7 Moments That Made Me Question If This Borderless Life Was Worth It

What No One Tells You About Living a Life Without Borders

The Freedom Was Real but So Were the Loneliness, Uncertainty, and Doubt

Imagine sitting in a moldy Georgian basement apartment in the middle of August, sweat dripping down your back as the electricity cuts out for hours.

There’s no AC, no internet, not even a fan to move the hot air.

You stare at the ceiling and ask yourself, “Is this really the escape and freedom everyone keeps posting about?”

That wasn’t even the worst of it.

The cracks didn’t come all at once. They crept in quietly.

A visa run crackdown in Ukraine that forced me to leave the country after living and working there for 20 years.

My grandmother’s 100th birthday party and the funerals I missed because the flights back to the States cost more than I made that entire month.

A simple question over a cheap glass of Georgian wine, Where are you headed next?, and realizing I didn’t have an answer.

I’ve spent over two decades bouncing between countries.

Teaching English in Ukraine.

Doing remote work from a tiny flat in Tbilisi during a pandemic.

Hiking Spain’s Camino de Santiago twice, because once wasn’t enough self-inflicted blistering and penance.

I’ve sipped ouzo in Greece, eaten street food in Thailand that made me question my intestinal fortitude, and accidentally offended people on the Metro in Kyiv just by smiling too much.

Everyone loves to talk about the perks of the borderless life.

The sunsets in Mexico.

The tapas in Spain.

The fact that you never have to go to your high school reunion.

But no one writes Medium articles about the 3 a.m. existential spirals.

The growing pile of expired SIM cards.

The moment you realize that while everyone back home has roots, you’ve got packing cubes.

This isn’t a rant, and it’s not a regret.

It’s something else.

Something most of us never admit.

These are the seven moments that made me question everything about this life I built.

The so-called dream. The escape. The freedom. The myth.

If you’ve ever had your own moment of what the hell am I doing, keep reading.

You’re not alone.

1. When I Missed a Funerals I Couldn’t Afford to Attend

I was sitting in a coffee shop in Tbilisi when the message came in.

My uncle, had passed.

It wasn’t unexpected, but grief doesn’t care about flight prices or conversion rates.

I checked anyway, just to entertain the fantasy of being there. The ticket from Georgia to the US might as well have been to Mars.

I didn’t go. My brother and cousins FaceTimed me at 3am instead on their 4th drink from a bar after the funeral, grieving together, which is somehow worse because I couldn’t be there at all.

The screen froze halfway through the conversations, the Wi-Fi glitched, and I sat there staring at a loading icon like it was a metaphor.

What to remember: Freedom can come with distance, but it also means choosing who you can’t be there for.

No matter how far you roam, the guilt finds you just fine.

2. When a Visa Delay Left Me in Limbo

In Thailand, visa runs are practically a rite of passage. Friends tell me you know it’s bad when border guards start recognizing you.

But Ukraine?

Oh no, Ukraine has other ways.

But, this time was different. I wanted to go legit.

No more visa runs, “overstay fines” or “impromptu cash gifts” at the airport with no guarantees of being allowed back in.

I did everything myself, without an employer or a lawyer, so I’d submitted everything.

Twice.

They wanted a notarized copy of something I didn’t even know existed. My bank statement, my rental contract, my entrepreneur business certificate, and apparently a blood sample.

Meanwhile, the expiration date of this “visa run” kept inching closer.

So I waited. Canceled plans. Checked my inbox like it owed me an apology.

So, while Instagram kept telling me I was “living the dream,” I was just trying not to get deported.

What to remember: Bureaucracy doesn’t care about your curated lifestyle.

Always assume a visa delay will hit right when you need your life to function.

3. When a Polyclinic Visit Made Me Realize How Alone I Was

Kyiv, Winter, 2002. A polyclinic that had seen better days and Zhenya, built like a female Soviet shot-put champion and just as gentle.

My back had given out after a gym injury and I needed help.

Fast!

There was no receptionist with a clipboard, no friend waiting in the hallway.

Just a gruff command in Russian to strip, a table that looked like a coroner’s slab and felt just as cold, and a massage that walked a fine line between therapy and punishment.

It worked. Thank God!

But, Zhenya…. she will always have a special place in my heart.

Even so, I still remember lying there at the time, eyes fixed on a water stain on the ceiling, thinking, “If this goes south, who would even know?”

What to remember: Travel insurance is one thing.

A human safety net is another.

If something happens, who would pick up your phone?

4. When I Had No One to Call at 3 a.m.

It was one of those nights. You know the ones.

Heart racing, mind spinning, a thousand thoughts all yelling at once.

All I wanted to do was talk to someone who had known me before all of this.

But it was 3 a.m., yet again, in Tbilisi.

The lights were off, the streets were silent, and my inbox was just as quiet.

My phone contacts read like a collection of expired friendships and WhatsApp ghosts.

It wasn’t that no one was awake. It’s that no one felt close enough to call.

Too much time. Too much silence. Too many chances I thought could wait. Too many connections I let slip away or never tried to fix.

I stared at the ceiling for hours. Nothing dramatic happened.

That’s the thing. It’s just quiet.

The kind of quiet that lingers and reminds you of just how alone you are in this big world of ours.

What to remember: Time zones don’t just separate clocks, they separate comfort and life long relationships.

So, build relationships that transcend geography before you need them.

5. When Old Friends Stopped Reaching Out

At first, it was little things. Missed birthdays and weddings.

Fewer emails, back when that was still how people kept in touch. Then the calls stopped.

The invitations and news stopped coming.

I wasn’t left out on purpose, just slowly forgotten.

They were having kids. Mortgages. Thanksgivings and Christmas parties.

I had SIM cards from 4 different countries and questionable Airbnbs above kebab shops.

It wasn’t a dramatic goodbye.

It was just silence, stretched over years.

What to remember: Distance doesn’t always create drama.

Sometimes it just creates… nothing.

Stay intentional, have a purpose, or it all fades faster than you think.

6. When I Couldn’t Remember the Last Time I Felt Settled

Spain. France. Ukraine. Georgia. Albania. Then back again.

I’ve traveled with three types of jackets for all seasons, three cellphones, four SIM cards, 4 chargers, 4 pairs of shoes, and no idea where the hell I stuffed my winter socks.

The romantic idea of mobility started to feel like a sitcom where I was playing the role of a person with a life.

Except the background set kept changing along with the cast of supporting characters.

I realized one day I couldn’t remember the last time I bought anything bigger than a new suitcase, let alone the last time I hung a picture.

What to remember: If you never settle, you never stay.

After a while, even constant motion starts to feel like standing still.

7. When I Asked Myself What’s This All For

I was in North Macedonia, sitting in a park full of stray dogs and pensioners, journaling like it was still 2004.

I’d just finished writing an article about why I’d never move back to the US.

But, for the first time in a long time, I didn’t believe myself.

Was I still chasing something or just running out of places to be?

What to remember: It’s one thing to choose a lifestyle.

It’s another to become trapped by the version of yourself you keep selling to others.

Ask yourself if you still mean it.

Even Freedom Has a Price

This isn’t a complaint. It’s a confession.

A clearing of the air for anyone who’s ever felt the ache behind the adventure.

I’ve built an interesting life across borders, but not without its cracks.

So I’d rather be honest about them than keep pretending the cracks aren’t there.

What about you?

What moments made you question the lifestyle you’ve chosen?