Learning to Embrace the Unknown, the Unexpected, and Serendipity when Traveling to Foreign Lands

Updated: Feb 27, 2018

"Cat: Where are you going?

Alice: Which way should I go?

Cat: That depends on where you are going.

Alice: I don’t know.

Cat: Then it doesn’t matter which way you go.”

Extended travel isn’t everyone's cup of tea, but it's my beverage of choice and I couldn't imagine a life without it. I’ve always loved to travel, but I’ve never had the opportunity to do it for an extended period of time as an adult ("responsibilities" and whatnot). I’m passionate to write this blog for both audiences: those who are obsessed with traveling, and those who hear the call but are apprehensive to embrace it. After nearly 3 months on road, rail, air, and sea, I have more real-life examples to help me understand what about traveling really turns me on.

Serendipity, and the flexible mindset that allows you to take full advantage of it.

Serendipity is EVERYWHERE in life, but you especially start to realize it's frequency when traveling to new places and meeting new people. If you embrace serendipitous opportunities, keep your travel schedule as flexible as possible, and keep a positive and open mind, anything can, and often will happen. 

When I boarded my first flight to Phuket on December 8th, I had zero idea what I was getting myself into: no hotel reservations, and no set schedule or firm plans. That decision played out better than I ever imagined.  Lesson learned: be prepared but don’t over-plan. 

Some abbreviated examples: 

I met Gabe on my first day in Thailand. We were both on a ferry in Koh Phi Phi Island, Thailand. I still hadn’t booked a hotel for the night, but Gabe and I struck up a conversation. From our quick chat, we learned that we were both from Florida and had a dozen close mutual friends. Now basically best friends, I ended up staying in Gabe’s extra bed in the Ibiza Bungalows. The bungalows and their location were so perfect, that we ended up booking these bungalows for all of our guests for Now or Never Trips #destinationTHAILAND. Gabe also introduced me to an incredible videographer who we ended up booking for Now or Never Trips. In Koh Phi Phi, I also met up with the owner of Treehouse bar, a guy I had met on a trip to the island 2 years prior. He immediately recognized me and was excited to work with us on the Koh Phi Phi excursion events we are planning for the trip.

From there, I decided to join my Hong Kong favorites, Evan (Brutal Force) and Madison at a music festival in Pattaya. WonderFruit (coined the burning man of Thailand) was the one of the weirdest and most wonderful experiences. At the festival, I met two additional people, Roe and Simone, who have quickly become some of my best friends as well as incredible advocates for Now or Never Trips. I now have a lovely family of friends in Hong Kong.

In Cambodia I had a perfect trip planned out for me because a friend I had met prior, Victoria, had lived there for 6 months. She introduced me to many friends, and showed me all the best spots. 

After that, courtesy of Gabe's introduction, I got invited to watch an incredible up-and-coming Chicago DJ, Tony Arzadan preform in the biggest club in Macau, Club Cubic. Being part of his entourage that night was one of the wildest nights of my trip. All the awesome guys I met on that trip are now meeting me in Bali in 2 weeks. I’m also working with him and his team to set up additional gigs in Asia (hopefully a few for Now or Never Trips).

Through introductions from friends, friends of friends, or random meetings, I have become close with business owners and millionaires in tech, travel, investment, hospitality, crisis PR, and video production just to name a few. It's intimidating because many of these people have already “made it;” they have profitable and sustainable businesses that are growing. Yet when I get to know them, they have as much interest in my story as I do in theirs. 

These experiences are not unique to me. These encounters happen to all adventurous travelers who allow it. Never underestimate what can come from random chance, or if you believe in it, from serendipity. Embracing the unknown will provide some of the most incredible memories, friendships, and experiences that you could ever imagine.

I feel so fortunate for my personal journey, and that is what we are creating with Now or Never Trips (with a little less uncertainty and planning on the part of our guests). I hope serendipity will bring you to our first trip in April or our next trip in November!

Much love,


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