One Month & 7 Years Of Big Questions

One Month & 7 Years of Asking Big Questions

By: Michael Youngblood, Co-founder, Unsettled.

Last month was one of the most Unsettled months I’ve lived.

I sailed one of the longest passages sailors tend to make these days: 5,150 nautical miles through the Panama Canal and onto Hawaii on a 45 foot sailboat with three Unsettlers.

In true Unsettled style, I realized the most meaningful aspect of this trip wasn’t the adventure itself. Rather, it was the time and space this trip gave me to process a really big question that’s been on my mind for a while.

How’d this sail from Panama to Hawaii transpire? 

We started Unsettled 7 years ago by asking a big question, ‘How can we live and adventure given all the new ways of working in the world?’.

We haven’t stopped running (literally & figuratively) these trips – both the sailing trips, like our next one in Ibiza in June, and our traditional coworking retreats for remote workers.

Since our founding, my co-founder Jon and I have always thought of living Unsettled as a positive state full of questions to explore and possibilities to pursuit. When our lives are unsettled, they’re full of opportunity, potential, and movement precisely because something in life is fluid and open. 

Unsettled. Adj. Not yet resolved. Not fully stable. 

We’ve tried to design our experiences with this in mind. It’s why everyone who sails with us is part of a crew; not passengers on a cruise. We take the stance that there are no passengers on spaceship earth. Only crew. It’s how we’ve operated and co-created all of our experiences over the last 7 years. 

Fast forward to a couple of months ago. In early December, I was leading our Unsettled British Virgin Islands sailing adventure. Midway through the trip, I received a text message from Jose Castillo, one of our regular captains (Unsettled Baja ’19, The Bahamas ’20, and Croatia ’22) asking if I’d be interested in delivering a sailboat to Hawaii with him.

I was ‘in’ from the start. I literally grabbed another participant who was on that BVI trip with me, Raul (Unsettled Tahiti ’21 and BVI ’22), and asked if he wanted to go. We had a shot of rum and decided then and there that we were both sailing across the Pacific. 

Lesson: You never know what you’re going to get out of an Unsettled trip. Being pulled into a month-long sailing passage shouldn’t surprise anyone who’s been on an Unsettled trip. We can’t even count the business partnerships, relationships, marriages, career changes, and life turn-up-arounds that we’ve witnessed.  

So we had a boat. We had a plan. We had a crew. Jose, his friend Andy, Raul, and me. Like any good Unsettled trip, we all brought something to contribute. Jose was was our captain and overall leader. Raul is a sharp sailor and has an engineer’s mind to fix problems. Andy was trained as a chef and specializes in sushi (for all of our planned fishing).

And me? Well, yeah, I can sail, fish, and lead adventures, but more than anything I brought some questions along… 

Why not take your work on the road?

An Unexpected Realization 

We crossed the Panama Canal in wonder. We updated some unsettled alumni who were from Panama, had worked there, or were following our journey. 

We learned about the history of the Panama Canal from books and from an Unsettled alum who shared the story of her indigenous grandfather’s home being uprooted and working on the canal as we were crossing it.

The trip was starting right as I’d hoped, connecting people, place, and purpose all together in a great adventure. 


Why not take your work on the road?

We left land behind on New Year’s Day, fitting. Routine set in pretty quickly. Raul and I did night shifts from sunset to sunrise. The days quickly turned into weeks as we crossed the Pacific.

About halfway across, I realized that we were about as far from civilization as anywhere on earth. 

On a night watch on day 18, I watched the international space station fly 254 miles above us. That same night there was a pod of dolphins swimming around the boat, their bioluminescent trails shooting through the water all around us. 

Looking around the sky that night, I realized that for much of their time in space, astronauts were closer to civilization than we were at that moment. Were were thousands of miles away from the closest town. Space was all around, above, and below me.

Why not take your work on the road?

It wasn’t lonely, but we were clearly alone. 

It made me think how I hadn’t seen a plane in 18 days. I hadn’t seen social media, the news, email, or text. There was no outside noise. No expectations. Only me floating through this liminal state between civilization and a great void of space.

This is when I realized this was the real gift of this adventure. There was no one to influence my questions, decisions or next steps in life except me. 

I was alone out there to reflect on the last 7 years at Unsettled, and I loved it. 

I believe that taking time alone is one of the best ways to cultivate your true north in life, and this helps us ask and answer big questions. 

Once you start figuring out the answers, one of the best ways to bring it into reality is to surround yourself with a community of people who’ll be part of the solution. 

This is the essence of Unsettled to me. It’s your own journey to ask yourself big questions, and when you’re ready, to join a community of people living differently who are ready to make things happen. 

Naturally, the big question on my mind was about what’s next for me. What to do with Unsettled, the business Jon and I co-founded 7 years ago. 

Out there in the wilderness, I arrived at half the answer:

I’m ready for new adventures. Ready for change. I’m ready to find new ways to bring meaning and an impact into the world. I’m ready for Unsettled to find a new home, bring on new leadership, or merge with a new partner. 

This is the part that I needed to figure out on my own. The open sea gave me what I needed.

What I’d like to figure out next, is best done within this community:

What’s the best home for Unsettled? What should the future look like? How can we combine adventure and community better than ever?

We’re assessing opportunities at our doorstep, and are looking for community input. 

If you have something that you want to share, please reach out to  

Unsettled is a global community for those who embrace the unknown and value meaningful human connection. Our mission is to inspire a lifelong pursuit of growth, meaning, and adventure through travel and shared experiences.

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