Four recent “failures” and what they taught me

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.







19 thoughts on “Four recent “failures” and what they taught me

  1. I’m sorry you seem to have met so many of the arseholes of the corporate world in such a short space of time. The trouble is they love to pull others down and tear them apart in what they think is a show of personal strength whereas in fact it shows a personal weakness in them in that they look at scoring points with others instead of supporting the business.
    The woman who created and circulated a list of your personal faults will want to be the first to say “I never wanted them in the first place” has now proved to her colleagues what a small minded nasty piece of work she is, and will be looking to get rid of her in case they’re next.
    Fingers crossed 2016 is a year of the opposite and you meet charming genuine people who will honour their promises and understand why you’re the right person for the job.
    xxx Huge Hugs xxx

    1. Thanks. 🙂

      She was quite something, that one. The only satisfaction of quitting that position was drawing the cobra from its nest — so everyone could see what she had been subjecting us to privately. Done.

  2. The one thing I’ve always had with the Failure Is Awesome movement, is that its end point is always You Will Then Succeed. And if you don’t (in the corporate world, in my experience), you’re then a REAL failure. The kind no one wants to have anything to do with, despite all previous propaganda.

    I love the corporate world.

    Thanks for sharing your failures, and their lessons. And reminding us that they are valuable for moving on.

    Kudos, Caitlin!

    1. So true…As if it were contagious and then…OMG. NOW WHAT?????

      Especially in America, the land of winners. 🙂

      If I hadn’t already had plenty of success, I might be crushed. I certainly shed tears over a few of these, but the hell with it. In each instance, it took two to tango…

  3. Jan J

    Caitlin, These hurt, of course. Particularly because you have such a strong work ethic. But I can’t see how these “failures” were your fault. You had the misfortune of dealing with some seriously unpleasant people – some merely didn’t know how to manage an outside writer, and others were downright mean people. Yuck. Here’s to a better 2016!

  4. I often find that when your gut instinct tells you to walk, you should definitely walk. And, fingers crossed, because you walked, something better will come along.

    In 2012 I worked in a small French law firm. I LOVED the location (the office overlooked the Parc Monceau and most lunch hours I was in it), but I hated the lawyers I worked for. Towards the end of the year, we had our annual evaluation. We were handed a questionnaire and invited to express our feelings and opinions on a number of different topics relating to our jobs and the workplace. Well, because I had been “invited” to express myself, I did so. But also my gut instinct told me to. I hated the lawyers, so I figured “What the hell.” I didn’t care. And I let loose. They didn’t appreciate my candor. They fired me just before Christmas in 2012.

    And it was the best thing that could’ve happened! Even though I miss the Parc Monceau, I got a new and better job only two months later…at a higher salary and with very good benefits. I no longer work in law firms but now in a small investment bank. Until we moved two months ago, the new job was literally a 3-minute walk from my apartment. It’s now a 20-minute walk.

    I guess what I’m trying to say is if it FEELS WRONG, it probably is and you shouldn’t feel bad about resigning or walking away. And, hopefully, something better will come along. I sincerely hope that 2016 will be a great year for you and for all of us.

    1. Merci, madame!

      It is comforting to hear that others (as we all do) have faced similar situations. It’s such a taboo to discuss our mistakes or missteps in public, which gives the impression successful people never make them. They do!

      So glad you went on to better things!

  5. There is no person on the planet who could have made the board position work, from the sounds of it. Four ex-presidents on a 13-person board is the platonic ideal of “too many lions and not enough Christians.” Consider yourself the Kim Campbell of the situation and bail out of there to new and glorious positions where your contributions are respected and your leadership followed.

  6. As Churchill put it, ‘success is going from failure to failure without a loss of enthusiasm’. Rolling with the punches: and often, stuff that fails does so out of left-field despite best effort. I’ve just had an issue with a post-fact decision by a magazine not to pay me for one of my (very rare) feature articles – something I’d produced in good faith and from which they’re deriving income – it’s still behind their online paywall. It’s not the first time I’ve been shafted that way – I made a decision some time ago not to deal with certain of NZ’s media companies because they’d broken faith once too often, always to my dead loss. But this was one I hadn’t dealt with before – and I’d rather view strangers in positive light than tar them with the brush of past experience.

  7. Pingback: [BLOG] Some Thursday links | A Bit More Detail

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