7 Frustrating Errands Abroad That Made Me Miss America More Than I’d Like To Admit

The Embarrassing Hassles That Hit Harder Than Culture Shock

Nobody tells you that the errands abroad are what break you first.

Not the visa paperwork. Not the language barriers. Not even the terrifying moment in Kyiv when you realize the alphabet looks like someone dropped Scrabble tiles into a blender from bizarro world.

Nor the moment you find yourself in yet another country long-term, and realize you’d absolutely click on a shady “Learn Any Language in 7 Days” ad at 2 a.m. just to avoid asking where the bathroom is.

It’s walking into a French supermarket looking for cold medicine like you would back home, only to realize you’re searching an aisle that doesn’t exist.

You have to find a pharmacy, explain your symptoms, and hope your rusty French is better than your immune system.

That’s when America starts looking dangerously sexy again.

I’ve lived abroad long enough to know the glamorous expat dream usually dies somewhere between mailing a package, finding a barber (since solved by shaving my head, but I digress), and realizing one simple errand now requires confidence, humility, and possibly a local eye-witness.

Quick note: If this piece hits a nerve, it may be because the real question is bigger than this one story.

Maybe you’re wondering whether life abroad actually fits you, whether your second thoughts are normal, or whether the dream you’ve been carrying needs a more honest look.

“Is Life Abroad Really For Me?”

I built my Backroom, Guide, and Private Conversation around that very question, and I’ll link them at the end.

So here are the seven frustrating errands abroad that made me miss America for reasons I’m not proud of, but absolutely stand by.

1. Buying Medicine Shouldn’t Feel Like Solving a Mystery

In the U.S., buying cold medicine is simple. You shuffle into a pharmacy looking like death in sweatpants, grab something with the words severe, maximum, or nuclear strength on the box, then pray it works before your next Zoom call.

In France, I learned quickly that cold medicine isn’t something you grab at the supermarket between cereal and toothpaste. You go to a pharmacy, explain your symptoms, and hope you don’t accidentally describe a medieval plague.

This sounds reasonable until you’re congested, sweating, speaking broken French, and miming sinus pressure like you’re auditioning for a very depressing silent film.

The embarrassing part wasn’t needing help.

It was realizing I missed the American luxury of avoiding help completely.

Tiny Errand, Big Wake-Up Call: Abroad, even buying medicine reminds you that American convenience trained you to expect answers before you even ask the question.

2. The Grocery Store Humiliated Me More Than I Expected

The first time I had to weigh my own produce abroad, I stood there like a man trying to defuse a bomb with bananas.

In the U.S., grocery stores are basically theme parks with fluorescent lighting. You want peanut butter, cereal, cough drops, motor oil, birthday candles, and a rotisserie chicken sweating under a heat lamp?

Great. Aisle seven.

In Ukraine, France, Georgia, Albania, and Spain, groceries often made me work for it. Different layouts. Different brands. Different rules. Outdoor makeshift markets out of some parking lot.

Sometimes different bags, which I usually forgot until I was shamefully juggling tomatoes like a street performer with no talent.

Still, the grocery store became one of the best classrooms abroad. You learn what people actually eat, how they shop, and how badly you’ve been spoiled by 47 kinds of barbecue sauce.

Tiny Errand, Big Wake-Up Call: The grocery store didn’t just confuse me. It exposed how much I missed America’s ridiculous, beautiful, overwhelming ease.

3. Sending One Simple Package Turned Into an Afternoon Adventure

Mailing a package abroad is where optimism goes to get slapped.

I’d walk in thinking, this should take five minutes. Famous last words. Suddenly there were forms, stamps, windows, lines, rules I didn’t understand, and a clerk staring at me like my existence had personally delayed her lunch.

In Kyiv, I learned that the post office wasn’t just a building. It was a test of endurance, humility, and whether my Russian was good enough to explain why I needed to send something without accidentally confessing to mail fraud.

In America, even when the post office is annoying, you usually know the ritual.

Abroad, the ritual knows you’re foreign and smells fear.

Tiny Errand, Big Wake-Up Call: Mailing a package abroad taught me that patience isn’t a personality trait. It’s a survival skill.

4. Avoiding Haircuts Became My Strangest Expat Survival Strategy

Here’s the problem with writing about haircuts abroad. I haven’t really had one since 2000.

After my first long trip in 1998 and moving abroad permanently in 1999, I figured out the safest international haircut strategy of all time. I bought clippers and started shaving my own head.

No awkward chair. No mystery instructions. No tragic misunderstanding where “just a little” turns into “congratulations, you now look like a Ukrainian conscript.”

A fellow traveler I met in Georgia wasn’t so lucky. He went in for a trim, smiled confidently, pointed at his hair, and came out looking like his barber had been angry at NATO.

That’s when I realized shaving my own head was a form of self-preservation with clippers.

Tiny Errand, Big Wake-Up Call: Abroad, even skipping the haircut can become a survival strategy when you don’t trust your vocabulary near scissors.

5. Banking Abroad Made Me Appreciate Boring American Convenience

Nothing makes you miss the U.S. faster than realizing “just open an account” abroad can mean appointments, paperwork, registration with local authorities, stamps, signatures, copies, more copies, and one mystery document nobody mentioned until you were already sweating in the chair.

In the U.S., we complain about banking apps if they take three seconds too long to load. Abroad, I’ve had moments where moving money felt like I was negotiating an international hostage release.

Ukraine taught me paperwork had its own weather system. Georgia and Albania reminded me that every country has its own rhythm, and that rhythm doesn’tt care about my American desire to finish everything before lunch.

The trick is to arrive prepared. 

Bring documents, bring patience, and bring the emotional maturity not to say, “But back home we just do this online.”

Nobody likes that guy.

Tiny Errand, Big Wake-Up Call: Banking abroad made me miss the boring American systems I used to complain about.

6. Returning Something Was Way More Complicated Than I Expected

The U.S. has trained us to believe returning something is a sacred constitutional right. Isn’t that why we fought a revolution?

You buy the wrong shirt, wrong charger, wrong blender, wrong emotional support air fryer, and back it goes. No drama. No interrogation. Sometimes they barely look at it.

Abroad, returning something can feel like you’re asking the store clerk to donate a kidney.

I learned quickly that refund culture is not universal. Some places offer store credit. Some places inspect the item like a crime scene. Some places give you a look that says, “You bought it, genius.”

At first, I missed the American “no problem” attitude. Then I realized stricter return cultures make you think harder before buying useless crap you never needed in the first place.

Painful? Yes.

Financially healthier? Also yes.

Tiny Errand, Big Wake-Up Call: Returning something abroad showed me how spoiled I’d become by America’s “no problem” refund culture.

7. Finding the Right Store Became an Unexpected Treasure Hunt

In the U.S., one store can solve half your life before noon.

Need bread, socks, toothpaste, a frying pan, printer ink, and Halloween decorations in July? Somehow, it’s all there under one roof, because the U.S. looked at moderation and said, “No thanks, we’ve got parking.”

Abroad, I had to relearn shopping like a normal human being. Bread from one place. Meat from another. Hardware somewhere else. Electronics in a store I’d never find unless a local personally guided me there like a mountain sherpa.

At first, it drove me crazy.

One simple Saturday errand became a scavenger hunt with receipts.

Then something strange happened. I started liking it. 

The bakery knew bread. The butcher knew meat. The grocer knew which fruit and vegetables were in season and grown locally. The little hardware store had the exact tiny screw I needed, even if I had to mime “wobbly table” like an idiot.

Tiny Errand, Big Wake-Up Call: Running errands abroad made me realize one stop shopping isn’t normal. It’s an American superpower I’d taken for granted.

The Errands I Once Hated Became the Stories I Love Telling

Looking back, it’s embarrassing how many tiny errands made me miss America.

I never expected homesickness to sneak up on me in pharmacies, supermarkets, post offices, and banks.

But there I was, missing cold medicine, easy refunds, absurdly wide grocery aisles, and banking apps that don’t require a blood oath and three photocopies.

Living abroad taught me that convenience is cultural. What feels normal in one country can feel completely absurd in another, and what frustrates you today might become the story you laugh about tomorrow.

Those errands didn’t ruin expat life. They made it real.

So, what’s the tiny everyday task abroad that caught you completely off guard?

Life abroad can be incredible, but the dream still has to become a life you can actually live.

That means the doubts, the distance, and the weird daily stuff nobody puts in the glossy version.

The Expat Backroom gives you the more candid layer behind my public stories. Is Life Abroad Really For Me? helps you think through the bigger question. A Private Conversation lets you talk through your own situation with me directly.

The Expat Backroom

A quick note: I’ve added a private Expat Backroom section to the Substack version of this piece.

The public article here is complete, but the Backroom is where I add the more candid version behind selected stories: what I left out, what I think really happened, and the sharper life-abroad lesson underneath it.

Read about The Expat Backroom on Substack here.