Earlier this summer, On Running reached out and offered to send a pair of its new CloudMonster shoes for me to sample. Naturally, I said yes. At the time, I expected this to be a typical product review of a shoe that could soak up some mileage amidst a marathon training plan. But two months after receiving them, my review of the Swiss brand’s latest release has become anything but typical.
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Ever since taking up running years ago, my goal has always been to qualify for the Boston Marathon. I can’t point to precisely why that race became my Holy Grail. Maybe it’s because it’s become such an internationally-renowned course. Maybe it’s the challenge. Maybe it’s because, when I was a kid, my violin teacher ran Boston every year and asking her about it was the only way to avoid admitting that I didn’t practice. I like to think it’s been a combination of all three.
But for years, I never thought much about racing, instead reserving running as something purely therapeutic. Then, in late 2021, I broke the seal to join my local run club on an ultra-relay from Toronto to Montreal and, over the course of a three-day race, I became addicted and the goal of Boston started to materialize.
For the next year, I trained for several shorter races that I hoped would carry me into my marathon debut in the fall. This past spring, I ran a half-marathon personal best (1:20:40) before placing fourth in the Mississauga 10k (35:07) later that month – not up to elite standards but not bad for someone who types for a living. Throughout the summer, I continued following my marathon plan to the letter, increasing my mileage week by week in the lead-up to the Hamilton Marathon. Hamilton tends to be one of the latest races of the year, taking place at the beginning of November, so it felt like the perfect way to cap off my first full year of races.

Yet each week felt increasingly like a balancing act between health and performance. You sacrifice health to put up the mileage required, but you risk being able to produce the necessary miles if you happen to get injured along the way.
You have to get comfortable being uncomfortable.
Avid distance runners know the mantra all too well. It’s the type of corny, pseudo-philosophical quote that you might see those like Joe Rogan and David Goggins spouting on viral Instagram reels. But I internalized it (and still do, as clichéd as it may be). Over the years, I’d gotten used to going to bed with soreness, I’d grown accustomed to nagging shin splints, and my girlfriend had accepted waking up next to feet that looked like they’d just climbed to the top of Mount Doom. But what Rogan and Goggins don’t tell you is that you can only endure so much discomfort before your body hits the emergency brake.

In the last week of August, with my mileage reaching its highest peak since the spring, I was out for an easy run with the Parkdale Roadrunners down by Toronto’s waterfront. We were trotting at an easy pace. My shoes were worn down and my legs were sore but that was normal. Then, midway through the run, I took a step and – seemingly out of the blue – a sharp pain ran up my foot. At first, I thought it was merely a bad cramp, so I ran home gingerly and massaged the foot, first with my hand and then a little rougher with a tennis ball. That only made it worse, so I put some ice on it and went to bed. After all, I’m sure that’s all David Goggins would’ve done.
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But the next morning, my foot had swollen up and the pain had intensified to the point where I could barely stand. I went to the doctor before getting referred to the fracture clinic at the hospital. The verdict: one stress fracture and a broken bone.
Throughout the appointment, the doctors seemed to talk a lot, but all I really heard was that my November marathon hopes were crushed. There was no running for six weeks and no real speedwork for another six weeks after that (meaning the full recovery time would far exceed my marathon date). But after a couple of days of feeling sorry for myself, I’d accepted that my quest for Boston would have to wait until the spring. All I really wanted was to return to the roads and run as freely as I once did before I was chasing times.
But the closer I came to the initial six-week mark that would allow me to return to running and finally unbox the On CloudMonsters waiting in my closet, I felt a pang of anxiety I’d never felt before. After weeks of hobbling around in a walking boot, watching fellow runners glide past me on the sidewalk with their marathon plans still intact, I realized I’d grown uncomfortable being uncomfortable.
I hadn’t broken my foot by tripping or running recklessly in the middle of a bike lane (both of which I’d been known to do). I broke it taking a step, like any other. I broke it doing what I would have to do thousands and thousands of more times before I would ever get to Boston, with no warning. As excited as I was to run, part of me was terrified I’d take a step and feel the familiar sharp pain course through my foot. I’d been wearing a walking boot for over a month, so I had no idea how my foot would fare without the thick plastic armour protecting it. But when six weeks rolled around and I heard the doctors say I was free to run (responsibly), I couldn’t wait another day.
The moment I got home from work, I tore into the On CloudMonster box that I’d waited so patiently to open and put them on. I went outside and took a few cautious steps before breaking into a light jog. I had friends from Parkdale rave about On’s latest release and knew they had signed one of the country’s best distance runners (Ben Flanagan) but, other than that, I didn’t quite know what to expect from the Swiss brand.
What I felt on that first run was something I’d never think to put a price on: security. With its springy Cloud cushioning system, the CloudMonster is genuinely the softest, most cushioned trainer I’ve ever worn. Over the past few weeks, I haven’t even considered putting on another shoe.
Still, despite how good they felt, my scepticism lingered. It wasn’t a reflection of the shoe, but rather the irrational fear that my foot was just waiting to snap again on the next step, or the next one, or maybe the one after that. Distance running is oftentimes more of a psychological exercise than a physical one. It’s why most marathoners achieve their fastest times years after they’ve left their physical peaks behind; the marathon requires a calloused mind. And as I gradually returned to the roads, it felt as if I was forced to rehab my psyche alongside my body. But with each step, I knew my foot was growing stronger with the support of the shoe’s massive cushion. Eventually, I stopped worrying about potential setbacks and simply got comfortable feeling comfortable.
As the soreness in my foot continues to subside, I’ve started ramping up the speed, not quite running full-on tempo workouts, but at least getting the legs turning over with some confidence again. For both easy Zone 2 jogs and faster, longer runs, On’s CloudMonster transitions seamlessly between workouts with a balance between cushioning and responsiveness.

The Clouds on the bottom of the shoe compress with each foot strike, resulting in a dynamic, trampoline effect. But more than anything, it was the shoe’s exceptional stability and deep cushioning that set it apart from other foamy trainers. For those with mechanical issues in their gait or those wanting a steady base to return from their own nagging injuries, I’d proudly recommend the CloudMonsters, even more so than my previous go-to trainers (the New Balance 1080s and the Hoka Bondi 7s).
As far as shoe reviews go, I typically avoid making any promises to brands. Months ago, another rival shoe company reached out asking us to sample their new collaboration and offer a review. After several runs, I admitted to them that I couldn’t, in good conscience, offer the positive review they were hoping for (I ended up donating the shoes). It might seem trivial but, when it comes to long-distance running, finding the right footwear often requires the same careful consideration as the training plan itself.
Now, as I start reconfiguring my plan to run through the winter and lead into the spring, I have a slightly different relationship with the incessant pain I used to embrace like some sort of trophy for my hard work. Of course, I still believe there’s inherent value in seeking discomfort; marathon training is hard and any sustained progress means pushing through your preconceived limitations. At the risk of turning this into a hackneyed self-help essay, I think that’s one of the great values consistent across not only running but life in general. Yet if the past few months have taught me anything, it’s that blindly chasing discomfort leads nowhere (except straight into a walking boot).
Distance running is hard, chasing personal bests is an exponential challenge, and whether you’re training for a Boston-qualifying time or your first 5km, racing is an intimidating endeavour. But if there’s one thing that the On CloudMonsters have taught me, it’s that pushing one’s limits is still productive, even if you’re doing so with 30mm of thick cushioning.

So, while the David Goggins and Joe Rogans of the world urge you to get comfortable being uncomfortable, I – a mere civilian without a podcast nor a New York Times Bestseller – offer one caveat: get comfortable being uncomfortable, but do so with intention. Despite how heroic it seems, discomfort without intention is reckless and leads to little more than diminishing returns. Sometimes “intention” is as banal as taking the time to stretch before a workout. Other times, it means reconfiguring your sleep cycle to your running schedule. In my case, it meant adopting the right shoe to make sure I stay healthy through the upcoming fall/winter training block.
Of course, every foot is different (and I’m severely underqualified to prescribe a shoe), but if you’re a runner who’s grown overly accustomed to the pain that comes with heavy mileage and fast paces, consider the On CloudMonster. The road to Boston might require a few more months to pave than I had originally planned, but the trainer’s stability and support have me exactly where I need to be: back on the roads, chasing the next stage of discomfort in the most comfortable shoes available.