1. Cynicism: The Slow Death of Wonder
Early Warning Signs:
✓ Eye-rolling at others’ enthusiasm
✓ Assuming the worst in people
✓ Calling realism "just being honest"
Antidote:
✓ Hunt for good news daily
✓ Reconnect with your younger, hopeful self
"Cynicism is what happens when you stop being disappointed and start being disgusted."
2. Compromise: The Ethics Slippery Slope
How It Happens:
✓ "Just this once" exceptions
✓ Small moral shortcuts
✓ Isolating yourself from accountability
Recovery:
✓ Establish non-negotiables
✓ Find truth-tellers who’ll call you out
3. Disconnection: The Loneliness of Leadership
Danger Zone:
✓ Canceling personal plans for work
✓ Only having transactional relationships
✓ Feeling unknown in crowds
Reconnection Plan:
✓ Schedule unprotected time with friends
✓ Share struggles, not just successes
4. Irrelevance: The Fear Every Leader Secretly Harbors
Symptoms:
✓ Defensiveness about new ideas
✓ Overemphasis on past achievements
✓ Avoiding younger colleagues
Relevance Hack:
✓ Have a reverse mentor (<30 years old)
✓ Spend 30 mins/week learning something irrelevant to your field
5. Pride: The Achievement Trap
Subtle Indicators:
✓ Unconscious name-dropping
✓ Feeling offended by minor slights
✓ Believing your own press
Humility Builder:
✓ Regularly do something you’re bad at
✓ Celebrate others’ wins publicly
6. Burnout: The Ambition Tax
Stage 1: Working 24/7 with pride
Stage 5: Numbness, insomnia, emotional detachment
Recovery:
✓ Mandatory unproductive time
✓ Physical movement before emails
✓ Redefine "enough"
7. Emptiness: The Success Paradox
The Lie: "When I reach ___, I’ll be happy."
The Truth: Achievement amplifies who you already are
Filling the Void:
✓ Serve someone who can’t repay you
✓ Create meaning beyond metrics
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