My sister and I spent a week in Santorini to celebrate my 30th birthday. Somehow that became a sacred tradition, and for the next decade I made a trip every year to celebrate my birthday. I called one birthday road tripping from Seattle to San Diego in a Mustang convertible and another touring castles and
My sister and I spent a week in Santorini to celebrate my 30th birthday. Somehow that became a sacred tradition, and for the next decade I made a trip every year to celebrate my birthday.
I called one birthday 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 aging by eating tapas and watching flamenco groups perform during a solo stay in Madrid, and another, I ziplined through the Monteverde cloud forest in Costa Rica with my mom.
For my 39th birthday, I spent an afternoon on a floating spa on the St. Lawrence River during a trip to Montreal. In each of these places I had the excitement of discovering new neighborhoods, languages, customs and cultures.
For my 40th birthday, I planned a whirlwind trip through Europe with several stops with a friend to kick off the next decade. It was in the final stretch when I realized that this tradition had run its course.
One trip a year was no longer enough: I wanted more.
my 40th The birthday trip ended up being the last.
My 40th birthday trip included a stop in Copenhagen. Hannah Wesley
This tradition had started during the time in my life when I was making less money, had fewer vacation days, and held junior positions where taking too many days off was discouraged.
The limited PTO I had was used to celebrate friends and family when they reached traditional “adult” milestones: weddings, engagements, bridal showers, and baby showers.
My birthday week abroad was a way to make sure I remembered to celebrate it too.
By 40, the wedding season was over and the friends had settled into lives focused on their partners, children, homes and careers.
Meanwhile, I was single and childless, and after diligently climbing the career ladder, I looked around and realized I really didn’t want to be there.
I celebrated a birthday in Costa Rica with my mom. Hannah Wesley
The thought of spending the next 25 years working at jobs that brought me very little joy, motivated only by the promise of a week or two living “the life that could have been,” suddenly felt intolerable.
Somehow, this tradition created to expand my travel experiences had, in fact, reduced them to a box on a shelf that I only removed once a year and then put back 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.
Over time, I have built a life more focused on traveling.
While I was trying to figure out how to travel more, I spent some time in Croatia. Hannah Wesley
So, a few months after that 40th birthday trip, I adjusted my budget, started saving as much as possible, and looked for a tenant to rent out my house so I could also have passive income.
Shortly after I left my job and two weeks later I took a flight and spent the next three months traveling through Croatia, Bosnia and Herzegovina and Slovenia.
I returned home long enough to figure out how to make a travel-focused life more financially sustainable.
I got freelance work at my old agency, found new long-term tenants for my house, and began earning a certification in astrocartography, a practice that uses the birth chart to identify the best places in the world to travel.
Now I can work from anywhere in the world on a schedule that I set, and at the same time I gain experience in that practice.
It feels good to finally be building a life centered around travel instead of one where it’s a rare pleasure.
