We rolled out of Great Malvern train station with two laden bikes, a dentists nightmare of a snack bag, and a plan that, on paper at least, erred on the side of ambitious. It took less than two minutes for that plan to completely fall apart.

“I’m done with these hills!”

A strong and entirely understandable early statement from a 9 year old boy who had unknowingly signed up for 200m of elevation within the first 2km. (There were several others climbs over the course of the day that I’d also chosen to keep to myself).

I stood there, already sweating like a lasagne in a dishwasher, looking up at the climb I’d chosen, then back at the face of a furious riding partner and wondered, not for the first time, why I have this habit of making things a lot harder than they need to be.

I could have definitely picked a much easier route closer to home; flatter, shorter and far less likely to trigger an argument before we’d barely got the wheels rolling. I could also have scrapped the idea entirely and taken us to the cinema. Or a trampoline park.

But I didn’t. 

And I rarely do, for some strange reason.

I’m a big fan of pedal-powered adventures.

A 38,000km ride from England to Australia in my twenties showed me a version of travel that asks a lot, but gives back tenfold. When you move that slowly, the world opens up in ways it just doesn’t when you’re flying over it or blasting through in a car; all those small, wonderful details you’d otherwise miss. The occasional arse boil is a small price to pay.

So as soon as Jet could turn pedals, it felt inevitable he’d be dragged into this with me. We’ve done a handful of overnight trips over the past few years, and while setting off into the hills with him still gives me a slightly giddy excitement, tapping back into that old vagabond part of me, every single one has moments where I find myself wondering what on earth I was thinking.

The Malverns were no different, I just didn’t expect it quite so soon.

As we stood there negotiating the opening climb out of Malvern, I felt that familiar moment where expectation and reality come crashing together. I had a picture in my head of how this would go. He had other ideas.

It starts with frustration. A flicker of disappointment that it’s all unravelling this early. Again. Then, with a deep breath and a bit of internal recalibration, I shift into the role required of me: part motivational speaker, part pack mule, delivering short bursts of optimism that are received with varying levels of scepticism.

Then I remembered the peanut M&Ms! Like a low-budget remake of ET, I began coaxing him up the hill with the promise of chocolatey rewards at loosely defined intervals like a performance enhancing snack strategy. We inched upwards, the conversation hovering somewhere between encouragement and bribery while I lugged both bikes and all our gear up it.

By this point, my sweat patches had joined forces to form a single, unified Pangea of perspiration, but I also knew this was the moment that mattered. If I met his frustration with my own, it was game over.

But eventually, as it tends to, the climb broke. The gradient softened, the path levelled out, and the landscape opened up. Rolling hills stretched out in every direction. Apparently you can see 13 British counties from the top, although I was mostly focused on convincing my heart to return to a sustainable rhythm.

Jet was now back on the bike. The same boy who had declared the day over minutes earlier was now gliding along the ridge with a beaming smile and a gob full of m&ms, fully re-engaged as if the whole protest had been erased from the travelogue. We’d finally found our rhythm.

We moved across the hills at our own pace, stopping often to take in the magnificent views but mainly because stopping is one of the great underrated joys of doing anything with kids. The wind picked up to the point where it felt like we’d accidentally wound down the window on Artemis 2. We rode up and over an ancient Iron Age hill fort and then witnessed a Planet Earth-worthy mid air scrap between a Red Kite and a pair of particularly ballsy crows. At one point we took a wrong turn and followed a trail that slowly turned into a river, which felt like a fitting consequence for my navigational confidence. We stopped for a pint and a packet of pork scratchings too.

Threaded through the whole trip was what I’ve come to recognise as the swings. Those sharp, unpredictable, occasionally quite violent shifts between joy and resistance that seem to define most of the microadventures I do with my kids.

Moments where everything stops being a battle and just, somehow, works. The giggles after a deer explodes out of a hedge like it’s been fired from a cannon. The satisfaction of leaning almost 45 degrees into gale force wind. The silent appreciation of a sea of bluebells. The strange, fleeting sense that I might actually be quite good at this whole dad thing.

And then, often not long after, the opposite. A bike thrown to the floor. Voices raised. A surprisingly detailed critique of my route choice, my planning, and my overall decision-making as a human being.

It swings. Back and forth. And somewhere along the way I’ve realised that trying to eliminate that is a complete waste of energy. It’s baked in. The only bit I can really control is my side of it. Which, halfway up a climb carrying two bikes and sweating like a Labrador in a wetsuit, is easier said than done.

By the time we found a spot to wild camp, we were both ready to rest our arses. We set up quickly, ate a dehydrated meal that tasted far better than it had any right to, and crawled into the tent as the last of the spring light disappeared.

Everything had settled. The mini arguments, the effort, the moments of friction…all of it absorbed into the duck down of our sleeping bags. As I leant in to say goodnight, Jet gave me a hug and said, with complete sincerity, “You’re the best dad ever.”

It hit like being applauded by a small, invisible audience.

Unless I’m returning with chocolate brownies or announcing a trip to Legoland, my kids don’t tend to dish out that sort of feedback. And even when they do at home tucked up and half-asleep, it’s lovely, but it doesn’t quite carry the same weight. This did. For him to have gone through something that had properly tested him (largely off the back of my slightly overcooked planning) and still land there, that felt significant.

It made me realise that the bits that matter aren’t the smooth, well-executed days we try to engineer, but the ones where things wobble and we have to figure it out together. We spend a lot of time trying to remove friction for our kids, but real life has other ideas. It’s messy and unpredictable, and every now and then asks more than you’d like it to.

Maybe part of the job isn’t avoiding that, but choosing when to lean into it, and being there with them when it does.

That hill at the start? Turns out, that was the point.