Let’s Talk About Failure

8 min readMay 17, 2022


Yikes — did your stomach just lurch up a little bit towards your throat when you read that title? Did a shudder reverberate through your spine, emerging from a deeply guarded place in your past? Did you just feel a little bit of dread? fear? anger? sadness? It’s okay — you’re okay.

Let’s take a deep breath. Raise your arms high up in the air — and then as you breathe out — release it all down to the ground. Shake your arms out, roll your shoulders, shake your head.

We don’t like to talk about our failures. Failure feels icky in our bodies, and sticky in our minds. When we are deep in our failure-voice, we are trying to run through a muddy river with lead bottomed boots. We are dirty, grimy, ashamed — and we want to get out of here as fast as possible, and if we can avoid seeing the people involved in our failure- all the better. Maybe we grab some of the mud and rub it all over our faces. We gag. Failure makes us gag.

We would much prefer tell people how well we are doing, how much we are “crushing” our goals, and how good we are at “getting it done.” When people ask us how we are doing, we share the highlights — usually the same ones we might share on social media. We don’t want people to know that we tried something — and it failed.

We like to feel like our life is a highlight reel, because — well — it makes us feel better. As children, many of us were conditioned to believe that anything less than our best was not good enough, or that if we are not good at something — that we might never be. Never for a child is a long, long time. We might have been made to feel bad for failing to do something on someone else’s timeline. We might have internalized that if we are not perfect — not our best — constantly ready to go — then we are not quite going to get there. We might have been ill, weak, or frightened as children, and told that it was our fault — a failure of grit, stamina, or constitution. We internalize these voices, and they become our own. They re-emerge when we are failing to tell us that we are failures. Something as simple trying to bake a cake that didn’t rise can trigger that internalized voice of failure. It can become your “Tiny Spotted Elephant” ( Click here for more on that!) Instead of wanting to try again, we believe that we are made to fail. We believe that we, in fact, are what is causing the fail.

It is very hard to admit when we have failed at something, particularly something that we might have been telling people about.

For some the question, “how did it go?” can be a crushing reminder of disappointment.

The truth is though, we all do it. We all fail — all the time. We don’t respond to emails, we don’t say what we really feel when we saying it might make things better, we’re late, we check our phones while with other people, we find loopholes within loopholes so that we can justify something we’re doing. We fail at work, we fail at home, we fail sometimes just walking down the street (I see you texting and walking). We fail at things that are deeply important to us. We are failed by memories of our past, we fail to appreciate the hope in our futures.

Most glaringly — we fail to recognize just how worthy we are — especially when we fail. When we fail, we often fail rigidly — it didn’t work, it’s over, this will never succeed. I invite in the idea that we can fail flexibly — it didn’t work this way, let’s try again that way, let’s see how it can succeed.

Over the last few days, I have failed spectacularly at two pretty big goals that I had set for this year — one in the professional realm, and another in the personal realm. Both failures occurred basically within 24 hours of each other, and both brought with them a feeling that was quite unexpected: relief.

Yep. I felt relieved at the fact that I had failed at something — two things — that I had dedicated many months, quite a bit of energy, and so much hope to.

The personal goal required five months of hard, dedicated, precise physical, mental and emotional training. It required me to be willing to push through physical limits I thought I had, and mental limits I definitely had. It required that I be kept accountable to another person, who dictated said training and commented on it. It had a very specific goal outcome — with very little wiggle room. Sometimes it meant running 20 miles with a start time before 5am. It required sacrifice on the part of my family for me to have this time to try to reach this goal. On Sunday, a day I had been training for since the second week of January, everything fell apart within the first half hour, and the goal very quickly slipped out of my grasp. It didn’t matter. I was — quite literally — on top of a mountain, and I had to make my way down.

In what turned out to be one of the most grueling — and memorable — 3 hours 48 minutes and 18 seconds of my life, I pushed to get to a finish line in a body that wasn’t responding the way I expected to, and a mind that was reeling. I faced fear that I wouldn’t make it, anger at wanting to stop, and sadness at having to let go. I could feel my body shutting down, and I heard my mind screaming. I also had no cell service, so there was no one I could call. It was just me, on the mountain, making my way down. It might have felt meditative, had my insides not been writhing in pain the entire time. The pain was real, acute, and crushing. I felt the disappointment start to seep in when I knew my goal was out of reach. The voice admonishing me for wasting so much time and energy cleared its throat and began to sing in my ear.

I barely had the energy to contradict it — but I had enough energy to start asking questions. I wondered about how much value we attach to our goals, and what we are learning from constantly chasing them. I wondered about how we chase them, what they mean, and what happens when we fail. I wondered, “what is the point of all of this?”

I began to ask the question that I tell so many others to ask themselves in tough times: “Why is this happening FOR me?”

The answer didn’t come on the mountain. By hour 2, my focus was: get water, don’t get eaten by a bear, and get home. The answer came later, on my drive home, after blessedly having made it down: this happened today because again I see the strength I have to keep going. I know I can do hard things. I know I am resilient. I know that I am worthy. I failed, spectacularly, at this goal, because I am worthy of another try. The relief came with gratitude and hope.

We are all worthy of another try. If you look into the scripture of many of our organized faiths, there is messaging from The Sages on the virtue of trying again. (Pirkei Avot 5:22–24 for anyone interested in some Jewish text). We are worthy of the again! — at a physical goal, at something we want to accomplish professionally, even deeply personal quests that we aren’t sharing with the world quite yet. We can all fail flexibly.

The professional goal — this, as expected, is quite a bit more complex. It involves other people, it is tied to what I am most passionate about, and it is in a space that I love. Being in this work feels like being wrapped up in a yummy sweater made of the softest yarn. I am pretty obsessed with this sweater -and I wanted another party to experience it. Yet — a couple of months ago, I found a loose string, and I started to pull on it. Pretty soon, all I could focus on was the string — and the sweater began to unravel. I received much commentary on how quickly this sweater can unravel from others who had worn ones like it — and yet here I was, pulling at the string. Earlier this week — the sweater finally unraveled beyond wearability. No one could enjoy it — not me, and not the other party.

Again, I felt something odd: relief.

Although this time, rather than the gratitude and acceptance that came with Sunday’s failed goal, this relief brought with it sadness and disappointment. Sometimes, failing is public — and hard. Sometimes our reputations ride on it. Sometimes it feels like we are pulling a layer of skin off our face — in front of everyone.

Again, I asked the question, “Why is this happening FOR me?”

I resisted the answer. I didn’t want to hear it. I wanted to hear that I could fix it. That I could remake this sweater and share THIS sweater. I really couldn’t — the sweater was no longer wearable. The sweater, however, still had yarn that was perfectly usable. The yarn — beautiful, intricate, well made — could be re-used. Ah. The answer was: This is happening because you created something good. It might not be right for this place at this time — but it will be right for others. Use the yarn again. Share the yarn. Try again. Make a new sweater. Fail flexibly.

I don’t know yet what the next try looks like for either goal. The failure is too fresh, too sore. There are still raw, emerging feelings that I need to tend to, process, and release. The sadness still emerges at night, I still am having conversations about it in my dreams. I have no idea how I will try again — on either front — but just the knowledge that I can, that I am able to, that I am worthy of it -is a miracle.

We all love to win, to succeed, to get at it. It’s very exciting to share good news — it can uplift, spread joy, encourage others. Failure, though, as it turns out — can be a real gift too. Talking about our failures — openly, honestly, vulnerably — shows real courage. It can encourage others to try — and fail — and share about it. It can teach our children that it’s okay to try many times to get something right — or not. It can help someone who is struggling, but isn’t sharing about it. It can help heal our past — where we were told that we were not okay. We can fail flexibly, and show others that they can too.

We are okay. We are worthy of another chance, another try, another YES. Our challenges show us our strength, so that one day we can bask in the glow of our successes.

This life will leave us all with battle scars. When we fail flexibly, we learn how to get up again — stronger. We learn how to keep going.