by Kym O'Leary

The Milestone I Missed

by Kym O'Leary

While I was away for work, my four-year-old son David learned to ride a bike without training wheels.

I wasn’t there to see it.

For a long time, I assumed that missing moments like that would be one of the hardest parts of balancing work and family. But when my husband Stu sent me the video, the emotion I felt wasn’t sadness.

It was pride.

“The emotion I felt wasn’t sadness. It was pride.”

Four months earlier, at our first stop of the trip at Hastings Point, riding a bike had looked very different. Back then, we rode everywhere — to the water slides, to the shop for milk, around the caravan park in lazy loops. We spent a lot of time reminding David not to ride down the middle of the road, gently building his
awareness of the people and vehicles around him. There was alot for a four-year-old to take in.

Slowly, he improved. Not just his riding, but his confidence. We asked a few times over the following months whether he wanted to take the training wheels off.

The answer was always no.

Then we started meeting other families on the road. David began spending time with kids at caravan parks — watching them ride, watching what was possible, quietly recalibrating what he thought he was capable of.

Community has a way of doing that, even for four-year-olds.

One day while I was away, Stu asked him again.

This time, he said yes.

Over to a patch of grass they went. And before long, he was riding on two wheels.

When I watched the video, I couldn’t believe it. Later, we FaceTimed and David was absolutely beaming — the kind of pride that fills up his whole face. He knew what he’d done.

And so did I.

“What surprised me most was that I didn’t feel sad about missing the moment. I felt grateful.”

Grateful that he was growing. Grateful that he was building the kind of confidence that doesn’t come from being told you can do something — it comes from discovering it yourself.

It made me think about the pressure we put on ourselves as parents to witness every milestone. To be present for every first. To feel that if we weren’t there, we somehow
missed it.

But I’m not sure that’s actually the goal.

What this trip has reinforced, in ways I didn’t expect, is that the goal isn’t to witness every milestone. It’s to create the conditions for growth — an environment where kids feel safe enough to try, to fail, and to keep going anyway.

I wasn’t there when David rode without training wheels for the first time. But I was there for the hundreds of small moments that built toward it. The wobbly laps around the caravan park. The reminders about looking up. The gentle nudges when he
wasn’t quite ready.

“Not witnessing every milestone. Helping create the confidence for them to happen.”

Perhaps that’s what matters most. Not being there for the moment — but being the kind of parent who helps make it possible.

“What surprised me most was that I didn’t feel sad about missing the moment. I felt grateful.”

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