The walks, the wins, the failures — and what I learned along the way
Challenge Accepted!
IT STARTED WITH A WALK...
I didn’t set out to become someone who spent weekends walking marathon distances, 50km challenges and the occasional slightly ridiculous 100km.
For a long time, I wasn’t particularly fit. I smoked, exercise wasn’t exactly a major part of my life, and the idea of walking 100km would have sounded completely absurd.
Then I started walking.
Nothing dramatic at first. A few miles became longer walks. Longer walks became something I actively looked forward to. And somewhere along the way I discovered something about myself: give me a challenge and I find it very difficult to say no.
So the distances started creeping up.
10km. 15km. 25km. Marathon distance. 50km.
Then came the bigger challenges — long days, night walking, sore feet, ridiculous weather, spectacular scenery, finish lines…and a few occasions when there wasn't a finish line at all.
Because that's been part of the journey too.
I've completed some challenges I'm incredibly proud of. I've also failed at some spectacularly. And I've probably learned more from the latter.
That collection of medals above is only part of the story.
This page is about what happened along the way.
WHEN WALKING BECAME A CHALLENGE
My first proper organised challenge was the National Three Peaks Challenge.
Ben Nevis. Scafell Pike. Snowdon. Three mountains, lots of driving, very little sleep — and the small matter of trying to do the whole thing against the clock.
I didn't complete it.
And looking back, that's probably one of the most important challenges I've done.
I'd been walking more and getting fitter, but the Three Peaks taught me very quickly that a big challenge isn't simply about being able to walk a long way. There's the terrain, the climbing, the weather, the pacing, the fatigue — and what happens when things don't go according to plan.
Not reaching the end could easily have put me off.
It did the opposite.
I wanted to understand what had gone wrong, get better at this stuff — and try something else.
And that, really, was where the challenges began.
THE LESSON: Failure isn't necessarily the end of a challenge. Sometimes it's the thing that makes you want to come back better prepared for the next one.
THE DISTANCES STARTED CREEPING UP
After the Three Peaks, I didn’t suddenly decide that walking 100km sounded like a sensible idea.
It happened gradually.
I started entering organised walking challenges and pushing the distance a little further. 10km became 25km. Then came marathon-distance events. Then 50km.
Crossing the finish line of a 50km challenge felt like a pretty big deal. And it was.
Each step taught me something new.
How quickly you can go off too fast. How important your feet become after several hours. Why eating before you're hungry matters. Why the waterproof you nearly left at home suddenly becomes your favourite possession.
And, perhaps most importantly, I learned that you don't have to be an elite athlete to take on these events.
You train. You prepare. You turn up. And then you keep putting one foot in front of the other.
Somewhere along the way, the distances that once sounded ridiculous started to feel achievable.
And that's when 100km entered the conversation.
THEN CAME 100KM
Eventually, 50km wasn't enough.
Which is a ridiculous sentence when you think about it.
100km is 62 miles. For most walkers, it means starting in daylight, walking into the night and discovering just how differently your body and brain behave after you've been moving for hour after hour.
My first attempts taught me that doubling 50km doesn't simply make a challenge twice as hard.
It's a different beast altogether.
There are the obvious things — tired legs, aching feet, darkness and the sheer distance still ahead of you. But there are also the things you don't necessarily expect: struggling to eat, getting cold when you stop, the mental battle when another checkpoint feels impossibly far away, and how tempting it can become to simply sit down and call it a day.
I didn't get every 100km attempt right either.
But eventually, I crossed that 100km finish line.
And whatever state you're in by that point, there's something extraordinary about looking back and realising you've travelled 100 kilometres under your own steam.
THE LESSON: You can't bluff your way through 100km. Respect the distance, prepare properly — and when things get difficult, stop thinking about the finish. Just get yourself to the next checkpoint.
NOT EVERY CHALLENGE ENDS WITH A MEDAL
Most recently, I took on the North Yorkshire 50km Challenge. I'd trained for it and arrived expecting to finish. But the heat had other ideas, and after 26km I made the decision to stop.
Frustrating? Absolutely. But carrying on simply to say I'd finished wouldn't have made it the right decision.
THE LESSON: Respecting a challenge also means knowing when to stop. A DNF doesn't erase the miles you walked to get there — or what you learned from them.
THEN THE CHALLENGES GOT HIGHER
Distance wasn't the only thing that started escalating.
In 2022, I swapped UK checkpoints and finish lines for the Himalayas and headed to Nepal to trek to Everest Base Camp and Gokyo Lakes.
This was a different kind of challenge altogether.
There was no 100km finish line to chase and no medal waiting at the end. Instead there were long days at altitude, freezing mornings, basic teahouses, the crossing of the 5,420m Cho La Pass — and the small matter of trying to breathe when there didn't seem to be quite enough oxygen available.
But many of the lessons I'd learned on those UK challenges came with me.
Keep moving. Look after your feet. Eat when you can. Break the day into manageable pieces. And when things get difficult, concentrate on the next step rather than everything still ahead.
That trek changed my relationship with walking again.
It eventually led to Annapurna, more adventures in the mountains — and, slightly unexpectedly, a book.
THE LESSON: A challenge doesn't need a stopwatch, a medal or even a finish line. Sometimes it's simply about finding out where your own two feet can take you.
SO WHY KEEP DOING IT?
You'd think that after enough early starts, blisters, aching legs, freezing nights and moments of wondering why on earth I signed up, I'd have got it out of my system.
Apparently not.
The challenges have changed over the years, but the reason I keep coming back to them is actually pretty simple.
They give me something to aim for.
A date in the diary gets me outside. It makes me train. It takes me somewhere I might never otherwise have gone. And every so often it pushes me well beyond what I thought I was capable of.
But it isn't really about collecting medals.
Some of my best memories have happened miles away from a finish line — walking with friends, meeting complete strangers at checkpoints, watching the sun come up after walking through the night, standing somewhere spectacular and thinking, I got here on foot.
And there's always another challenge.
Another trail. Another mountain. Another slightly questionable idea that sounds perfectly reasonable when I first suggest it. 😄
That's really what Walking in Circles has become about: helping ordinary people discover just how extraordinary an adventure on two feet can be.
YOUR TURN
You don't need to start with 100km. You definitely don't need to head straight for Everest.
Start with something that feels just far enough outside your comfort zone to make you wonder whether you can do it.
Maybe that's your first organised 10km walk. Maybe it's a marathon. Maybe you've already done those and 50km is beginning to sound strangely tempting.
Pick something. Give yourself time to prepare. And see where it leads.
After all, that's pretty much how I ended up with that wall of medals.
You never know where one walk might lead you.