STRIVE Challenge 2016

Paul Williams
17 min readSep 15, 2016


WHY did I, a newcomer to serious cycling, just spend 5 days cycling 480 miles from the Alps to the heart of Italian Tuscany, climbing 22,000 feet, or, the equivalent of two thirds the height of Mount Everest?


I attended the Virgin Disruptors in Education event in London in October 2015 — a truly excellent, thought-provoking and inspiring day, but the thing that stood out for me was the passion I sensed when the work of Big Change was talked about — exemplified by two 12-year-old schoolkids from School 21 confidently interviewing Richard Branson, and Sam Branson eloquently describing ‘growth mindset’ — that growth happens when you step outside your comfort zone: in fact it is often the most challenging experiences in our lives that present us with the greatest opportunities to learn and develop. And as he said, “One thing I have been lucky about with my parents is that they’ve always let us be our people, to find our own passions and purpose. When you find your passion and that purpose, you can achieve great things. A by-product of that is that you create something that you are proud of, and that people around you are proud of”. He was explaining how Big Change supported projects that nurtured young people into looking for opportunity, and being ready to grab it with all their passion when it does arise.

Also, hearing the story of Karl Lokko leaving the gangs of London and becoming an influencer and leader for good was remarkable.

I came away knowing that I had to be part of this movement — the energy and passion I sensed in this group of people were truly infectious, and the causes seemed to be effective and transformative.

Meanwhile, I’d recently run my first London Marathon, having steadily trained from nothing for 4 years, and I was looking for a new physical challenge. As seems to be a common part of umpteen mid-life-crises, I got a road bike! And Strive Challenge 2016 came along. The challenge itself was a physical and mental one — travel under human power from the northern border of Italy in the Alps, all the way to Sicily — hiking, cycling, swimming and running. To accompany the core team doing the whole thing, there was an invitation for extra participants to join for part of the journey — each section an endurance event in its own right. It looked amazing, but all the parts of it looked virtually impossible for someone like me.

But in Richard Branson’s words: “If someone offers you an amazing opportunity and you’re not sure you can do it, say yes — then learn how to do it later”.

After multiple reassurances in emails from the organizers and trustees of Big Change, that I wouldn’t be surrounding by super-fit 30-somethings (although it turns out most were!), and that there would be a great support team with us of medics, mechanics and cycling experts, I took the plunge and signed up for the least hard cycle leg — the entire red line on the map below. And then tried to train hard for 2–3 months. Trying to prepare for something that felt impossible was my own growth mindset journey. Particuarly the prospect of multiple consective days of big rides, and very big climbs.

The journey.

So it began. After a short flight to Milan and a 3 hour bus ride into the mountains, we met with the core team of 25 who had already been hiking over Mount Zermatt for 5 days. The arrival was a surprise — Richard Branson, recovering from a recent nasty bike crash and also having just completed the hike — greeted us, as did STRIVE founders Noah Devereux and Sam Branson, and Big Change trustee Holly Branson, who I knew also cares passionately about helping kids find opportunity and make the most of it.

Welcoming words from Sam Branson

Noah and Sam gave us nervous, slightly bewildered but very happy-to-be-there STRIVErs a great welcome. I thought we should go and check on our bikes which had been shipped separately — they were all assembled, ready to go, thanks to the team from Halfords UK who had arrived early to prepare. We settled into our 6-man dorm room, then started to get to know each other over dinner.

Day 1: the hardest physical thing … yet

Rima to Alessandria: 112 miles, 2000 ft of climbing (according to Strava; officially 1082 ft), max gradient 19%

First night, I didn’t sleep. You know when you see the hands ticking round, over and over again, and they seem to move so slowly? One of those nights. Possibly nerves, maybe altitude (we were staying at 4,500 ft). I’d been put into one of the medium-speed groups — later to be a little over-ambitious on my part, but nice while it lasted — and we prepared for the initial 20 mile descent. Alberto Elli, an Italian cycling star who has worn the yellow jersey in the Tour de France, led us off and this ebbing and flowing snake of 60 riders found their way down the mountain. The scenery was stunning, and it was a great introduction not having to put much effort into pedalling initially — mainly braking!

Picture by Adam Slama

When we hit the bottom, we assembled into our peleton and started to power across the relatively flat landscape for another 75 miles — already the longest ride I had ever done. With the peloton, one rider takes the lead every 5–10 minutes, and the others tuck in close behind to benefit from the slipstream. It makes a huge difference — only the front rider needs to exert full power, and then gets to rest a little as he/she drops back to the rear of the peloton, thus only riding at top capacity for few minutes every hour or so. I was with a group of particuarly fit thirty-somethings (after all) but was able to keep up all while I was in the peleton.

We only really stopped for a coffee break (payed for by the Italian police force — grazie mille!), if someone got a puncture, and for lunch. It felt great motoring across the Italian plains like this.

The only problem is when you don’t keep close enough to the bike in front — you lose the slipstreaming effect, and have to work harder not only to catch up, but to compete with the efficient machine running in front. The team were happy to wait when this happening to anyone, but as the day wore on, I could tell I didn’t really have the stamina to stay with them. At mile 96 we hit the first large hill — in hindsight not that enormous — but for me I just couldn’t keep up with them, so dropped back and then actually ended up walking up part of the hill. I texted that they should go on, even though I knew they would have waited for me, and did the final, relentless 18 miles on my own. But this was my first ever ‘century’ ride, and I was happy about that.

Finally I made it to the end point, to be greeted by cheers and clapping, and an ice bath to jump into! It felt so good after 7 and a half hours on the road.

About half an hour later, there were more cheers as Richard Branson came into view — he’d just done the whole thing too.

Richard was firmly establishing he was here to do the entire adventure, including fitting other engagements around these full-on days. Fantastic.

Day 1 Strava data.

Day 2: The Giro D’Italia ruined me

Alessandria to Sestri Levante: 90 miles, 11000 ft climbing (officially 5968 ft), max gradient 20%

Day 2 was always going to be one of the big days. A long, slow climb in the morning, another longer slower climb, and then an enormous climb up part of the infamous Giro D’Italia cycle course.

Richard Branson, in remarkable shape considering his bad accident was only a couple of weeks before

But it started well — I found myself riding in a slightly slower group than yesterday, with Richard and Holly Branson, and Richard demanded a coffee stop soon after the first climb. This was more like it! Holly was asking how my fundraising was going, and I was explaining how generous my friends had been when I ran the London Marathon last year, so I was sensitive about going back to the same people for yet another “one off”, even though the cause was very worthy. Richard chipped in: “my advice to you is to pledge to personally match all donations given” — I took that as a challenge, and as soon as I announced it, my donations doubled overnight! (I did put a limit in — I don’t quite have the same capacity as Richard!).

Still — extra stat so far: 2 free coffees (police and RB).

The day did get a lot harder though. At the point were we hit the Giro D’Italia, I was on my own, and, even though I’d managed the hills this morning, as soon as I saw the next one I was daunted. A climb from 1,500ft (500m) to 3,500 ft (over 1000m), steep and twisty. I tried hard, but ran out energy, and ended up pushing my bike up over half of it. Not easy in cycling shoes — walking boots would have been more useful! Wherever I found a section that was slightly less steep, I would cycle, but it was just relentless.

Eventually I made it near the top, and determined to get back on my bike for the final section. The views were worth it though!

At 3,700 ft on part of the brutal Giro d’Italia

After the big big climb, there was an incredible downhill section —at this point I actually got quite emotional about that climb being now in the past, even though I hadn’t managed to cycle all of it.

And then it was a long ride to the seaside town of Sestri Levante. I was trying to maintain a reasonable pace, but at one point an older Italian gentleman cruised past me, grinning and chuckling — it took me a while to realise he had a motorized bike!

Because the walking section had slowed me down considerably, the sun was now setting — very nice as I was cycling along the seafront.

Day 2 Strava data. Day 2 in 3D.

Day 3: Digging so deep. Heat exhaustion, dehydration, energy sapped

Sestri Levante to Lucca: 88 miles, 8000 ft climbing (officially 3126 ft), max gradient 23%

So — day 2, the hardest day, was over. And now we had an easier day 3. Or so I thought. It started well with a stunning sunrise illuminating this picturesque town:

Sunrise in Sestri Levante
Holly Branson — her enthusiastic emails got me here!

In fact the first climb was vast. I kept with the same group as before, but gradually started to lose them on the hill, and again found myself cycling on my own.

We’d been told to keep our energy supplies up by eating specially-prepared Veloforte food en-route, which some people loved — however I was finding it increasingly hard to eat them, particularly on the move. And once you start losing energy, you don’t want to eat or drink, and quickly feel unwell — the vicious circle begins. By the time I got to the top of the climb, I was completely exhausted. Drained. But I knew there was a long downhill coming, so I kept going. This was followed by what seemed like an age of flat miles along the coast — nothing much to see, just relentless. And in the intense heat, I was really not feeling good. When I finally rolled in to the lunch stop, almost all the other riders had gone, and I went straight to the ambulance. Almost keeling over, I said I wanted to stop. Kathryn the chief medic calmed me down a bit — was happy to let me stop, but just wanted me to sort my head out first, so she made me a hairs-on-your-chest-strength cup of Yorkshire tea and found me a banana and some shade. But I was so ready to be swept up by the broomwagon that followed us all day at about 10mph, collecting signposts and broken bikes/cyclists. After all, being able to handle failure and move on is a part of the Big Change mentality — I thought I was going to experience that.

But after an hour of sitting mostly motionless trying to find some energy, Jo, one of the ‘chaperone’ pro cyclists arrived, with Richard Branson, who had clocked up another steady 55 miles. Never one to take ‘no’ for an answer, Jo persuaded me to ride the rest of the day with them, even though I knew there was still a reasonably steep and long climb to come. So a little group of us set off — and as we traversed the flat at a reasonable pace and the next ascent at a very easy pace, I learnt two things: Jo taught me how to conquer a hill by starting slow and staying within my aerobic capacity; and that Richard Branson is great conversational company — we spent the best part of 3 hours swapping stories, hearing about his best April Fool’s jokes, and hearing his latest thoughts on space tourism, the refugee crisis, the music industry, politics. What a privilege — I could not have ever imagined any situation where this would have been able to happen.

We finally arrived in Lucca — the last group in, to rapturous applause from the rest of the team — mainly for Richard of course, but word had got out that I had really struggled today, and it was great to feel such support from the other riders and the organizers. STRIVE together — the best way. And thanks to Jo, and Steve, one of the other bike leaders, I’d learnt a lot about conquering these hills.

Day 3 Strava data. Day 3 in 3D.

Day 4: Fell off. Got lost. Caught in a Thunderstorm. Swallowed a Fly

Lucca to Siena: 84 miles, 7200 ft climbing (officially 4901 ft), max gradient 17%

Just look at that terrain profile. I knew day 4 was going to be a big one, with two huge hills, both significantly higher than anything I’d encoutered in my training. But I was ready to try out my new enthusiasm and hill-climbing technique.

First, 30 miles of mostly flat — and my adventures started, As usual, the support vehicles parked at various points along the route to check on us, top us up with supplies, and clean up cuts and bruises. Good thing too — I pulled in, and got stuck in my pedal cleats — at which point there is nothing you can do except fall over — in my case, straight into the ambulance! Oops. But only damaged pride really, and we got going. And got lost. So there was an extra four miles to add to today’s stats. When we finally doubled back and found the route, I started to find my (slow) stride on the hills, and although the climbs were indeed relentless, I made them. Eventually stopping just outside San Gimignano for lunch, at least my slow pace was giving me an opportunity to appreciate the stunning Tuscany countryside.

Approaching San Gimignano

After a quick descent out of the hilltop town, the afternoon climb just kept going and going, up to a long ridge in the heat.

— and then the skies turned angry and a dramatic thunderstorm hit. The rain was actually refreshing — I even got cold, which was a senstation I hadn’t experienced for a few days.

The storm left an incredible sky, which I could see for the remaining part of this climb and then as I waited to speed back down into the valley — only to be greeted by another 10 miles of lesser but still evil climbing into Siena. But I felt good — despite the final mishap of the day, swallowing a fly on one of the descents — I had conquered this terrain. What a transformation from the previous morning.

Day 4 Strava data. Day 4 in 3D.

Day 5: Finito

Siena to Magliano in Toscana: 106 miles, 7100 ft climbing (officially 3687 ft), max gradient 21%

Day 5. Final riding day — another beautiful morning.

Starting early — climbing back out of Siena, which definitely woke our legs up. I found myself riding with Richard’s little group again, and we were talking about the best part of this adventure — the people — the organizers and support crew, the core team and the participants who, like me, had joined just for this week. Over the time here I’d come to realise that there were many influential leaders and successful entrepreneurs amongst us, but everyone had three things: passion, humility and graciousness. Richard remarked that in his experience most of the successful people he had met had those qualities — it was such a wonderful thing to be part of for a few days and I came away very inspired.

Nothing beats a good biscuit

Jo had been teaching me to ride close in the peloton, but now I found myself riding too close and I had to make a split-second decision — plough into her wheel and possibly take out one of the chaperones (not a good idea), or bail. So I bailed — thankfully off the road, but I did rip my leg up a little. As I’m writing this, remarkably this was my worst injury — very little muscle pain, just some nasty stabbing pains as the cuts heal.

Since we were already a little bit above sea level, the morning climbs were reasonable, but we knew there was a big one coming after lunch where we would drop right down to sea level, only to come back up to 1,800 ft / 600 m for the final climb. I settled in to my all-conquering steady cycling plod, and just kept going. And going. And going. Climbing for 2 hours to what I thought was the top — then finding there was some more, and thinking that must be the top, then finding a little bit of downhill … and more climbs. It just went on for ever.

But finally there seemed to be some real descent, and I got a chance to rest my legs, whilst still being wowed by the incredible scenery.

My Strava app clicked to 101 miles — theoretically the finish, so I put all the power I had left into a quick sprint towards the end, which I couldn’t yet see. Or round the next corner. Or along the next straight. Or the next corner. Or the next straight. Eventually I did an extra 5 miles at 15–20mph, completely using up any remaining energy by the time I found the finish line. I only learned later that a serious bush fire had caused a sudden diversion to the route to have to be found.

And that was it. Despite having to walk part of two hills earlier in the week, I’d done it — achieving something that, if I’d really thought about it sensibly, I was not prepared enough for. But I proved that basic fitness plus a mind that can be moulded by inspiring people around you can lead to almost impossible accomplishments. It felt great — the satisfaction of surprising myself, but most of all that through the support of others I felt part of this movement for change that we were trying to demonstrate and support by doing this.

During dinner, Richard got all the dads to stand up, and proclaimed that the next adventure like this would be designed by all the parents over 50 — with built-in coffee breaks, long lunches and early finishes, rather than this intense endurance test. But then it is called the STRIVE Challenge …

Day 5 Strava Data. Day 5 in 3D.

After the end — Reflections.

Looking out of the window flying back from Rome, the clear sky revealed an expansive vista of the Italian coastline, stretching miles into the distance. It was amazing to think that we had just cycled further than I could actually see across that landscape from the plane. I, and the other people in the team, had achieved something most of us thought almost impossible. Some preparation had helped — but the camaraderie, conquering spirit and incredible supportive environment from the crew and the other STRIVErs were the things that enabled us to do it. I think we all learnt that we can do more than we thought — and that, indeed, growth happens when you step outside your comfort zone. The core team we left behind to carry on this relentless, astonishing journey have my utmost respect — they are going to need those STRIVE principles so much! But I know they will put everything in to completing this.

In a crazy moment last night I wished I could go back to the two hills I ended up partially walking up and try cycling them again — it would be brutal but a little bit more knowledge and a renewed mindset might have made them possible … perhaps?

Thank you to everyone who has supported me on this journey — whether financially or through encouraging comments and likes on my postings during the trip. Cycling in a fast peleton is a thrill — but having to pace myself also meant many hours on the road on my own, giving me lots of time to think — and something I thought about was the way the people around me have given me fantastic opportunities in life that have enabled me to stretch and develop — and I, and Big Change, want to see that in many more people’s lives — particularly the next generation. If you would still like to support Big Change’s work, then please see my fundraising page here. Thank you.

And thanks to the dear people I met on this journey — Freeborn Bikes in Horsham for giving me a great discount and teaching a novice so much about road bikes; Kirsty at BikeBoxOnline for offering to FaceTime me to help pack my bike “as if I was in your kitchen drinking your tea”; Noah and Holly for convincing me to sign up and being so welcoming during the week; Essie, Karl and Sam for their inspiring vision and words for the Big Change cause; Jo and Steve for teaching me how to cycle properly and not letting me give up; Erin for giving me an excuse to stop and take pictures of the scenery (‘social media purposes’); Kathryn, Sally and the amazing medical and physio teams; the awesome roving mechanics from Halfords; Caitlin, Cassie, Mark, Scully and the ultra-efficient logistics folks; Leon, Jan and Diane in particular for encouraging me as fellow cyclists; many other new friends incuding Tarun, Richard R, Dan, Josh, Fredrik, Gaenor, John, Reinhard, Natalie, Harry, Victoria, Joanne, Warren, Marie, Jonathan (and some I’ve missed); as well as Andy, Bella, Keith and Richard B for showing me life can get even more energetic and fulfilling after 50!



Paul Williams

Systems Architect and Software Engineering Manager at Bloomberg in London. Passions: photos, music, space, tech, travel, philanthropy & STEM. Opinions my own.