What Entrepreneurs Can Learn from The Obstacle Is the Way
Every founder eventually meets a problem large enough to feel like the end of the plan. Holiday's framework — perception, action, will — is specifically about what to do in that exact moment, not before it and not after it's already resolved.
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 — seeing the obstacle before reacting to it
Panic and ego distort the size of a problem before you've actually assessed it. The discipline is separating what's actually true about a setback from your emotional reaction to it, which usually exaggerates it.
A founder reacts to a lost deal or a bad metric with an immediate, dramatic narrative ("we're finished") before doing the actual work of assessing what changed and what options remain.
The next time something goes wrong, write down the neutral facts of what happened separately from your emotional reaction to it, before deciding what it means.
Action — disciplined, practical steps, not a single clever move
Most startup obstacles yield to unglamorous, persistent iteration, not a single insight. The discipline is doing the next concrete thing, repeatedly, rather than waiting for the plan that makes the obstacle disappear all at once.
A founder stalls looking for the perfect strategic response to a setback, while a series of smaller, immediately available actions goes untaken.
Will — enduring what genuinely can't yet be changed
Some conditions (a downturn, a platform policy) really are outside your control right now. The Will discipline is holding steady through that specific part while continuing to act on what remains yours.
Using this well versus using it to avoid a real problem
If an obstacle is actually a sign the current plan is broken — not just hard — "push through it" is the wrong response. The honest test: is repeated effort producing any real change, or is the obstacle simply restating that the underlying plan doesn't work.
Persisting through a hard stretch and honestly recognizing a plan has failed aren't opposites — the discipline of Perception is precisely what lets you tell the difference instead of defaulting to either blind persistence or premature quitting.
Name one thing, honestly
Name your current biggest obstacle. Have you actually assessed it clearly, or reacted to your fear about it — and is continued effort producing any real change?
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
The next time something goes wrong, write down the neutral facts of what happened separately from your emotional reaction to it, before deciding what it means.