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I spent a decade taking annual trips to celebrate my birthday. Once I turned 40, I knew the tradition had to end.

July 13, 2026
in News
I spent a decade taking annual trips to celebrate my birthday. Once I turned 40, I knew the tradition had to end.
Woman standing overlooking aerial view of water, trees in Slovenia
Traveling for my birthday helped me realize I wanted to spend more of my time exploring the world. Hannah Wesley
  • From age 30 through 40, I took a trip every year to celebrate my birthday.
  • Then, on my 40th birthday trip, I decided that one trip a year was no longer enough. I wanted more.
  • I’ve found ways to make travel a big, sustainable part of my life that’s not limited to birthdays.

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

Woman smiling on boat in Copenhagen
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 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.

Woman smiling with another woman in Costa Rica
I celebrated a birthday in Costa Rica with my mom. 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

Woman smiling in Croatia
While 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 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.

Read the original article on Business Insider

The post I spent a decade taking annual trips to celebrate my birthday. Once I turned 40, I knew the tradition had to end. appeared first on Business Insider.

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