Let Go or Be Dragged: Adventures in The Last Frontier

I want to tell you a story about how an unexpected encounter with nature changed everything.

In the summer of 2021, my girlfriend Steph and I spent all of July working on a course designed to help people use technology to get more out of their time. By the time launch day rolled around, we were exhausted but had pocketed $20,000.

I decided that we should use those course winnings on a trip to Alaska. The Last Frontier seemed like a great place to unwind and recharge, and I planned a two-week trip that included epic hikes, a glacier tour, whale watching, salmon fishing, and good food.

As we boarded our first-class flight to Anchorage and took a sip of the free champagne, my mind fantasized about a magical Alaskan experience that would deepen our budding romance.

But as war strategists say, no plan survives contact with reality. 

The first few days of our trip were not the romantic fairy tale I had imagined. Upon landing in Anchorage, we spent our time quibbling about this and that as we drove through landscapes that belonged in a Bob Ross painting.

On the third day, we woke up at dawn to ride bikes through Denali National Park. I thought this biking adventure might turn things around, but during the first 10 miles, we continued bickering. If we had not been the only two people biking in the park, we probably would have parted ways and enjoyed the alone time.

I started wondering if we were going to have to cut our trip short, and that’s when life handed us an unplanned gift in the form of a snacking grizzly bear.

When we were five miles from the end of our bike ride, a tour bus driver stopped and rolled down the window. He said a bear was munching on berries close to the road about a quarter mile ahead. There was no way to predict how he would react to us, so he advised us to stop biking and go back. Before we could ask him the many questions we now had, he drove away and left us to fend for ourselves.

We were less than prepared for this news. While each of us had spent time in nature, we were not the type of people who carried first-aid kids, went overnight camping, or knew what the hell you do when a bear decides to eat lunch on your path.

But this little snafu proved to be the medicine we needed. As the reality of dealing with a wild grizzly bear sunk in, the tension and quarreling dissipated. With our lives on the line, we had to drop the drama and start working as a team on a mission to survive.

We agreed that we could not turn back. That involved biking 10 miles (mostly uphill), and neither of us had the water supply or quads for such an endeavor. That meant we either had to convince the next bus to let us on or that we had to bike past the bear. The team preferred the bus option.

We had no cell phone service or knowledge about the bus schedules, so while we waited for another bus to come, we moved closer to the bear to observe him. He would get sick of eating berries and move on at some point, right? Well, apparently not. This guy went on munching for the better part of an hour, ignoring our pleas for him to move on.

A bus eventually came and we waved it down. The driver said he couldn’t take us onboard, so we asked him about biking past the bear. He said it wasn’t smart, but we could give it a go and see what happens. He wished us luck and kept driving. Thanks man.

To his credit, his cheeky answer was another gift. Given our ignorance about the situation, his lack of a hard no for going past the bear gave us the confidence we needed to try it out. Steph and I hugged each other, exchanged nervous glances, and agreed not to look the bear in the eyes.

With that, we began to peddle, quickly realizing that we were moving uphill into a fierce wind. Neither of us was moving more than a few miles an hour, but we weren’t turning back now. I reached the bear first and tried not to look at him, but he looked up for the first time and gave me a long stare. I looked at him and realized just how big bears are. 

My heart thumped a little faster as I prayed that he didn’t chase me down. I looked back to see that he now had his eyes on Steph. She had fallen back quite a bit, and it wasn’t until she was a couple hundred yards past the bear that I took a breath. Mr. Bear seemed unphased and resumed his adventures in Berrylandia. We both peddled hard for a half mile and finally stopped to discuss what had happened.

We laughed about how stupid we were and how helpless we would be if the bear came after us. But he didn’t, and it was nice to feel the rush of connection that comes from dicey moments. The quibbles of the past few days already seemed like they were from another part of our lives. All that mattered was that we were together and safe.

We even recorded a video to remember the moment.

As we prepared for the last few miles of the journey, we caught our breath and passed an apple back and forth. Right as I handed the apple to Steph for the final bite, I saw something emerge from the woods about 50 yards away. It was moving fast and toward us.

Another grizzly, much bigger and more active than the other one. Oh boy.

My eyes bulged and I told Steph to come to me. A bear was walking toward us. She giggled and told me to stop joking until she looked back and froze in silence. I considered telling her to run, but she appeared unable to move her legs. My mind turned off as my instincts took over.

My arms raised high above my head and a series of tribal-sounding chants emerged from my mouth. I don’t know where these sounds came from or what they were, but I’m sure I could not make those noises again. Upon hearing these sounds, the bear immediately changed course. He made a hard right, darting into the woods on the other side of the road. My chants continued as I watched the trees closely. A bus driver pulled up thirty seconds later.

I pleaded for him to take us on the bus, and after deliberating for too long, he relented, helped us load our bikes, and cursed us for being dumb enough to bike through the park. The bears had become a lot more active with fewer people visiting Denali during the pandemic. Didn’t we know?

I had never been so happy to enter a hot, packed bus of chatty middle-aged tourists. As I sat down, the image of that bear walking toward us remained burned in my mind. Some passengers asked me what happened, but I was not ready to speak. Steph told the story while I remained in awe about the size of the grizzly, the sounds that came out of me, and our proximity to a violent death.

Let go or be dragged

When I’m surfing and the ocean holds me underwater, I often think of the Buddhist saying: “let go or be dragged.” It’s a reminder to let go of the desire to breathe, relax, and wait for the ocean to allow me to resurface. It always does. Over time, I’ve learned to shortcircuit my desire to fight the ocean. That’s an unwinnable battle that only makes the experience worse.

While I’ve learned to let go in the water, I sometimes forget to apply this idea to land life. 

The Alaska trip is a good example. I had an idea in my head about what our trip should be. The plan was to have the BEST TRIP EVER, and when reality deviated from those expectations, I resisted. And that resistance dragged me and Steph further away from enjoying our time.

But sometimes life has a few tricks in its book that force you to let go of your expectations. In our case, that trick came in the form of two Alaskan grizzlies. While neither bear did anything other than be a bear wandering around, the experience of being that close to and helpless against a bear in the wild put everything into perspective.

I don’t — and I doubt Steph does either — remember what we were even quibbling about at the start of the trip. Almost certainly something silly. 

But I do remember the joy and gratitude that bubbled to the surface after we came out unscathed from the encounters with the bears. The opportunity to continue enjoying this life and the experience of being together, even for one more day, felt like a gift.

After the bears, all expectations went out the window. I let go of all my ideas about the trip and simply lived out the experience of being in Alaska with someone I love and everything that came with it. And once I let go of the plans and expectations and started living more fully in the moment, one of the more magical and unexpected events of our relationship played out.

At the end of the first week of our trip, I woke up groggy and exhausted. We were supposed to go on an all-day trek up to a glacier, and I didn’t feel like going. I nearly bowed out until I thought about how those bears had given us a second chance to live more fully. So I got myself together, and Steph and I headed for the trek to the Harding Icefield.

After five hours of intense hiking, we reached a stunning view of a glacier that stretched for miles and looked like it belonged to some land other than Earth. As we sat down to enjoy some snacks, I surprised us both by taking out the ring that I had carried around for the last 9 months and asked Steph to marry me.

She said yes.

Making sense of the experience

Looking back on the proposal, marriage, and many good times that followed, I can’t help but consider the role of those grizzlies.

I had no plans of proposing on that trip or on the day that it happened. Sure, I carried a ring, but I figured I might use it in the next 5 years if and when the moment felt right. Even 15 minutes before the proposal, the idea had not crossed my mind.

In my attempts to make sense of it all, I like to think about what John Lennon said In “Beautiful Boy (Darling Boy):” “Life is what happens to you while you’re busy making other plans.” 

I didn’t know what he meant until the Alaskan journey that led to an unplanned proposal. You see, it was the bears that allowed me to let go of my original plan and focus on simply being present with life as it unfolded. And paying attention to the full beauty of our experience together is what gave me the courage to take the leap with Steph at that glacier.

As I noodle on that experience now, it’s humbling to realize how the random unfolding of life leads us in directions that no plans can account for.

I mean, had we started biking 20 minutes earlier on that day in Denali, maybe we would not have seen any bears. Maybe we would have been killed by a bear. Maybe we would have continued quibbling and missed the chance to start over and take our relationship to the next level.

I can’t know for sure because you can never know the counterfactual. All you know is what happened, and the rest is conjecture.

What I do know now is that regardless of how it happened, the process of letting go is what allowed us to stop getting dragged during our vacation and to embrace the unpredictable twists and turns of the experience. We needed to chill and roll with it to allow the beautiful moments to emerge.

Zooming out beyond that trip, it’s clear that so many of the most important forks of life follow a similar path. There is some plan, and while I grasp onto it with all I have, the randomness of the world causes me to lose my grip and chart a new path.

Whether that randomness comes in the form of people, things, experiences, or bears that I did not forecast, these deviations all play a role in moving life in a new direction. Sometimes that direction is a good one; other times it isn’t. And often we don’t even know whether it’s good or bad until enough time has passed for us to connect the dots backward.

What I take from these experiences is that my desire for control over my life and the world is a fool’s errand. Life does not offer certainty or control, no matter how much we want it. There are no guarantees in this world. None. And when you begin to see that this is the fundamental, unalterable nature of life, you can learn to let go and surrender to the unknown.

I think this is what Lennon meant when he said, “life is what happens to you while you’re busy making other plans.” He was reminding us that life is fundamentally unpredictable and uncontrollable. No matter how diligent we are with our planning, intentions, and goals, there will be surprises that muck it all up.

That doesn’t mean that we shouldn’t try to plan or direct our lives, but it does mean that we should remain open to the flow of life that does not care about our plans. Or at the very least, we should recognize that life becomes easier and more enjoyable when we stop resisting.

To do otherwise is no different than fighting a wave that will hold you down as long as it wants. If you’ve ever found yourself in that situation, you understand that the wave is not what will kill you; it’s the panic and fear and grasping to get to the surface that does you in.

It’s only in learning to let go that we can finally be free to exist as we were meant to be.