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Don’t tell my kids, but sometimes, a little bit of eavesdropping can be good for you.

I wasn’t supposed to be listening to any conversations that night when I stopped off at the school building long after the last bell had rung.

I was there to make photocopies for work, to check things off my to-do list and then make my way home where the dishes, diapers, and drama awaited me.

But my curiosity got the best of me when I realized there was a class for adults in session. I walked up to the door of the classroom, read the sign posted beneath the window, and nearly laughed out loud.

An emotional intelligence workshop? Really?

Who has patience for those kinds of things?

Why would anyone need a class to tell them how and why they feel their emotions?

I went back to the photocopier, rolling my eyes a little as I fed my papers into the machine.

Some of us had important things to do with our time.

But I shouldn’t have been so smug.

Because when the whirring of the machine quieted down and I removed my papers from the machine’s ledge, a few words from the workshop drifted down the hallway and caught my ear.

“If you knew you wouldn’t fail, what would you do?”



In the silence that followed, I could hear some murmuring and then pens scratching against paper. I could hear people far less cynical than I am taking the time to consider what they would do if they knew they could not fail.

“If you knew you wouldn’t fail, what would you do?”

My superiority evaporated as I let that question sink in.

I suddenly realized there were millions of things I don’t do because I’m scared of messing things up.

Simple things:

I’ve never made those gorgeous cookies from the magazine because what if I can’t get them to look as beautiful as they appear on the pages? Why waste my time? I might as well just buy dessert.

And important things:

I’ve never had that non-religious couple over – the one my husband works with – because I’m so afraid I’ll say the wrong thing or do the wrong thing and inadvertently turn them off from Yiddishkeit. Better not to invite them at all than risk letting them down, right?

Or wrong.

Standing in that empty hallway, with reams of paper in my hands, I realized that my fear of failure was holding me back from so many things – big and small – and it nearly blew my mind.

If I knew I could not fail, what would I do?

Would I strive to cure cancer?

Would I strive to teach all Jewish children to love Torah and mitzvos?

Would I strive to be the very best version of myself: the best mother, the best wife, the best daughter, and the best friend?

It was a tantalizing, intoxicating thought. Of course – I would do all of those things – and it would be amazing!

But despite the workshop instructor’s optimistic tone, that cynical voice still whispered in my ear:

Why dream about not failing at anything if failure in life is inevitable?

Why dream about all the things you wish you could do if you know in reality you’ll never be able to do them?

I didn’t stay for the emotional intelligence workshop.

I drove my realistic self back to my realistic life, where my long list of Yom Tov preparations awaited me. I left the philosophizing for the people who actually took the time to sign up for an emotional intelligence workshop, and I left them my rose-colored glasses to enjoy.

But as I readied for the Yomim Noraaim – shopping, cooking, reflecting, and taking on kabbalos – I couldn’t help but let that question marinate in my mind.

“If you knew you wouldn’t fail, what would you do?”

I couldn’t help but think about Yom Kippur, and the impact real-life failure has had on my ability to do genuine and lasting teshuva.

When I was younger, when I would stand rooted to my spot in shul during Neilah, when I could feel the very gates of Heaven closing before me, I used to believe – deeply and truly – that I would be a new person in the coming year.

As I would cry into my siddur, I would make promise after promise after promise about how things would be different this year:

I would daven three times a day – every day!

I would have more kavanah during davening!

I would not lose my temper with my children!

I would be patient, considerate, loving, and kind toward every person in my life, even the ones who often got under my skin.

I believed it.

I could all but see it.

But then Yom Kippur would pass and the year would unravel, and that passion – that conviction – pushing those promises would fade.

Without the Yom Kippur-induced adrenaline, I let reality set in.

First, there was the day I didn’t find time to daven Maariv.

Next, the day I didn’t find time to daven Mincha.

And then, eventually, the day I didn’t find time to daven Shachris.


Those promises about being the best wife, the best mother, and the best friend?

Before I knew it, I got tired or stressed or worried – and I said things I shouldn’t have said or did things I shouldn’t have done.

So much for keeping my promises.


I had failed myself and I had failed Hakadosh Baruch Hu. I was a failure

But until I heard the workshop facilitator ask that question, I hadn’t realized how deeply that sense of failure had seeped into my psyche. I hadn’t realized how brutally damaging failure can be.

Failure hardens you.

Failure makes you doubt yourself.

Failure inures you to the possibility that everything and anything is within your reach.

Suddenly, I realized why my tefillos each Yom Kippur have been getting weaker and weaker instead of getting stronger.

It’s because I no longer believe in myself.

How can I make promises if deep down I believe I will never be able to keep them?

How can I set new, ambitious, lofty goals for myself if I believe I can never attain them?

But if I knew I wouldn’t fail, what would I do?

That question is a game-changer. It gives an entirely revolutionary way of looking at Yom Kippur.

When the Ribono shel Olam gives us the gift of Yom Kippur, it is the miracle of a clean slate.

Our failures from the previous year? They are erased.

Our failures from years past? They no longer exist.

We can erase those failures not only from the Heavenly ledgers, but also from our hearts, from our psyches, from our promises for the future.

Sure – we might fail, but maybe we won’t.

We can have more kavanah in our davening, even if we didn’t manage to do so in the past.

We can be more patient mothers, more understanding wives, more considerate friends, even if we failed to do so last year or the year before that.

We can go into Yom Kippur believing that failure is impossible.

That real change is probable.

That real change is right within our grasps.

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