Failure? Let’s discuss



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?


35 thoughts on “Failure? Let’s discuss

  1. SUCH a good post. I’ve come out positive more recently but 2014-2016 included a lot of “failures” for me, personal and professional. At the time, going through some of them felt like I was being gnawed on constantly. However the great life lesson I’ve taken away from that time has been: failure isn’t fatal. I see in retrospect that I was experiencing things for the first time, including big, adult-level failures which meant I took them probably more personally and with less resilience than I would now. I’ve failed at other things since then, but my ability to fold them into a bigger context is much better, and thus also is my resilience. I don’t like failing, it still gnaws at me. But I now know that in some cases its inevitable. We move to the next square as best we can.

    1. Thanks!

      I thought of you and other driven/talented friends as I wrote it.

      I know it’s damn hard to “forgive” ourselves for “failure” when — let’s face it — we’re usually just doing the very best we can with the skills, stamina and $$$ we have AT THAT MOMENT.

      I loathe debt. LOATHE it…and yet we now have some (again.) It sure ain’t fancy duds but a pile of $100 co-pays for my diagnosis and so many lost days for me and Jose (no work = no income) as a result. I could feel like a failure but I’ve cranked out 4 major stories and a bunch of blog posts and pitches in spite of it. And applied to the NYT for a job, dammit!

      Half the time we need to step back and re-frame it all in (a forgiving) context.

      Like you, I am always so much harder on myself than others.

  2. The thing I really like about failure is that it’s so democratic. It affords everyone the opportunity to say things like “Failure is not an option” and “Do or do not, there is no try” and then find new and creative ways to back out of their positions once it becomes clear that failure is always an option and do or do not, there is only try. It takes a stable genius not to fail and a fuzzy little space hobbit to succeed without trying.

    1. I have said “failure is not an option!” (because when you work freelance, you can’t eat or pay bills if you consistently fail) but I take your point.

      The problem with the media (ahem) is that they/we endlessly go on and on and on about people who have succeeded — and very little is said about all the failures that are highly likely to occur before (and help to create) that success. Some, yes — like J.K. Rowling’s endless rejections.

      But then it’s also framed ONLY when the final success is HUGE fame and $$$$, and not…Hey, I got out of bed and was able to walk unaided down the hall after surgery.

      I wish failure were something we talked about so much more, and more freely with one another. I was whining a few months ago to a good pal here in NYC who finally snapped “Your problem is you’re used to being successful!”

      Well, hell yes. That IS my goal. 🙂

      1. Roger that. People aren’t too interested in all the times you lose until you win. Sometimes I feel a bit insulted, like when I wasted two hours of my life watching Pearl Harbor. They just couldn’t leave it alone; They had to put in the August, 1945 scene at the end so all the babies could have their bottles and nobody would leave thinking the Japanese had won.
        Professional wrestling is much better. Bitter, abject failure is, in actuality, the thing that gives that desperate struggle for victory at the pay-per-view main event all its sweetness. It’s the most important part of any story. It’s why Iron Man is big business and nobody cares about Richie Rich.
        It is a lovely day, so I think I’m going to go outside and shoot up a couple rolls of film. See ya.

  3. in spite of our best efforts, and time and energy expended, the universe chooses not to give back in equal amounts at times. i’ve had many ups and downs, and it means nothing more about me than does anything else i endeavor to undertake. all that being said, it gets old and is hard to swallow when it continues on for a long period of time. i always find you inspirational, in your refusal to surrender under duress.

    1. Thanks…

      This summer, (blog post coming on that topic) has been very very tough with more tears, fears and anxiety — about health, work and income — than in many long years. It’s pushed me to my emotional and physical limits so it’s not that I HAVE refused.

      I agree, if shit goes ON, it really wears you down…beyond my diagnosis I’ve also had a breast infection last week and stomach issues (likely due to antibiotics) but ENOUGH!

      These aren’t “failures” per se, but stressful anyway.

      I’ve gotten through some very tough times in my past so I know I can do it. That’s half the battle; if you’ve never been tested, you don’t know you can survive it.

  4. Jann Jasper

    Caitlin, thanks so much for this. In my opinion, this is one of the most insightful and deep essays I’ve ever seen on your blog. A comment about one particular lesson: “Don’t marry someone who won’t do the work to go the distance.” I have found out, the hard way, that this information about a partner can remain hidden for quite a long time. It’s not necessarily that he inspires to deceive you. People have limits regarding what they are willing and able to look at in themselves. Limits they are not aware of. A well-meaning and loving partner can turn out to have psychological problems that may remain hidden for quite some time. Perhaps it was a tiny issue when he was young, and with the passage of time, he becomes more extreme. Depending on what challenges life brings, your partner may hit a bump in the road that he cannot navigate. Then you see another side of him, another side that makes it impossible to continue the relationship, even if both of you do your utmost to save it.

    1. Thanks.

      Of course.

      I had doubts going into my 1st marriage (sorry to say) and so its abrupt and adulterous end (his move) was not, in some ways, a surprise.

      I sure learned about the fragile male ego.

      Luckily, my 2nd husband is a much happier guy and a much better fit.

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  6. But why do you consider Montreal, New Hampshire, first marriage, rejected book proposals, etc. as failures? They’re not failures. They’re life experiences. That’s what life is all about, and you know that. You went out into the world, you had those experiences, and now you’re the richer and wiser for it.

    Do you want to know the number of times I’ve been fired for “insubordinancy” (don’t you hate that word?) A lot. But I don’t consider them failures. The people (French ASSHOLE lawyers) and institutions I worked for failed, not me. In fact, the last job I was fired from in 2012, I consider myself a winner because I took the asshole lawyer to court for wrongful dismissal and won 10,000 euros. Every single one of my dismissals were wrongful. They fired me (all in France, not in Canada or the U.K.) because I spoke out against abuse and general assholery. Frankly? I see my conduct as an achievement.

    You need to turn your narrative around, Caitlin. Abolishing the word “failure” from your POV is a start. (Don’t be so hard on yourself :)) Despicable people like Donald J. Trump are abject failures, not people like us.

    As far as social media is concerned? Who gives a crap what other people think, envy or look at.

    Last night I accidentally stumbled across a glossy spread of Alec Baldwin’s wife, Hilaria, who had just given birth to her fourth child. And while I’m looking at the photos of her holding her mewling newborn – minutes old! – on her chest, all I can see is this massive diamond ring that she’s flaunting, and diamond necklace. And I’m thinking, wait a minute, wasn’t she a yoga teacher before she met Alec? And are you even allowed into the birthing room (or whatever it’s called) wearing diamond and gold jewellery?? I had a good laugh.

    It’s all a joke, these Instagram and social media accounts. Really!

    1. It’s a fair point.

      I have expected (silly moi) to “succeed” at what I try, bringing high energy and intelligence and decent social skills to most endeavours. When these fail me — as they did in Montreal and NH for sure — it’s tough on my self-confidence. NH was very very rough. I had never lived anywhere (including Paris, albeit on a group fellowship) where I felt so utterly socially shunned. It was brutal.

      Social media may mean nothing in some industries, but for me, still, it’s a needed proof of street cred — and without which you can barely hope to sell any book proposal. Your “following” is key to publisher interest.

      You are a very strong-minded person. More than the average bear, I suspect.

  7. I try to operate under the philosophy that ever failure is a teacher and a lesson for going forward. I also admitted on social media when I didn’t pass my driver’s exam the first time (I passed the second time, though).

  8. A wonderfully insightful and honest post, Caitlin! We all have lots of “mixed experiences” or “challenging chances to learn” that feel really really hard while they are happening.

    All I can say is you deserve every success, writing job, and good relationship or experience you have, and I am pulling for you! I suspect that I speak for many of your readers who don’t necessarily comment, but tune in post after post because we like and respect you and know you are the real deal.

    Thanks for your consistent hard work and integrity.

  9. It’s amazing how online lives always seem to be so perfect – and often, built around social terms of ‘success’. Projections and shadows! Apropos the world of writers – I think what others define as ‘failure’ is integral to the business; too many people competing for too few resources. It’s normal to swing at something, miss, and move on. The only real problem, as you point out, is the scale of work needed to create a proposal. I think that’s been climbing of late even in the bread-and-butter work.

    1. It’s very intimidating to see everyone bragging about their grants and fellowships and book deals. But it doesn’t do a thing to move me toward my own goals…

      This summer has been a nightmare — and all my pals are in Europe on vacation, posting images! (But I was there last year, and very happily so.)

    2. Same in my world of music, Matthew. The easy gigs are gone – every job requires more prep and takes more time, in part because of the higher expectations raised by the online world.

  10. It’s true I think, we should celebrate mistakes more than we do. I have a great book recommendation for that topic, it’s called ‘Failed it!’ by Erik Kessels and it’s hilarious 🙂

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