A possibly irresponsible, albeit quick, trip to Portugal: Part 1

Letter #2: I shouldn't have booked a solo trip to Portugal when I knew I wanted to blow up my entire life anyway and go on the road. But my therapist also told me I need to be done with "should's".

Towards the end of summer my desire to travel internationally became very strong again. That desire had been quiet for most of 2022 as I was working longer days in the beginning of the year, and so focused on improving my self-care by the summer, that I was okay with not making travel a big focus in 2022.

Several years ago I had made a 5 year plan, which included traveling internationally at least 3 times a year. I realize it sounds like a lot, but I included work travel and my sometimes yearly trips to Mexico in my plan. But this year was different. I had only planned a few trips home to the Midwest, a long weekend to New Orleans with my childhood best friend, Alie, and a visit to Montana for my high school friend’s wedding. I had plenty of exciting plans coming up, but inevitably my urge to get out of the country and go somewhere unknown, exotic, and exciting became so strong, I felt I was going to burst with unhappiness of having to stay in one place.

So, around August 1st, I checked with mom regarding family plans for Thanksgiving. My parents keep many wonderful holiday traditions, and, while I love being part of them, I sometimes cause heartache when I choose to do something different with my paid leave from work.

For reference, I had been at my last company for nearly 10 years, and only had 15 days of paid vacation time per year. Not enough to travel the world AND spend meaningful time with family and friends across the country. It has been quite a pain point for me over the years (as I mentioned in my previous post).

My parents’ Thanksgiving plans were different this year, and I was so gracefully “let off the hook” from having to book $350 roundtrip tickets from NYC to Milwaukee.

I immediately hopped onto Google Flights Explore to see where I could get to with direct flights under 9 hours. Between Jamaica and Portugal, Portugal won. With roundtrip tickets at $430, how could I resist heading over to Europe? I hadn’t been to Europe since 2016 and had never been to that coast. It’s been talk of the town around New York—everyone going to Portugal for the easy European living, inexpensive wine, and amazing seafood. “Better get there before tourism blows up and it reaches the prices of Paris.” It seemed like a knock out of the park. Perfect for solo travel and inexpensive enough that I wouldn’t have to worry much about saving money for the trip. Only 5 days and 4 nights!

I had it in my heart for years that I wanted to blow it all up. Quit my job, travel the world, and start over. But I kept putting it off. An opportunity at work would come up. I was too fearful about walking away from a consistent paycheck. And dammit I just LOVE my life in New York!

Because I continuously put off this dream of mine, I needed the band-aid of a quick trip to calm my anxiety of not living the nomadic lifestyle I deeply wanted to experience. So there you have it. A possibly irresponsible band-aid trip to Portugal when I should’ve saved money to live out my greater dreams.

Little did I know in that moment I would decide just a month later that I was actually doing it. Quitting my job, letting go of my apartment, selling my worldly goods. Keeping the Portugal trip in November seemed silly since I’d be going international anyway. But the flights would’ve cost so much to cancel, I decided to keep them and treat this as a little celebration for my momentary retirement from capitalist America. And, yes, in case you are wondering, I will 100% have to go back to work at some point.

Stay tuned for my next post, where I will share reflection of my time spent in Portugal and the wonderful friends I made on a wine tour in the Douro Valley.

I realize I need a more original title than “On The Road”, although I have the read the book by Jack Kerouac, chronicling his cross-country adventures by car with his friend, Neal Cassady, and it feels fitting at the moment. That said, I am open to suggestions for title updates and feedback on my writing as I learn how to share my thoughts and experiences with my audience. XOXO, HK.