The Logistics Operation

There is a specific kind of anxiety that comes from ‘optimizing’ a hike. You spend 32 hours researching the exact weight of your socks, comparing 12 different brands of merino wool, all so you can ensure the maximum ‘return on investment’ for your physical effort. You aren’t walking in the woods; you are performing a logistics operation. You’ve brought the office with you, even if you left the laptop at home. The tools have changed-from Slack to AllTrails-but the mindset is identical. You are a manager, and your vacation is the underperforming employee you are trying to coach into greatness.

I think about my grandfather, who once drove 1202 miles across the country with nothing but a paper map and a sense of profound indifference toward where he ended up. He didn’t have a Trello board. He didn’t have 102 tabs open to find the cheapest flights. He had a car and a direction. If he got lost, he wasn’t failing a project; he was just somewhere else. Somewhere else-what a terrifying concept for the modern traveler. To be ‘somewhere else’ without a pin on a digital map is to be practically non-existent.

We fear the void of the unplanned. We fear that if we don’t schedule every 12-minute interval of our trip, we might miss something. And in our desperate attempt to not miss ‘something,’ we miss the only thing that actually matters: the feeling of being present. You can’t be present when you’re checking the next card on your board. You’re always three steps ahead, living in a future where the train arrives on time and the restaurant still has a table.

The Sickness of De-Risking

I recently spent 52 minutes-nearly an hour of my finite life-reading reviews of a public park in Osaka. A park. I was reading what strangers thought of grass and trees. I wanted to ‘de-risk’ the experience. I wanted to ensure that the grass was of a sufficient quality to justify the 12-minute walk from the station. This is a sickness. It’s the inability to trust our own senses to evaluate reality in real-time. We need the data. We need the social proof. We need the project to be successful.

When the weight of the logistics becomes its own kind of trauma, I start to realize that the only way out is to surrender the management of the experience to someone else, or to the universe itself. You have to find a way to stop being the CEO of your own fun. It is why some people find solace in pre-arranged journeys that don’t feel like a corporate retreat. For example, trusting an experience like Kumano Kodo allows you to finally drop the clipboard. You move from being the ‘Project Manager’ of a trek to being the person actually walking the trek. There is a massive, soul-level difference between those two states of being. One involves looking at a screen; the other involves looking at the moss on a centuries-old stone.

The Vocabulary of Rest

I’m back at my crossword grid. 12-Across: ‘To move without purpose.’ I type in ‘AMBLE.’ It feels like a foreign concept. When was the last time I ambled? My Trello board doesn’t have a label for ambling. It has a label for ‘Transit’ and ‘Sightseeing,’ but ‘Amble’ doesn’t fit the taxonomy. It’s too inefficient. It doesn’t contribute to the completion of the project.

Maybe the open fly is a sign. A sign that even when we think we have everything under control-when we’ve checked the boxes and aligned the columns-there is always something we’ve missed. There is always a vulnerability. We are messy, biological creatures who forget to zip up their pants, yet we try to plan our vacations with the precision of a SpaceX launch. It’s a hilarious contradiction.

The Compulsion to List (122 Food Spots)

If you find yourself color-coding your packing list, stop. If you find yourself setting ‘deadlines’ for when you need to have your hotel booked, take a breath. Ask yourself if you are preparing for a joy or if you are preparing for a performance. Are you the traveler, or are you the project lead? The project lead gets the promotion, but the traveler gets the life.

The Gentle Surrender

I think I’m going to delete the Trello board. Not all of it-I’m not that brave yet. I’ll keep 12 cards. The essentials. The rest? I’ll leave it to the gods of the open road. I’ll leave it to the possibility of getting lost, of eating at a mediocre restaurant that happens to be right there when I’m hungry, of sitting on a bench for 32 minutes and doing absolutely nothing productive.

The crossword puzzle is finished now. The grid is full. Every letter has its place. Every conflict is resolved. It’s a satisfying feeling, but it’s a temporary one. The real world doesn’t fit in a 15×15 box. It’s loud, it’s disorganized, and it’s frequently embarrassing. It’s a world where your fly is open and you don’t know the bus schedule and the rain starts just as you reach the summit.