Shawn Jenkins Blog

Greece Shawn Jenkins

Discovering Inspiration in Greece

Stepping off the plane in Thessaloniki, Greece, my wife and I wondered if anyone would be on the other side of baggage claim to pick us up and take us to our hotel. We had somewhat blindly signed up for an event called Chautauqua a few months earlier and were now about to see what it was all about.

It was our first time traveling to Europe. We were excited, enthusiastic, and a bit nervous. We were certainly outside our comfort zone, and yet doing something we totally wanted to do.

Thankfully, our luggage made it, and as we broke though the pushing and pulling crowd, we saw a man holding the sign we had hoped to find: Chautauqua!

Rewind: Four or five years earlier I began to read a series of blogs on lifestyle design, mindfulness, personal finance, and this new-to-me Financial Independence (FI) Community. One of the first blogs I discovered in the FI community was by Jim Collins. It was Jim’s blog that ultimately lead to me climbing into a van in a far away land.

As we huddled around the back of this van we were simultaneously meeting new friends, stacking our luggage, and wondering where this journey was about to take us. It sounds a bit dramatic but that’s exactly how my mind processed it; as I lifted my left leg to climb into the van with these Chautauquans, I felt myself climb from the digital world of the online FI community into the 3D, real people, here-and-now world of the FI community.

Strangely, I had to go all the way to the Aegean Sea to have my first conversation with people about this lifestyle of retiring early. Fortunately, these strangers became fast friends and we began to share our stories and be absorbed into the community with open arms.

As a matter of fact, when we arrived at our hotel in Thessaloniki we were literally greeted with open arms. Our hosts, Katie and Alan Donegan of Pop Up Business School, ran up and gave us huge hugs and welcomed us. They pulled us over to a group of guests and our network of FI friends expanded exponentially.

It’s a strange thing to read the writing of an author and then to actually meet the author in person. We build these imaginary personas of the people we read. Perhaps stranger still is listening to audio of someone and then to meet them. On this trip we would do both. And in each instance our internal picture was confirmed and expanded.

The term Chautauqua is an Iroquois term loosely translated as “meet up.” And while this week would be filled with plenty of social time, chatting over meals, and excursions, there was also a series of talks planned from guest speakers, such as Brad and Jonathan of ChooseFI, Millennial-Revolution, and Jim Collins himself.

A common thread of this financial independence community is a sense of living an intentional life. It was inspiring to hear the stories of the guest speakers and the participants as they told of their personal journeys. The presentations during the week centered around ideas such as designing a life of intention, strategies for being bold in your endeavors, and practical approaches to investing your time and resources in ways that provide you the greatest return. 

One observation I came away with was the wide variety of paths people are taking to create for themselves both financial margin and flexibility with their time. At the event we met people who had started their own businesses, who were working at government jobs, who were in technical vocations and others in trades. Also of note, was the global nature of the group. People came from Switzerland, England, South Africa, Japan, Toronto, Dubai, and from the U.S.: Atlanta, San Diego, Seattle, Napa Valley, Arizona, Virginia, Wisconsin, South Carolina, and more. 

I believe what drew us all together was a desire to use our time, the one life we have, to do something unique and special. I plan to write more about the presentations and stories we heard during the week in future blog posts. 

The setting for our week was a boutique hotel overlooking the Aegean Sea at the foot of Mount Olympus. As I stood on the lawn of the property, I turned my head to the left to see the powerful mountain with the seat of Zeus atop, partially covered in snow. I turned my head to the right and saw the aqua-blue Aegean Sea with fishing boats out making their catch for the day. Scattered in between were charming small towns dotted with cafes and coffee shops.

My wife and I rented a car one day and journeyed out on our own. I am not sure why it was such a big deal to me, but driving a car around Greece was so thrilling and carried some sort of significance for me. It felt like we were taking a summer off right out of highschool and backpacking through Europe. The sense of freedom and unplanned adventure surged through me. My heartbeat escalated as we deciphered the mysterious Greek road signs and whirled our way down the coast.  

On our drive we visited the Castle of Platamonas. As we walked around the grounds we talked about ways to encourage our children to explore the world. A fire was lit in us to expand our experiences with our family and friends.

We met up with some of our group in the alpine village of Ampelakia. It was such a unique feeling to be in a new place and then see familiar faces. And yet the faces were not known to us just a few days prior. The contrast of completely new experiences with familiarity, similar to the contrast of the mountain and sea, was woven through the week. It had awoken our senses with the expectation of seeing something new, yet provided the comfort of being with friends.

As the week went along, I observed a platform emerge below my feet: Chautauqua.

It’s fascinating to me how people create all manner of platforms. Chautauqua, which began in Ecuador, with Jim and some friends gathering to experience a cool place and have cool conversations, has become a platform. It is forging new friendships, sharing ideas that help people create the future they want, and leading to new blogs, podcasts, documentaries, and who knows what else.

Similar to when I climbed into the van from the airport, I had a second experience that was like a “click” snapping two ideas into place in my head. It was during Jim Collins’ presentation to the group. He explained to us that his original idea for his blog was to document his philosophy on money and life so his daughter would be able to have them as she made a life for herself. In that moment, I fused together my desire to write with my desire to help my own children create for themselves a life they enjoy.

Perhaps we need to travel to new places and meet new people to find what we have been carrying around all along. I knew in that moment I had discovered the inspiration to begin this blog.

I have been thinking about starting this blog for a while. I registered the domain a year ago. It was this trip to Mount Olympus that provided the final nudge I needed to bring it to life. To do the work of founding something once again.

Thank you, Jim and Jane, for trusting your instincts enough to propose such an outlandish idea. It is those outlandish, outsized, ideas that lead to big things.

Thank you, FIRECracker and Wanderer of, for your inspirational presentation. You ignited a spark in us to travel and explore the world.

Thank you, Jonathan and Brad of, you inspired us to join and help build a local FI community in Charleston.

Thank you, Katie and Alan of Pop Up Business School, for the hug and for the opportunity of hosting your event for entrepreneurs in our home town.

And thank you to all of the Chautauquans for the open arms and wonderful stories. We cannot wait to see what you all do on your journeys.

Jocelyn and I with Jim Collins at outdoor cafe dinner
On Mount Olympus with FIRECracker and Wanderer of Millennial-Revolution!
The Seat of Zeus atop Mount Olympus
Jonathan and Brad dialing us in on designing a well lived life

Bumping in to friends for lunch at Ampelakia

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