Getting Out Of Your Own Way

I heard someone say recently that one of the habits quietly ruining many of our lives is judgment.

Not judgement in the sense of wisdom or discernment, but judgment as a reflexive tendency to approach people, situations, and experiences with pre-formed conclusions already in place. In other words, we walk into life already deciding how things should be, and then react negatively when reality does not cooperate with our expectations.

That idea caught my attention.

Because I think there is an important distinction here between judging and having good judgement.

Judging is the semi-automatic process of forming and imposing opinions.
Judgement, on the other hand, is discernment, wisdom, and the ability to make thoughtful decisions.

Good judgement is desirable.
Being judgmental is what often gets in our own way.

And the more I thought about it, the more it reminded me of complaining. The two are closely related. Both create a kind of rigidity that blocks openness to experience. Both narrow our capacity to encounter reality as it actually is.

That got me thinking about the Enneagram personality system and whether it might help explain some of the deeper motivations behind our judgmental tendencies.

I think it can.

So let’s walk through the nine types briefly and look at how each one tends to get in its own way. I’ll also use myself as an example throughout where it fits. Personally, I believe I’m primarily a Type 4 with a Type 5 wing and a 471 tri-type structure, so many of these dynamics are very familiar to me.

Type 1 — The Perfectionist

Type 1s often get in their own way through moral rigidity and self-righteousness. They can begin treating their personal standards as universal truths that everyone else should naturally follow.

For example, I have a very strong bias against debt. I genuinely believe one of the best things many people pursuing FIRE can do is eliminate debt and stay out of it.

But my “One” energy can become judgmental if I start assuming everyone should see the world exactly the way I do. Some people view debt as a useful financial tool, and they are entirely free to think that way. My responsibility is to recognize where my convictions end and where imposing them onto others begins.

Type 2 — The Helper

Type 2s can get in their own way when helping becomes entangled with control, validation, or resentment. They may unconsciously judge others as selfish, incapable, or insufficiently appreciative.

When unhealthy, Type 2s often become martyrs.

As a Type 4, when I regress under stress, I move toward unhealthy Type 2 tendencies. I can become overly generous or overly emotionally invested in “fixing” situations for people. Then, when things do not unfold the way I hoped, resentment can quietly emerge underneath the surface.

That is the trap:
helping in order to manage emotional discomfort or gain emotional reassurance rather than simply helping freely.

Type 3 — The Achiever

Type 3s tend to get in their own way through status consciousness and dismissiveness. They can begin judging others as inefficient, unsuccessful, slow, or irrelevant.

This one makes sense to me even though it is not one of my dominant types.

Whenever I slip into intense “get it done” mode, I can absolutely begin viewing people primarily through the lens of whether they are helping me move toward the outcome I want. When stressed, I can become impatient with anything or anyone that feels like an obstacle.

That is not exactly a beautiful way of relating to people.

Type 4 — The Individualist

This is my home territory.

Type 4s often get in their own way through aesthetic or emotional elitism. They can judge others as shallow, conventional, vulgar, or emotionally asleep.

In other words:
the unhealthy Type 4 becomes a snob.

Type 4s deeply value authenticity, beauty, uniqueness, symbolism, emotional depth, and meaning. But when this becomes exaggerated, it can create alienation and disconnection.

I see this in myself all the time.

Part of me does not actually want to fit into conventional social structures. There is a romantic attachment to being the outsider, the misunderstood wanderer, the lone figure standing above the sea of fog in some dramatic Romantic painting.

And yes, there is a subtle superiority complex hidden inside that posture.

Type 5 — The Investigator

Type 5s often get in their own way through intellectual arrogance and emotional detachment. They can begin viewing others as uninformed, irrational, intrusive, or mentally lazy.

This is my wing type, and I absolutely recognize it.

Curiosity and analysis are wonderful strengths, but they can easily morph into “I understand this better than everyone else” energy. When that happens, genuine connection becomes difficult because the person is relating from intellectual superiority rather than openness.

Type 6 — The Loyalist

Type 6s often struggle with suspicion and anticipatory judgment. They can become quick to categorize others as unsafe, deceptive, reckless, or untrustworthy.

At the core, this usually reflects anxiety and a longing for security.

Type 6s value loyalty, preparedness, and honesty very deeply. But when fear takes over, they can begin projecting their own anxieties outward onto other people and situations.

Type 7 — The Enthusiast

Type 7s get in their own way when they become overly attached to possibilities, stimulation, excitement, and future-oriented thinking.

They often judge others as boring, pessimistic, limiting, or overly serious.

This one is very alive in me.

The “7” energy in my tri-type is probably part of what fuels projects like writing and posting a blog article every single day for a year. I get energized by possibilities, vision, momentum, and enthusiasm.

And when someone immediately responds with caution, practicality, or reasons something may not work, my internal response is often:
“Please do not derail my energy right now.”

The challenge for Type 7 is that realism can start feeling emotionally threatening, so they label it negativity and tune it out.

Type 8 — The Challenger

Type 8s often get in their own way through intensity, aggression, and condemnation of weakness.

They can judge others as cowardly, incompetent, passive, or fragile.

Type 8s respect strength and resilience. They want to push forward, overcome obstacles, and lead from force of will. But the shadow side is that vulnerability starts to feel unacceptable — both in others and in themselves.

Anyone who slows the momentum or threatens the vision may become a target for frustration or dismissal.

Type 9 — The Peacemaker

Type 9s often get in their own way through avoidance and passive resistance.

Rather than directly confronting conflict, they may withdraw, disengage, make sideways comments, or quietly disappear emotionally.

Type 9s crave peace, comfort, and inner stability. As a result, they may judge others as disruptive, dramatic, demanding, or exhausting.

But the cost of avoiding conflict is often the suppression of their own feelings, desires, and boundaries. Over time, that suppressed frustration tends to leak out indirectly.

So what do we do with all of this?

Is judgment itself the problem?
Should we try to completely stop judging?

I’m honestly not sure.

Personally, I do not think it is possible — or even desirable — to eliminate all forms of judgment entirely. That sounds somewhat dissociative and inauthentic to me. We need discernment. We need values. We need preferences.

But I do think it helps enormously to become more aware of the unconscious narratives we carry into situations.

For me, the real work is noticing when my pre-formed mythic structures are taking over automatically at the Relatively Unconscious level of my personhood.

And at the Character level, I actually find paying attention to my complaints especially revealing.

What am I repeatedly criticizing?
What annoys me disproportionately?
What themes keep showing up?

Those reactions often reveal where I am getting in my own way.

And then there is the Existential level of my personhood — the level of choice itself.

Because regardless of our personality structure, myths, habits, or conditioning, there remains the possibility of pause.

This is the key.

One of my mentors used to tell me that Rollo May often spoke about “the power of the pause.”

And I think that is exactly right.

Because it is in that pause — however brief — that we regain the possibility of exercising judgement rather than merely reacting through judgment.