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Every two weeks, I share my writing on investing, career transitions, meaningful work, parenting, living intentionally, and other topics that engage me.

In my fifties, I'm still trying to figure stuff out.

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Vacation Fear

As my turn approached, I climbed the last steps to the zipline platform, and panic set in. My heart pounded. I struggled to control my breathing. Since the friendly family from Florida wasn’t looking to battle, my fight-or-flight response focused on finding a way out of this mess.

Our recent family trip to Costa Rica was supposed to be about spending time together in the presence of monkeys and sloths. And it was. But I didn’t expect it would also teach me a subtle yet important lesson in courage.

Months before the trip, our family gathered to book our activities. As we reviewed the resort’s suggestions, my wife, Liza, zeroed in on the half-day ziplining tour. She’d always wanted to go, and Costa Rica seemed like the place to do it. So, she proposed that experience to the family.

The kids immediately rejected the idea, and I felt a wave of relief.

Smart kids.

And then Liza turned to me and asked if I’d go with her. I paused, forced a smile, and replied, “Sure.”

The words “for better or worse” came to mind, so I accepted her offer. But inside, I hoped she’d reconsider the plan when the kids opted out. Instead, she seemed excited to share the experience with me.

Our first day in Costa Rica went exactly as we hoped. We woke to the sounds of howler monkeys marking their territory, swam in the Pacific, and even spotted a sloth from our deck. The ziplining tour was scheduled for day 2.

The next morning, I was ok at first, but the anxiety started to build.

We arrived at the ziplining site and joined the other tourists gearing up. What struck me most were the kids, some as young as eight or nine, brimming with excitement and fearlessness. Watching them, I felt a mix of awe and embarrassment. How could I, a grown man, back out when these kids were ready to take the plunge without a second thought?

The guides picked up on my tense smile and widening eyes. I appreciated their playful teasing and diligence in helping me secure my harness.

By the time the safety lesson started, I was already starting to tune out. If the anxiety hadn’t already taken over, I might have been more concerned. I might have understood less than half of the warnings due to the guide’s thick accent.

It was time.

For the record, I’m not exactly afraid of heights. That would be irrational.

Instead, my fear was rooted in sound logic. With everything to lose, why should I have confidence in this outfit’s rigorous testing process? I’d be suspended hundreds of feet above the ground with only a cable to hold me.

My guide could have been distracted, hungover, or quiet quitting. Besides, accidents happen, right? The list of seemingly reasonable concerns multiplied quickly.

Oh, and I should mention that I’ve had one prior experience with ziplines, and it didn’t end well. See the footage below and forgive the language.

Back to our story.

As our group ascended to the first platform, my legs felt like lead. The higher we climbed, the more intense my breathing became.

I saw one of the kids approaching the first zipline just as Liza and I hit the halfway point. The young girl giggled and leaped. She screamed excitedly as the gear carried her along the cable into the green abyss of the jungle canopy.

The line crept higher and higher toward the platform. We were in the second-to-last group in line. Behind us were two parents from Florida, who also happened to be grandparents, and their teenage daughter.

Sensing my trepidation, the couple assured me I’d be fine. Apparently, they’d done this sort of thing several times and loved it. I appreciated the gesture, but it helped not at all.

People do all sorts of stupid things. I try not to follow those folks. And here I was, paying for the privilege. My list of very good reasons to bail continued to grow.

Finally, Liza sensed my hesitation (read: total panic). With a knowing smile, she said, "Come on. You’ve got this. It’s safe. And besides, this is exactly the type of stuff you write about. It’s time to face your fear.”

Well played.

Her words were meant to encourage me, and she wasn’t completely wrong. But somehow, this situation felt different from battling existential angst associated with professional uncertainty, parenting, or managing risk.

What was I playing for? What was the payoff? Was it absolutely necessary to experience an hour of ziplining in a Costa Rican jungle like tens of thousands of American tourists before me? I still wasn’t convinced.

We approached the platform.

My wife went first. Her laughter echoed back as she soared away. Then it was my turn.

Standing on the edge, every nerve screamed at me to stop. But then I remembered the kids ahead and the young girl behind me, their eager faces waiting their turn. And I knew if I bailed, I’d have to complete the climb of shame past the grandparents and their teenage daughter. They’d have to let Liza know I couldn’t do it.

That wasn’t happening. It was my turn.

I approached the awaiting guide and allowed him to clip me in. He gave me the thumbs-up sign and said a few other things I didn’t hear and wouldn’t remember anyway.

I took a slow, deep breath and stepped off the platform. The initial moments were terrifying. But as more seconds passed, I began to believe I’d survive. And eventually, I had.

On to the next platform.

Each platform was higher and faster than the last. The flow was designed to build confidence. And it did. At the seventh platform, I summoned an additional dose of courage to zip upside-down, arms extended toward the ground (evidence below).

Reflecting on that experience, I realized that overcoming fear isn’t just about bravery, self-talk, or mindset; it’s about pushing boundaries and surprising yourself.

Here’s the honest truth.

My wife’s encouraging words helped, but they weren’t enough. Reason has precious little firepower during bouts of panic—at least, that was my experience. Instead, an unspoken, perceived challenge from the others in the group, mainly the young kids and grandparents, put me over the edge.

Call it pride, peer pressure, or a greater fear of shame, but that’s what got the job done.

Fear is a natural part of life, but it doesn’t have to control us. This zipline adventure was another reminder that courage isn’t the absence of fear; it’s the decision to move forward despite it. Of course, that’s the main message, but we also need to know what works for each of us.

So, here’s to facing fears, pushing boundaries, and finding inspiration in the most unlikely places, possibly even in the carefree faces of young kids and grandparents.

Other Stuff

Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member | Uri Levine (co-founder of Waze) Lots of useful takeaways from Lenny's interview with Levine. One idea that resonated with me is scheduling a review of key decisions in 30 days to reassess. We often accept the status quo and forget we can undo our mistakes. Most decisions can be reversed. Levine initially recommends the approach related to hiring but extends the practice to other areas, too.

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​Listen to the podcast (1 hr 22 mins)

"The Glass Bead Game" by Herman Hesse Despite winning the Nobel Prize in Literature, I had never heard of this book until I received a copy as a gift from the co-founders of Napkin. The story is set in a 23rd-century intellectual utopia around the Glass Bead Game, an abstract synthesis of arts and sciences. The protagonist, Joseph Knecht, becomes the Master of the Game but questions the value of his intellectual life in his search for deeper meaning. Key themes include the tension between intellectual pursuits and practical life, spirituality and self-discovery, and a critique of pure intellectualism. It's certainly not an easy read, but the effort is rewarded with thought-provoking insights.

​Read the book (I don't think it's an affiliate link)

Vix / Soccer Now that the NBA and NHL seasons have wrapped up (Congrats, Celts!!!), more sports fans might consider watching more soccer. At least, that's what I'm doing. With the Copa America and Euro '24 ongoing, my son and I have been obsessed with the matches. If, like us, you don't have cable or streaming live TV, you'll have to get creative. Vix has been a great solution. They cover both major tournaments. It costs only $6.99 per month through Amazon. Cancel anytime. Yes, the broadcast is in Spanish, which makes it even more fun. For those not paying attention, here's Jude Belingham's incredible goal in the 95th minute to save England from elimination. Amazing stuff.

​Watch more soccer on Vix! (not an affiliate link)

And a Farewell Photo...