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Facilitator or Personality? Retreat – Know Thyself! - No-Location

When it comes to running a retreat, retreat operators fall into two categories: “Facilitators” and “Personalities”. What is the difference between these two?

The Facilitator:

Facilitators are tour operators that arrange experiences and aren’t a pivotal part of the participant’s experience as a personality. If you are running a week long coding retreat where students learn from different instructors and have ample free time to explore the surroundings themselves then you would be a facilitator – in this case you are free to engage in the logistic side of the retreat yourself with little to no damage to your program because the various aspects of your program are centered around the group of participants as a decentralized unit.

The Personality:

Personalities differ because their retreats live and die based on the personal connections participants develop with them. If you are running a retreat where your participants interact with, travel with, and learn from you then you are a Personality. In this case you can’t afford to be bogged down in the logistics of the program’s day to day operations because each operation you attend to personally detracts from the connections you build with your clients and devalues the expertise they have come to learn.

So you know what you are…now what?

For any retreat it is incredibly important what image the participants develop in regards to the content and quality of the program but this is accomplished in different ways for Facilitators and Personalities. Knowing what kind of program you run lets you know what you should personally focus on and what you should delegate.

Facilitators need to focus on the integrity of the program’s pre-designed function – in this way they are similar to the director of a play – while they may not act as Personality to the clients of the retreat they most certainly act as personality to the crew who help them run the retreat. Facilitators, like directors, are integral in making sure the stage is set, the players are ready, the tech crew is prepared, and the show runs smoothly. The director chooses the vision of the event and has it built and prepared by delegates who act on instruction.

As a retreat operator you are responsible for choosing the venue, designing the program, overseeing delegated work, choosing delegates, and managing both the expectations of the clients and any problems that arise during the event. Initially this is a lot of work but once a Facilitator finds the right people and they are able to function autonomously with minimal oversight things become easier and the complexity and quality of the program is free to grow.

Personalities need to focus on the feelings and experience of the clients – in this way they are similar to street magicians. They must create an atmosphere of intrigue, turn spectators into players, and figure out how best to work with assistants to make sure the experience is effective. The important thing is this: The Personality is the event and chooses how the event ebbs and flows based on preparation and feedback from the audience both in real time and in reflection afterwards. The assistants must be able to work with little to no oversight from the personality and it is the job of the Personality to manage expectations both beforehand and during the event. This kind of retreat is pretty straight-forward and, if done correctly, is fairly easy. Growth is tricky though as the Personality must attain complexity through an array of near-autonomous assistants and the program will have to shift to more and more spectacle.

It is of course possible for a facilitator to become a cult of personality and vice versa but this usually requires an overhaul of the entire product. Because of this it’s easier for one to blend into the other without fully crossing over. For example a facilitator can take a central role in the interaction with participants, resembling but not fully becoming The Personality and a Cult of Personality can let their assistants take on side-kick roles while they go do something else themselves.

From here you can tweak and optimise your setup and really start creating wonderfully complex and beautiful experiences that aren’t just business – they are art.

What makes a retreat, a retreat

Retreat is a trending word among travelers – you can find yoga retreats, digital nomad retreats, and even forex trading retreats…but what exactly is a retreat? Is it a workshop or is it just a group traveling and doing an activity together?

According to Dr. Sheri Rosenthal from Wanderlust Entrepreneur, a retreat is a custom-crafter life-changing experience that most commonly takes place in a group format at a gorgeous location. The emphasis here is on the “life-changing experience” and, dare we say it, the very purpose of a retreat in the first place. This experience is a result of multiple parts working together; destination, location, activities, information, and message. Retreat facilitators and operators should all understand these parts and how they work together to craft a life-changing experience.

Here are the three things that make a retreat, a retreat.

The Information

Most retreats exist to solve a problem. Healthy eating, better yoga, connection to the self – these are all areas where people are looking for information to resolve an issue they are having. Destination and activities are important but the essentially you as the facilitator are providing a space in which your client’s problems are solved. Information is often passed along formally or informally through teaching, both in classes and in excursions and trips. A proper retreat allows for a traditional classroom setting but it also has a lot of emphasis on spending time outside of a classroom. The difference between a workshop and a retreat is this aspect of how information is transmitted. Workshops are more utilitarian and straightforward while retreat are more multi-sensory and experientially focused. This is what provides a retreat with value over a workshop.

The Location

While a retreat can technically happen anywhere, including the backyard of your childhood home, a more inspiring location is probably called for. Retreats are crafted experiences and you want your client to feel detached from their everyday problems and ready dive into the experience and learn. A new and inspiring setting means a new and inspiring mindset. You need to understand the environment that best suites your client – for example getting your clients to adopt a healthier diet would be easier in the jungles of Ubud than it would be in hubub of Bangkok. Be sure to connect your information to your location. Instead of a “Women’s Weight Loss Retreat” why not try “Eat, Love, and Become Healthy in Bali Retreat”?

The Needs

Traditional wisdom states that retreat facilitators should focus on marketing their program and experience – but reality states that the most important factor in a facilitator’s success isn’t about meeting basic needs at high quality. This consumes a lot of energy and time that would be better used elsewhere because the most important factor in your success as a retreat facilitator is YOU – your client’s personal connection and time spent interacting with and learning from you. So have someone else take care of the little things while you take care of your people.

Cut the Shit: Becoming and Entrepreneur and the Only Two Ways to Do It

All over the world people dream of being an Entrepreneur – someone with their own business who does things their own way. Who wouldn’t want to do away with bosses and overlords forever? Who wouldn’t want to receive 100% financial returns on their efforts instead of an hourly pay? Who wouldn’t want the freedom to choose when to work and what to work on?

Sadly many people are filled with illusions about what being an entrepreneur is as well as how to become one. So I’d like to cut the shit, dash the illusions, and get to the heart of the matter to help as many people as possible.

First off, lets be honest – an entrepreneur is simply someone with a business, that is to say someone who provides a product or service and has full control over what happens with the profits – even if they don’t necessarily have full control over the product or the service they are selling. Chris Guillebeau famously stated that business needs but three things: Something to sell, a place to sell it, and a way to get paid. So lets define an entrepreneur as someone who has something to sell, a place to sell it, a way to get paid, and has control over what happens with the profits.

With this in mind we can start to see that the world is full of entrepreneurs – it isn’t just digital nomads, followers of the 4-Hour Work-Week, or people drop shipping on the internet. Au contraire! The woman pushing a food cart around Jakarta selling noodles is an entrepreneur, the kids selling candy on the subways of New York are entrepreneurs, and the guy selling weed in the back alleys of Bombay is an entrepreneur.

This brings me to an important point – necessity truly is the mother of invention. There are more entrepreneurs living in or under the poverty line than above it, and more entrepreneurs operating outside the law than within in it. When human beings are faced with a do or die, sink or swim situation they usually rise above the challenge, discover the minimum viable laws of business, and find their niche. From there it’s just a matter of building and honing skill, being able to adapt, and being willing to learn – either from experience and observation or by mentorship and education.

The best way to intrinsically understand anything is to have faced it’s opposite without getting locked into a cycle of fear – appreciation of life comes from facing death, understanding love means having been used, etc. The next best way is to have simulated facing it’s opposite, such as imagining a situation in detail, or having been told of someone else’s direct experience. Being able to learn from someone else’s mistakes is a skill that can propel you forward very quickly.

This is the part no one likes to talk about – becoming an entrepreneur usually results from facing the deep dark well of having and controlling nothing, becoming and entrepreneur usually comes from having to because it is the only way to get what you want – for some it’s the only way to feed and house themselves and their children, for others it’s the only way to avoid being under someone else’s power and authority. Whatever the reason, a man or woman will usually only succeed in their transformation if it is the only option available. In this is power, self-reliance, and freedom – from this is possible the shift from a mindset of scarcity to one of abundance. You simply have to know what you want and the best way to know exactly what you want is want what you absolutely need.

There is however another path to entrepreneurship – this is the path of pleasure. You see, not everyone grows up in a media saturated environment having sh*t pumped into their ears since birth, not everyone is raised in bubble of constant fear and instilled with a mindset of scarcity (I’m looking at you America…). Additionally, not everyone who comes from such abject circumstances continues to propagate them – some people evolve and so, for an increasing number of people there is no need to hit that rock-bottom point of finding out what they want by wanting what they absolutely need. Instead they live in the very human world of pleasure-seeking and enjoyment.

This is the natural state of humans – to do what we enjoy and enjoy what we do. In such a world and in such a mindset it is only natural that as a being attains mastery over a skill set, craft, or discipline they will simultaneously build a business or industry as well – in a pleasure-seeking world the only way to attain greater pleasure is to attain greater complexity, and the only way to attain greater complexity is to provide greater pleasures to greater amounts of people.

For those with illusions casting shadows of fear and scarcity in their lives I have but one sure-fire piece of advice. Risk everything, lose it all and become totally and abjectly f*cked. Once that happens you’ll know what-is-what, you’ll know exactly what you want, and you’ll magically find a way to get it using the skills and knowledge you’ve built over your life-time. For those living for pleasure’s sake just keep doing what you are doing.


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