My most hardcore outdoorsy friends all fantasize about owning Jeeps. They don’t want a sprinter van or an SUV – no, they want a real Jeep. You know the ones I’m talking about? The ones all jacked up with super high clearance and with the spare tire hung outside the back door like a trophy. The ones with tops that looks like you could peel them off if you decided to go on safari. The ones that, if they could, would bully other cars by asking them: “What’s it like? I honestly don’t know how I could be happy if I couldn’t drive across the sand.” 

Me… well I want to be able to go anywhere, but… maybe I could say I aspire to aspiring to it? It’s just I haven’t exactly had a lot of luck with them to date. For instance, when I was in Texas, desiring to no longer be limited in my adventures in any automotive way, I rented one. But even before I was able to take it off road, hours into the endless nothingness of West Texas I thought I was about to die. My real Jeep, going 80mph on the highway, began to shake so violently without warning that I thought either ALL of my tires had blown out simultaneously or the suspension might be literally detaching from the undercarriage. Miraculously, the shaking stopped as I slowed down, only to start again an hour later. When I called Hertz to complain and demand a new car, the kid on the line suggested, “Weird, I don’t know… with Jeeps, well… I mean, you have to know how to handle them.” Clearly I didn’t.

I’m sure an SUV can get me everywhere I want to go, I tried to assure myself.

So, when my mother and I were planning our trip to the Virgin Islands National Park, and I found out there was only one rental car company with availability still, and it had only one kind of car remaining (a real Jeep, obviously) I was … not happy… but determined to make the best of it. Maybe Texas had been a fluke? Maybe I’d be able to prove I knew how to handle them after all?  

~~~

Mom and I arrived in the US Virgin Islands in the middle of the night after a series of delays resulting from a combination of de-icing problems, an overheated passenger who had to deplane, a missing baggage handling crew, airline union rules that required a new crew to be found after our initial delay, unclear issues that required us to get a new plane, one of the new pilots going AWOL for 2 hours, and a broken jet bridge. Despite it all, we congratulated ourselves for being in such good spirits when we landed.

“It’s part of the adventure!” Mom kept saying along the way.

Thankfully, while en route we found out we’d still be able to pick up our Jeep when we got there. And Jennifer, the woman who managed the house we were renting, was still available to show us the way. “I’ll pick you up at the ferry! I don’t want you to worry about a thing.”

Our trip wasn’t quite over. After landing in St. Thomas, we had to take a 40 min cab to the ferry, and then take a boat about 20 minutes to St John. On the way we texted Jennifer our arrival time and she promised again to pick us up. But once ashore, there was no sign of her. We called her. She didn’t answer. 5 minutes passed – finally she called us back: “Sorry, sorry! I’ll be right there. Such crazy traffic.” I looked up the road, there were about 5 cars. “Island time,” I thought, and shrugged.

“Part of the adventure!” added mom. 

When Jennifer finally did arrive and we got in her pick-up, and she asked us if we were: “Ready to for our adventure in paradise?” I chuckled.

60 seconds later we arrived at the rental car company, two blocks from the ferry.

The rental car man was all business. “No Amex, insurance highly recommended.” After signing the paperwork, he showed us our Jeep. It was giant, and mustard colored. (Seriously, who would order a mustard colored car?). Walking us around the beast he spoke to a dozen tiny scratches on the doors and bumper, sometimes without even looking at them. “I know every inch of my cars,” he told us proudly. My mom was impressed. “Don’t forget,” he told us as we got into the car, “Drive on the left side of the road.”  

And off we went…. and immediately had issues, starting with our first turn. Despite the fact that I was making a left-hand turn into the left-hand lane, the turn radius of our Jeep was so wide that I literally had to cross the entire left lane and swing through oncoming traffic on the far side of the road in the right lane before getting back to the correct lane. 

Once in the correct lane, Jennifer pulled in front of us, and led us out of town onto an empty mountain road. It wasn’t long before we were driving in the dark except for our headlights and the moon, all other manmade lights were long behind us. Meanwhile, the road had substantially narrowed and its grade reached up to 20 degrees. “Thank goodness for this hardcore Jeep!” I thought. 

Then weirdly, and seemingly out the blue Jennifer stopped in the middle of the road. She got out of her car and came to talk to us. “Follow me. Turn here. I’ll stop just past your driveway.” 

“Where?” I thought. I didn’t see any turnoff.

But to our right was a small, single lane that turned sharply up and disappeared into the thick brush. It was steeper than any road I’d ever seen in my life. I shifted into 4WD. “Part of the adventure!” I said with a chuckle before hearing the bottom of the Jeep seem to scrape the ground as we turned up the hill. The back wheels spun, slipped, and finally caught – propelling us up, up, up. 

More winding in the dark. Then again, Jennifer stopped and got out of her car. She approached my window, “Okay you go down here.” I could see the house far below us. Mom and I both got of our car to look at the narrow spur leading straight down to the house at an angle even steeper than what we’d just driven up. 

“Isn’t it nice that’s it’s paved after the dirt section?” Jennifer asked cheerily. 

We said nothing. Our eyes still not sure we were seeing this thing correctly.

Trying to fill the silence, she went on: “It looks scary, but it’s not so bad! I sometime turn around up here, you know, pop, pop, pop, pop, pop” she swung her arms as if she was having so much fun imagining the 5-point turn, “and then I reverse straight back down. You might have to work up that though. Probably not the first time.”

Meanwhile, another car had pulled up behind us, an aqua blue Jeep. We needed to move or we’d be blocking their way I thought.

Jennifer threw in: “Oh it might look scary. But it’s okay – there’s no cliff you have to worry about.”

I looked down, that wasn’t true. I looked back her. 

“Well,” Jennifer added, “Not a steep one. It’s set back from the edge a bit. It’s not like you’d die immediately if you went too far.”

Those were the magic words for Mom. And with that, she took off down the hill on foot. “Jill! Don’t do that. It’s very steep and slippery.” Jennifer called out after her. 

As she shimmied down the hill perpendicularly like a crab, Mom yelled out over her shoulder: “I fell off a cliff once. I’d prefer to walk.”

Turning to me, in a whisper, Jennifer asked: “Did she say she fell off a cliff?” 

I shrugged. I didn’t want to get into it. I waited to make sure mom got to the bottom and got back into the Jeep. 

Pulling up to the edge and peering over the steering wheel, I literally couldn’t see the driveway in front of me the hill was so steep. As I inched the Jeep forward I felt the front of the car tip forward. A rush of adrenaline. Still nothing to see but the hood and trees above the home, then tip, tip, tip …  the roof of the house, my mother at the bottom the hill, the driveway before me. Slowly, slowly I eased down the rest of the hill. 

That night as I laid in bed, channeling my inner gangster, I feted myself: “I handled those crazy steep roads in the dark in a freaking hardcore 4x4 with mothering F’ing aplomb. Who says I can’t handle a Jeep?” 

I knew I’d have to turn the Jeep around in the tight circular area at the base of the hill in the morning, but thanks to my new swagger, I wasn’t worried, even if it was hard, it’d just be “part of the adventure”.

In the morning as we loaded the car up with gear for the day, I looked up the hill and noticed the blue jeep hadn’t moved from where it’d been the night before. I guess we weren’t blocking them? I wondered. A mother and son got in and drove away. 

But soon I forgot about them. Surveying the area in which I’d need to enact my own 180 degree turn, I imagined how it’d go. I saw it clearly in my brain: pop, pop, pop, pop, pop, easy, just like Jennifer said.

We got in, I shifted it into reverse, and.. almost backed into a wall of rocks. I’d been expecting a beep to warn me. But there was no back-up camera or sensors like in my car at home. My mom was a little rattled, but I shook it off: “You got this gangster,” I told myself, “Old school skills time.” 

I shifted into forward, turned the wheel hard, tapped the gas, and … barely turned the car at all. So, I put it back in reserve and inched back. Pop, pop, pop, pop, pop I went – but after completing my 5-point turn – I realized I hadn’t even made it a 10th of the way there. 

So, Mom volunteered to get out of the car and help direct me. She scurried forward and backward, side to side, directing me to go: “3 more meet, 1 more foot, a few more inches, stop, stop!” over and over. 

After 10 turns, I no longer felt this was a part any adventure I was interested in. But, finally, finally, we got the car facing up the hill. 

“Okay, maybe not so Gangster,” I said to myself as I tried to breathe deeply and regain my composure. Looking down at my watch I noticed my heart rate had spiked. 

Later, when we returned from exploring the island and before heading back down the driveway, we found the spot where the Blue Jeep parked the night before. We realized it wasn’t blocking traffic because it had been tucked into a small pullout immediately in front of a hidden staircase going to another home. The spot was just barely big enough for one car. We looked for other pullouts along the road, but found none. 

We had to go down again. And so, we did. Which, to my surprise wasn’t so bad. In fact, the dropping down over the hill onto the unseen pavement gave me a thrill. I felt bold, daring, even inspired. As I inched down I even thought maybe my turning problems early had been solely due to the angle at which I started. I’d tried pulling up to the opposite side of the turnaround area. Getting out, I yelled up to mom, who was still crab walking down the hill “I’m getting the hang of this!” 

But no, as I’d learn 30 minutes later, I wasn’t actually getting the hang of it. 

This time, despite my mother’s direction from the outset, after 10 turns I found myself incomprehensibly a tad past perpendicular, with the passenger side tires a foot above the driver’s side, and the front of the car slightly pointing down the hill. It was then that I first learned about reversing a Jeep while it wants to roll downhill. Tap the accelerator too slowly or too softly, no gas will make its way to the engine, and the car will roll dangerously forward until you can jam the break again. Tap too hard and you’ll shoot back quite a bit – in this case, straight into a rock wall. 

A breathed deeply, focused hard, and somehow over the course of many, many turns, managed to damage the landscaping quite a bit, but also avoid both the cliff and rock wall. Once on the road to dinner, Mom went to give me a high five: “Nice job! What an adventure!” 

I tried see it that way and re-summon up my gangster swagger, or to see this as part of the adventure -- but my positive attitude had long since left the island. I was mad at the car for being so big and poor at turning. I was mad at the rental company for only having a real Jeep. I was mad at the islanders for making such narrow roads. I was mad at the home’s owner for making this nonsensical driveway. I was mad at the other guests on VRBO for not writing in their reviews about the death trap driveway. I was mad at the island for being so hilly! 

I knew blame wouldn’t change anything. I knew on a deeper level I was angry at myself. I felt shame that I couldn’t handle the Jeep. I felt shame that I couldn’t maintain a positive attitude. And I feared that I’d have to park and un-park so many more times during the week — getting stuck, or doing real damage, seemed inevitable — and thinking about it all felt paralyzing.

But I didn’t want to talk about that. That all seemed like weakness. Both my complaints and my fears. Better to fight it, right? My words are my world. I thought to myself. 

So, I just clenched my jaw, breathed deeply, and tried to exude “Zen” to my mother – “This was our special trip together – stay present to that!” I scolded myself. But I wasn’t. As I drove away I silently imagined what unparking it again in the morning would be like. 

~~~

That night when we came home I refused to go down the driveway. 

“I’m parking up here.” I told my mother angrily.

“But this is blue jeep’s spot. They don’t have a driveway, remember?” My mom reminded me softly. 

“I don’t see a sign!” I snapped back, then trying to be more reasonable, I added “It’s late and they aren’t back. Maybe they aren’t coming back?”

My mom looked incredulous. 

I felt that anger welling up again: “If they want to park there, they can wake us up and I’ll move it in the night!”  

No one woke us up. But when I woke up in the morning I kept looking up the hill nervously, anticipating their arrival any moment. I called the rental company. “Do you have anything smaller?” I asked them. “No. All booked out.” “Please? Are you sure? What about tomorrow?” Nothing. 

While I was increasingly agitated Mom seemed cheery and ready for adventure as we ate breakfast. “What do you want to do today?” she asked. With an exaggerated yawn, I replied “How about enjoying this incredible view? Maybe we can just read, relax, and unwind here?” 

I’m sure she saw through me, but she agreed, until finally around 4pm we decided we had to get out. We decided to go to the beach. “Should we bring our clothes for dinner so we can go straight from there to town?” I asked.

“I don’t think there are showers there. Shouldn’t we come home and rinse off?” 

“Hmm… let’s just be ready in case?” 

Two hours later we went to dinner sandy and salty.

That night my heart jumped as we approached the driveway and I saw the blue Jeep still had not returned. “Maybe they’ll never come back!” I imagined dreamily. 

The next day I again resisted making “unnecessary trips” to and from the house. I pleaded with the rental company (on the phone and in person) for a new car to no avail. Whether at home, driving, or out hiking, part of me was always dreaming about that driveway, fearing what it would be like if the blue Jeep returned. 

I knew my constant fear was impacting my experience of the island, but how could it not? I vacillated between absolute confidence that disaster was near, and a counter belief that with enough willpower I could avoid it. Back and forth it went in my mind as I went on hikes, ate dinners with mom, and tried to relax in the water. 

The next morning, while eating breakfast, Jennifer re-appeared out of nowhere: “I hope I’m not bothering you. Just here to make sure you’re having a great adventure!”

“Yes, thanks. So good.”

After some pleasantries, she added nonchalantly, “I see you parked up on top of the hill”

“Yes.” 

“You should park down in the driveway, you know. It gets easier.”  

“Oh…”

Seeing I wasn’t going to help her, she tried to be more direct: “That’s the neighbor’s spot.” 

“Hmm. Is that right?”

“Yes, you can’t park there,” 

“I guess... it seems like they’re gone.”

She turned to me, trying a different tact, whispering conspiratorially, “There is a family there, but the dad… He’s unpleasant. Very unpleasant. He’s a real grouch. Other people have had problems…” she trailed off and resumed her forced smile. “Anyway, you need to park in the driveway. I promise, it’s gets better.”

“Well gosh, thanks for letting us know!” 

When she left… I didn’t move the car.

~~~

Late that afternoon I dipped into the rental house’s small plunge pool for the first time, luxuriating as I floated in the water and listened to the sound of the ocean far below. In the water I began to forget about the stupid Jeep

But then vroom vroom... Looking up the hill, I saw it, “Blue Jeep!”

I jumped out of the pool, grabbed the keys, and ran up the hill barefoot. Getting to the top I looked into the car window and saw a gray-haired man’s form still behind the driver’s wheel. He didn’t seem to notice me.

I jumped into my Jeep, turned on the ignition, and sped down the hill. Looking in my rearview mirror, I saw the man had gotten out of his car. He was standing at the driveways’ edge, looking down at me. “Oh God,” I thought, and imagined what a real grouch would do.

My mom ran up to the car and tapped the glass, “Come on! Get out of the car. He wants to talk to us!” 

I waved at her angrily, “I can’t, I can’t – I’m trying to turn around!” as if that made any sense as an excuse. But then having said it, I felt I had to make it true. And turn around I tried to do as she walked up the hill to talk to the man alone. I turned, and turned, and turned until I’d gotten myself into a worse position than ever before. Like last time I was down below, I gotten the jeep entirely perpendicular to the driveway. But this time all four wheels were on the steep hill. Suddenly, I had flashbacks to Qatar and the feeling of a Jeep before it seems like it might tip over. 

I turned the wheel hard, shifted into reserve, lifted my foot off the break, tapped the gas, and kept rolling. I hadn’t pressed hard enough. The front of my car rolled into a large wooden plank propping up a tree. I saw it pop out from the trunk. In a panic, I now really hit the gas, I shot back and … CRUNCH. I felt the rock wall behind. Oh god! I shifted forward. Then slammed the breaks again. 

Looking out the passenger window I saw both Mom and the man staring in disbelief at what was happening below. Mom had kicked one leg into the air and outstretched both of her hands straight in front of her as if to ward away an approaching evil spirit. 

“I can’t stop now!” I thought. Back, forward, back, forward, back, forward I went. 

I don’t know how long it took. But somehow, somehow, I got it turned around.

As I looked up I saw the man was now gone and mom was slowly sideling down the driveway. “Well,” she started, trying to be positive, “He says you did better than some of the other guests. Others have gotten stuck entirely.” 

She walked past, shaking her head, “He also said his wife and son are gone for the week, so we can park up in their spot at the top of the hill the rest of the week.” 

She disappeared into the house, but not before adding disappointedly: “Why didn’t you just go and talk to him?”  

I sat in the car for another minute. Kind of shell shocked. Finally, I got out of the car and inspected the damage. I’d hit a tree – but it was still standing. I reattached the support beam. I discovered I’d run over a few LED lights. But they all could be popped back into their casings. There were deep tread marks on the dirt. But most consequentially, the back bumper was badly scratched and dented.

Without even closing my eyes, I could see the rental car man’s face and hear him saying: “I know every inch of my cars.” This was going to be expensive…

I felt enveloped in a growing cloud of shame: “You are such an idiot. Why didn’t you just talk to him? Why couldn’t you do this? Why can’t you drive a real man’s car? Why do you always fail when it counts most?” 

I stood in that for a while. My head slumping lower and lower. 

But then, over the din of my internal critics, I also became aware of the sound of the ocean. The rhythmic crashing far below—completely unchanging and unaffected by the petty dramas or triumphs in my life. I felt the warmth of the sun on my face. I looked around. Everything was so lush. “How absurdly lucky am I to be here?” I thought: “This is paradise. I’m alive in paradise. How unfair and wonderful.” 

Suddenly, I also felt a huge weight of anxiety lifting. All the uncertainty about whether I’d damage the car was gone. I had! And I saw it was just a bumper. No one was hurt; no one’s life would be forever altered. Of course, I knew it’d cost something to fix. That’d be annoying, but I had the insurance and savings to deal with it. Plus, from a cost side -- I no longer needed to fear damaging the bumper again. I reasoned they’d charge me for a whole new bumper whether I put 1 or 6 dents in it. That idea, gave me the confidence to drive with complete lack of fear about dinging it again the rest of the week. I felt so much freer, and as consequence, I actually became much more skilled at driving.   

Over the next few days, I still felt somewhat anxious about what the rental car company would say, and how much they would try to charge us for the damage, but I also realized it was out of my hands. With time, I stopped thinking about the car at all except with gratitude for the way it helped us get up the steeper portions of the island safely.

The last morning, when we went back to the rental agency, mom and I took a bet on how much he’d try to charge us. We held our breaths as the agent who “knew every inch of his cars” carefully inspected the damages and shook his head. He poked at the dent. He seemed to grab the whole bumper with his hand as if to pull it all off, but it didn’t budge. 

He looked at us, and then said, how about $100? 

Was he joking I thought? It was only then that we realized that while we couldn’t fix the special real Jeep bumper, he probably had some way to pop it back into shape with ease. There was no need for a whole new bumper as there would be on any car other than a real Jeep. 

As we walked the two blocks from the agency to the ferry (no 60 second Jennifer shuttle this time), we shook our heads and laughed.

$100. I let the fear of paying $100 consume my thoughts, keep me from exploring as much as I could have, and damage the quality of my conversations with Mom over many days for what turned out to be $100. How silly! And how strange that if I had never crashed then my fear of crashing would have been a contributing and limiting factor to our whole time on the island (not just several days). Instead, by confronting my fear due to my desire to avoid it, I actually found freedom from its weight.

Of course, this is not the first time I’ve fallen into this dynamic in my life. I can think of so many times that amorphous fears of discomforts (of things which actually weren’t that bad) kept me from having conversations I should I had, changing behaviors I knew didn’t serve me, and taking risks that could have helped me grow. But as with the bumper, so what? It does not help to obsess on counterfactuals. The bumper is dented now. I must live with the consequences of that.

But that’s not bad. It’s a gift! This moment and this insight is an invitation for to me to step back and ask with clear eyes: what (small) fears are controlling me even now? How and where am I hiding from them? And how can I move from insight to action in facing them today?