5 Reasons to Study the Enneagram

We move through this world under the impression—some would say the illusion—that we’re consciously choosing all of our thoughts, feelings, and behaviors. But most of the time we’re operating on autopilot, stuck on the hamster wheel, doing the same thing over and over again, in spite of our best intentions.

The Enneagram provides a window into our habits of thinking, feeling and behaving. The result is that the more we know, the less we’re at the effect of the programs that are usually running us.

As a system for describing our basic temperament or personality, the Enneagram is comprehensive, multifaceted, and accurate. It requires a bit of effort to fully grasp, so if you’re wondering why you should bother–what’s in it for you–here are five good reasons to learn more about the Enneagram:

1. You’ll Be Able to Let Yourself Off the Hook.

A surprising amount of what we perceive of as our own individual quirks, flaws, and shortcomings are not the result of our upbringing or personal experiences—or the fact that we’re stubborn, wrongheaded, or lack any semblance of willpower. It’s just the way we’re wired. That means we don’t need to continue expending time and energy trying to figure out why we’re that way or attempting to fix ourselves. The Enneagram offers a short-cut to self-awareness and self-acceptance, which is very powerful ground to stand on.

2. Other People Will Make You Less Crazy.

Even when you don’t know what someone else’s type is, just being aware of the fundamentally different perspectives and attitudes of each type can be eye-opening. That awareness makes it a lot easier to cut the other people in your life some slack and stop expecting them to be who they’re not. It also makes it less likely they’ll be able to push your buttons as often and as easily. Our differences don’t always have to be frustrating or divisive. They can be a source of humor and even a way to connect.

3. You Can Stop Banging Your Head Against the Wall.

Do you ever feel like your life is the one Narcotics Anonymous was referring to when they defined insanity as doing the same thing over and over again and expecting different results? If so, take heart. The Enneagram explains how we get into our particular ruts of behaving, thinking, and feeling—and then offers a range of alternatives to try out from among the other types. Knowing your type is also extremely helpful—maybe even essential—if you are in the process of attempting to change your behavior.

4. It’ll Make You Smarter, Improve Your Memory and Mood, and Keep Your Brain Healthy.

Learning about the Enneagram may not add measurable points to your I.Q., but brains crave challenge and stimulation in order to maintain their plasticity. Learning something new actually changes your brain physically by not only increasing synaptic connections, but also growing new neurons—no matter how old you are. That’s one of the main ways to keep your mind sharp and flexible and your memory intact. These neuronal interconnections in our brains affect our behavior, thoughts, and feelings on a daily basis. You can definitely nurture your neurons by learning about the Enneagram.

5. It Has What You’re Looking For.

On the psychological level, the Enneagram is a great tool for anyone who’s on a journey of personal exploration or wants to change old, outmoded patterns of behavior. On the interpersonal level, it can help you deepen your relationship with your partner or develop clearer communication with friends and family members. At work, it can help you get along better with your co-workers, understand your boss, and become more effective. What you take from it depends on how you come at it and what it is you’re looking for.

I learned about the Enneagram 20 years ago when I was working as a substance abuse counselor and trained to become a Certified Enneagram Instructor. Not only did the Enneagram help me get a handle on some of my own automatic (System 1) behavior, it was the single most effective tool I ever found for working with my clients.

The work I do now is based on the most recent understanding of the mind and brain that neuroscience and psychology can provide. And once again I have found the Enneagram to be an invaluable tool, in this case for identifying my clients’ automatic behavior and tendencies.

Many of us want to increase our self-awareness, but we can’t pay attention to everything. The Enneagram points us in a direction that allows us to see how we tend to operate, in both positive and constructive ways and in negative and sometimes destructive ways. It’s one way to find out some of what’s in our particular mental model. Since the contents of our mental model are not directly accessible, I see the Enneagram as a short-cut to self-awareness.

E Is for Enneagram


The Enneagram is a straightforward, yet rich and complex system that describes our individual strengths and weaknesses, deeper-level motivations, and most importantly, the compulsions that often rule our lives. Although we’re wired to operate under the impression that we’re consciously choosing what we do, most of the time we’re at the effect of unconscious impulses. We’re living our lives on autopilot; asleep at the wheel, doing the same things over and over again, expecting different outcomes.

As I wrote in A Is for Autopilot:

Estimates are that close to 80% or more of what we do every day we do on autopilot, which means without conscious intention or volition. It’s not just what we do, either. The majority of our thoughts, feelings, and behaviors are the result of automatic brain processes.

As neuroscientist David Eagleman says:

Our brains run mostly on autopilot, and the conscious mind has little access to the giant and mysterious factory that runs below it.

When you look outward at the world—or even inward at yourself—you see things not as they are but as you are. You view the world through your own set of filters, biases, opinions, judgments, personal experiences, and temperament. You act and react as you do—and not as someone else might—because you’re looking out from within your own model of the world. Your model of the world influences what you pay attention to, how you interpret and react to events, the meaning you assign to them, and most of what you think, feel, do, and say. When it comes to trying to change the status quo, your preexisting model of the world is your most formidable obstacle.

In order to create and sustain positive change, you have to change your model of the world. But how can you change something you can’t see—the very lens you see through?

That’s where the Enneagram comes in. It offers each of us a window into our particular model of the world so we can develop the self-awareness that’s essential for creating change.

The Enneagram is the most practical and accurate tool I’ve found for describing our basic temperament or personality, and therefore our habits of thinking, feeling, and behaving. (Other typing systems include the MBTI, OCEAN [a/k/a Big Five], DISC, and Social Styles.) The Enneagram is comprehensive and multifaceted, so it requires some effort to fully grasp. But it’s worth it. When you identify your type, you may find that the Enneagram knows you better than you knew yourself. It isn’t the personality equivalent of a Theory of Everything, but it gives you a place to look, a way to pay attention to what you’re doing, thinking, and feeling.

In a Nutshell

Enneagram is a Greek word that means nine points. The Enneagram symbol is composed of a triangle and a hexad within a circle. The triangle connects points 3, 6, and 9. The hexad connects points 1, 2, 4, 5, 7, and 8.

The 9 points represent 9 basic, or core, personality types, each of which has a unique perspective and approach to life. We tend to polarize near one of those points, as a result we overdevelop some areas and underdevelop others. That polarization strongly affects how and what we perceive of the world around us—and how we respond to what we perceive. Our perceptions and responses become so much a part of us that they occur automatically, without any conscious thought.

alphabet-changeOne way to think about the Enneagram is that each point represents a particular kind of imbalance. (It’s easier to spot imbalances in others than it is to recognize them in ourselves. So it can be tempting to “helpfully” point out those imbalances to friends, family members, and co-workers. It is also tempting to stereotype people because categorizing is an automatic process of the brain.)

The Enneagram can make you more aware of your particular autopilot behavior. It can show you how you tend to operate, in both positive and constructive ways, as well as in negative and sometimes destructive ways. Your core personality type doesn’t change over the course of a lifetime, but as you become aware of your tendencies and imbalances, you gain the ability to moderate them. You’re no longer run by them.

Some people believe that being typed diminishes them somehow, that typing puts them into a box. But typing doesn’t put people into boxes; it identifies aspects of the boxes we’re already in. It points out what’s inside the box and what’s outside, both of which are equally important.

The Nine Types

Very briefly, these are the nine types:

Type 1: The Good Person, the Achiever, the Reformer, the Perfectionist. Principled and responsible, but can also be rule-bound and critical.

Type 2: The Helper, the Giver, the People Pleaser, the Partner. Compassionate and altruistic, but can also be co-dependent and manipulative.

Type 3: The Performer, the Succeeder, the Motivator, and the Status Seeker. Self-assured and accomplished, but can also be competitive and performance-driven.

Type 4: The Individualist, the Tragic Romantic, the Artist, the Sensitive Person. Creative and inspiring, but can also be overly dramatic and fault-finding.

Type 5: The Observer, the Investigator, the Knowledge-Seeker, the Thinker. Perceptive and curious, but can also be cold and detached.

Type 6: The Loyalist, the Questioner, the Guardian, the Devil’s Advocate. Organized and hard-working, but can also be indecisive and overly-vigilant.

Type 7: The Adventurer, the Epicure, the Generalist, the Enthusiast. Cheerful and multi-talented, but can also be acquisitive and thrill-seeking.

Type 8: The Challenger, the Confronter, the Leader, the Asserter. Courageous and magnanimous, but can also be combative and domineering.

Type 9: The Peacemaker, the Preservationist, the Mediator, the Universalist. Deeply receptive and serene, but can also be disengaged and inattentive.

When it comes to creating change, the greatest benefit of learning about your Enneagram type is discovering how you repeatedly get in your own way. Without that knowledge, your efforts are likely to lead to frustration more often than to success.

For more information about the Enneagram, visit ninepaths.com.

Part of the series A-Z: An Alphabet of Change.

Permission to Fail

Here’s a handful of quotes to inspire you to fail and fail again because failure is an essential part of the creative process. It’s also a part of life.

If you’re not failing, maybe it’s because you’re not trying hard enough.

So go out there and fail better, fail faster. Rack up as many failures as you possibly can!

An essential aspect of creativity is not being afraid to fail. –Edwin Land

Success is going from failure to failure without losing your enthusiasm. –Winston Churchill

The man who makes no mistakes does not usually make anything. –E. J. Phelps

It takes sixty-five thousand errors before you are qualified to make a rocket. –Werhner von Braun

If you’re not prepared to be wrong, you’ll never come up with anything original. –Ken Robinson

Forget your perfect offering. There is a crack in everything. That’s how the light gets in. –Leonard Cohen

I have missed more than 9,000 shots in my career. I have lost almost 300 games. On 26 occasions I have been entrusted to take the game-winning shot… and I missed. I have failed over and over and over again in my life. And that’s precisely why I succeed. –Michael Jordan

To develop working ideas efficiently, I try to fail as fast as I can. –Richard P. Feynman

Would you like me to give you a formula for success? It’s quite simple, really. Double your rate of failure. You are thinking of failure as the enemy of success. But it isn’t at all. You can be discouraged by failure—or you can learn from it. So go ahead and make mistakes. Make all you can. Because, remember, that’s where you will find success. –Thomas J. Watson

Failure is a bruise, not a tattoo. –Jon Sinclair

An inventor is almost always failing. He tries and fails maybe a thousand times. If he succeeds once then he’s in. –Charles Kettering

I failed my way to success. –Thomas Edison

Ever tried? Ever failed? No matter. Try again. Fail again. Fail better. –Samuel Beckettt

To be wrong is nothing unless you continue to remember it. –Confucius


The best way to have a good idea is to have a lot of ideas. –Linus Pauling

If I have a thousand ideas and only one turns out to be good, I am satisfied. –Alfred Nobel

I’m a perfectionist, which I think is a mistake. –Michelle Shocked

So try not to be too attached to any of the ideas you currently have or to take failure personally. Use the results—good or bad—as feedback not as evidence. And begin again.

Ready to Amp up Your Creativity?

An article in 99U offered its readers 10 “creative rituals” used by various creative professionals, including writers, entrepreneurs, and designers. Of course, you don’t have to be a creative “professional” to be creative. Creativity is an approach to being in the world.

And, as the article’s author Sean Blanda says:

Sustained creativity doesn’t come from a flash of brilliance or a single afternoon of inspiration. It comes from a consistent routine that serves as the bedrock for getting things done.

There’s a difference between rituals, routines, and habits. Jack Kerouac touching the ground nine times before writing is a ritual. Writing every day is a habit. “Brainstorming at the bar” (item 9 below) is a routine. There’s value to be had from all of these suggestions, but some are more valuable than others. (Hint: Don’t miss #7.)

#1 Take a Quarterly Vacation

Venture capitalist Brad Feld says that taking a week off every three months with his wife is the most impactful thing he’s done. He leaves his computer at home and turns his smart phone over to his wife for the duration. While away from home, Feld reads, relaxes, sleeps, and generally enjoys himself, returning home refreshed.

Maybe taking four weeks of vacation a year is feasible for you, but even if it isn’t, the recommendation to take time away from your regular work and routines is a good one. The amount of time you spend away isn’t as important as getting away—and really disconnecting when you do.

#2 Hold a “Retrospective” After Projects

Harper Reed (former Obama campaign CTO) said his team relied on meeting at the end of each project to ask what the experience was like, what went right, and what went wrong. They didn’t wait till the end of the campaign to do it; they conducted many such meetings along the way. That allowed them to pay attention to feedback and adjust course.

It may be easier to hold a retrospective meeting with a team, but even if you work solo you can incorporate a reflective activity into your workflow. It’s difficult to identify what’s working and what’s not working if you don’t stop, even briefly, to assess. Another way of using this process is to stretch your thinking by asking those questions near the start of a project or goal from the perspective of having completed it.

#3 Write Every Day

Cheryl Strayed, author of Wild, is a professional writer who also uses writing “as a tool for self-discovery” when she’s trying to work through something or make a tough decision. She believes that “writing forces you to locate your clarity.”

I’m a big fan of developing a writing practice, but I think writing only leads to clarity if you use it deliberately and intentionally. As I wrote in W Is for Writing, “in order to get the best results, you need to be clear from the outset about what you want from your writing.”

#4 Create an “Interesting People Fund”

Writer and entrepreneur Ben Casnocha invests in an “interesting people fund,” which he describes as a pre-commitment strategy. He pre-commits both time and money to meeting interesting people to make it more likely that he’ll actually do it. As he says, it takes time to develop any kind of relationship.

I think that allocating resources (time and money) to cultivate relationships with interesting people can, over time, alter your mental model. You’ll be on the lookout for people who interest you and you’ll get into the habit of reaching out to them to make a connection on more than a superficial level. This may be more important in our high-speed, digitized lives than it has ever been!

#5 Keep “Tear Sheets” to Get Inspired

Designer Sarah Foelske gets stuck once in a while; that’s when she “visits her tear sheets.” (Tear sheets are pages clipped or torn from a newspaper or magazine that show a client’s ad.) She’s saved things she likes or that inspire her, including books, beautiful packaging, or pages from magazines. She finds that getting away from the project she’s working on and flipping through her tear sheets, even if for a few minutes, can spark new ideas.

This is really an inspiration file, so it could take almost any form, depending on what inspires you. There’s such an abundance of new brain and behavior information that my habit is to either bookmark or print copies of the articles that interest me to check out later. That may seem like research more than inspiration, but it’s really both. I often get new ideas from what I read and make new connections, which energizes me—and that, I think, is the point of an inspiration file.

#6 Nap Every Day

News anchor Pat Kiernan takes a nap. Every day. He says he’s “super protective” of his nap and keeps a hard line about it. “You have to learn how to say no.” He wants to be rested and healthy, so he has learned to resist the temptation to do everything he’s invited to do.

There’s a lot of research to support the benefit of daily napping, and I know several people who swear by it. But I confess that I’m not one of them. If a nap during the day recharges you, then take Kiernan’s advice to heart and treat nap time as you would any other important appointment on your calendar. If you’re intentional about making it a habit, you’ll find that much easier to do.

#7 Envision What You Will Be Remembered For

Rapha founder Simon Mottram writes “faux business pieces,” articles for Financial Times or Wall Street Journal as if the company had already accomplished their current goals. In one article, he described how Rapha had revolutionized the cycling market and was “leading more people to discover road racing as a lifestyle and a fundamental part of their lives.” He was very specific about what that looked like and how many customers the company had. Five years later, he says, the article pretty accurately described the company’s reality.

“Envision what you will be remembered for” doesn’t go far enough. This is an example of identifying and visualizing your desired outcome clearly and specifically enough to try it on for size—and to use as a benchmark to tell when you’ve gotten to where you wanted to go. The desired outcome is not the same thing as the goal. A good goal is S.M.A.R.T., but that’s not enough. You have to identify what’s going to be different afterward and what it’s going to feel like and look like—for you and for others. (Essentially, why do you want to achieve this goal or create this thing?) Taking the time to identify your desired outcome is a habit that pays spectacular dividends and one that you can incorporate into planning anything of any nature in any area of your life.

#8 Brainstorm at the Bar

Designer James Victore says he does his “think-work” at the bar and his “work-work” in his studio. He sketches on paper, usually in a bar or restaurant. His routine includes going to the park to write (longhand) for an hour or so in the morning and then taking his writing to the studio to work on. Afterward, he goes to a bar or restaurant, has a beer, and refines his idea or does some sketching. He uses his studio for “putting stuff together” rather than coming up with ideas.

I can relate to this one! I discovered that while I can do all kinds of work in my home office, one thing I cannot do there is any kind of long-range planning. I’d tried taking the planning to various coffee shops, but that wasn’t effective, partly because I don’t—and apparently don’t want to—equate coffee shops with work. But I discovered, almost by accident, that taking my planning materials to the nearby library allows me to get an amazing amount of work done in a relatively brief amount of time. So notice how your environments affect you and figure out which environment is the most effective for the task or process you’re working on. Develop a routine around what works rather than around what you think should work.

#9 Get Out of the Building

Garrison Keillor credits getting out into the “observable world”—as opposed to sitting and looking at a blank page—as providing him with “the start of something.” He recommends walking around with scrap paper and pen to take notes on what you see in the world. These observations and notes are valuable even if they don’t make it into your final work because “everything—everything—starts with the observable world.”

Your brain usually determines what you pay attention to, so you attend to things selectively. We all do. Check out The Invisible Gorilla video on YouTube for verification. Creating a practice of not just noticing what you notice (the usual suspects), but consciously directing your attention can definitely change your perspective. Tell your brain what kinds of things to look for and it will find them. It will also make connections and see patterns that might otherwise have been invisible.

#10 Engage in “Morphological Synthesis”—or Not

Artist and filmmaker Ze Frank uses morphological synthesis to segment his thinking process into parts. He says, “You take 4-5 adjectives or characteristics and then brainstorm in that direction.” He then “flips back and forth between extremes until something interesting comes out of it” and then repeats the process. He likes it because it “forces you to explore the outside boundaries of things.”

OK, that’s interesting, but what Frank also said in the same interview is that he makes something every single day. He said it’s the only design habit he has. “No matter what, I make something.” Developing the habit of making something every day is awesome. It doesn’t have to be big. It doesn’t have to be “successful.” It doesn’t have to be totally original. Just make something. If you’re a writer, write something. If you’re a cook or a chef, cook something. The result doesn’t need to be a tangible object, however. This is about creativity, after all. Create an idea or a concept. Make a new connection between ideas, objects, or people. Have some kind of impact.

I think this is a wonderful agenda to take on: what did I make today?

Look for Limitations

When Phil Hansen was in art school, he developed a shake in his hand that prevented him from drawing a straight line. He was interested in pointillism at the time, but the technique exacerbated the problem to the extent that eventually he gave up art. The shake in his hand didn’t go away. The neurologist who told him he had permanent nerve damage suggested he “embrace the shake.” So he did.

Embracing the shake meant embracing limitation, which is what led him to discover that working on a larger scale with bigger materials was easier on his hand.

This was the first time I encountered the idea that embracing limitation could actually drive creativity.

In the video below of his TEDx talk in Kansas City, Hansen says:

I realized that if I ever wanted my creativity back I had to stop trying so hard to think outside of the box and get back into it.

He set out to impose all kinds of constraints on the art he created. The image at the top of this post was the result of his intention to create something for under a dollar. (When he asked someone at Starbucks for 50 empty cups, he got them.)

You become more creative by actually looking for limitations.

He’s written a book about creating art aimed at “kids” from 8 to 70 titled Tattoo a Banana: And Other Ways to Turn Anything and Everything Into Art.

Looking at limitations as the source of creativity changed my life.

It’s impossible to create anything, do anything, or just be (alive) without experiencing limitations. The trick is not only to look for limitations, but also to embrace them.