Being A Bit Unsettled in Tuscany

Wendy Castleman
Jul 1 · 6 min read

Sixteen women from around the world arrived at the Podere San Giorgio in Palaia, Italy at the beginning of June. These women had never met and yet they formed a close and supportive community within a couple of days. They blended work and play over 14 days and are carrying their relationship forward as a virtual community that is thriving weeks later.

I was one of those 16 women at the Unsettled Tuscany co-working retreat in Tuscany. It was a fantastic experience and taught me quite a few lessons about what work/life balance can really look like in an ideal world. I’d stumbled across Unsettled when I was researching sabbaticals last fall. The idea of a coworking retreat intrigued me and I decided that I needed to find out what it was about.

A co-working retreat is a gathering of people to work and play at some location away from your everyday office. The retreat that I participated in was held by Unsettled which is a company that offers retreats worldwide with a global audience. The two week retreat was coincidentally all women who were ranging in age from the late 20s to early 50s. All of us were professionals who had success in various fields. All of us were fiercely independent and most of us were at a moment of transition in our personal or career life.

In my case, I was pivoting from one business model to another and I wanted to take some time to really create a strategy for moving forward. I also had some important decisions to make for the upcoming year and my involvement in various work situations. I did some writing and had some meetings too.

At the retreat some of the women gave workshops on various topics. Other women did other things for the group including hosting dinners, parties, dance lessons, yoga sessions, karaoke nights and other adventures.

Since we were in Tuscany, of course food was central to what we were up to. We shared meals most of the time. There was a lot of gelato. There were gallons of olive oil. Pasta! Bread! Prosciutto! Mozzarella! It was indulgent and glorious.

We also did optional day trips, traveling to various locations in the area including the Cinque Terre, Florence, San Minato, Sienna, Lucca and Volterra. I went on some of these and skipped others to focus on work. I didn’t feel that I missed out, though, because I did make sure to immerse myself regularly in the present of being in Tuscany.

We spent a lot of time getting to know one another and building community, which was really one of the most important pieces of the experience. I was particularly struck by the things that our host did to very quickly create community out of the 16 strangers.

The audience was global. We had a doctor from South Africa, a supply chain manager from Dubai, A former human rights lawyer and now breath coach from Zimbabwe, a former lawyer and now law recruiter from Derbyshire, a lawyer from London, a neurosurgeon from Pakistan, a hotel manager from Lebanon, a college professor from Montreal, a television programming director from Puerto Rico, a design director from Miami, a woman who sells thoroughbred race horses in Lexington, Kentucky, a finance professional from Dublin Ireland, a travel facilitator from Cyprus, a branding design professional from St. Louis, the two digital nomads (one from New Jersey and the other from Vancouver Canada), and me (from California). It was a melting pot of people who all were so different and yet, so… similar.

I was certain that the best part would be getting time to myself to think to be creative to be inspired. However the best part, when you have an amazing community, is the people. This set of women were supportive, smart and funny. We almost instantly became best friends. Yes, of course I had time to think and be creative. BUT, I was able to think and be creative with other awesome people. It gave me a sense of belonging and confidence in what I was doing and how I was going about it.

What fascinated me about this experience was the concept of blending work and play. In my experience researching sabbaticals last fall, I spent some time chatting with people who have chosen to have a digital nomad life. This is a life where you can be on the road and maybe not even have a home. You stay and work in various locations including things like unsettled. In fact we had two digital nomads out of the 16 women who were at my retreat. One was a former physician who is now working remotely as a hospitalist. One was a controller and business ops person who had just moved on from her last position and was spending this time figuring out what her next remote position was going to be. Like all of us, they had a deep passion for play and enjoyment in addition to work. These two just did it all the time.

This two week retreat gave me an idea about what that could look like and how to embrace it in my own life.

Today, we are always on. Since we are connected to the internet, email and our phones all the time, we are always reachable. And thus, we are always working… Unfortunately, that doesn’t translate to that we are also always playing.

These days, most Americans don’t take all of their vacation. Realistically, even when we’re on vacation, we still do some work. So this idea of blending work and play is really important to our mental well-being and probably physical health.

It wasn’t a vacation. In my case I did quite a bit of work a lot of writing met with clients and also created strategy during this two-week period.

Some of the things I learned are going to roll into some of the new programs I am developing.

Although Unsettled is focusing more towards vacationing with people and community (in fact they’ve been introducing one week experiences lately including the one in Tokyo and the one in Beirut, Lebanon), I am interested in the reverse. I am interested in how to blend work and play in a way that is focused more on work but including play.

I intend on following Unsettled’s lead and rely heavily on a curated community. There’s nothing better than coming together with new people and doing great things. That’s my style, so that’s what I’m up to. Look for some of my new offerings including a retreat for new executives and a mastermind group for new UX and design thinking leaders. I’m looking for new people to bring together in a way that will effectively blend work and play. Wanna come get work done and play?

Wendy Castleman

Written by

MasterCatalyst, Coach, Facilitator, Wife, Mother, Dreamer

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