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Maui: Road to Hana – The Jump & The Dark

I discovered something funny about myself when we were in Hawaii. It was probably something I already knew and just didn’t want to acknowledge, but when it’s staring you in the face while on vacation, it’s something you notice and think about.

Here’s the thing: I am not very good at relaxing, being on vacation, taking it slow, etc. I’m no good at it. I am too Type A. Too “what’s the next thing on our list?”

From the minute we stepped off the plane in Maui, Anish was exclaiming, “Oh MAN, I feel relaxed already. Doesn’t this feel nice? Vacation here we come. This is GREAT.” Meanwhile, I had already fast-walked down the terminal to find the Hertz place to rent the car > get on the road > get to our lunch place > check-in to the hotel. Go-go-go! I was still in agenda-mode.

One day into it, on our Road to Hana day, I was definitely feeling happy about being in Hawaii, that’s for sure. But I wasn’t relaxed. The whole drive I was checking the time / reading the travel guide / getting irritated by other drivers / stressing about parking on the side of the small, windy road, etc. I wasn’t slowing down. And so, it was a battle of wills between Relaxation-Central Anish and Task-Master Taylor.

Luckily, the Road to Hana was just what I needed in a lesson of patience. It was endlessly frustrating at first, but I really had to to be able to enjoy it. Once you were past a certain point on the road, you had to keep going. There was no fast lane or instructions or clock to be followed. We arrived in Hana late that afternoon/evening, and by that point, the only way to go was to keep going, ’round the bottom part of the island until it curved northwest in the direction of Wailea, then Lahaina, then Ka’anapali. Estimated time almost 3 hours.

Two things helped me switch off the Type A, No Relax mode:

1// THE DARK — As we drove around the island, past Hana, the sun set quickly until we were driving alone in pitch-black darkness on winding, country roads. We knew Haleakala Crater was to the right of us the whole time, but we couldn’t see a darn thing. It was just us and random herds of cattle that roam the ranches on the southern part of the island.

We were out there, in the dark, with only one option — to keep driving. We had no place to be. No destination but the hotel. We drove slowly and carefully through the intense darkness. I’d never seen a night so black, but it wasn’t scary. We stopped multiple times and put the convertible top down to look at the stars. They gleamed brighter than I’d ever seen them before, and it was wonderful. Something we would have never seen if we had raced along earlier that day.

2// THE JUMP — Earlier on the Road to Hana, we came across a favorite spot of the local’s called “Ching’s Pond.” If you were driving by, you’d pass directly above it on the bridge and never know it’s there below — a pretty swimming hole with one very deep narrow hole for jumping. We stopped there to cool off in the pond and watch the folks that our guidebook said jumped off the high ledges above (and sometimes the bridge) into the deep pool. At this point, we were more than halfway along the road and our moods were finally lightening up, although I was still counting down till Hana.

As we waded into the water, a guy climbed up onto the highest ledge while his family watched from the rocks and jumped straight off it into what appeared to me to be the smallest diving hole known to man. We made conversation with them as the man swam back to his family, exclaiming, “Oh! I lost my wedding ring!” and then laughing it off. Anish was mildly interested in taking the leap and said so, and the guy agreed that he should try it. It was no big deal, he said. You just have to make sure you jump in the darkest blue spot and look out for the shallow ledge underwater just below the place you jump. Oh… okay.

This is where Task-Master, Type A Taylor has a mini heart attack and side-eyes the guy while encouraging Anish not to do the jump.

But it was already too late. Anish was swimming across the pond with his GoPro in hand. The guy with the endless encouragements and missing wedding ring swam alongside him to offer advice and heckling. Lovely.

Anish climbed up to the first ledge and thought he might try to lower jump first to make sure he could hit the target, etc. That’s when the guy proceeded to heckle and tell him that local kids jumped from the highest spot, so why shouldn’t he? Never underestimate the power of peer pressure. Before I knew it, Anish was on the highest ledge looking down into the sapphire blue pool, about to jump.

It was at that moment that the constricting cords wrapped around my soul started to come loose. The Type A ones that try to control everything around me, all at once. I was standing in the pool, while Anish stood on a high ledge about to take a leap of faith.

All of the sudden, I let it go. My childlike sense of adventure and bravery crept back up to me and tugged my heartstrings. I found myself shouting, “You can do it, babe!” I was smiling, and I knew it would be fine. It would be exhilarating actually and worth the jump.

So he did it! TWICE, no less! And we were both grinning and shaking every time.


It’s amazing how one day can help you learn so much about yourself. All you need sometimes is a little bit of bravery and the gumption to take a leap of faith. Who knew that the next day — Tuesday, August 19 — I would be facing an even bigger adventure and the biggest leap of faith I might ever take. 🙂





  1. Robin Snellgrove Robin Snellgrove

    I laughed out loud at the peer pressure…guys never outgrow that. Great article. I’m also type a….no hope for me. ☺

    • I know, right? So funny! No hope but at least we Type A’s can stand together. 😉

  2. If there is a perfect place to let go and learn to relax, it’s Hawaii. Glad you let it happen!

    • Indeed, Pat! Me too. I’m ready to go back. 🙂

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