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5 Continents & 30+ Retreats Later... Here's What I've Learned

I graduated from Arizona State University in 2016 and immediately dove into the corporate world. For a long time, I demonized corporate bureaucracy, and while I don't believe it's for me, there's a lot I still look back on fondly from my time at Hyatt... let alone the incredibly education they provided me on the job.


A few years later, I was asked to help them open a new property, Andaz Scottsdale. As part of my negotiation, I asked for the ability to launch a yoga & fitness studio on property, to which they obliged with minimal resistance.


Fast forward 12 months, the property's Director of Operations saw what I had created and requested a 50/50 revenue split with the resort (... and for what reason is still unknown to this day because he in no way benefitted from it) which triggered a series of, in hindsight, fortunate events.


I created a proposal to build a wellness program that expanded to Hyatt as a whole and was told that the space would never be big enough to warrant a corporate partnership. I submitted my two weeks notice, took the list I had generated, realizing what I had learned about hospitality, resorts, wellness, and people, and launched a retreat business.


I'm proud to say that I'm writing this from a stunning beachfront resort on a tiny island in the Azores archipelago, the Hawaii of the Atlantic. It's my last retreat of 2023. To date, I've facilitated retreats on five continents, soon to be six, and have had hundreds of people go through my Align Your Purpose curriculum.


Change can be scary, yet it's in the unknown where all growth happens. This business has led me to create others, including opening my own resort in Costa Rica. The reason all of this has been possible is because I trusted myself with my future more than anyone or anything else.


Here are five lessons I've learned from facilitating retreats on five continents:



1: Positioning Creates Perceived Value

Last year, I did a resort site visit in Morocco with other retreat leaders. To pass the time on one of our drives, the topic of 'best practices' was brought up. To my surprise, everyones focus was on class programming, not experience.


It's not uncommon because the majority of facilitators are viewing retreats as an extension of their weekly classes... and because of this, they see the trip through the lens of 'classes taught equals money earned'.


What I've found to be true is the opposite. You're being paid to cultivate an experience, and its value is directly tied to the perceived value of the experience.


Most frame a retreat as 'practice with me in a resort abroad,' which commands a much lower price point and retention rate than 'transform your subconscious beliefs and immerse yourself in a new culture'... which makes the trip outcome-based and anything productized is infinitely more scalable.


2: Set Expectations Day One

A retreat is not a vacation... read that again. Anyone can book an all-inclusive stay at a resort in Mexico and spend their days engaged in unconscious activities. There is nothing wrong with that. However, creating a transformational experience demands intentionality.


On my early retreats, I used to not set expectations... which led to the trip taking the form of what each person desired, leading to disorganization and habitual excess. Now, I sit the entire group down day one and walk them through the week. I cover what is mandatory, what is optional, what is included and not, and what to expect as they go through our 8-day, 7-night Align Your Purpose curriculum.


Reflecting back on the site visit last year, none of those facilitators made anything on the trip mandatory... and their CSAT scores and retention rates were hurt because of it. People don't know what they want until they're told... don't believe me, watch this.


3: No 24/7 Scheduling

In opposition to the above point, you DO need to give the group free time to tick off what they want to do on the trip outside of your programming. You're a facilitator, not a dictator, and when I was starting out I felt the need to control every moment.


In line with facilitation, if done correctly, the group will form bonds day one and begin to schedule things together and form new relationships. When this happens you can take a step back and watch beautiful friendships form right in-front of your eyes.


Remember, the experience is not about you.


4: Problems Are Opportunities

One of my favorite sayings from Dr. Jordan Peterson is, "Conflict delayed is conflict multiplied," and in any group setting, this rings true. Being a facilitator it is your job to create group cohesion, but, it is not your job to brush aside conflict.


Problems are the pressure we push against which allows us to craft our character... and when you're pushing people past their comfort zones, emotions often bubble to the surface. Not only is this a beautiful opportunity for a participant to work on themselves, it's a great opportunity to act as a mirror for each other.


My 2c... don't ever try and make things all butterflies and rainbows, that's not how people grow. I care more about people growing because of me than being liked... and when I made that shift my retreats gain another layer of transformational depth.


5: Do Something You've Never Done

You don't need to put someones life in harms way, but you do need to create a container that pushes them past their imagined limitations. On every retreat we have a 'fear' day... which is always my favorite day of the trip - and often the hardest physically and emotionally.


Scary, hard, and challenging are all relative, and while I often have to put up with some choice words, this day becomes the most memorable point of each trip. The best part, those who complain the most are always the ones who come back at the end and say thank you for helping them unlock a new level within themselves.


Our minds and bodies are stronger than you can even comprehend... and if you don't choose your challenges in life, your challenges will choose you.


If you'd like to see upcoming retreat availability, click here.



Quote On My Mind:


"Your purpose is not the thing you do...

It is the thing that happens in others when you do what you do."

﹣Dr. Caroline Leaf


Purpose exists in becoming the best version of yourself.

... and becoming your best is more about saying no than yes.


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Shane Gillis has a new, and pretty rowdy standup set on Netflix. It's titled Beautiful Dogs and is the funniest thing I have watched this year... specifically the George Washington, Trump, Navy SEAL, and Down Syndrome moments.


Watch on Netflix





In last weeks edition, I wrote about my weekend with Dr. Joe Dispenza, expanding on the top 5 things I learned:

  1. Why look for your future if you've already created it.
  2. What feels right is familiar. The unknown is always uncomfortable.
  3. Genes don't create disease... the mismanagement of emotions do.
  4. Become so conscious of your unconscious self that you never revert.
  5. If you can't think greater than how you feel, then you're thinking in the past.

If environment signals the gene, then your perceived reality is within your control.

It may be challenging to see in the short-term, but the long-term reward is worth it.

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