5.14cs Didn’t Exist When I Started Climbing. I Finally Sent One at Age 50.

“One move at a time,” I say to myself out loud at a precarious rest partway up The Green Mile (5.14c/8c+). My hands swap back and forth in the “soap dish,” a slick, two-pad edge/pinch for the left hand and one-pad edge for the right. Meanwhile, most of my weight teeters between two flimsy kneebars—the left one just a kneecap scum on an inch-wide rooflet.

Less than a quarter of the way up this 130-foot marathon, I’m already pumped. From here, I’ll encounter many insecure boulder problems, dozens of opportunities to fall, and nearly 40 more minutes of fight and focus to the anchor. So I zero in on one move at a time, a mantra I audibly repeat every chance I get.

The Green Mile is the hardest sport route I’ve put any real time into, and it’s a grade I assumed I’d never be skilled enough to climb. But in 2020, after a couple of 5.14b redpoints (and, at 45 years old, with time passing faster than ever), I figured I should at least try something harder. After all, sometimes it’s worth investing time and energy into wild possibilities, even when failure feels likely.

Worst case scenario: You learn a few things, including the priceless knowledge of where your limit lies at that particular time. Best case? For me, the greatest meaning in life often stems from a leap into the unknown, regardless of how it turns out.

My conscious mind dwells on one perfect move, and then the next.

I’ve sampled a few 5.14cs, but the ones I dogged up seemed unrealistic for me to redpoint. The cruxes felt too hard and the climbing seasons were finicky. I needed a route more suited to my strengths.

My ideal project would be long—say between 30 and 50 meters. It would be overhanging, highly featured, endurance-oriented, full-body climbing, with bouldery sections separated by rests or shakes. The number of hard sections wouldn’t matter as much as their difficulty. Single-digit V-grades only please!

The Green Mile seemed to match all the criteria. It also has the bonus of a potentially long season: October through May, depending on the year. The glaring downside is that it’s at Jailhouse Rock in Northern California, a whopping 1,200 miles away from my home. The logistics of a long-distance project are complicated, especially considering I had to leave my wife and two year-old son for five to 12 days at a time. But even if I managed to iron out the details of travel and family life, the idea of investing in a route so difficult made me squirm.

As a teenaged newbie in the late ‘80s and early ‘90s, 5.14 was a hallowed grade, reserved for mutants and demi-gods. Believe it or not, when I started climbing in 1988, 5.14c didn’t yet exist. The magnitude of a route that hard was unthinkable. Besides, for me at the time, climbing wasn’t about performance—it was my door to a seemingly boundless dimension of freedom and exploration. That’s why I chose objectives like kicking steps up the Ingraham Glacier on Mt. Rainier, with the crunch of crampons on névé amid the frigid, buffeting wind.

On weekends, I’d bike 12 miles each way to climb on the University of Washington rock—an outdoor artificial wall built in the ‘70s. Early on, I had no gear and no partners. I’d lace up my green and blue Merrell Flashdance hightops with their pink triangle logo and try to emulate the stinky, shirtless climbers who seemed to float up its cracks and rock-studded walls.

In my early years as a climber, I summited the North and South Early Winter Spires at 17 years old, and had my first look into the North Cascades wilderness, with its glaciers, deep valleys, and jagged peaks. My heart burst with excitement and desire to explore it all, to ascend every summit.

Now, my heart feels like it’s bursting in my chest from a long bouldery section. My forearms are ballistically pumped, just a second or two from failure. When I lock in the best rest on the route, I’m less than halfway up. I’ll try to recover here for a full nine minutes. My legs are tucked into a square-cut recess, with a left kneebar so wide, I’m on my tiptoes. Tiny muscles in my calf visibly twitch as I try to relax, changing hand positions between a two-pad edge and slippery slopers out left. I swap legs in the kneebar just before the loaded calf collapses.

At least I’m accustomed to burning calves, a discomfort I’ve experienced since I first learned to climb frozen waterfalls in loose-fitting, double plastic boots. Back then I also taught myself how to aid solo on the granite walls of Index in the Cascades, and I clipped bolts in the sun at Smith Rock. I attempted—and occasionally summited—big mountains in Alaska and the Canadian Rockies in between working at a rock gym, bouldering on plastic, and goofing off after hours.

“… sometimes it’s worth investing time and energy into wild possibilities, even when failure feels likely.”

Each discipline held value beyond its specific purpose; the skills and, more crucially, mindset, bled into all aspects of my climbing. That said, I didn’t excel at any one thing. I wrestled with staying fit for 80 feet of pockets and micro edges, while snow-slogging, humping packs, and swinging tools in the mountains. Another few years would pass before I started taking sport climbing more seriously—a decision that would ultimately lead to my campaign on The Green Mile.

“One move at a time,” I repeat, this time at an awkward backstep-kneebar at the first anchor, halfway up. I grip small edges loosely, and allow myself to scan the rightward traverse into the hardest moves of the route. But I stop short of imagining it. One move at a time always works.

I commit to the traverse, trusting my body as it moves through the sequence. Anxiety surfaces, but I focus on relaxation and precision. I try to grab each hold exactly how I’ve practiced. On a route this long, over-gripping is the enemy. Wasted energy has already contributed to three falls I’ve taken higher up on redpoint attempts.

It’s November 24, my last day of this trip, and I won’t have a chance to return for several weeks. But this doesn’t register in the moment. My conscious mind dwells on one perfect move, and then the next. Soon, I slot a tight left kneebar under a large roof.

In October 1996, I redpointed Shark Walk, my first 5.13a, at Red Rock, Nevada. Four years later, at the Virgin River Gorge, I did F-Dude, my first 5.14a. It happened during my first long road trip in my Eurovan, camping with like-minded climbers. Being well-rounded remained my priority, but I learned the importance of dedicating blocks of time to clipping bolts in order to improve.

In the early 2000s, I climbed at Jailhouse for the first time, after getting rained out of Yosemite. It’s a common “Plan B” when the Valley is too wet to climb. Over the years, this happened repeatedly. I began to love wrestling the steep, technical basalt so much that, even while immersed in North America’s granite mecca, I secretly looked forward to a rainy forecast.

What I love about limit redpointing is that it’s the absolute opposite of other climbing disciplines, where the key challenge is often to keep climbing despite antagonistic factors like fatigue, hunger, fear, cold, storms, etc. Redpointing asks the critical question: What are you capable of when everything is stacked in your favor? If you’ve done your prep work, there should be zero adventure, very little risk and, for the most part, no excuses.

It’s also precisely why redpointing is so intriguing. When everything else is lined up and ready, your mind becomes the only wild card.

Had I trained my mind enough for the hardest route of my life? I honestly wasn’t sure.

I launch into a nearly horizontal boulder problem that revolves around a wide, left-hand pinch. As I move my feet, my left hand starts to open up … but just in time, I slam an overhead kneebar. A few moves higher, I get a final shake before the long crux. It’s my fourth time here on redpoint. Am I less pumped this time? Not really. How will this try be any different? I fly back home tonight. Realistically, this is my last attempt until mid-December, and sometimes the route is wet by then.

“One move at a time.”

After 14 years and long stretches without sport projects, I dedicated dozens of days at Rifle to send my first 5.14b: Stockboy’s Revenge. It was 2014, I’d just turned 40, and I was psyched to achieve what I assumed was a final new letter grade.

But as the years rolled by, I continued to improve in subtle ways. Five years and two more 5.14bs later, it felt like the right time to invest in a wild possibility. In December 2022, my wife, one-year-old son, our nanny, and I spent nearly three weeks in Sonora, California, climbing at nearby Jailhouse. My goal was Flower Power, the 5.14 first half of The Green Mile. If that went well, I’d at least check out the extension—also a 5.14 on its own.

I honestly never gave my age much thought when I considered diving into my hardest sport project. Physically, I felt stronger than ever. It seemed like consistent training had more than offset whatever decline had taken place due to aging. If anything, my mental focus and redpoint tactics were peaking.

The main challenge these days is the responsibility of having a child, now three years old. Parenthood feels like adding a few more balls to life’s juggling routine. The only way to keep up is to juggle faster and more efficiently, while also keeping an eye on one ball at a time.

Leaving the shake, I squeeze each hold just hard enough to stay on. I grab the key left-hand sidepull above my head, setting each finger just so. I’ll need to hold the sidepull for three big right-hand moves, until it’s down by my knee. One move at a time. I’m sideways, straining for balance as I grasp a fingertip undercling, then a three-finger sloper. I’m moving left now past the hanging refrigerator, through insecure kneecap bars, toward the end of the crux.

If there’s a key to hard climbing at any age, it would have to be motivation. The climbers who finish projects are the ones who want it the most. When you really want something, you do whatever it takes to make it happen.

Redpointing asks the critical question: What are you capable of when everything is stacked in your favor?

The other necessary ingredient is confidence, which, for me, takes time to develop. On The Green Mile, for example, I didn’t really believe I could do it until I’d sent each half of the route independently. That was nearly a year after I first attempted Flower Power. Even then, it took another 20 days of rehearsal and beta refinement (especially after the six-month off-season) to gain the confidence to give it an honest redpoint effort.

Yes! I’m through the hardest moves and into an awkward rest with a sharp kneebar and flared hand jam. The final 30 feet are intricate, weaving back and forth toward the top of the cliff. One move after another, fighting nerves and exhaustion. I latch a small sidepull, stand to a jug, heel hook out right and clip the anchor.

Relief overwhelms me as I finally acquiesce to gravity. With a racing heart, I collapse onto the rope, my body, and my mind, utterly spent. I’m 50 years old and have sent my first 5.14c.

It’s not until I’m back on the ground that emotions begin to swell. I’m with Skyler, my close friend and climbing partner, and some other good friends I’ve made during the 59 days I’ve tried this route over the past two years. Before I have a chance to untie, they embrace me.

Then, I feel everything.

Photos by Jon Glassberg, who has been a professional climber for 20 years. Jon has traveled the world, climbing rocks up to 5.14 and V15. Now, his focus has shifted from the rock to the camera as a director who captures the heart and soul of cutting-edge outdoor sports.

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