Lessons from Hosting 4 Days and 4 Nights in Tuscany

People hanging out next to a big pool

Welcome to my Tuesday Newsletter. Every week, I share one leadership tip, one public speaking tip, and one adventure tip.

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Now, onto the 10.24 Issue.

4 days at a villa in Tuscany

Each year, I host a retreat for members of my Samita Lab Mastermind.

The retreat was in May of this last year. The goal was to harvest deeply personal stories in service of the TED x style talk each woman would be delivering in November.’


What we we did

The objective:

  • Created the whitespace to allow the stories to bubble up by going to a remote and beautiful place


We were an hour outside of Florence at this castle-turned-villa, surrounded only by olive trees and mountains. Given the remote nature of the home, we had a chef on premise, making breakfast, lunch, and dinner. In addition to the writing exercises, the retreat featured a cooking class, a wine and bike, and an olive oil tasting to

  • deepen their relationships with each other
  • deepen their relationships to themselves
  • cultivate vulnerability
  • get them outside their comfort zone


Why I did it

Adventure is my top value.

It changes people. See this graph by thought leader Justin Welsh.

When I took a film crew of 5 guys to Tamil Nadu, India in 2010 to shoot my first feature length documentary, I noted that the 5 men who returned from India were not the same men who had boarded a flight at JFK 6 weeks before. They had indelibly changed. In their relationship to themselves. In their relationship to themselves to one another.

Specifically, what I wanted to get out of this retreat in Tuscany:

  • Take the women from their “comfort zone” to the “learning zone” to the “growth zone
  • Take the women on beautiful adventures inside the adventure for inspiration
  • Cultivate courage. It takes real courage to ‘go there’ and lay yourself bare on a stage with personal stories.


I’ll share 6 lessons I learned from the experience.

  1. Face Challenges

When I first created the deep writing and reflection retreat, I offered it up to any woman leader. I got no commitments. I even had a cohost for the retreat. But she was clear she would only be teaching at the retreat. She would not take on the burden of filling it. Geez.

In small business, one has to pivot and pivot fast. The deposit for the house had already been put down and it was risk management time.

My lesson was to fill the Mastermind, there by creating a built-in community. The retreat then served a bigger purpose: Harvesting stories for the TEDx style talk later in the year.

2. Acquire new skills

While we locked travel plans in January (fly into Milan, train to Florence, drive to Florence, fly into Florence) for a May retreat, it all went to shit. Italy had been experiencing torrential rains retreat week. A 4 hour drive from Milan into a 6 hour drive. There was a missed flights. Lost luggage. Transfers left unused. Extra transfers.

I plan these retreats a year in advance to mitigate as much risk as I can. When things go sideways, I’m not the most graceful in those moments. My lesson was to push outside my own comfort zone weekly to gaining more psychological flexibility.

3. See opportunity

In the cooking class with Chef Antonella, there was an astonishing number of steps in hand making pasta. It’s slow. Its deliberate. There is a reason it tastes different from pasta from a box. It can’t be rushed.

FYI, Chef Antonella does not speak English.

Google translate got us through.

It reminded me how impatient I am on a daily basis — with myself, my partner, with the person in front of me on a NYC sidewalk.

I saw the opportunity in slowing down more. Let go. Trust and let things unfold.

4. Expand comfort zone

As a group, we were at varying levels of athletic readiness. The company hosting our wine and bike supplied us all with electric bikes. The extra boosts built into them made us feel like rockstars, allowing us to climb the highest of hills with the greatest of ease.

Sometimes everyone needs a boost. Help is okay. Even though it was pouring rain, there were smiles all around.

5. Problem Solve

The last evening had given enough time to build trust among the group. The shares were getting more personal. More raw. More deep.

My lesson was to offer some kind of ritual, act of passage, or exercise to integrate back into everyday life. When I take people that deep, there needs to be an integration back.

6. Learn

Having led 11 retreats over the years, I’ve grown accustomed to that one person not being happy.

I wasn’t disappointed on this trip.

There were complaints about who got what room in the villa. Who paid what for what. There were complaints about the drive times to activities.

I had to absorb each complaint and thoughtfully maneuver around them.

Everyday, we face “complaints’ of different kinds.

My learning has been to make people feel seen, heard and understood.


A quick recap of the 5 lessons adventure offers:

  • Face Challenges
  • Acquire new skills.
  • See opportunity.
  • Expand comfort zone.
  • Problem Solve
  • Learn


I hope some of these resonate with you and impact your next adventure like they have mine. I’m currently enrolling the 2024 Class of the Samita Lab Mastermind. Walk away with one key digital asset, which is a filmed TED x style talk on stage. Receive your application here.


One Leadership Tip

7 ways to optimize your brain for better leadership.

My favorite is #2. I didn’t know that sugar, alcohol and carbs weaken focus.


One Public Speaking Tip

Below is a boundary-setting template.

While there’s no one-size-fits-all to conflict management, use this framework to help guide your approach:

  • Ask: “Is now a bad time?”
  • When you _____, I felt _____.
  • I have a personal rule where I only allow/don’t allow _____.
  • If you keep doing _____, I will have to _____.
  • I hope we can make this work and continue to _____.


My podcast interview with “Boundary Boss” author Terri Cole

One Adventure Tip

I did this exercise laying out my 10 year vision.

It was an exercise Debbie Millman, founder of the “Design Matters” podcast shared with me. I put the visuals to it in my Notion. It was the best part of my Saturday.

recorded a video taking you through my board.

If you don’t know the platform, video on how to use Notion here.


I’m currently enrolling the 2024 Class of the Samita Lab Mastermind. Walk away with one key digital asset, which is a filmed TED x style talk on stage. Receive your application here.

If a 12-month container is too much, I also offer one day intensives called VIP DAYS to work on your thought leadership.

Got questions? Email me at joya@joyadass.com

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