Chapter 8

Shadow Work Meets Stoicism

The Stuff You're Hiding From

Your ego shows up daily. It protects, deflects, rationalizes. But underneath is the stuff you don't want to look at.

Carl Jung called it the shadow. The Stoics called it vice. Modern bros call it "that thing I know I should fix but definitely won't."

Your shadow is the collection of parts you've rejected, suppressed, or refused to acknowledge:

  • The anger you pretend isn't there
  • The insecurity you mask with confidence
  • The pattern you keep repeating despite knowing better
  • The fear that drives decisions you won't admit

If you don't face it, it runs you.

Stoics Did Shadow Work

Marcus Aurelius constantly confronted his worst impulses:

He didn't pretend he was above anger, fear, or anxiety. He interrogated it. Wrote about it. Named it so he could face it.

Seneca did the same. Every night: What did I do wrong? What temptation did I give into? Where did I fail to be who I want to be?

This isn't self-flagellation. It's self-awareness with action.

The Monthly Deep Dive

Daily journaling catches the surface. Shadow work goes deeper.

Frequency: Monthly (not daily—too heavy)

Shadow Work Template

1. THE PATTERN

What recurring problem keeps showing up in my life? (Relationships, work, self-sabotage, anger, avoidance)

2. THE TRIGGER

When does this pattern appear? What situations, people, or feelings activate it?

3. THE ORIGIN

Where might this come from? (Childhood, past relationship, fear, belief)

4. THE BENEFIT

What does this pattern protect me from? What payoff am I getting?

5. THE COST

What is this pattern actually costing me?

6. THE ALTERNATIVE

What would a Stoic response look like? What would Courage, Justice, Wisdom, or Temperance say?

7. THE COMMITMENT

What's ONE small action I can take this month to interrupt this pattern?

Chad's Shadow Session

The Pattern

"I self-sabotage relationships. Things get real, I pull away."

The Trigger

"When someone shows genuine interest. When vulnerability is required."

The Origin

"Dad left when I was 12. Mom checked out emotionally. Love = eventual abandonment."

The Benefit

"If I leave first, I can't be left. If I don't care, it can't hurt."

The Cost

"I'm 32. Never had a real relationship. Deeply lonely. Pattern confirms itself."

The Alternative

"Courage says: Stay when it's scary. Wisdom says: Past isn't destiny. Temperance says: Don't let fear drive."

The Commitment

"Next time I want to pull away, I'll stay one more week. Just one."

Two months later: "Stayed when I wanted to run. It was terrifying. But she's still here. Maybe love doesn't always leave."

Warning: This Gets Heavy

  • Don't do this daily. Monthly max. This digs up real shit.
  • If trauma surfaces, get help. Shadow work isn't therapy. If something serious comes up, talk to a professional.
  • Courage, not punishment. The goal is awareness and growth. Not beating yourself up.

Marcus Aurelius: "If it's not right, don't do it. If it's not true, don't say it." Simple compass. Hard execution.


Stoic Slap

"No man is free who is not master of himself."

— Epictetus
Your Move

Set a monthly calendar reminder: "Shadow Work Session."

  1. Block 30 minutes alone
  2. Open the template
  3. Be brutally honest
  4. Pick ONE commitment
  5. Track it during daily journals

Face the shadow. Or it runs you.


Chapter 9: Systemize Your Mind →