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Exercises in Big Thinking: Island Hopping for 1/2 the Year

I’m a firm believer in Thinking Big when it comes to designing your life.

Following the path that's traditional or aligned to the status quo, or even popular isn't a significant priority to me. I don't actively try to be unconventional but I am invested in creating my ideal life, regardless of how unconventional that may look - and when I learn about other people who are living in a unique way, I lean in and try to learn more.

Like Ramit Sethi - after talking to a friend and learning that they took a honeymoon that lasted for a year, he and his wife decided to take a six-week honeymoon through Italy, Kenya and Thailand - inviting their parents along for part of the journey to treat them to a trip and make new memories as a family together.

I absolutely love that. I plan to have an extended honeymoon and a family bonding experience with my life partner - and that's something that I may not have ever considered if I hadn't left my bubble.

I want to highlight and share these Big Dreaming and Big Thinking experiences that I come across regularly - including my own. Because one thing that I’ve discovered on this journey is the importance of leaving room for serendipity. And as much as I love planning, I have to leave space for opportunities that are Bigger than what my imagination had even dreamed up. It may have never occurred to me to start a one-person online business, live on the road or travel the world if I hadn’t been exposed to it. And I want to keep exposing myself, and you, to the many different paths taken by Big Thinkers and Big Dreamers.

I was reading one of my old tweets from 2010 (on my super secret anonymous Twitter account) and I came across one that essentially said: Wow, I would love to spend a month in Italy. That would be a dream come true.

And there’s nothing wrong with that dream. But as someone who now lives and spends indefinite amounts of time in places where I once fantasized about vacationing, spending a month there is a small dream.

So, my most recent exercise in Thinking Bigger and Dreaming Bigger:

I’m spending the next six months island-hopping through Southern Europe, the Caribbean & Latin America.

The current plan is starting in Greece (where I currently am) and then moving to Southern Italy, the Canary Islands in Spain, and then jumping to Mexico, Cuba, the Dominican Republic, Jamaica, Aruba, Curacao, and the Bahamas, with a possible transition to Ecuador, Colombia, and Brazil.

As usual, I’m not holding these locations too tightly - maybe I’ll fall in love with a place and want to stay for a while or discover a new place that I hadn’t considered. Maybe I'll end up shifting to Asia and exploring the Thai islands, more of the Philippines and different parts of Indonesia. Who knows? But I’m excited - for the food, for learning how to sail, for scuba diving and landmarks like the Underwater Ruins, and for the sun. I’m excited for the sense of freedom and reduced inhibition that I feel when I embrace island living and I'm excited about the time that I’ve carved out every day for my art. I’m excited for the burst of creativity that comes with being in a new place and as always - I’m excited to see what I’ll learn.

Here’s to Thinking, Dreaming and Living Bigger.

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