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During 2019's Rapha Festive 500, I devised a slight twist to the challenge — I had wanted to finish the entire 500km in 1 continuous ride. And if I am being honest, it was something born out of sheer boredom; cycling 500km over 8 days is a question of logistics rather than physical fitness, and I had been eager for some more physical challenge since my bikepacking trip earlier that year. Riding it all in one go was most definitely a challenge.

I pitched the idea to my usual Festive 500 partners-in-crime and to my surprise, the idea took root... then blossomed. We had a pre-ride lunch meet-up to figure out the food and gear, and decided on a there-and-back route at Tanah Merah Coastal Road, approximately 32km per loop. Due to logistical issues, we only had the 24th to do it, as we couldn't miss Christmas and the other days of the week were unfortunately work days. This meant that we had to start our ride at 24th Dec, 1201h.

Arriving at our crime scene at around 2339h

This would prove to be a big mistake, as we would later find out; a much better starting time would have been at 1600h-1700h so that we get a few hours of riding in the daylight in and avoid having to stay awake almost 6 hours additional.

We were high on adrenaline and raring to go, and our first few laps passed by without incident. Being cautious and on a mission to "stick to the plan", we settled into a pace of about 27-28km/h, which was easy to maintain given our 4-man strong "peloton" and the relative lack of headwind.

Then around 0600h, something bizarre started to happen; I started to fall asleep while pedalling my bike. At this point, I had been awake for about 21 hours, and we were on our 5th lap. Not ideal, but at least our pace were steady. Falling asleep while you are physically exerting yourself is weird. While I've had this while route-marching during my army days, I was confident that it wouldn't happen on this ride. I mean, we're chasing a goal that we actually care for, not walking around aimlessly with heavy field packs!

I kept spinning as I didn't want us to fall further behind our schedule; this was, on hindsight, a mistake. Taking short power naps would have made sure that both our bodies and our minds would be able to take a break and no doubt help with morale, which was starting to thin a little.

We did end up taking a nap at around 0900h though, which was a good respite.

At ~0930h, after 6 laps, we decided that we really need to stop to have some real food and this was, in my opinion, our biggest mistake — once we got into our heads that we should — no, NEEDED TO stop, the inertia to get going again was too much to overcome. Breakfast took almost 2 hours and heading back out after that to face the same monotonous route and the now-blazing sun was too much for us to handle. Our 4-man became 2-man after the lap, and one more lap after that both of us tapped out as well.

Basically, we were hamsters on the wheel for 15 hours.

I did a total of ~250km, or exactly half of what we had planned for. It had taken us just a little over 15 hours to finish. We were way off schedule, no doubt because of our long breakfast and our long breaks between laps. Either way, it didn't matter. Mentally, I was exhausted and the thought of doing even just 1 more lap was too much for me to bear. I had come up with this challenge in hopes of breaking myself and while I don't think I was broken, I was at an all-time low. Physically, it was definitely one of the most intense things I've ever done.

And if I were being honest to myself, I was not expecting to finish the ride. I would have been happy if we had done 300km in that ride, or almost double what I've ever ridden in a day.

While it was no doubt an achievement for me personally, it was an even more remarkable feat for one of my friends. I'm not sure he has ever done a ride longer than 60km before that day and yet on that day he did a beautiful 7 laps, for about 220km, staying with us all the way.

After some celebratory high-fives, we all went home. I promptly fell asleep for around 14 hours.

A week later, we gathered for our celebration feast, even though we did technically fail. You know, count the small victories, be kind to yourself, and all that.

Our crazy celebratory 1.6kg Tomahawk at High Steaks. Left to Right: Me, Alex, Suan. Missing: Chong, the forementioned hero who had never done more than 100km in a ride
Yup, 1.6kg is a lot of meat.

Since then, 5 months has passed, and I can feel that restlessness in me again. As athletes (though I am honestly still a bit uncomfortable with calling myself that), we often get that question, "what's next?", whether is it from others, or ourselves. After a 10K run, comes a half marathon. After the half marathon, a full marathon. Then an ultra. Or an Ironman. Or both. Or an Ultraman (yes that's a real thing).

There are people who have asked me why I decided to do this, and my standard answer has always been, "Why not?". To quote Rosie Swale-Pope, who ran around the world while pulling her own food, water, clothes and shelter (all 20,000 miles on foot), "I believe that if you can keep your strength in a difficult situation, that strength is still yours for ever when you need it."

Just like how I decided to go on my solo bike-packing trip earlier in 2019, I decided on this 500/1 challenge on a whim because of boredom and curiosity. I've since learnt that I have the tendency to set lofty fitness goals, only to fail rather unremarkably at them. But I'm failing upwards, and that's perfectly all right by me.

I'm pretty sure one day I will revisit this "500/1" goal, but for now I've reverted back to another earlier goal that I had my eye on. Let's just say I need to start doing more climbing on my bike.