✦ Part of Italy Trip 2026

⌖ Florence, Italy

Meaningfulness runs inversely to convenience

We went to go visit the statue of David today, because it is something you must do when you go to Florence. We forayed northeast across the Arno River to the touristy side of the city. It was 37°C and 80% humidity. We arrived there and saw a line stretching down the block, exposed to the sun, and a mob of other clammy, cranky tourists and decided to abandon our places.

Later that day a timely essay came through from David Cain about bucket lists and travel checklists are not only impractical but are quickly outdated (past versions of yourself, inherited lists from others).11. David found many old goals no longer mattered and thinks lifetime lists are often impractical. Now, he focuses on meaningful personal challenges and relationships instead of ticking off exciting experiences. Then I remembered that other piece I read recently about people who are trying to race to visit every country in the world22. “Last year a record 82 people claimed to have achieved the feat of travelling to all 193 countries.” (and undoubtedly sharing it on social media), and how this pervasive (potentially status-driven) mentality of quantity over quality33. And it’s no surprise that the conveniences, technology of modern travel actually enabled this is so misplaced, and misplaced for the same reasons that this “choosing friction” essay44. “Today’s cult of convenience fails to acknowledge that difficulty is a constitutive feature of human experience. Convenience is all destination and no journey.” talks about: when you forgo friction you miss out on learning the things about yourself, you miss out on the challenges that make these events and occasions meaningful.55. Sweating through your clothes on a walk to a rose garden to re-read our vows on our one year anniversary

As I’ve been feeling on this trip, you miss out on the depth of experience and interaction with others when you don’t choose to go the more meaningful route.66. We wouldn’t have met the couple that runs the pizza shop and the olive oil shop if we were there for a day and only focused on the places that other tourists say we should go. It’s also quite rewarding to watch locals light up when you ask them about their favorite places. There is a difference between the cheaper highs of novelty-seeking and frictionless convenience and the meaningful experiences that require us to step out of our comfort zones. In fact I would even say that meaningfulness is often directly proportional to the discomfort faced.

I’m much more interested in a meaningful personal experience in the current moment; Yes, the Renaissance was incredible, and yes, I’m super inspired by Da Vinci, but what was far more meaningful was the dinner we had the night before served in that small Enoteca by that short, quirky, and energetic Italian guy and his equally eccentric and stern (yet sweet) Italian-speaking German wife.

It’s important to honor and understand the history of a place (the Medici palace, David and Michelangelo), the parts of the whole that make it special, just as I’ve been thinking it’s important when I go camping to learn about the names of all the trees and plants, birds and animals.