the impossible

This is how I learned to ride a bike: My father held the back of my seat and ran alongside me, shouting encouragement in his vowel-breaking Irish brogue, and next I know I’m flying along, impressed that my father – who seemed ancient to me, as all fathers do – was flying along with me. That glorious feeling lasted until I realized his voice was receding into the distance behind me, having let me go fifty feet back.

My point in relating this is that I have first-hand knowledge that riding a bike is not impossible.

Lucy, however, was insistent that it was.

“How am I supposed to ride this thing?” she said, shaking one of the handlebars. “It doesn’t even stand up! You just fall right over!”

“You just have to get going,” I told her.

“But how do you get going if you can’t ride it?”

She had me there.

“I’ll run along behind you, holding the seat. You can feel what it feels like.”

“And you won’t let go?” she asked, eyes narrowing.


“You promise?”


“I know you’ll do great!” I exclaimed vaguely.

I did let go, of course. And she did ride for a little bit before realizing I wasn’t there and fell over into the grass.

“You promised!” Lucy called back to me, upset.

“I didn’t promise promise,” I insisted. “You did amazing!”

“I didn’t do amazing! I fell!! That’s not amazing!

I bring all this up to ask you this one specific question:

Have you ever tried to give that speech to your kids about how It’s Okay to Fail?

And if so, has that speech EVER worked?

Because we just finished our orientation for NYU Stern and that motif came up time after time for the MBA students: Don’t Be Afraid to Fail! And they were kind of nodding along but I knew they weren’t going to be okay with failing, any more than Lucy was okay with it. And those are MBA students.

The whole “It’s okay to fail” trope  is one of my secret pet peeves. Which is difficult because it is practically a mantra in business school. And it is, to be fair, fundamentally true in business – at least they way that people mean it. I just don’t like hearing it from the tech billionaires at Davos trying to inspire the masses.  

I have two problems with the It’s Okay to Fail thing: 

The First Problem is that this expression isn’t something that actually works in advance. You can’t tell somebody beforehand and have them mentally prepared to just…fail.

Because why would I ever be okay with creating something that I knew would fail? Every time I try something, I genuinely believe that might the final product.

I don’t try making a birthday cake and think, “Well, I haven’t really tried this before, but it’s okay to fail!”

No – I pour the cake mix into the pan and I am confident in a couple of hours I will be setting a stunningly fabulous cake in front of my child.

But that’s not what happens. This is what happens.



I made this. It is supposed to be a cake. 

The whole It is Okay to Fail is only retroactively encouraging, once I’m standing on the podium of the Great British Bake-Off or whatever those shows are called and I’m retelling this inspiring story about how my earlier cakes looked like I made them with my feet so don’t give up because It’s Okay to Fail! 

But those inspirational stories you hear up there on stage from that great speaker? They are all success stories! Where are all the inspirational speakers who are still in the middle of failing?  I’m waiting on the speaker to get up there at some culinary world showcase and be all like, “For years I tried to make beautiful birthday cakes – years! And you know what? I’m still failing. I never got it right. Check out this cake – you want a bite? Of course you don’t, because it looks like a swamp monster. Okay, well, I guess we should just bring up our next speaker…”

I pretty much gave up on cakes (at least cakes that had any chance of being eaten by anyone other than my kids). I gotta be honest – the failure was getting to me. I give up on things because they can feel impossible, and no amount of It’s okay to fail! will get me past that.

But there are a few things in this world that we don’t give up on. And that’s what makes them special. That’s what makes them our thing.

The thing I refused to give up on was writing.

Writing is my favorite thing to talk about.

Not my writing, which can be frightfully dull for me to talk about, but other people’s writing, which is actually fun to talk about. (I work with high school students on college admission essays, which is hugely entertaining – I get to discover their story and figure out how to help them tell that story instead of telling another one of my dumb story about how much I love Doritos or whatever.)

When I speak to high schools or colleges (or even middle schools) about writing, the thing I always share is This Hard Truth:

The first draft of whatever you write is going to be terrible. You WILL throw it away.

One time a student in a class raised his hand.

“It’s not always terrible,” he insisted. “I only wrote one draft of my last paper and I got an A on it.”

I answered, respectfully: “You got an A on it because your piece of trash was better than everyone else’s piece of trash, and your teacher is grading on a curve. But it was, unfortunately, still trash.”

I quickly assured this student that every first draft I have ever done was also complete trash. It’s a simple inevitability.

And that brings me to my Second Problem with the whole It’s Okay to Fail thing: 

I have written millions and millions of words over thousands and thousands of hours and there are thousands of pages in the trash. Draft after draft is part of the process. But THAT IS NOT FAILURE. That is LEARNING HOW TO WRITE. 

Failure is giving up on something. And it is okay to give up on stuff. It’s okay to fail. But if you are persisting, then that is the opposite of failing.

Writing is one thing I personally never, ever gave up on. I’m telling these students that if they want to do this writing thing – and I know it can feel impossible – then they have to persist and they have to do it again and again and they have to decide that they are going to do it

Lucy got back up after she fell off her bike. Not because she heeded my sage words about it being okay to fail, but because this was going to be her thing. She was going to ride that bike, like her brother before her and her father and mother before that. So she didn’t give up, not when she scraped her knee or when she fell in front of the guy walking his dog and was super embarrassed. She persisted. And she did the impossible.

But speaking of actual, red-blooded American failure, here are…

The Top Five Random Things I’ve Failed at:

1. Learning Italian.

In college I took Italian, and I imagined myself vespa’ing through the alleys of San Gimignano shouting to Italian passersby as they raised their espressos at their fellow native Italian. But I failed the first quiz and bailed like a fighter pilot in a flat spin.

2. Growing my own herbs.

The first house we got in Connecticut, I was so going to have a little herb garden. People would come over and I’d be like “Can you just grab me a few sprigs of thyme?” and they’d come back with rosemary and I’d laugh gently and guide them back out to get the proper herb. NONE of that happened. (I don’t even use fresh herbs. Also, I wouldn’t be able tell different herbs apart if they were wearing dog tags. Also, I’m still working on cakes.)

3. Categorizing my inbox.

Every year I make like 20 folders and I put all the emails in there and I’m like “I’m organized!” And then it lasts maybe a day and then I just have these emails in folders that I never open again and can never find again and so my inbox now has literally nineteen thousand emails in it.

4. Become a birder

How hard could that be? My dad knows every bird, he’ll pause when he hears one and then identify it. How many different kinds can there be? Six? I can memorize six stupid bird calls. But every time I hear one I have no idea and Finn asks what kind of bird it is and I’m like “I don’t know, owl?” and he’s like “It’s three o’clock in the afternoon, aren’t owls noctural?” And I’m like “Who’s the birder here??”

5. Eat super spicy food

I actually genuinely thought I could practice this, eating spicy food. My secret dream is to go to an Indian restaurant and say “I’ll have the vindaloo, as hot as you can make it,” and they bring something out and I taste it and throw down my spoon and shout “Hotter!!” until the entire cooking staff is gathered around my table, wide-eyed as I lounge back having consumed an entire plate of the hottest food they have ever served. (I don’t really know what comes next, maybe they cheer or something? When I write it down it doesn’t seem as exciting…)

Anyway, if I can just leave you with some last advice: It’s okay to fail.

By | 2018-09-05T09:08:24-04:00 September 5th, 2018|28 Comments


  1. Crista Mathew September 5, 2018 at 10:06 am - Reply

    SO glad you kept learning to write and I like that refreshing perspective on failure! Great wisdom Conor!

    • Conor September 5, 2018 at 11:52 am - Reply

      Thanks Crista!!

  2. Sharon September 5, 2018 at 11:32 am - Reply

    Love your writing. Your random musings at the end always make me laugh 🙂
    PS – you don’t fail at cakes if they still taste okay in my humble opinion!

    • Conor September 5, 2018 at 11:54 am - Reply

      Right, cakes are for eating. And so we should judge them solely on their edible merit. Enough of cake decorating! Petition time!!

  3. Ellette September 5, 2018 at 11:40 am - Reply

    This is spot on!

    • Conor September 5, 2018 at 11:55 am - Reply

      Thanks Ellette!!

  4. Judith Hochhauser Schneider September 5, 2018 at 12:26 pm - Reply

    I have started looking forward to your posts. Your messages always resonate and your humor keeps it compelling. I quite literally laugh aloud. I will subscribe, both for the pending gift and to have one less reason to check FB. BTW, I do have an herb garden and do exactly what you suggest about laughing when people can’t simply clip the correct herb I request. I will get more pleasure from it now that I have in the past. Second, my mother was a self taught birder and I never knew how she did it. Horrifying considering I took ornithology in college! Third, I have dreams of being multilingual and yet I’m barely conversant in Spanish. Luckily my 6 year old is helping me out when I back myself into a corner since he’s fluent in a Spanish Immersion school. Lastly, I have fond memories of your dad’s brogue. If you find yourself in Portland, my new home, please look me up.

    • Conor September 5, 2018 at 3:05 pm - Reply

      Judith!! Hi! I love childhood friends :-). And you took ornithology in college?? I downloaded a bird call app. So there’s that, I guess… Portland! We will make it there, I’ve never been!

  5. Susan Flanagan September 5, 2018 at 1:39 pm - Reply

    My smile is already “on” each time I start reading your blogs, Conor, knowing I will be entertained–but “herbs with dog tags” brought on a quite audible chortle. I’m pretty good with salt and pepper but Parsley, Sage, Rosemary and Thyme is just a pretty song. Loved the encouraging “It’s okay to fail”, and I know for a fact Lucy is now an accomplished cyclist.

    • Conor September 5, 2018 at 3:05 pm - Reply

      She IS an accomplished cyclist! So proud of her!

  6. Glenna September 5, 2018 at 2:05 pm - Reply

    I love your writing so I’m glad you didn’t give up. Keep these blogs coming! And I think you need to make another cake. That first one was your
    first draft.

    • Conor September 5, 2018 at 3:05 pm - Reply

      I need a good cake editor.

  7. D September 5, 2018 at 3:42 pm - Reply

    Good one! Successful, no question. Life is drafting, God help us!

    • Conor September 5, 2018 at 6:29 pm - Reply

      Life is drafting. I’m totally stealing this phrase.

  8. Mark September 5, 2018 at 5:44 pm - Reply

    I love your Charlie Brown Christmas Tree Cake.

    • Conor September 5, 2018 at 6:30 pm - Reply

      That’s what it is!! A Charlie Brown Christmas Tree Cake! Smartest thing you’ve ever said :-).

  9. Laura September 5, 2018 at 7:39 pm - Reply

    If it makes Lucy feel any better, the first day I rode my bike down our street with my mother next to me, I was so proud that the neighbors were praising my new accomplishment that I forgot to look where I was going. Why my mother didn’t warn me is still a mystery. Anyway, there I was flying along when WHAM my little tiny tire got wedged under some rude persons bumper, and flying off the bike I went. I landed on my face and was so upset…what WAS this car doing parked here in the street IN MY WAY??!! I think I was pretty bloody and drowned in humiliation to boot. But kids are made of tough stuff. I got back on that bike and conquered the street. And forever resented that cars took up so much space!!! I’m proud of Lucy!!!!

    • Conor September 6, 2018 at 8:11 am - Reply

      I would give literally one million dollars to see photos of sweet little Laura!!! (I LOVE this story!!)

  10. Rachel Nicholls September 6, 2018 at 2:27 am - Reply

    I used to decorate cakes, birthday cakes… wedding cakes etc. I haven’t decorated a cake for years because I just got so over it! It’s my son’s 15th birthday next month and it’s school holidays here in Australia. No cake decorators available!!! Oh dear! It’s up to me!!! Wish me luck! Hope all the kids don’t laugh!!
    Love your posts, I read them at work and giggle. People around me wonder what the hell I’m doing. Let’s keep them guessing 🙂

    • Conor September 6, 2018 at 8:14 am - Reply

      Send a photo when you finish! Will you? Maybe to my Facebook page? I would totally love to see it!

  11. Carolyn with a J September 6, 2018 at 11:11 am - Reply

    Let me know if you happen to come to Iowa. We have the last bird in our nest ready to launch to college next year and we keep hoping we will figure out the college essay thing. A private lesson could be the ticket. 🙂

    • Conor September 6, 2018 at 12:46 pm - Reply

      Thanks Carolyn! I feel like we need more reasons to come to Iowa. Why don’t we get to travel more? I feel like we should drive back and forth across the country at least once every two years. And congrats on the upcoming college departure!! And also yikes!! And also I’m sure that bird will do awesome on the essays – sounds like you’ve been through this already :-). But if you need help lemme know, I can see what I can do!

      • Carolyn with a J September 6, 2018 at 1:56 pm - Reply

        Iowa has the absolute best sweet corn and it becomes the center of the political universe every four years. Oh, and we have the Best State Fair. . Coincidently, NYU and UVA are on his short list. Unfortunately or fortunately, he has lived an easy life as the youngest of three brothers in an intact family in middle America. I’m hoping he can make that into an epic story.

        • Conor September 7, 2018 at 12:42 pm - Reply

          You had me at State Fair. Nothing better.

  12. Jackie Lyons September 7, 2018 at 10:08 am - Reply

    Am I ‘subscribed’? Probably not, but I’m trying to be. Sometimes it’s not ok to fail!

    • Conor September 7, 2018 at 12:43 pm - Reply

      Good question! If you put in your email, you’ll probably get an email sent to you asking you to confirm it, and you click that button. Thanks Jackie!!

  13. Kelly Frasca November 8, 2018 at 10:17 am - Reply

    currently rereading this in an effort to ignore the plethora of work I’ve yet to do and “different herbs apart if they were wearing dog tags” just made me snort out loud in Spanish class.

    • Conor November 8, 2018 at 4:18 pm - Reply

      Thanks for reading Kelly!!

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