Character and Values Misalignment
Take a minute and think about one of the worst jobs you’ve ever had—something you stuck with for at least a few months, maybe longer.
What was it, exactly, that made it so bad?
I’ve had a couple like that. Jobs that didn’t just annoy me… they actually made me feel physically ill.
One of them stands out more than the others, so I’ll use that one here.
I was in a sales role. Cold calling businesses, trying to get in front of decision-makers to sell office equipment. And when I say cold calling, I mean cold—walking in unannounced, interrupting people’s day, trying to convince them to do something they had no interest in doing.
I would have done just about anything to avoid that part of the job. And sometimes… I did.
I played hooky.
I’d go into the office, make the rounds, have the small talk, and then head out as if I were going to make calls. And instead… I’d disappear for a while.
At the time, I told myself all kinds of stories about it. But underneath all of that, the real issue was pretty simple:
I felt like I was living a lie.
Like I was being asked to be someone I wasn’t, and to push something I didn’t believe in, in a way that didn’t sit right with me.
That created a kind of low-level—but very persistent—existential angst.
I’d wake up with it.
A knot in the stomach. A sense of dread. A mood that was… off before the day even started.
And then, of course, my behavior made it worse.
Because now I wasn’t just misaligned with the job—I was also not doing the job I’d been hired to do. So on top of everything else, I started to feel like a fraud. A scammer. A loser, if I’m being honest.
Not a great place to live from.
But something interesting happened.
At some point, my awareness caught up with me. I could see what was going on—internally and externally—and I started to adjust.
Because I had a large geographic territory, I realized I had some freedom in how I approached the role.
So I made a decision.
Instead of hitting the same dense, competitive areas over and over again, I started driving out to smaller, “under-served” towns—places where fewer salespeople were showing up.
Two things happened almost immediately.
First, I could actually get in to see people. Conversations were easier. Sales started happening. At one point, I even became salesperson of the month—which, given how this story started, is kind of amusing.
Second—and maybe more importantly—I started to enjoy parts of the job.
Those long drives? Two hours out, two hours back?
That became thinking time. Music time. Space.
Time to be my authentic Self.
It’s the year I really got into David Bowie and Bob Dylan—not just casually, but actually sitting with full albums and letting them unfold.
And I realized something else along the way.
This shift wasn’t just about tactics. It was about fit.
I had unknowingly moved closer to a way of working that matched how I prefer to exist in the world—what I’ve been calling ecological embeddedness.
I like space. I like movement. I like being out of the fluorescent-lit office and into something that feels a little more open, a little more alive.
(And let’s be honest… does anyone prefer fluorescent-lit Business offices?)
Looking back, I’m actually grateful for that job.
At the time, though?
It felt like a hellscape of my own making.
Because I had convinced myself I should be able to do sales. That I should enjoy it. That it made sense on paper.
But internally… it wasn’t aligned.
And that brings me to the point I said I’d get to today:
How does existential angst show up across the 9 Enneagram types?
At a high level, it’s actually pretty simple.
It shows up when we’re out of alignment with our core values.
Each Enneagram type has a set of values it naturally organizes around. When those values are expressed in day-to-day life—at the character level—things tend to feel… right.
Not perfect. But aligned.
When they’re not?
That’s when the friction starts.
And that friction doesn’t just stay at the surface.
It shows up at the Existential level of personality:
A “bad” mood, lack of willpower (your choices), and that nagging sense something is off
In awareness → you know, even if you can’t articulate it
In imagination → rumination, daydreams
And dreams and nightmares (at the Relatively Unconscious level of personality)
In your environment → where and how you’re living and working
So here’s a simple way to look at it.
The “Good Life” Values by Enneagram Type
Type 1 – The Idealist
Integrity
Fairness
Self-improvement
Type 2 – The Helper
Reciprocal connection
Generosity
Belonging
Type 3 – The Achiever
Achievement
Competence
Validation
Type 4 – The Individualist
Authenticity
Meaning
Self-expression
Type 5 – The Investigator
Understanding
Autonomy
Objective truth
Type 6 – The Loyalist
Security
Trust
Preparedness
Type 7 – The Enthusiast
Freedom
Stimulation
Optimism
Type 8 – The Challenger
Impact
Justice
Intensity
Type 9 – The Peacemaker
Harmony
Wholeness
Consistency
And if you want to understand what creates angst for each type?
Just flip those.
The “Hellscape” (Misalignment) Values
Type 1
Hypocrisy
Chaos
Stagnation
Type 2
Isolation
Selfishness
Exclusion
Type 3
Incompetence
Mediocrity
Invisibility
Type 4
Fakeness
Shallowness
Anonymity
Type 5
Confusion
Dependency
Irrationality
Type 6
Instability
Betrayal
Helplessness
Type 7
Restriction
Boredom
Despair
Type 8
Impotence
Injustice
Apathy
Type 9
Discord
Fragmentation
Volatility
You don’t need to memorize any of this. There’s a lot to unpack when it comes to the Enneagram personality types.
But it’s worth noticing when you feel “off” and understanding why.
Because when you find yourself in a situation that consistently produces dread, resistance, or that low-grade “something’s not right” feeling…
There’s a good chance you’re living inside a set of conditions that run directly against what you value most.
And that’s potentially a doorway back out.
So I’ll leave you with a couple of questions to sit with:
What do you think my Enneagram type might be, based on that “hellscape” job?
And more importantly…
What has your version of that experience been?
Not just what the job was—but what, exactly, made it feel so off?
Because that answer tends to tell you a lot more than you might expect.