Some moments in parenting never leave you.

The big ones arrive as anticipated, yet still manage to completely floor you when they finally happen. No amount of mental rehearsal prepares you for their seismic wallop.

The phone call from Susi telling me there were two lines on the test. Cutting the chord through tears to hold my freshly baked son for the first time. The first stumbly steps. The first ‘dadda’. They’re out-of-body experiences that fundamentally alter who we are and how we continue as men and as fathers.

Painful memories carve their way in too, and there’s one that stands above the rest.

The day my son’s teeth met the tarmac.

Jet took to riding bikes remarkably quickly.

I like to think this was down to his raw pedalling talent, but in truth it probably had more to do with my poorly concealed desire to raise a riding buddy. He skipped stabilisers altogether and at three years old, just one push across the garden was enough - he took off down the street and, figuratively speaking, never looked back. I spent that evening Googling “best bikepacking rigs for three-year-olds.”

By the time Jet was four, we were a two person peloton riding longer loops through town. He was getting confident. Cocky, even.

And this is where the story really starts.

I remember it with an uncomfortable level of clarity.

The plan was simple: ride a couple kilometres to a football field with a cycling track around it that’s smoother than the inside of Kim Kardashian’s elbow. We’d ride a few laps before returning home, but we got there faster than expected and it was clear that riding in circles wasn’t going to cut it for Jet. He was thirsty for more.

We moved to Plan B: continue into the estate, drop back down the hill, and ride the long way home, a five-kilometre loop I ran most Monday mornings.

The gradient of the hill made me pause though. It was a gradual, quiet, 200m descent, not overly steep or technical but long enough to build speed. I convinced myself that with enough brake use and me riding alongside coaching him, it would be a great introduction to downhill riding.

Jet’s pleading to do “the big one” sealed the deal.

At the top of the hill he was giddy with excitement.

Even though I’d run this road hundreds of times, it suddenly felt much bigger.

I stopped him for a final pep talk.

“Stay right by my side. I’m right here with you. Control your speed. Tap the brakes. Enjoy yourself. Be careful.”

We pushed off.

Almost immediately we picked up momentum.

I’d never seen him smile like that. Full ear-to-ear joy. He was using his brakes. He looked in control.

“That’s it buddy. Tap those brakes. Good job.”

We gathered speed and he edged slightly ahead.

“Slow down Jetty. Tap them a bit harder.”

That’s when it changed.

He began to panic.

The motor neurons controlling his braking fingers seemed to collectively decide they were under-qualified for the task and quit without notice.

I caught up beside him and watched his face morph from pure joy into raw terror, his mouth agape and eyes bulging. Unable to physically help him, all I could do was witness what was about to unfold from the front row of the worst horror film I’ve ever seen.

“Use your brakes Jet! USE YOUR BRAKES!”

He wasn’t slowing down. He was getting faster.

His front wheel started to wobble, a violent shudder that anyone who grew up riding bikes knows only ends one way. His wrists were being whipped side to side as he fought to regain control.

I spotted the grassy verge at the edge of the road and shifted into damage control.

“Ride onto the grass Jet!! Go left!”

His hearing had followed his braking fingers and was no longer open for auditory business. He was now staring straight down the barrel of his first proper crash.

He fought hard. Bravely. But it was always going to end the same way. One final aggressive wobble and his hand slipped from the handlebars. The wheel kinked then jammed, and his momentum launched him clean over the front.

He landed face-first, the rest of his body catching up in a tangle of four-year-old limbs.

I slammed on my brakes and ran to him.

His oversized blue helmet lifted from the tarmac as he turned towards me, his screams revealing a mouth already coated in crimson. I could see empty spaces where parts of this teeth had been seconds earlier. A deep cut ran from his lip to his nose. Gravel embedded in the scars across the right side of his face.

As I lay there holding him, overcome with guilt and the certainty I’d failed as a father, he forced out his first blood-filled words.

Words that still haunt me.

“Why did you make me do that daddy?”

I called Susi as calmly as I could muster, told her what happened and she came to pick us up. I kept reassuring Jet he was going to be okay, whilst simultaneously searching for fragments of salvageable teeth.

Once home he had his favourite peach yoghurt pouch and the sobbing eased. He leaned into me like he always did when he was tired, except this time his face was swollen and bloody and my chest felt like it was caving in.

Writing this has been therapy. It’s still so vivid and uncomfortable. Jet only remembers the yoghurt. But what do I make of the experience now?

I didn’t ignore the risk that day and I wasn’t reckless, but I definitely misjudged it. That difference matters, even if it doesn’t feel like it when scraping gravel out of my kid’s face.

There’s a line all parents are constantly trying to read, between danger and growth, protection and preparation. We want them strong, but not broken. Brave, but not hurt. Independent, but safe. We find it by feel, and sometimes we find it by crossing it.

That hill was probably too big for a first go and I’ll be reminded of it every time I see the scar on his lip; a permanent footnote to my failure. But I also know that if I never let my kids point their wheels downhill, they’ll never learn how to handle speed or fear or themselves. 

The instinct after experiences like this is to clamp down and keep them close and safe. I can’t do that. We can’t keep them from intimidating situations forever. Our job is to introduce challenge carefully, then step back. Slowly handing responsibility from us to them, showing them we trust them, so they can learn to trust themselves.

I’m not sure if mine or Jet’s scar runs the deepest, but I can tell you Jet still rips on a bike. In fact, he was back in the saddle the very next day, encouraged by me (I can’t put my future riding partner off for life after all) and when he drops into something that scares him now, he doesn’t even look back for the thumbs up.

That’s the trade-off. We can keep them perfectly safe - free from failure and mistakes - or we can prepare them.

Sometimes the preparation hurts.