Warning: Honesty ahead. And mixed verb tense.
Planning days are the worst. Sitting in front of a laptop for hours, sometimes days, on end… working every possible combination of transportation and accommodation, balanced with equal parts budget, adventure and relaxation in mind… and just when my eyes begin to cross and my head wants to run screaming into the wild blue… the perfect itinerary finally emerges. Flights get booked, Airbnb or hotel reservations are made, and, of course… my Google spreadsheet gets updated.
Today will be one of those days. I find myself in Santorini, a tiny spec of an island sitting just at the cusp of the Mediterranean and Aegean seas… in a fantastic suite nestled in the volcano cliffs… with a reservation that ends in just four days, and not a single plan made after that point.
Where will I go from here? Where will I stay? How will I get there?
Just over two weeks ago I left Ireland after an amazing three month tour (including a long weekend trip to Paris to visit a high school friend, like ya do). I spent a few days in Brussels, bumming around the city center and gorging myself on waffles. I breezed through Luxembourg, taking in as much as I could in just one night. I was then whisked off to Germany for the wedding of another dear high school friend, where I met many fantastic people, made some lasting friendships, and got just a taste of German culture and family life. Then only a week after leaving Ireland, I was off on a 645am flight headed to Athens, Greece… with friends new and old… and spent a few quick days exploring the ruins, laughing and eating our way through the massive, ancient city. Just two days later, we were off on a pre-dawn ferry through the Greek islands and into the village of Oia (ee-ah) on the island of Santorini. After another whirlwind few days of sightseeing, laughing, eating and drinking (raki!!)… it seemed just as soon as our week together had begun, my friends were headed back to Germany, and once again I slipped back into the peace and quiet of isolation. I moved just a few kilometers around the edge of the island into the main village of Fira, and have spent the last few days soaking up the sun, the views, and the magical sunsets.

Truly amazing adventures. Yet, at the same time, constant travel is exhausting. Overwhelming, in fact. Sights, sounds, tastes all come in a flash… memories that will certainly last a lifetime, but little time to process. Somewhere, sometime, during these last few weeks… I started to break. I believe it was inevitable. Mentally, physically, I was feeling drained. Homesickness started to creep in. One morning shortly after arriving in Santorini, while surrounded by pure and intense beauty, I awoke in a panic. Emotions rushed over me… words can hardly describe what I was feeling, words which I’ll save for another post for another day (working title: “Fear is the Mind Killer,” or “What the Fuck Am I Doing?!?”).
My head, bombarded by emotion, was screaming to go home. I craved purpose, direction. My heart, however, urges me on.
So back to the question… what’s next?
This afternoon I have an interview over Skype with a program called Unsettled. The program lasts one month, from mid November to mid December, and is based in Porto, Portugal. Unsettled is a semi-structured coworking, coliving retreat for individuals just like myself. The program brings together 25 people from creative and entrepreneurial backgrounds to live, work, and explore the historic city of Porto together. Seems like the perfect opportunity at the perfect time. A chance for me to collect my thoughts, finally begin posting the thousands of pictures I’ve taken, and begin the planning process for my return to reality. All while collaborating with other like minded individuals. For more information, check out this recent article in the New York Times.
Assuming I’m accepted into the program, that just leaves a gap of a few weeks to fill between Santorini and Portugal. Since starting this post, I’ve already extended my stay here in Santorini for a few extra days. I’m hopeful that the rest and relaxation recharges me enough to push through.
While in Porto, I’ll decide how much further I’ll go. However, at this point, I’ll most likely be back stateside for the holidays.
So The Gap Year may not last a full 365 days… but who’s counting? It’s the challenges, both behind and ahead, that matter most.
Stay tuned for updates… wishing you all much peace… #namaste #tooblessedtobestressed #bepresent