What Leaders and Managers Can Learn from The Obstacle Is the Way
How you personally react to a team-level setback becomes the model your team uses for their own reactions — Holiday's three disciplines are as much about what you demonstrate as what you privately practice.
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.
0 of 3 selected
The core lessons, applied to you
Perception — modeling a clear-headed read of a setback
Fear and ego distort a setback's real size before an honest assessment happens. A leader who reacts with immediate, dramatic framing teaches the team to do the same.
A manager announces a missed target with language that treats it as a crisis before establishing what actually happened and what options remain, and the team's anxiety escalates beyond what the facts warrant.
Before communicating about a setback to your team, write the neutral facts of what happened, separately from how alarming it feels, and lead with the facts.
Action — disciplined, practical steps your team can actually see
Persistent, unglamorous iteration usually resolves team-level obstacles better than a single bold pivot. Naming the next concrete step, rather than a grand plan, gives a team something to actually do.
A leader announces a dramatic strategic reset in response to a setback that a series of smaller operational fixes would have resolved, creating unnecessary disruption.
Will — holding steady through what's genuinely outside your control
Some obstacles (a market condition, a decision made above you) are real constraints your team has to endure rather than solve. Naming that honestly, while still pointing to what remains actionable, is the Will discipline applied to leadership.
Using this well versus using it to avoid a real problem
If a struggling initiative keeps failing despite genuine disciplined effort, that's information the plan is wrong, not evidence to push harder. A leader who reflexively reframes every failure as "the obstacle is the way" risks keeping a broken plan alive too long.
Encouraging persistence and being willing to kill a failing initiative aren't opposites — the Perception discipline is what tells you honestly which situation you're in.
Name one thing, honestly
Think of your team's current biggest obstacle. Is your framing to them based on an honest assessment, or on how alarming it felt to you initially?
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
0 of 1 selected
Run this for seven days
Before communicating about a setback to your team, write the neutral facts of what happened, separately from how alarming it feels, and lead with the facts.