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? We take the long way.
Of course she did.
We were on our second rental car of the trip, a Cadillac SUV we’d swapped for the Infiniti after a dead battery stranded us back near Hana. The Caddy handled the switchbacks better, but my hands still stayed locked at 10 and 2 the whole way up. The road climbed sharply, coiling through cow pastures and patches of fog. Chickens darted across the pavement. A few goats gave us the side-eye. There were stretches with no guardrails at all.
We kept climbing. And then we hit the clouds.
Thick, white mist swallowed the rearview. I could barely see the road ahead and could see nothing in my rearview. It was like we’d crossed some kind of threshold—into something quieter. Higher. I didn’t say anything to Jocelyn, but I couldn’t help thinking: this might be the closest I’ve ever come to heaven.
By the time we reached the summit, the temperature had dropped nearly 30 degrees from what it had been at the beach. We stepped out into crisp, thin air and looked out over the crater. It stretched out like the surface of Mars. The sun was shining overhead, but below us? Clouds. Miles of them. We were standing on a volcano, 10,000 feet above sea level, and for once in my life, the noise in my head went quiet.
We made our way from one overlook to the next, taking photos and breathing it all in. At nearly every stop, we kept bumping into the same group, and in that group, a woman. Petite, blonde, probably in her forties. She had this confident energy about her, like she belonged here.
Eventually, we overheard her talking. She mentioned that she worked as a personal assistant. Then came the part that made me stop mid-step.
She was Tony Robbins’ assistant.
She was on break from one of his exclusive retreats, One of those high-altitude, high-ticket events, right here on the mountaintop.
I didn’t say anything to her. We just nodded at each other once, like travelers passing on the rim of the world.
For years, I’ve said that I want to be the Tony Robbins of healthcare. That’s not just a line—I mean it. I’ve imagined what it would look like to inspire people the way he does: not just with hype, but with heart. I’ve envisioned giving hope to patients, caregivers, anyone navigating pain or loss or diagnosis, and helping them rediscover their strength.
And Oprah? Making her book club is on my vision board. Always has been.
So here I was, taking the long road to the summit because Oprah blocked the shortcut, only to cross paths with someone from Tony’s inner circle at the top.
Coincidence?
Maybe.
But as I stood up there above the clouds, it felt like something else. Like the universe was letting me know I was still on the right road, even if it wasn’t the easy one.
Back in the car, I sat for a moment before starting the descent. The road disappeared behind a curtain of cloud, like it had never been there at all.
Just sky ahead. Just silence.
And somewhere down the mountain, the long road home.