What Coaches and Mentors Can Learn from The Obstacle Is the Way
A large part of coaching well is helping someone else move through Holiday's three disciplines in order — seeing a setback clearly, acting on it practically, and enduring what genuinely can't be changed yet — rather than skipping straight to reassurance.
The whole book, compressed
This edition works through 4 core lessons — take them one at a time, not all at once.
What's different for your conditions
Tap whichever ones sound like you. Nothing here is sent or saved — it's just for your own noticing.
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The core lessons, applied to you
Perception — helping someone separate facts from their reaction
When someone you coach reacts to a setback with catastrophizing language, the useful move is asking what actually happened, specifically, before addressing how they feel about it.
A coach responds to someone's distress with pure reassurance, skipping past the more useful step of helping them see the situation accurately first.
The next time someone you coach is reacting strongly to a setback, ask them to describe what actually happened, in specific, neutral terms, before responding to the emotion.
Action — helping someone find the next concrete step
When someone is stuck, identifying one small, specific, doable next action is usually more useful than a big motivational push toward an overwhelming overall goal.
Will — helping someone endure what's genuinely outside their control
Part of coaching well is naming, honestly, what part of a person's situation can't be changed right now, while still pointing to what remains theirs to act on — rather than promising a fix that isn't available yet.
Using this well versus using it to avoid a real problem
If someone you coach keeps hitting the same obstacle despite real, sustained effort, your job is to name that honestly as information, not to keep encouraging pure persistence when the approach itself needs to change.
Encouraging someone to keep going and being willing to tell them a specific approach isn't working aren't opposites — good coaching does both, in the right order: perceive clearly first, then decide.
Name one thing, honestly
Think of someone you coach who's currently stuck on an obstacle. Have you helped them see it accurately, or moved straight to encouragement?
Good. Now look back at the "Try this" line under whichever lesson feels most connected to what you just wrote, and treat that as this week's actual assignment — not all 4 at once.
The practices from this edition
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Run this for seven days
The next time someone you coach is reacting strongly to a setback, ask them to describe what actually happened, in specific, neutral terms, before responding to the emotion.