who don’t give a shit how much copy you sold this week. Get over it.

No one will ever admire or respect me

I think this is a fundamental, unacknowledged and undiscussed part of why people are SO freaked out by rejection. Since when (really) is rejection 100 percent final? You’re reading the blog of someone who applied eight times to the Globe and Mail before being hired. Who interviewed three times at Newsweek and never got hired.

No one will ever know how great I could have become

This is such self-indulgent bullshit. You either want it more than anything, or you don’t.

united states currency eye- IMG_7364_web
united states currency eye- IMG_7364_web (Photo credit: kevindean)

I will starve to death and live under a bridge in a cardboard box

I doubt it. Get a day job and keep it as long as you have to. Or make the leap of faith (with six months’ expenses in the bank and no debt. And, ideally, no dependents.) Those of us who have leaped have little patience for the endless hand-wringers.

I have nothing new or fresh to offer

Really? Then why do you want to bother?

No one wants to work with me

EQ (emotional intelligence) is the new black. EQ is the new IQ. If you’ve grown up in the U.S. in an affluent community (and many of you did not), then being really smart is often deemed the most important thing you can be. Wrong! Being someone able to get along really well within seconds with a wide range of people who are very different from you is going to move your career along a lot faster and further than only hanging with people who drive the same car and went to the same college(s.)

No one wants to help me succeed

Really? What sort of person are you? A taker, giver or matcher? Are you a selfish little wretch who rarely, if ever, returns calls or emails? Who has yet to write (yes, really) a hand-written thank-you note on very good paper and sent it through the mail to someone who gave you an interview or mentored you? There’s an inverse relationship between how greedy you are and how much anyone is interested in helping you be even more greedy.

Everyone else is doing great!

As if! The effect of Facebook on millions of fragile egos — mine included — is to make us all feel Utterly Inadequate all the fucking time. Just don’t read all those perky, upbeat, how-great-my-life-is status updates!

Who actually posts: “I hate my agent. S/he never returns my calls. My book isn’t selling. I’m living on credit cards. I owe $10,000 to American Express and everyone is paying me late.” They should. Because that’s all too often the Glamorous Reality of being a writer.

Now go kick some butt, my dears!

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The value of doing something really badly

English: The picture being uploaded is a from ...
English: The picture being uploaded is a from Evergreen Golf – Driving Range located in Martinsburg, Wv (Photo credit: Wikipedia)

When was the last time you tried something new — making an omelet, writing a screenplay, drawing your dog?

Were the results really awful?

What did you do next?

I bet some of you wailed in (premature) despair: “I suck! I am the world’s worst cook/screenwriter/artist!” And possibly swore that was the last time you would road-test that particular patch of hell.

But I think there’s tremendous inherent value in doing something very poorly. Because, unless you’re an absolute genius (ooooh, lucky you!) you will not be amazing at pretty much anything new right out of the gate.

So, being lousy at something doesn’t mean you’re always going to be lousy. It means you’re a beginner. If you don’t indulge in the ego massage of frustration, (says the chick who once threw her fencing helmet across the salle), you’re bound to start getting better if you keep at it.

Babies fall down a lot when they start walking. It’s a new skill.

They don’t form complete lucid sentences when they begin speaking, nor do we expect them to. It’s a new skill.

When I took up fencing in my early 30s, when I moved to New York and didn’t have a job and didn’t know anyone beyond my fiance, I was pretty lousy at it for a while. Being a driven, stubborn perfectionist, (in New York, the equivalent of having a pulse), I did not take kindly to being shitty at something.

I hadn’t sucked at anything in ages.

One night, worn out and sore and deeply frustrated by my lack of progress, I went and wept in a stairwell. I never cry. I didn’t come back to class for about a month. Then, to my coach’s surprise, I did. A two-time Olympian, he knows how hard it is to get good at fencing. To get really good at anything.

I needed to get comfortable with “failure”, to dredge up the necessary humility to learn something new, and do it poorly for a while until I improved. Or gave up.

But I very rarely give up. For the next four years, I was a nationally ranked saber fencer, knocked out at nationals each year just before the final eight. I learned a great deal about myself in those years, most of it about mental blocks and anger and what a toxic waste of time it is to beat yourself up for being lousy at something.

Who isn’t?

This past weekend, I suggested to my husband, an avid golfer, we go to the driving range. He couldn’t believe his ears. My standard line is that I hate golf.

I haven’t learned a new skill in far too long, so I had him teach me as we ploughed through a large bucket of balls.

Some of my swings were so shockingly bad that I didn’t even get near the ball. I’m a highly athletic person, still, with terrific hand-eye coordination. So I cursed and sulked a bit.

Then I took a long deep breath and reminded myself that I had deliberately chosen the exercise of doing something completely new and unfamiliar.

In my work life, as a full-time freelance writer, I’m expected to be excellent all the damn time. I need the relief of being awful. To try new stuff out in privacy. To see if I can still learn, and how I’ll handle the frustrations that come with that process.

So, when I whacked that ball soaring into the air, landing a satisfying 150 yards away, I was ecstatic. Then I did it again. And again.

I was wildly inconsistent.

That’s what it means to be a beginner, a learner.

In an era of rushrushrushrushallthetime! we often don’t allow ourselves, (or our sweeties or our kids), the luxury of failure and experimentation. Of being a beginner.

High school students feel tremendous pressure to get good grades to get into the right college, where they feel tremendous pressure to choose only the classes they know will get them the high grades to get them into the right grad or professional program and into the right job and…On it goes.

We’re squeaking our lives away in a hamster wheel of perfection.

When was the last time you savored being lousy at something you’re simply new at?

Are you still willing to be a bumbling beginner?