4 Reasons I Believe in Leadership Through Adventure

My next adventure come September 20th is the northern tip of Africa:

The women in my Samita Lab Mastermind are headed to Morocco. We will visit a hammam in Marrakech, stay in a tent in the Agafay Desert, hike the Atlas Mountains, and ride a horse on the beaches of Essaouria.

Why am I so committed to adventure as a means of leadership development?

LadyDrinks SkyDiving Retreat

#1 Travel is a Metaphor.

I’m huge fan of pushing women out of their comfort zone. If I push you so far, what else becomes possible for you? Both in business and in life?

Years ago, I hosted a skydiving retreat. We hosted a debrief before and after jumping out of the plane. The question we posed to all 7 attendees: “What blocks are you experiencing? Where do you wish for a breakthrough?”

One woman said she unilaterally says ‘no’ to everything. She wanted to say ‘yes’ to more things.

She signed up for my retreat and in a few hours, she was jumping out of a perfectly good plane. I was on the aircraft with her. Normally, there is unbridled excitement as a plane is ascending into the sky. Our thoughts traditionally go to “What I will do when I land?” But, we were going to hit that peak and then jump out of this darned thing.

She felt the fear.

She did the jump.

She landed.

Since the retreat, she has built a real estate empire of 300+ multi family units. For the first time she is building a fund, with money that is not friends and family money.

All because she is now saying ‘yes’ to everything.

In Morocco, we are going to be hiking the Atlas Mountains. How do you navigate the physical challenges? How do you deal with interpersonal challenges? How do you work collaboratively to get up the mountain?

LadyDrinks Trapeze School Retreat


I hosted a retreat at the New York Trapeze School on the West Side Highway of Manhattan. I don’t know that I have done something more complex or unfamiliar, two building stories above Manhattan, with peripheral views of both New Jersey and the New York City. I could feel the oxygen slipping from me as I climbed up the skinny ladder.

Stretch goals like this made me realize how much ‘fear’ hampers me. I had a harness as a safety. A net below me to catch me. I wasn’t going to die. Afterwards, I learned to recognize that voice: ‘Oh, there you are fear. Here again, are we? Not today. Today, we are going to do this risky thing anyway.’

We are going to be in the Agafay dessert, living in a tent in Morocco with probably no cell reception. We have to give over trust to the guides who are bringing us out there.

How is this forcing us to step up in new ways? What’s stretching our leadership?

Women’s Leadership Lab (Formerly LadyDrinks) 10 Year Anniversary in Croatia

#3 It’s preparation with purpose

Leadership, much like any adventure, requires mental preparation. Logistical preparation. Tomorrow I will share my packing list for Morocco.

My friend Jane is a news anchor and had prepped for a year to be gone for 8–10 days with me in Croatia — the longest she had ever been away from her own business. I’m normally the replacement when she travels. But now, both she and I were away on the same trip. She prepped another person to fill in. She brought in an extra set of hands to assist. She would log onto the boat wifi every morning to help as best she could. But then — she had to let go, and trust that the team back home would handle the rest. The only thing to do, when out to sea on this most recent trip to Croatia was— to relax. It was a new step in her leadership. How to disconnect from her very busy day to day and — just be.’ She’s now thinking critically about how she will vacation in the future.

#4 You have a continuous feedback loop

Similar to an adventure, there are real life ramifications for when things go terribly wrong.

I had drummed it into everyone that the boat, much like planes at the airport, are governed by the port authority. Just because I had done a buyout, didn’t mean the boat could sit there all day waiting. The next island was 6 hours away. I said, “Please organize your mornings to be on board by 1pm GMT. I silently couldn’t believe it. Thirty people had crossed the Atlantic Ocean and was on the boat in Split, Croatia, by 1pm GMT, the yacht’s departure time. Given all the horror stories I was hearing about summer travel. Given where the yacht was anchored in the port, this took collaboration, extreme and clear communication, and leadership to get everyone on board.

There were activities each day (buggying, cycling, kayaking) There was opportunity to do, reflect and get out there again, with a new challenge.

I host a mastermind for women with a goal and a desire to make it their reality in a year. You show up. I put the right group and the accountability around it. Take this assessment to see if you are ready to get your goals. www.goalsscorecard.com

In this HBR article, Mike Doyle and Christopher Myers say companies spend so much money on leadership retreats. Guess what? Research shows they don’t really work. You know why? You pretty much replicate the office environment by moving to another conference room. “That doesn’t really push people to realize something about themselves or their leadership.”

They are both bigger fans of taking teams on wilderness expeditions. Mike is Director of Experiential Learning at the Johns Hopkins Carey Business School and has led adventure-based leadership programs for more than 20 years.



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Joya Dass

Joya Dass


If you have a goal and want the steps to make it your reality, I have a solution. www.joyadass.com