My sister and I spent a week in Santorini to celebrate my 30th birthday. Somehow, that turned into a sacred tradition and, for the next decade, I took a trip for my birthday each year.
I rang in one birthday by road-tripping from Seattle to San Diego in a Mustang convertible and another touring castles and distilleries in Scotland with a friend.
One year, I celebrated getting older by eating tapas and watching flamenco troupes perform on a solo stay in Madrid and, for another, I ziplined through the Monteverde cloud forest in Costa Rica with my mom.
To mark 39, I spent an afternoon in a floating spa on the St. Lawrence River during a trip to Montreal. In each of these places, I had the thrill of discovering new neighborhoods, languages, customs, and cultures.
For my 40th birthday, I planned a whirlwind multi-stop European trip with a friend to kick off the next decade. It was on the final leg that I realized that this tradition had run its course.
One trip a year was no longer enough — I wanted more.
My 40th birthday trip ended up being my last
Hannah Wesley
This tradition had started during the time in my life when I was making less money, had fewer vacation days, and was in junior positions where taking too many days off was discouraged.
The limited PTO I did have was used to celebrate friends and family as they achieved traditional “adulting” milestones: weddings, engagements, bachelorette parties, and baby showers.
My birthday week abroad was a way to make sure I remembered to celebrate myself, too.
By 40, wedding season had died down, and friends had settled into lives centered on their partners, children, homes, and careers.
Meanwhile, I was single and child-free, and after diligently climbing the career ladder, I looked around and realized I didn’t really want to be there.
Hannah Wesley
The idea of spending the next 25 years working in jobs that brought me very little joy, motivated only by the promise of a week or two living “the life that could have been,” was suddenly intolerable.
Somehow, this tradition created to expand my travel experiences had, in fact, shrunk them into a box on a shelf that I only took down once a year, and then tucked away again for 50 weeks.
I wanted to know what it was like to experience the places I visited on a deeper level, not just as a tourist.
In time, I’ve built a life more focused on travel
Hannah Wesley
So, a few months after that 40th birthday trip, I tightened my budget, began saving as much as possible, and searched for a tenant to rent my house so I’d also have passive income.
Soon after, I left my job, and two weeks later, I boarded a flight and spent the next three months traveling around Croatia, Bosnia and Herzegovina, and Slovenia.
I returned home for just long enough to figure out how to make a travel-centered life more financially sustainable.
I secured freelance work with my old agency, found new long-term renters for my home, and began a certification in astrocartography — a practice that uses one’s birth chart to identify the best places in the world to travel.
Now, I am able to work from anywhere in the world on a schedule that I set, while also gaining lived experience in that practice.
It feels good to finally be building a life that’s centered on travel rather than one where it is a rare treat.
