I Was Too Afraid to Travel Alone. Then One Month Away Turned Into Five Years

For years, I had a very specific version of the life I wanted in my head. I wanted to work online, move between countries, spend a few months somewhere instead of rushing through a city in four days, and have the freedom to decide where I wanted to wake up next month. In other words, I wanted the life people now casually call being a digital nomad.

There was only one fairly serious problem: I was terrified of actually doing it.

I was extremely introverted. Traveling alone sounded romantic when I was looking at photographs online, but when I imagined the practical reality, my brain immediately produced a list of everything that could go wrong. Who would I talk to? What would I do alone in a restaurant? What if I arrived somewhere and couldn't make any friends? What if I hated the city? What if something happened and there was nobody nearby whom I knew?

Even the idea of approaching a stranger and saying hello felt uncomfortable.

So instead of traveling, I worked from an office.

And I hated it.

I kept waiting for the right moment to start living differently

There wasn't anything particularly dramatic about my office life, which was almost the problem. I went to work, did what I was supposed to do, came home, and repeated it. From the outside, it looked perfectly normal.

Inside, I constantly felt that I was living the wrong life.

I would sit at my desk and think about countries I wanted to see. I would read travel blogs, look at apartments in cities where I had never been and imagine what it would be like to simply take my laptop and leave. Sometimes I would mentally plan entire lives abroad without ever buying a ticket.

But there was always a reason not to do it yet.

I needed more money. I needed a remote job first. I needed someone to travel with. I needed to become less shy. I needed to feel ready.

The last one was especially convenient because I never felt ready.

I thought confident people traveled alone because they weren't afraid. I didn't understand yet that many people become confident precisely because they do things while they're afraid.

Then I got fired.

At the time, losing my job obviously didn't feel like some wonderful gift from the universe. Suddenly the stability that had kept me in one place disappeared. But something else disappeared with it: my biggest excuse.

I didn't have an office to go back to anymore.

And that changed everything.

I went to the United States for one month

My first decision wasn't, "I'm going to become a digital nomad and travel the world for five years."

Nothing remotely that brave happened.

I went to the United States to visit friends for one month.

That felt manageable because I wasn't completely throwing myself into the unknown. I knew people there. I had a reason to go. There was a return point in my head. I could tell myself that this wasn't a huge life decision; it was simply a month away after losing my job.

That distinction mattered enormously.

One of the things I've learned since then is that fear becomes much worse when you present a decision to yourself as permanent. "I'm leaving my old life and becoming a solo traveler" sounds terrifying. "I'm going somewhere for a month and seeing what happens" sounds possible.

So I went.

And somewhere during that month, my thinking started to change.

Being away from my normal environment gave me a strange sense of distance from the person I had been. My office routine suddenly wasn't the default anymore. It was simply one possible way of living.

For the first time, I seriously asked myself: If I don't go now, when exactly am I going to do it?

At 50? When everything is perfectly organized? When I'm magically no longer introverted?

There was never going to be a perfect moment.

And we really do get only one life.

That sounds like the sort of sentence people put over sunset photographs on Instagram, but it feels considerably less clichéd when you suddenly realize you've spent years postponing something you desperately wanted to do.

I decided I didn't want to keep postponing it.

I found work I could do online.

And I kept going.

The one-month trip eventually became a five-year journey.

The beginning wasn't the glamorous digital nomad life I had imagined

People tend to tell travel stories backwards.

Once someone has visited dozens of countries, you see the confident version of them. You don't see the person standing somewhere unfamiliar at the beginning, checking Google Maps every thirty seconds and wondering whether they've made an enormous mistake.

I had plenty of those moments.

There were cities where I arrived knowing absolutely nobody. I would check into a new place, put my suitcase down and suddenly become very aware of the silence.

When you're traveling with somebody, the first evening is easy. You go out together, find somewhere to eat and talk about the trip.

When you're alone, you have to create the evening yourself.

At first, even going to a restaurant alone made me self-conscious. I imagined everyone noticing that I was sitting by myself, although in reality nobody cared. I would look at my phone far more than necessary simply because it gave me something to do.

Making friends was even harder.

I had spent years thinking of myself as "an introvert," and somewhere along the way I had turned that description into a rule: I don't approach people first.

Unfortunately, that rule doesn't work particularly well when you repeatedly arrive in cities where nobody knows you exist.

Eventually I had to choose between temporary awkwardness and permanent loneliness.

So I started saying hello first.

Travel didn't turn me into an extrovert. It made me braver.

This distinction is important.

I didn't suddenly become the loudest person in the room. I didn't wake up one morning desperate to make conversation with everybody around me. I still needed time alone, and I still sometimes felt nervous in new social situations.

What changed was my relationship with discomfort.

I learned that feeling awkward for thirty seconds wouldn't kill me.

If I was sitting near somebody who looked friendly, I could ask where they were from. If I met another traveler, I could suggest getting coffee instead of waiting for them to invite me. If I liked talking to somebody, I could say, "I'm going there tomorrow. Do you want to come?"

These things sound ridiculously small.

For me, they weren't.

Every time I initiated a conversation and the world didn't collapse, something shifted. Every time a stranger became someone I spent the afternoon with, my old belief that I "couldn't make friends" became slightly less convincing.

Of course, not every attempt worked.

Sometimes conversations went nowhere. Sometimes I met people I had absolutely nothing in common with. Sometimes I thought I had made a new friend and never heard from that person again. Sometimes I spent days mostly alone.

That was part of the education too.

You don't need every social interaction to become a friendship. You don't even need every destination to become a success.

Solo travel became easier when I stopped treating every imperfect experience as evidence that I wasn't capable of doing it.

Forty countries later, I see cities completely differently

Over the years, I visited around 40 countries and lived in very different places.

After a while, I stopped experiencing destinations purely as a tourist.

I became interested in what actually makes a city livable.

A place can be wonderful for a weekend and exhausting after three months. A beautiful neighborhood can be terrible if you're trying to work online. A city everyone describes as "friendly" can feel incredibly lonely if its social life revolves around established groups. Somewhere that looks chaotic on your first day can become surprisingly comfortable once you understand how daily life works.

I started noticing things I had barely thought about before: where people actually meet each other, whether it's normal to sit alone in cafés, how easy it is to work remotely, which neighborhoods feel comfortable after dark, how expensive ordinary life becomes once you're no longer behaving like a tourist, and why some cities make newcomers feel welcome while others keep them permanently on the outside.

I also started noticing how different reality could be from what I had read before arriving.

Sometimes I would search for very specific information and find twenty articles essentially repeating the same generic advice. The writer had clearly researched the destination, but I couldn't tell whether they had ever tried to build a normal Tuesday there.

I had.

And eventually I realized I had accumulated five years of these experiences.

That was how The City Theory digital magazine about expat life began.

Why I created The City Theory

I didn't want to create another travel blog telling people about "10 amazing things to do" in places they can already find on Google Maps.

I wanted to write about what cities actually feel like when you stay.

The uncomfortable parts included.

What happens when you move somewhere alone? How do you meet people when you're introverted? Which places work when you have deadlines rather than a two-week holiday? Why can one neighborhood completely change your opinion of a city? Why do certain cultural habits initially seem rude, strange or confusing to outsiders? Why do some places look perfect online but become difficult when you actually try to live there?

The City Theory grew out of all the questions I had during those five years.

In some ways, creating the blog also felt like connecting two versions of myself.

There was the woman sitting in an office, looking at other people's travels and thinking, I could never do that alone.

And then there was the woman who had eventually traveled through 40 countries, lived in different parts of the world, worked online and learned how to walk into unfamiliar situations without automatically assuming she couldn't handle them.

I wish I could go back and tell the first version of myself that she didn't need to become fearless before leaving.

She just needed to leave once.

If you're afraid to travel alone, don't start with "traveling the world"

This is probably the biggest piece of advice I can give.

Don't sit at home imagining yourself alone for six months on another continent if that idea terrifies you.

Make the experiment smaller.

Go somewhere for a week. Or two weeks. Choose a place where getting around is relatively straightforward. Book accommodation in an area where you can walk to cafés and restaurants. Make sure you have enough money for emergencies. Give somebody you trust your itinerary.

Then see how you feel.

You don't sign a contract promising to become a solo traveler forever when you buy a plane ticket.

You are allowed to dislike it.

You are allowed to come home.

Knowing that actually makes leaving easier.

And don't wait until you find somebody who wants exactly the same life. I wasted a lot of time believing that travel required a companion. The problem is that other people have their own jobs, relationships, budgets, fears and plans. If your life depends on somebody else being available at exactly the right moment, you can postpone it indefinitely.

Being alone and being lonely aren't the same thing

This was another thing I had to learn.

Yes, solo travel can be lonely.

I don't like the overly romantic version where people claim you'll instantly make lifelong friends in every hostel and spend every night surrounded by fascinating strangers. Sometimes you won't.

There will probably be evenings when you're eating alone.

There may be weekends when everybody you know is busy or has already left the city.

You may arrive somewhere and simply fail to connect with the place.

But loneliness isn't unique to travel. I had felt lonely while living a supposedly stable life and going to an office every day.

At least traveling forced me to do something about it.

If I wanted company, I had to participate in creating it.

That meant going somewhere instead of staying in my room. It meant accepting invitations when my instinct was to hide. Most importantly, it sometimes meant becoming the person who made the invitation.

That skill changed much more than my travels.

Learn to say the first sentence

If you're shy, forget about becoming "good at networking."

That's too big and artificial.

Learn one much smaller skill: say the first sentence.

"Have you been here before?"

"Where are you from?"

"Do you know a good place to eat around here?"

"Are you working remotely too?"

That's enough.

You aren't responsible for manufacturing an amazing conversation after that. Sometimes the other person will respond enthusiastically and you'll talk for an hour. Sometimes you'll exchange three sentences and go back to whatever you were doing.

Both outcomes are fine.

The goal isn't to make a friend every time.

The goal is to stop fear from making every decision for you.

Don't mistake fear for intuition

This one took me a long time to understand.

There are situations where something genuinely feels unsafe and you should absolutely leave. Solo travelers need common sense, awareness and the ability to say no without worrying about appearing rude.

But there is another feeling that can look surprisingly similar: ordinary anxiety.

"I shouldn't go to this meetup because I'll know nobody."

"I shouldn't eat there because I'll be sitting alone."

"I shouldn't speak to them because they probably don't want to talk."

"I shouldn't move to that city because what if I don't make friends?"

For years, I treated those thoughts as useful warnings.

Most of the time they weren't.

They were fear trying to preserve the life I already knew.

Learning the difference between this situation isn't safe and this situation is unfamiliar and I'm nervous changed my life.

You don't need to become a different person

I think this is what I misunderstood most when I was dreaming about becoming a digital nomad from my office.

I imagined that there were two types of people.

People like me: introverted, cautious, scared of arriving alone.

And "travel people": spontaneous, confident, sociable people who could land anywhere with a backpack and immediately make ten friends.

I thought I had to somehow transform into the second type before I could start.

I had it backwards.

The experiences created the confidence.

Every flight I figured out alone made the next one easier. Every city I navigated made another unfamiliar city less intimidating. Every problem I solved gave me evidence that I could solve the next one. Every conversation I started made saying hello slightly more natural.

Confidence wasn't the prerequisite.

It was the result.

The life I was waiting for started with something much smaller

If someone had told me when I was working in that office that I would eventually spend five years traveling, visit 40 countries and create a blog from those experiences, I'm not sure I would have believed them.

I certainly didn't have a five-year plan when I boarded that first flight to the United States.

I had one month.

That's all.

Then one decision led to another. I found online work. I stayed on the road. I learned how to live in unfamiliar places. I learned how to make friends when nobody approached me first. I became more independent and, eventually, much braver than I had thought I could be.

And somewhere along the way, the person who used to sit in an office dreaming about another life actually started living it.

That's ultimately why I created The City Theory.

It's a blog about cities, travel, remote work and living abroad, but underneath all of that, it's also about something much more personal to me: what happens when you stop assuming fear means no.

If you're currently sitting somewhere dreaming about traveling alone but telling yourself you're too shy, too introverted or simply "not that kind of person," I understand that feeling extremely well.

Don't promise yourself you'll travel the world.

Don't promise yourself you'll become fearless.

Just make the first experiment small enough that you can say yes.

Mine was supposed to last one month.

It lasted five years.