I spent years building a 'perfect' life and career in Chicago. Then, I left it all behind to move to Portugal.

I built the life everyone told me I should want.

I was the chief operating officer of a growing company.

From the outside, everything looked like a success.

Yet any chance I got, I would leave.

Sometimes with friends, sometimes solo.

Traveling was the only time I felt truly like myself.

When I came home, I’d start planning the next escape — sometimes before I had even unpacked.

I spent years creating a life I perpetually needed breaks from.

I dreamed of leaving corporate, starting my own business, and moving to Europe.

But three fears kept me frozen: losing financial security, disappointing my mom by leaving as her only child, and having to rebuild a social life from scratch in a foreign country.

Yet despite the fears, the pull to leave grew stronger with every trip.

I was just waiting to feel truly ready.

After some conversations with a therapist, I realized I was waiting for a feeling that wasn’t coming.

I was going to have to do it scared and accept that I would disappoint people in order to choose myself.

I put everything I owned into storage and, in April 2023, left the US with two suitcases and a one-way ticket to Europe to test-drive being an expat.

Roughly two weeks into the trip, I was sitting in my Airbnb with the sun shining in through the open window, the sounds of the lively Lisbon streets outside, and a cup of espresso when it hit me: This is it.

The feeling surprised me, but I was as certain as I’d been in a long time.

A month later, on my birthday, I was in Bodrum, Turkey, overlooking the sea when I watched a video tour of an apartment in Lisbon.

It checked every box on my wishlist.

Then came the part I dreaded the most: telling people I was essentially quitting my current life.

She cried when I told her I was leaving.

But after some time to process, and a promise that I would return home for Christmas, she said more than anything, she wanted me to be happy, and she would learn to cope with my decision.

She said she knew this was coming eventually.

She even sent me off with clients to help me get started in my new business venture.

Paperwork, appointments, and a whole lot of Google Translate.

It wasn’t easy, but it also wasn’t the impossible task I had built it up to be.

It was mostly just navigating government websites, following steps carefully, reading fine print, and a major lesson in patience.

At last, it was time to face the final fear: building a new life from scratch.

I joined every expat community I could find.

I slid into the DMs of local Instagram influencers.

I attended dinners designed for singles to make friends.

I went to parties where I knew one person and tried not to cling.

It was awkward at times, but if I walked away with one new friend, I would consider it a success.

Slowly but surely, my friendship circle grew.

By the end of that year, as I posed for a photo at a holiday dinner with friends, I looked around and realized I had built exactly what I had been afraid of losing.

A sense of stability I didn’t expect to find so quickly.

I had a busier social calendar in Lisbon after six months than I did after a lifetime in Chicago.

My mom and I started taking trips together, something we never did when we lived 20 minutes apart.

The distance made our time together far more intentional, which actually deepened our relationship.

Three years later, I’m starting another new chapter in Amsterdam with a level of confidence I never had before — something I never could have imagined when I boarded that one-way flight to Lisbon.

This time, the excitement far outweighs the fear.

What once felt like rebuilding a life from scratch now feels like an opportunity to meet interesting new people and embrace a new culture.

The friends I made in Lisbon are already planning to visit.

I’m leaving Portugal with far more than I came with.

My only regret in this journey is spending too many years waiting to be “ready.” All I ever really needed was a big dose of courage and forward momentum.

But it was far more manageable than I had imagined.

The fear of taking the leap was much harder than the leap itself.