8 Packing Disasters This American Still Makes After Years Of Living Abroad!

Still Screwing Up My Suitcase: Packing Fails From Years Abroad

Here’s what no one tells you about long-term travel and why that useless item in your bag says more about you than you think…

I once packed a linen shirt for Albania thinking I’d suddenly develop a Mediterranean glow and an effortless sense of style.

Instead, I spent the summer sweating through it in a Greek bus terminal, looking less like a coastal fashion icon and more like a tourist who lost his tour group.

And yet, I packed it again for my return trip to Albania. Twice.

After years of living out of suitcases across Ukraine, Georgia, Bulgaria, Romania, Albania and North Macedonia, and a few deeply regrettable Airbnbs in Greece, you’d think I’d have mastered the fine art of packing.

But somehow, I still manage to drag around two scarves I never wear, a bulky paperback novel that mocks me from the bottom of my bag, and a pair of leather dress shoes that have seen fewer dinner parties than a monk in a monastery.

The truth is, packing for long-term travel is never just about the stuff.

It’s about the fantasy of who we think we’ll become in a new place.

That we’ll start journaling by candlelight in a French café, take up spontaneous tango in a Spanish plaza, or, I don’t know, hike up a volcano called Duvalo in North Macedonia despite getting winded climbing the stairs to our Airbnb in Saranda.

And even after years abroad and a dozen or so countries, I still make the same ridiculous mistakes, some out of habit, others out of hope.

So, here they are!

The eight dumb packing mistakes I keep making, and the ones I’ve should have learned by now to stop repeating.

1. Packing Too Many Shoes (That All Do the Same Thing)

I once packed five pairs of shoes for a month-long stint in Bulgaria.

Five! 

As if I’d suddenly develop a personality that switches between salsa dancing, trail running, and rooftop bar-hopping in Sofia.

Instead, I wore the same beige suede flat tops every day, which were not waterproof, but semi-breathable, and a little stylish (if I do say so myself).

But hey, they were already on my feet, and that counts for something when your Airbnb’s three flights up and there’s no elevator.

What I Should Have Learned by Now: Unless your feet are planning a solo trip with their own itinerary, keep it to two pairs, max!

One for walking everywhere, and one that can pass as “nice” if you squint.

2. Bringing “Maybe” Outfits for Imaginary Versions of Yourself

Somewhere between packing and boarding, I convince myself I’ll become a whole new person overseas.

The kind of person who wears crisp linen shirts in Greece and looks breezy, not like a sweaty lost American melting into a park bench in Athens.

Or the guy who brings a blazer to North Macedonia “just in case” there’s a jazz bar that requires one.

There never is.

What I Should Have Learned by Now: If you didn’t wear it at home, you won’t wear it abroad.

Pack for the you that gets “hangry” and lost, not the you that exists only in a romantic montage set to European café music.

3. Forgetting a Power Strip (Every. Single. Time.)

I don’t know how many times I’ve stared at one lonely outlet in a crumbling studio in Craiova, Romania trying to decide whether my laptop or phone deserves to live.

Once, I plugged my power bank into a socket that buzzed like a dying bee and sparked every time I touched it.

Meanwhile, my travel adapter sat useless in my bag, because I forgot the extension cord that would’ve saved me.

What I Should Have Learned by Now: Always pack a compact power strip.

It’s the cheapest solution to the eastern bloc epidemic of crappy Airbnb outlets in crumbling post-communist apartment blocks.

4. Skipping Rain Gear Because ‘It’s Summer’

The logic: “It’s July, I’m going to Thailand. What could go wrong?”

The answer: Everything!

In Chiang Mai, I got caught in a rainstorm so intense, my clothes clung to me like they owed me money.

Locals passed by in perfectly dry ponchos while I stood under a palm tree, using my passport wallet as a sad little umbrella.

What I Should Have Learned by Now: Rain doesn’t care what season it is.

A compact poncho or umbrella takes up almost no space, but your dignity will take up plenty of room if you don’t have one.

5. Ignoring Local Dress Norms (Until It’s Too Late)

It was my second week in Tbilisi, and I figured I’d blend right in.

So I spent a Saturday night wandering the Old Town, popping into wine bars, checking out the local restaurant scene and soaking up the vibe.

And oh, I got the vibe… just not the one I was going for.

There I was, dressed like I’d taken a wrong turn on the way to a hiking trail: cargo shorts, scuffed-up hiking boots, a sun-faded t-shirt, and a baseball cap that screamed, “lost his tour group.”

Didn’t think much of it… until I started catching the looks.

Locals strolled by in jeans, button-downs, actual outfits.

I, on the other hand, looked like the star of a low-budget travel doc called “Americans Abroad: What Not to Wear.”

Or the time I visited a church in Mtskheta, Georgia with bare shoulders and got handed a light see through scarf by a stern-faced woman who looked like she had personally wrestled saints.

What I Should Have Learned by Now: Check the cultural dress norms before you land. Especially for religious or rural areas.

Better to cover up than get called out.

6. Bringing Real Books… Because Apparently, I Hate Myself

There’s something romantic about reading a physical book on a train, right? 

Until that book becomes dead weight in your bag and you end up sleeping on it because your hostel ran out of disposable pillows.

I brought a 1300-page Count of Monte Cristo on my second Camino de Santiago trek through Spain.

I ended up reading just 20 pages!

But I still lugged it around in my backpack for 3 more weeks, refusing to admit defeat.

I finally surrendered and left it at a Pilgrim’s hostel in León with a passive-aggressive note that just said: “The movie’s better!”

What I Should Have Learned by Now: Kindle. Library apps. PDFs.

Anything but the hardcover or softcover bricks you think you’ll read.

7. Skipping the Laundry Essentials (Then Overpacking Instead) 

I’ve packed 6 pairs of socks just to avoid doing laundry.

Not 5. Not 4.

“Six”!

As if I were trekking across the Sahara, and not Spain with no access to water, or soap, or shame.

However, while in Spain, I did find myself crouched over a hostel sink, trying to wash my underwear with some leftover shampoo I “borrowed” from the shower shelf.

No sink stopper, of course, so I let the water run like I was baptizing each pair individually.

Another traveler handed me a single clothespin with the gravity of someone handing over state secrets.

What I Should Have Learned by Now: A basic laundry kit takes up less space than your emotional baggage.

Toss in a sink stopper, a few detergent sheets, and a portable clothesline (you know the one that doesn’t need separate clothes pins).

Unless, of course, you’re into paying strangers to fondle your t-shirts while you sit in a café pretending you’re writing a novel.

8. Packing Based on Emotions, Not Logic

Every item in my bag is a negotiation between practicality and irrational sentiment.

A hoodie from my first year in Kyiv? Doesn’t fit anymore, but it reminds me of a snowy December and a young woman named Anya. 

A t-shirt from a Legends of Rock festival I picked up on a trip back to the USA? Still smells like cheap beer and freedom… and now looks as old as the legends themselves.

A 100% Irish wool newsboy cap I picked up in Ireland? I still wear it! I don’t care what anyone says, I think it’s stylish and I love it!

What I Should Have Learned by Now: It’s okay to bring one or two sentimental items.

But if your backpack starts to look like a scrapbook, it’s time to make some emotional cuts.

Packing Isn’t Just Packing… It’s Self-Sabotage in a Carry-On

Let’s face it: packing is less about logic and more about the lies we tell ourselves. 

That we’ll become someone different abroad.

That we’ll need six outfit changes in Bulgaria, three scarves in Spain, and a classic novel that we’ll definitely finish this time so we can say we’re well read.

We won’t. But we’ll keep trying.

So, is the anything you, “Should Have Learned by Now”?