The Art of Packing Smarter

Why I Stopped Packing for Anxiety and Started Packing for Joy

I used to pack like a man preparing to survive societal collapse in another country. Ok… maybe that’s a little hyperbolic. I wasn’t bringing generators or dehydrated food buckets. But if I were employing any kind of strategy, I was absolutely packing from a place of “what if?”

What if I need extra clothes?
What if I suddenly decide I need to style my hair in a tropical climate when i know I’m going to wear a hat?
What if my glasses break?
What if I unexpectedly need a towel?
What if I become deeply committed to grooming my beard while on vacation, despite never doing that once on a trip?

And little by little, all those “what ifs” start stacking on top of each other. That’s how you end up hauling around things you never touch.

I don’t think I fully realized how much I was overpacking until I got home from trips and started unpacking. I’d find entire categories of items I never used. Clothes that never left the packing cubes. Toiletries that survived the trip untouched. Backup plans for scenarios that never happened.

At some point, I started leaving myself notes after every trip.

Literally.

In Apple Notes, inside my travel folder, I keep trip post-mortems for future me. What worked. What didn’t. What I wore constantly. What I never touched.

Some of the notes are basically me yelling at myself. “STOP BRINGING PANTS TO THE CARIBBEAN. YOU DO THIS EVERY TRIP, AND YOU NEVER WEAR THEM!”

And honestly? Putting that system in place has changed the way I travel more than any piece of gear ever has.

Packing for the Trip You’re Actually Taking

I think one of the biggest mistakes people make when packing is preparing for imaginary versions of their trip rather than the real one they’ll actually be on.

If I’m going somewhere tropical and informal, why am I packing multiple pairs of jeans? Everyone is wearing shorts and sandals anyway, even out to dinner.

If I’m staying in Iceland in the fall, that’s different. On that trip, I needed base layers, insulated boots, and rain gear because the environment actually demands it.

Now, before every trip, I try to think about two things:

What kind of trip am I taking? And what version of myself actually shows up on those trips?

That second question matters more than people think.

Vacation-me does not style his hair every morning. Vacation-me wears hats unless I have an upscale dinner reservation with a dress code.

Vacation-me does not carefully groom his beard with an electric razor every day.

Vacation-me is much more interested in comfort, movement, good food, cocktails, scenery, and exploring than maintaining some hyper-curated version of himself.

Once you accept that, packing gets easier.

The Joy of Walking Straight Out of the Airport

I will always still check a full-size bag for bigger trips. I’m definitely not trying to become some minimalist monk carrying two black t-shirts and a passport in a sling bag.

But I’ve absolutely started traveling lighter whenever it makes sense. And walking off a plane and straight out the airport doors without waiting at baggage claim?

Delicious.

There’s real freedom in that. Not just physically, but mentally too. It changes the pace of the entire travel day. Suddenly there’s less friction. Less waiting around. Less babysitting your own belongings.

Part of that realization certainly came from letting go of over-preparedness a little bit. It took a whole lot of looking inward to accept that I don’t need to solve every hypothetical problem before leaving the house. It took work to realize that most problems are solvable once you arrive anyway, particularly the inexpensive stuff.

I used to waste luggage space packing things I could easily buy at a grocery store or pharmacy twenty minutes after landing. Places that I would be hitting up anyway to stock the vacation property.

Now I’d rather use that space for things that actually improve the trip.

My Luggage Looks Like a Traffic Cone

The company that manufactured my luggage appears to have gone extinct. The brand was called OOO Traveling, which stood for “Out of Office,” and they seem to have vanished into the retail afterlife sometime around 2021.

But their luggage did something important, you’ll never lose it in a crowd, you couldn’t miss it if you tried.

My bags are the most obscenely obnoxious shade of neon orange imaginable. You could probably spot them from orbit.

And honestly? I love that.

After durability and capacity, visibility is probably my biggest luggage priority. In a sea of anonymous black bags rotating endlessly around the baggage claim, mine practically announces itself like a drunk guy yelling my name across a parking lot.

Nobody is ever accidentally walking off with this thing.

When I’m on line at the airport baggage drop, people always comment on my suitcase and carry-on.

Usually something along the lines of, “Damn, that’s bright.”

Yes… Yes, it is… and they’re mine.

The Packing Cube Revelation

Packing cubes felt like witchcraft the first time I used them. I bought a set almost on a whim. Suddenly, one entire side of my checked bag became exceptionally organized for clothing, while the other side handled everything else.

That was the moment things clicked. Tops in one cube. Bottoms in another. Underwear and socks. Swimwear. Miscellaneous items. Everything compressed neatly into place like a game of travel Tetris.

The funny part is that my packing cubes matched my luggage. Wild orange again, because apparently subtlety was never part of this system.

The company that made them folded too, because apparently, I’m personally cursed when it comes to travel brands surviving long term.

But the specific company honestly doesn’t matter anymore. The philosophy does.

Packing cubes create categories, and categories simplify. Reducing complications while traveling is one of the best gifts you can give yourself.

The Washer and Dryer Rule

One of the biggest shifts in how I travel happened because of something unbelievably boring: Laundry.

I specifically seek out Airbnbs with washers and dryers whenever possible because it fundamentally changes how I pack. For a two-week trip, I only need to pack for one week if I have the ability to do laundry halfway through.

For carry-on-only travel, it matters even more.

That one decision creates flexibility everywhere else.

I’ve taken trips where I couldn’t make that work and ended up spending part of a vacation sitting in laundromats in Ireland or Curacao waiting for clothes to dry. I can say with complete confidence: having an in-unit washer and dryer is infinitely better.

It’s not glamorous advice, but travel gets dramatically easier when you don’t need to pack an outfit for every day of the trip. And all of that space gained is space that can be reallocated for other things that can make your travel better.

Pack for Joy, Not Anxiety

This is probably the real lesson underneath all of this. I think overpacking is usually driven by anxiety and control. You’re trying to solve every possible future problem before it happens.

But eventually, I started approaching packing differently.

Not: “What could go wrong?”

But: “What will genuinely improve this trip?”

That shift changes everything.

A tiny cocktail kit that lets me make a proper Negroni at an Airbnb after a long travel day? Worth it.

A compact Bluetooth speaker for music while getting ready in the morning or lounging on a beach? Worth it.

A small flashlight and multitool that will solve problems without taking up space? Worth it.

Five pairs of pants for a tropical island? Absolutely not.

The goal stopped being preparing for every imagined scenario and became building a travel setup that supports the experience I actually want to have.

Carry-On Travel Becomes a Game

When I decide a trip can be done carry-on only, my brain approaches it completely differently. That’s when it becomes a game.

How much can I cut while still being comfortable?

Can I make the whole trip work with the shoes I’m wearing on the plane?
Do I really need another pair of pants?
Can I pack for the whole trip and still comply with TSA liquid restrictions?
Can I make this work without sacrificing the parts of travel I actually enjoy?

I genuinely love solving that logistical puzzle, untying that knot.

Not because I’m trying to suffer through travel with as little as possible, but because there’s something deeply satisfying about a system that works cleanly and accomplishes the goal.

What Actually Matters

Expensive gear doesn’t automatically make travel better.

More gear definitely doesn’t make travel better.

The right gear makes travel better.

That’s a huge difference.

I’ve brought giant tripods on vacations, thinking I’d spend nights doing astrophotography, only to use them once.

Meanwhile, smaller tools I almost didn’t pack ended up becoming indispensable.

Over time, I’ve realized simplifying travel isn’t really about bringing less.

It’s about making room for the things that actually matter.

And once you figure out the difference between packing for joy and packing for anxiety, travel starts getting a whole lot easier.

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