On our last night in Europe, my husband Jason and I were hurrying through the streets of Dublin, dressed for the opening night of Hamilton and ready to meet his colleagues at the theatre. But a sudden thud from a skateboard crashing into the street stopped us in our tracks.
Our eyes dart toward the sound, and we see a kid lying flat on his back, midway through a set of three stairs in front of an office building.
“Oh my god” I cry out a little too loudly. “That kid just wiped out. Is he okay?”
Wordlessly, we watch the kid lie on the ground for a minute as his two friends crowd around him. One friend holds out a hand and helps him stand up. Then the skater picks up his board and turns away, back up the stairs.
“Wow I’m glad he’s okay,” I remark to my husband
“Seriously.”
We continue to walk down the street but our ears perk up again at the sound of rolling wheels. We turn just as we notice as the same kid skating along the upper platform, right back toward the same stairs. Faster, faster, faster, until he clears a jump, catches air. There’s a brief moment of suspense until he lands flat on his back with a muscle-tightening thud. He does a half-roll to recover.
His skateboard scoots off the stairs, toward the street with incoming traffic in both directions. But a friend is there, at the bottom of the second set of stairs to receive it.
My eyes widen when I realize what’s happening. He didn’t crash accidentally. He’s conditioning himself.
I notice for the first time there is also a third person, with a video camera, seemingly waiting to catch a recording of the perfect landing. He has a team with him. And a vision.
Once again, the skater wordlessly gets up, picks up his board and heads back up the stairs.
“Can we watch again?” I ask my husband.
He nods.
As he continues up the stairs and down the platform, we watch his friends get into a receiving position, and he launches into the run again. He sprints down the drive, jumps onto the skateboard with both feet, slides toward the 10-step stairs and makes the jump. His skateboard flies past the landing down the lower step of stairs and his friend catches it with the skill of a baseball catcher, while the skater boy lands flat on his back again. I am transfixed.
“Again.”
He takes off his hoodie now, exposing just a t-shirt to the concrete ground that he’s knowingly going to crash into. He misses again, but manages to catch himself on his feet with a few stumbles this time, instead of rolling onto the ground. Progress.
I glance back at my husband.
“Last time” I promise, even though I know I’m lying.
It’s an addiction now, watching this 20-year-old hurtle himself off a set of stairs and injure himself on a missed jump again and again. I start to get nervous about our obvious voyeurism.
“Is this wrong for us to be standing here?” I quickly gut check. “Watching like this, I mean.”
“Well, he is recording it himself,” Jason reminds me, gesturing toward the camera. “And he is in public.”
“Ok great,” I say quickly, thrilled to have bought at least one more round.
He’s back on the board now. I hold my breath as he clears the landing, then release it sharply when he wipes out again.
He collects himself and stars up the stairs again.
As I stood there watching, I realized how rare it is to see someone willingly fail in such a public setting, again and again. It struck me that this is the very thing we shy away from, despite the endless talk in industries like tech about the value of “failing fast” and “working in public.”
“Opening night is just that way…” Jason reminds me.
“I know, I know.” I take a few feeble steps with him but turn back as soon as I hear the sound of rolling wheels on pavement again. I turn and wait.
Damn. Another miss.
Watching that skater crash over and over again in full view of strangers on their way home from work, rush-hour traffic, and theater-goers like me, felt like a rare glimpse into something we usually try to hide—failing publicly, without apology, as part of the process of leveling up.
In my work with founders and entrepreneurs over the past decade, I’ve seen how powerful it can be when people are willing to embrace honesty and vulnerability. The sooner a team drops the façade of constant success, the easier it becomes to both offer and receive help. But even in an industry that celebrates the idea of “failing fast,” there’s still a natural hesitation to share those messier, more difficult moments.
Of course, this is easier said than done. Even though we know this to be true in theory, you still don’t see many people crashing and burning publicly on social media, day in and day out. Why so many of us still hold ourselves back, even when we want to be a little bit braver. Why we’re still so captivated by the idea of public failure.
Almost a decade ago, a video went viral of a skateboarder named Christian Flores who shared a 5-minute short video testimonial of his 2,000+ attempts to land the same jump. You can watch it here:
In that video, Flores talks about how he visited the location 10+ times over two years of trying, making the attempt to land the jump 100 times in a row on each visit. He was hospitalized twice. Bruised and bloodied more than once. He openly admits that he’s not by any stretch the greatest skater in the world–he falls more times than not–but still, he perseveres until he finally lands the jump perfectly. Just once. He ends the video by inviting any viewers to introduce him to other stair challenges that he might take on next.
To him, even after all that time, and all those injuries, the work is never over. He barely skipped a beat before inviting in the next challenge. I imagine that is likely true for the skater we saw in Dublin, too.
Lately, as I’ve embraced AI to enhance my workflow, I’ve found myself getting ahead for the first time in years. After five years of post-pandemic life in NYC—raising two babies across three apartments and navigating four job changes—I’ve finally been clearing out the cache of old ideas. I’m dusting off half-written blog posts from the forgotten corners of my Google Drive and putting thoughts on paper that I’ve been mulling over for years.
But what’s surprised me most is that even after completing a long-delayed project, the feeling of unfinished work doesn’t go away. Another unresolved idea always bubbles to the surface, waiting to be tackled. The more I dive in, the more I realize this may be true for all of us: The work is never over.
It’s not about landing perfectly every time; it’s about staying in the game, even when the next jump feels like another wipeout. Whether it’s skating, writing, or anything else, the real work is just continuing to show up. Maybe more of us should take our work to the streets.
Over 500 subscribers
Collect this post as an NFT.
