How to free yourself from fear-based decisions

The Enneagram for entrepreneurs

Welcome Entrepreneurs. I’m so glad you’re here.

I played 36-holes of golf on Monday with a dear friend. Didn’t do a lick of work. I feel some fear in admitting to that publicly, as if I’ll be judged as lazy or self-indulgent. And in my first draft of this intro I left it out because of that fear of judgement.

It’s remarkable how pervasive fear is in our lives. As people who like to golf, sure, but also as CEOs and leaders (who are, remember, also simply people. Some of whom golf). Even for those who are willing to admit to being scared (far from the majority of leaders in my experience), it can be challenging to work with it. It’s difficult in the moment to realize that our fight/flight/freeze reflex has been activated and is insidiously guiding us toward “safety.” Quotes ironic.

Today I want to introduce a tool that I use with clients to help them identify and defang their fears in the moment, opening up the possibility of greater choice in every circumstance.

Hope you enjoy.

PS> if you haven’t yet subscribed, I invite you to please join our community of Purpose Driven Entrepreneurs by subscribing below.

How your fears run your company (and how to see, and overcome them)

As long as our subconscious thought and behavior patterns remain unseen, we have no choice but to follow them. We act out the same scripts over and over again, wondering why we’re not improving. We might even begin to let go of the growth we want, thinking we simply don’t have the personality for it.  

It doesn’t have to be this way. 

As a coach, my role is never to help founders make decisions, rather it is to help founders see the patterns and frameworks that underlie their choices so that they can make their own decisions more consciously. By training ourselves to see our thought and behavior patterns objectively, as something apart from ourselves, rather than as part of our immutable “self,” we are presented with a choice:

Follow the automatic pattern you’ve always followed and get the results you've always gotten, or choose differently.

So much of my work is centered around this process: moving the mind from subject to object, so it can be consciously managed and improved. This means helping a founder see  her purpose clearly, those things that she most wants to move toward, and also her fears, that which she wants to move away from (although in my experience, moving away from discomfort is rarely the answer to the change we seek. More often, the better course of action is to know our fears, and therefore ourselves, better).

I wrote recently about two powerful tools I use to help founders become intimate with their desires (the death context and present-focused purpose). Today, I want to share one of the most powerful tools I use in helping founders become intimate with their fears. 

Maybe you’ve heard of the Enneagram. 

Put together by Oscar Ichazo in the sixties, the Enneagram is a modern synthesis of a number of ancient wisdom traditions, designed primarily to help uncover the relationship between a person’s essence and their ego (or personality).  In Ichazo’s own words: 

"We have to distinguish between a man as he is in essence, and as he is in ego or personality. In essence, every person is perfect, fearless, and in a loving unity with the entire cosmos; there is no conflict within the person between head, heart, and stomach or between the person and others. Then something happens: the ego begins to develop, there is a transition from objectivity to subjectivity; man falls from essence into personality."

In one sense a personality profile similar to DISC, Kolb or Meyers Briggs, the Enneagram is in another sense completely different-- it is an amazingly effective tool to help people identify and become familiar with their fears. Specifically how, more often than not, their fears run their lives. 

Why in the hell would I want to become familiar with fear? 

Because until you see and understand fear as an object, with its own characteristics, causes, and effects, it controls you. Fear is what decides how you allocate your budget. Or whether you let go of a faulty strategy or a problem employee, or hang on until it’s too late. Your fear sees these situations as matters of life and death, and in trying to keep you safe, your fear decides your life even if you think it’s just your personality.  Or fate.  

“Until you make the unconscious conscious, it will direct your life and you will call it fate.”― C.G. Jung

The Enneagram divides people into one of nine personality types based on the fear that drives them. Regardless of your type, fear plays a bigger role than we like to think in our decision making process. It’s not that fear always makes bad decisions (for most founders their fear is highly adapted to their environment, as it’s gotten them to where they are), it’s simply that it’s automatic, and will follow the familiar patterns in all similar situations. In other words, fear-based decisions will get you the results you’ve always gotten. 

I’ve written before about the problems this type of fear-patterned behavior causes in organizations, although since we are not generally comfortable talking about fear directly we usually deal with the symptoms rather than the fear itself. It’s easier to address  bad board management or cofounder infighting than it is to tackle the fear pattern that drives both of them. But while we may be able to force ourselves to act differently or learn different skills in the boardroom, until we recognize and deal with the fear pattern itself, we will continue to make boneheaded decisions in the moment and wonder why the hell we did that.

The alternative is to train yourself to see your fears in action in the moment. Once you see your fear truly, as a set of automatic impersonal patterns triggered as a response to some environmental stimulus, you can choose to let them go. Or to embrace them, or heavens to Betsy, maybe even to confront them head on. If you do that, all of a sudden, you can see what lies beyond their limits. Nothing creates artificial limits quite so effectively as fear. And nothing in life is quite as rewarding as what lies beyond those limits.  

Fear as the bedrock of personality

Let’s approach this distinction between subject and object, particularly as it relates to the contents of your mind, head on.  Nothing screams “subject” quite so much as one’s personality. It’s nearly the definition of a subject. It’s who I am. My personality. These are synonyms, right? 


Far from being “you,” from the perspective of the Enneagram your personality is a direct response to your deepest fear.  The process goes like this:

  • When you were very young (<5yo) something important happened, from which you learned something bad about yourself.  Something that scared the crap out of you. Maybe you already know what this was.  

  • For example, you might have seen mom and dad arguing, and you wanted to stop them, but as a three year-old, you couldn't. So at that moment you realized that you weren't good enough.  (Other learnings take different forms -- not strong enough, not smart enough, not lovable -- each one corresponding to one of the nine Enneagram types.)

  • In response to this terrifying realization, you commit to yourself that you will never again feel that feeling.  The fear of this feeling is so strong, you are willing to do anything to avoid it. And so you develop your personality, with all its wonderful attributes and quirks, as a kind of barrier between you and that feeling. 

  • For example, when you learn that deep down you are not good enough, you might develop a personality of an achiever, someone who works their ass off to get accolades from the world in an attempt to cover up innate feelings of worthlessness with ceaseless mounds of praise. If this describes you (raises hand), know that this describes a lot of entrepreneurs, and Alice Miller talks about this dynamic at length in The Drama of the Gifted Child

  • As you grow, confirmation bias does its thing and you see evidence of your not-good-enough-ness everywhere, continuously reinforcing and strengthening your belief.  The boundaries between you and your personality dissolve, and you forget that you ever had a choice. 

The vast majority of adults are their personality. They have no choice in their personality, because they don’t see the distinction between those two things. That’s where the Enneagram is so powerful.

How the Enneagram helps you become familiar with your fears

By outlining our most intimate fears in high definition, along with the personality they gave rise to and support, the Enneagram allows you to see these things as an It, a (sometimes unhelpful) pattern that controls your actions and thoughts when you’re not paying attention, rather than You. Once you see your fear as an object out there, rather than an inalienable part of who you are, you have a choice of how to deal with it.

Easy to say, but when the fight/flight/freeze reflex kicks in, it’s hard to find the mindfulness to notice it amidst all the reacting. You could meditate for 10 years to train yourself to see your mind in action, or you can provide your mind a high-definition photograph of the specific language your fear uses, so you’ll be more likely to notice it because you know what you’re looking for. Just like you see your unique Volkswagen everywhere the moment you buy a new car.

Over time, as you become more and more intimate and familiar with your fear patterning, both at a language level as well as at a somatic level (what fear feels like in your body and where it lives -- the next level of training after the Enneagram), the unlearning process begins. Your fear-supported personality (there is no other kind) doesn't go away, but it has progressively less control over your day to day actions.  In other words, you gain more conscious choice over your life.

And giving you that, in a nutshell, is my mission as a coach. 

Feeling ready to get started? Find a free 30 minutes and $12, and take the RHETI test. (Yes, you can take free versions.  No, it’s not the same.)

(HT: Julie Mosow, David Burt, Nanya S and Foster for editing!)

Liked this article? I’d be honored if you’d share with others who might find it valuable. 


Who is Ryan Vaughn? 

I’m an executive coach for startup founders, a role in which I get to help high-performing founders expand into extraordinary leaders. I’m a 3x Founder/CEO who’s raised $20m+ in VC and built a market-changing company, as well as two other companies that taught me things. I’m an avid writer, meditator, reader, athlete, father, husband, amateur physicist, student of leadership, and adventurer. I’m also none of those things. But I am glad that you’re here.  If that’s not enough, here’s a more detailed bio.


One: How to Lead in the Stakeholder Era (HBR)

Hubert Joly, the former CEO of Best Buy, is the latest to thumb his nose at Friedman, saying in his Declaration of Interdependence in Business:

Now is not the time to retreat. Instead, it is the time to accelerate. The profound multifaceted crisis we are facing has made it even more obvious that business and society cannot thrive if employees, customers, and communities are not healthy; if our planet is on fire; and if our society is fractured. Doing the same things we have been doing for decades while expecting different results would be, in Einstein’s words, the very definition of insanity. What we need today is a refoundation of business and capitalism so that we can build a more sustainable future. It is time for business leaders to embrace a declaration of interdependence that prioritizes the common good and recognizes the humanity of all stakeholders. 

I know, based on my own experience and reflections over the past 40 years or so, that shifting a business from maximizing profits to serving employees, customers, suppliers, communities, and shareholders is not easy. It requires leadership. In this article, I share the philosophy I have developed throughout my career and that was at the core of the resurgence of Best Buy. Ultimately, it is about much more than piecemeal CSR or ESG. It is about fundamentally redefining your company around purpose and learning how to unleash the best people have to offer. It’s about putting purpose and people at the heart of business.

My experience says the same in the startup world. The key to outsized returns (as an outcome, not a goal) is “putting purpose and people at the heart of business.” Might take a while for everyone to get on board, but this genie is not going back in the bottle.


Two: Selling Hours (Seth’s Blog)

Loved this inquisitive, challenging take on work-from-home’s impact on the relationship between a company and its employees. I’m surprised by how many founders still manage their employees’ hours, creating terrible incentives and making people miserable for a metric that is proven to have little correlation with output. I get that it’s scary to let go and trust your employees to do the work in their way, and in their time, but if you aren’t losing employees to companies treating their employees like professionals yet, you will.


Three: Why Navigating Emotions in the Workplace Matters (Mindful)

Decades of cognitive psychology have taught us that repressing emotions doesn’t make them go away, instead only holding them back for a time before they explode in unpredictable and unhelpful ways. And yet we repress our emotions every day and call it “business.”

For those struggling to keep everyone monotone at all times, I offer this article as a fine entry point into why emotions matter in the workplace:

“As a friend, as a colleague, and as a leader, being able to understand and recognize the emotions of those around you is incredibly valuable in any organization.”

Emotions exist (can’t believe I just wrote that), and as a leader you ignore them to your detriment.


Four: UFOs? (Cabot Phillips)

I haven’t done the research here, so I’m hoping someone can either validate this thread with all the details about our multitude of UFO discoveries, or prove it’s BS. Note that I’m certainly vulnerable to confirmation bias here because I love the idea of finding aliens in our lifetime, but if all the stuff here is true (including a 60 Minutes report) I can’t figure out why it’s not the top story everywhere.


Five: Overwork killed more than 745k people in a year (NPR)

Goodness this stat.

Working long hours poses an occupational health risk that kills hundreds of thousands of people each year, the World Health Organization says.

People working 55 or more hours each week face an estimated 35% higher risk of a stroke and a 17% higher risk of dying from heart disease, compared to people following the widely accepted standard of working 35 to 40 hours in a week, the WHO says in a study that was published Monday in the journal Environment International.


A Poem for a Founder

“The Dexterous Butcher”

By Chuang Tzu (Translated by Thomas Merton)

Prince Wen Hui’s cook

Was cutting up an ox.

Out went a hand,

Down went a shoulder,

He planted a foot,

He pressed with a knee,

The ox fell apart

With a whisper,

The bright cleaver murmured

Like a gentle wind.

Rhythm!  Timing!

Like a sacred dance,

Like “The Mulberry Grove,”

Like ancient harmonies!

“Good work!” the Prince exclaimed,

“Your method is faultless!”

“Method?” said the cook

Laying aside his cleaver,

“What I follow is Tao

Beyond all methods!”

“When I first began

To cut up an oxen

I would see before me

The whole ox

All in one mass.

“After three years

I no longer saw this mass.

I saw the distinctions.

“But now, I see nothing

With the eye.  My whole being


My senses are idle.  The spirit

Free to work without plan

Follows its own instinct

Guided by natural line,

By the secret opening, the hidden space,

My cleaver finds its own way.

I cut through no joint, chop no bone.

“A good cook needs a new chopper

Once a year–he cuts.

A poor cook needs a new one

Every month–he hacks!

“I have used this same cleaver

Nineteen years.

It has cut up

A thousand oxen.

Its edge is as keen

As if newly sharpened.

“There are spaces in the joints;

The blade is thin and keen:

When this thinness

Finds that space

There is all the room you need!

It goes like a breeze!

Hence I have this cleaver nineteen years

As if newly sharpened!

“True, there are sometimes

Tough joints.  I feel them coming,

I slow down, I watch closely,

Hold back, barely move the blade,

And whump! the part falls away

Landing like a clod of earth.

“Then I withdraw the blade,

I stand still

And let the joy of the work

Sink in.

I clean the blade

And put it away.”

Prince Wan Hui said,

“This is it! My cook has shown me

How I ought to live

My own life!”

(If this poem resonates with you, send me an email. I’d love to discuss.)


Top Posts

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Executive Coaching for Entrepreneurs

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At Inside Out Leadership, I’m privileged to work with amazing humans every day to help them grow into extraordinary leaders, and support them in building the company of their dreams. As a 3x founder and CEO for 15 years myself, I coach entrepreneurs how I want to be coached:

  • Focused on the person, not the role.

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