Posts Tagged ‘failing’

Four recent “failures” and what they taught me

In aging, behavior, business, life, women, work on February 10, 2016 at 12:32 pm

By Caitlin Kelly


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.


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.


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.


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.


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.


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.







The value of doing something really badly

In aging, behavior, business, children, culture, education, life on August 22, 2012 at 12:04 am
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?