I’ll be honest. We weren’t exactly excited about another long, winding drive the day after doing the Road to Hana. But our time in Maui was running out, and every local we talked to said the same thing.
“You can’t leave without seeing Haleakalā.”
So we looked at each other, sighed, and got in the car.
Apparently the drive shouldn’t have taken three hours. One local told us that back in the day, you could cut across from Wailea and be at the summit in no time. But then Oprah bought a bunch of land up there and closed off access. She has a private road now. The rest of us take the long way.
I’ve been saying for years that making Oprah’s book club is on my vision board. I gave a speech once in Savannah, and it turned out Oprah and Gayle King were staying in the same hotel that weekend. Somebody on our side was trying to get a copy of my book into her hands. Nothing came of it, but that’s the kind of thing that keeps happening to me. I fly close enough to the sun to have a story about it. Never quite close enough to touch it.
We were on our second rental of the trip, a Cadillac SUV we’d swapped for the Infiniti after a dead battery stranded us near Hana. The Caddy handled the switchbacks better, but my hands stayed locked at ten and two the whole way up. The road climbed through cow pastures and patches of fog. Chickens darted across the pavement. A few goats gave us the side-eye. Long stretches had no guardrails at all.
Then we hit the clouds for real, not mist drifting past but a wall of white that swallowed the road in front of us and the mirror behind us. I couldn’t see ten feet ahead. I couldn’t see what was on either side of the car, and up there, what’s on either side of the car is usually a drop. I’ve driven through fog before. I have never driven through a cloud. It is a different kind of scared, the kind where you go quiet because talking feels like it might jinx something.
We climbed for what felt like a long time inside that white. Then, without any warning, we broke through it, and the sky opened up clear and blue like the cloud had never happened.
By the time we reached the summit, the temperature had dropped nearly thirty degrees from what it had been at the beach. We stepped out into thin, cold air and looked out over the crater. It stretched out in front of us, rust and ochre and sanded-down red, more like standing on Mars than standing in Hawaii. The sun was shining directly on us. Below us, clouds stretched for miles in every direction. We were standing on top of a volcano, ten thousand feet up, looking down on the weather.
Mason and Colby wanted to keep going. There’s a trail that runs along the rim, and somewhere along it a peak that’s a little higher than where the parking area sits, and the second they saw it, that was the whole plan. They took off up the trail together, the way teenage brothers do when there’s a highest point involved and neither one wants to be the one who didn’t make it.
I made it about as far as the building with the bathrooms and a row of benches outside it. My legs had other ideas about the rest of the climb. I stood there for a second doing the math on it, whether I could push through, and I already knew the answer before I finished asking myself the question. So I sat down on a bench instead and watched my sons walk up a mountain without me.
Jocelyn sat down next to me. She didn’t say anything about it, and I didn’t either. We just watched the two of them get smaller against the rock, two dark shapes climbing toward a ridge that used to be something we all did together and was now, apparently, a thing they did and I watched.
I want to say I was fine with it. Mostly I was. They’re at the age now where letting go isn’t a metaphor anymore, it’s just Tuesday. It’s the trailhead at the bathrooms. It’s a bench. A couple of years later I can look back and see it clearly for what it was, one of the first times the answer to “can Dad keep up” was genuinely no, and everybody adjusted and kept moving, including me.
While we sat there, a group of four came through, and one of them, a woman, petite, blonde, maybe in her forties, asked if Jocelyn would take their picture. Jocelyn did, and handed the phone back. We didn’t think much of it until we overheard her talking a few minutes later. She worked as a personal assistant. Tony Robbins’ personal assistant, on break from one of his retreats, one of the high-altitude, high-ticket kind, being held somewhere on that same mountain.
I didn’t say anything to her. We just nodded at each other once, like travelers passing at the top of the world.
For years I’ve said I want to be the Tony Robbins of healthcare. Not the hype, the heart of it, giving people who are scared or sick or grieving something real to hold onto. And here I was, on a bench I hadn’t planned on needing, watching my kids get small on a ridgeline, having just handed a stranger’s phone back to a woman who works for the guy. Oprah’s land blocking the shortcut. Tony’s assistant on the same trail. Me, in the middle of it, legs done for the day, feeling like I was standing exactly where I was supposed to be even though it wasn’t where I meant to end up.
The boys came back down eventually, out of breath and pleased with themselves, already arguing about who got there first. We climbed back in the Cadillac. The fog took the road again on the way down, the same wall of white, except this time it didn’t scare me the same way. I’d already been through it once.
Somewhere on the descent I looked in the mirror and the summit was gone, folded back into the clouds like it had never been there. Just the road ahead, and my family in the car with me, and the long way down the mountain that Oprah made us take.
About the Author
Matt Cavallo
Author, keynote speaker, healthcare leader, and storyteller. Twenty years with MS, turned into stories that move readers, audiences, and healthcare leaders alike.