How Much Do You Need to Carry With You?
It’s the height of travel season, and I’ve been thinking about how the best trips aren’t just defined by where you go, but by what—and who—you bring with you, and what you choose to leave behind.
Kevin Kelly, in a piece called “50 Years of Travel Tips,” offers this thoughtful distinction:
“There are two modes of travel: retreat or engage.”
We retreat when we need some R&R (rest and relaxation). The goal is recovery, not discovery. You go where it’s easy, relaxing, and familiar enough to be comfortable. Maybe it’s our favorite bed and breakfast or a home by the water with a good book.
But travel can also be a means of engagement; a form of learning, exploration, and connection. As Kelly puts it,
“You move to find yourself by encountering pleasures and challenges you don’t encounter at home.”
That distinction hit home for me. Our family vacations most often fall into the latter camp, especially with young kids who cannot sit still.
Good planning—financial, travel, or otherwise—is about first knowing what you want at the most basic levels: Are we seeking ease? Or experience? Comfort? Or growth? Each has its place.
One travel tip in particular stood out to me :
“Your enjoyment of a trip will be inversely related to the weight of your luggage. Counterintuitively, the longer your trip, the less stuff you should haul. Travelers still happy on a 6-week trip will only have carry-on luggage. That maximizes your flexibility, enabling you to lug luggage up stairs when there is no elevator, or to share a tuk-tuk, to pack and unpack efficiently, and to not lose stuff. Furthermore, when you go light you intentionally reduce what you take in order to increase your experience of living.”
This feels like more than just practical advice.
Packing light is not just about saving your back on cobblestone streets. It’s a mindset. The lighter your load, the more flexible you can be. You’re freer to say yes to unexpected detours, to try something spontaneous, to move with less friction.
This got me thinking: What other things are we hauling through life that are weighing us down? Old habits and familiar routines? The physical stuff we’ve accumulated? A cluttered calendar? The stories we tell about ourselves? Perfectionism and the need for control, or just keeping up appearances?
In financial planning, I sometimes talk about “decluttering” your financial life—simplifying accounts, automating decisions, and reducing complexity. But maybe it applies more broadly.
Packing light isn't just about luggage. We are often carrying more than we realize: fears, regrets, habits, busyness, expectations. Some of that “stuff” once served a purpose. But it can also be a burden.
What relationships or adventures have you postponed because life feels too crowded?
What would it look like to unpack some of that—to let go, simplify, and move through life with a little more curiosity and a little less drag?
Insights inspired by Kevin Kelly and his “50 Years of Travel Tips.” Thanks to Jonathan Yagel for sharing it with me on his excellent substack: 1, by Jonathan Yagel
