Boy Scouts ruined me as a packer.

When you’re miles from the trailhead, “be prepared” isn’t a just a motto, it could be the difference between life and death.

First aid kit. Snacks. Water. Backup shoelaces. You name it, you’d better have it covered, because there’s no gas station around the next bend.

Maybe “life and death” is a bit dramatic, but you get the idea.

Then Came Kids

Then came kids, and packing for family vacations felt exactly the same.

Do we have the pack and play? Do we have the fitted sheet that goes inside the pack and play?

Enough wipes? Snacks? The right charger for the iPad?

I was still packing like I might get stranded twenty miles from the nearest trading post.

Are We Out of the Woods Yet?

Here’s what I finally realized: most places we go now have more open at 11pm than the small city where I live has open at 2pm.

If I forget something, I’m not in trouble. I’m a ten-minute walk from a store that sells it.

The wilderness taught me to prepare for isolation, and then it took me a long time to notice I wasn’t in the wilderness anymore.

More Relaxed, More Stressed

Here’s the strange part: I stopped packing for every scenario, and I’m both more relaxed and more stressed than I’ve ever been about packing.

More relaxed because I’m not lugging around stuff for every contingency.

More stressed because packing light means every choice actually matters.

Team Checked Bag (Most of the Time)

Let’s be clear: for most leisure travel, I’m still team checked bag.

When it’s a family vacation, why fight for overhead bin space? Check the bag, bring what you want, stop thinking about it.

The Game of Packing Light

Solo business travel is where the real shift happened for me, and now packing light has turned into a bit of a game for me.

A recent Sunday-to-Wednesday trip: two pairs of Lululemon pants, two Turtleson polos, a button-down, and a lightweight sweater. Sneakers and loafers. Something to sleep in. Toiletries. That’s it.

All of it fit (with room to spare) in my Steele Canvas duffel.

Even that wasn’t as lean as it could’ve been.

A Sunday-to-Tuesday trip to drop my daughter off at a summer program: two pairs of shorts, a pair of pants, a button-down, two polos, a hoodie, sleep clothes, one pair of sneakers. I came home having never touched one of the polos.

I’d already told myself I was packing light and I still packed something I didn’t need.

So even inside “I’m a light packer now,” there’s a second level: not just fewer things, but the right fewer things.

The Questions That Actually Help

Here are a few questions that can help you figure out what to pack:

What am I actually going to do while I’m there? Not what’s possible. What’s real. A city can offer you fifty experiences but you may only have time for four of them. Pack for those four.

Am I walking or Ubering? Walking means relaxed clothes and shoes that can take a beating. Ubering buys you the luxury of dressing a little nicer, since your clothes and shoes aren’t earning their keep on the pavement all day.

Am I going to shop while I’m there? If you like to shop when you’re in a new city, you can always wear some of those new pieces once you’ve bought them. You also need to make sure you’re not packed beyond capacity before you go shopping, because then you’ve got a problem. Especially if you’re buying shoes.

Smarter, Not Just Lighter

I’m getting more honest with myself about where I’m actually going and what I’m actually going to do when I get there. That’s made me a smarter packer.

I still like feeling put together, since for some reason I hate looking like a tourist. But let’s be honest: everywhere I go except the small city I call home, that’s exactly what I am.

I still think about that Boy Scout mentality sometimes. That instinct to prepare for every scenario, just in case.

It served me well in the woods. It didn’t serve me in TSA lines, in overhead bins, or unpacking a bag full of things I never touched.

Deciding on Purpose

These days, packing comes down to deciding on purpose.

I know where I’m going, I know what I’ll actually do when I get there, and I trust that if I forget something, the place I’m visiting has got me covered. No need for extra shoe laces.