The Longest Hike
“What’s your criteria for a good hike?” I asked.
“It has to be at least 10 miles,” Ben replied without hesitation.
This was over a year ago, maybe six months after I’d met Ben at church. We were on our way to Muir Woods (my first time!), and I was still getting to know him. His answer caught me off guard…because didn’t people hike for the views? And to enjoy nature? Apparently, distance was more important for Ben.
That should have been my first clue that going to Yosemite with him was going to be…intense. But nothing could have prepared me for this hike. Still, I’ve come to believe that everyone needs friends like Ben–someone who pushes you beyond your comfort zone, and maybe even beyond your physical limits. A friend who convinces you to do something that sounds mildly insane, but that you’re glad you did anyway.
Rounding out the Yosemite trip was Cooper, a friend of Ben’s I’d met a few times, but didn’t know all that well. Cooper’s one-day hiking record was 35 miles, though, so he was going to be fine.
We rolled into Yosemite Valley just as the sun was setting and went for a brisk 6-mile walk to stretch our legs. I walked fast (maybe to avoid mosquitoes, maybe to impress my hiking partners). It was a good warm-up. In retrospect, too good of a warm-up.
“You ready to hike 18 miles with 6,000 ft elevation gain, Ted?” Ben asked.
“Sure,” I said, then backpedaled. “Actually, I don’t know if I can do it.” Yes, I was doing the modest Asian thing. But also–I genuinely wasn’t sure. The last time I’d done anything over 10 was…Muir Woods. With Ben.
Cooper sized me up. “You’ll be fine,” he said.
The next morning, we set out from Curry Village.
“Wait–it’s 10.5 miles one way?” I asked at the trailhead sign. We had already walked a mile just to get there.
“Oops,” Ben said, grinning as if he had planned it all along. “Oh well…what’s a few more miles?”
You learn a lot about people on a 20+ mile hike. Cooper had been home schooled, but you’d never guess it: he played sports, did policy debate, earned his Eagle Scout rank (which only 2% of Boy Scouts do), and now works in cybersecurity. He also trains in Brazilian jiu-jitsu. Basically, he’s the guy you want nearby if a bear shows up.
I learned more about Ben, too, thanks to the list of hard-hitting questions he prepared for such an occasion. Questions like:
- What are your spiritual gifts?
- If you could ask God one question and you knew he would answer, what would it be?
- What’s your favorite trait about yourself?
- What are your biggest regrets?
- Who outside your family has had the biggest impact on your life?
- What near-death experiences have you had?
We were 3 hours in, with 3,000 feet of elevation already behind us, when Ben directed a question at me.
“I can’t talk right now,” I said, breathing hard. “Cooper can go first.”
“Ted, the point is to talk so it takes your mind off the pain,” Ben replied.
Touché.
At one point, Ben and Cooper got excited about some mysterious wildlife sighting near a bush (possibly a lizard, possibly nothing), while I stood off to the side, amused by their enthusiasm. It was one of those moments where you appreciate how different everyone is—and how those differences somehow work on trips like this.
When we finally reached the top of Clouds Rest, we took off our shoes and socks, and just took it all in. I wish I had more eloquent words—or better photos—to capture the view. But let me just say this: it was breathtaking. A full 360-degree view of Yosemite, with Half Dome sitting below us. The mountains stretched out in every direction, and above them, a patchwork of soft, cotton-like clouds drifted across the sky. In that moment, Clouds Rest felt like a perfect name–like even the clouds had stopped to admire the view.
The forecast had called for scattered thunderstorms, but the conditions couldn’t have been better: it was sunny, but not too hot, and 80% of the trail had been shaded anyway.
And the cherry on top? There weren’t many people at the summit. Far less crowded than Half Dome, and with an arguably better view. We lingered up there for a couple hours, chatting with a few fellow hikers (one of which was a park ranger), taking photos for them (and asking them to return the favor), and soaking in the sense of accomplishment.
Eventually, we peeled ourselves away and started the long trek back. We filtered water at the first stream we came across–cold, crisp, and just what we needed to keep moving.
Somewhere along the descent, it hit me that this wasn’t just a hike. It was one of those rare weekends that goes deeper than you expect. The kind of trip where the combination of effort, scenery, and conversation leads to real connection–even with people you barely knew at the start.
Would I do it again? Maybe after I’ve recovered–and if someone brings a fresh set of deep questions to distract me from the screaming in my lungs.
But if there’s one thing I’ve learned, it’s this: sometimes the best views–and best conversations–come during the longest hikes.




Your risk tolerance is also not low. Just saying ;)