Who Is the Most Difficult Kind of Person?
Pick your poison, who would you least like to be in the back seat of a cab with?
When she was good,
She was very good indeed,
But when she was bad she was horrid.
–Henry Wadsworth Longfellow
Below I’ll give descriptions of how each type acts when they are unhealthy with examples of celebrities who exhibit these qualities. Sneak peek… each type is a different flavor of horrid. I’m using the framework of the Enneagram, but don’t stress if it’s unfamiliar to you, just read along and see if you recognize these archetypes.
We’re all super unpleasant when we’re unhealthy.
The Savior — Perfectionistic hypocrite who’s angry you won’t help them save the world by following the impractical, rigid rules they spent their life carefully crafting. They fume “Why are you so disappointing and incorrect?”
Unhealthy 1s: SNL’s “The Church Lady”, Osama bin Laden
Healthy 1s: Confucius, Plato, Michelle Obama, Nelson Mandela, GandhiThe People Pleaser — They’re so sickly sweet that you don’t want their unsolicited advice. They get angry when you say no to their help. They plead “Why won’t you just let me fix you?”
Unhealthy 2s: Elizabeth Taylor, Jim Jones, “Cinderella”
Healthy 2s: Dolly Parton, Bobby McFerrin, Guru Ammaji (The Hugging Saint), Byron KatieThe Overachiever — They’re working so damn hard to get you to like them that you can’t get close to them. They beg “Why can’t you just see how shiny and impressive I am?”
Unhealthy 3s: Elvis Presley, O.J. Simpson, Whitney Houston, “Don Draper”
Healthy 3s: Oprah Winfrey, Michael Jordan, Lady Gaga, StingThe Big Mood— They’re totally absorbed in the drama of their own specialness and just wishing to belong somewhere. They are too ashamed to ask “Why can’t you be my therapist for free for ten hours a day?” and go back to drowning alone.
Unhealthy 4s: “Eeyore,” Cher, Amy Winehouse, Hank Williams
Healthy 4s: Rumi, Frida Khalo, Edgar Allen Poe, Anne Frank, PrinceThe Know-It-All — When they finally emerge from their cave they shove everything they’ve been working on down your throat. They dismiss “Of course you’re so stupid that you can’t understand my brilliance.”
Unhealthy 5s: Kurt Cobain, Nietzsche
Healthy 5s: Albert Einstein, Eckhart Tolle, Agatha ChristieThe Worry-Wart — They freak out about every possible way life might go wrong. They mutter “Why can’t you live your life in a hermetically sealed bubble so I can stop worrying about you?”
Unhealthy 6s: Mike Tyson, “Charlie Brown,” Richard Nixon, Marilyn Monroe
Healthy 6s: Bruce Springsteen, Lord of the Rings’ “Frodo”, Katie CouricThe Flake — They chase fantasies of happiness till they’re miserable. They seem super fun until you try to rely on them to commit to anything. They roll their eyes “Why don’t you have infinite patience with my shenanigans?“
Unhealthy 7s: Robin Williams, Elton John
Healthy 7s: Jim Carrey, Ram Dass, Russell BrandThe Bull In A China Shop — They’ve decided that you need a kick in the ass, and they’re just the boot the universe has hired to give it to you. They growl “Why aren’t you stronger?”
Unhealthy 8s: Howard Stern, Pablo Picasso
Healthy 8s: Beyonce, Toni Morrison, Barbara Walters, Martin Luther King, Jr.The Phantom — When you need them most they disappear into the wallpaper. They mask their alarm “Why can’t you be ok so I can be ok?”
Unhealthy 9s: Ma Anand Sheela (Osho’s mastermind)
Healthy 9s: “Winne the Pooh,” 14th Dalai Lama, Morgan Freeman, Carl Jung, “Mister Rogers”
Which is the worst?
It’s all a matter of personal taste. We often don’t like people who are an unhealthy version of the same type as us as it offers too strong of a mirror of what we don’t like about ourselves. Ouch… I know. But, if you’ve found this article you’re on the right track! Keep going! There’s much revelation and realization on this path. When we find that someone is exhibiting a characteristic we find unacceptable or intolerable, it’s pretty much always a clue we have a hook or blindspot there asking for some loving attention.
Another possible dynamic on which type is most difficult is the similarity to your parents and siblings. I kept falling in love with Enneagram Sevens and having frustratingly unfulfilling relationships until I realized that my dad is an unhealthy Seven.
The trickiest thing about the Enneagram is it’s hard to tell which type you are.
This system pulls back the ego blindfold to show us how we’re hiding from our truest, essential selves. Because of this, your ego defenses are actively trying to get you NOT to know this information. If you’ve tried Enneagram in the past or took a quiz and found you didn’t quite “get it,” it’s probably because you mistyped yourself.
I mistyped myself at first too. I wanted to think *I* was a fun, freewheeling Seven like my dad. I’m a (recovering) workaholic Three. Oops.
When you finally do get your type right, you’ll see yourself in the pages of its description and say “Oh no, is this what I’m doing to myself?” Then you’ll uncover the patterns of self-sabotage that have kept you stuck and massively change your life.
secrets of the dragon
The Becoming Dragon deck is organized by the framework of the Enneagram. Each color represents the core struggles of that personality archetype. The red cards are Three, for example. You’ll notice three dots at the bottom of each red card, and the guidebook is organized thusly. The purple cards are for Four and have four dots, etc. The blue cards are for the Five, the teal cards for the Six, and so forth all the way around the pinwheel.
If you lay together the cards of the same color you’ll see that the themes are quite different.
The workaholic Three struggles to connect to the authenticity of their heart and gets distracted by seeing themselves through everyone else’s eyes. Those cards are Ancient vs. Impatient, Empathy vs. Narcissism, Flow vs. Frustrated, Leader vs. Manipulative, Transcend vs. Comparison, Truth vs. Self-Deception, and Voice vs. Choked.
Compare that to the free-wheeling Seven who struggles to stay with things — always chasing the next high and running from their fears. Their cards are Being vs. FOMO, Bliss vs. Hooked, Decisive vs. Maybe, Free vs. Trapped, Presence vs. Addiction, Revelation vs. Illusion, and Sacred vs. Bored.
I use the Enneagram in my Zoom sessions and in-person medicine retreats to clear out those dusty boxes of childhood trauma so you can (finally!) be yourself. You don’t need to keep carrying all that dusty baggage. Get in touch if you’re curious. Just hit reply to this email.
Love from Oaxaca,
Cris and Team Dragon