Measure in Hundreds
If your unit of measurement is one hundred attempts, five failures means you have effectively tried zero times.
- Difficulty
- Starter
- Time to result
- ~ongoing to results
- Steps
- 3
- Confidence
- 92%
Kilpatrick's personal life motto, kept on a post-it note behind his camera. When someone says 'I tried this and it didn't work', the hidden variable is almost always sample size — they tried five times. If your mental model measures attempts in hundreds, five failures registers as zero attempts, which removes the emotional weight from early failure and reframes it as not having started. It is a re-anchoring device for anyone at the beginning of a long compounding journey.
Origin
Logan Kilpatrick's own motto, shared as his life motto on Lenny's Podcast (Feb 2024). He keeps it written on a post-it note behind his camera.
Core principles
- 01Everything meaningful is built on compounding and repeated attempts.
- 02The denominator, not the failure, is the thing to examine first.
- 03Failure at attempt five is not evidence about the thing — it is evidence you haven't started.
- 04If you don't try enough times, you will never be successful at it.
- 05Changing the unit of measurement changes what counts as a setback.
How to run it
- 1
Set the unit of measurement to one hundred
Before starting any long-horizon effort — cold outreach, content, product experiments, a new skill — explicitly declare that the meaningful sample is one hundred attempts, not five or ten.
Pro tip Kilpatrick writes it down physically — a post-it note behind the camera — so the frame is present when the discouragement arrives.
- 2
When you want to quit, count the attempts
At the moment of 'this isn't working', state the actual number of attempts out loud. Against a denominator of one hundred, five failures is a rounding error, not a verdict.
Pro tip Reframe: 'I've tried five times and it hasn't worked' becomes 'I have effectively tried zero times'.
Watch out This is a persistence frame, not a validity frame. It tells you whether you have enough data to judge — it does not tell you the thing is worth doing.
- 3
Keep going long enough to let compounding start
Continue until the sample is real. The premise is that outcomes are built on compounding and multiple attempts, so the returns arrive far later in the sequence than intuition expects.
In the wild
Kilpatrick says he talks to people all the time who report that they tried something and it didn't work. Applying the hundreds frame, their five attempts amount to zero real attempts — they abandoned before the sample was large enough to mean anything.
→ The diagnosis flips from 'the approach is wrong' to 'the sample is too small to know', which changes the decision from quit to continue.
Kilpatrick's favourite recent film is Gran Turismo — a kid from London doing virtual sim racing who ends up a real professional race car driver competing at Le Mans, a story of accumulated repetitions converting into a real outcome.
→ Kilpatrick cites it as the kind of inspirational human story he is a sucker for — the compounding-attempts thesis in narrative form.
Common mistakes
Judging an approach on a sample of five
Five failures carries no statistical or practical information about whether the approach works. Treating it as a verdict is the most common quitting error.
Using the frame to justify a genuinely bad bet
Measuring in hundreds tells you to keep going, not that the destination is right. It must be paired with an independent judgment about whether the goal is worth a hundred attempts.
Is it for you?
Best for
Anyone at the very beginning of a compounding journey — building an audience, learning a craft, cold outreach, or shipping experiments — who is about to quit after a handful of failures
Not ideal for
Situations where each attempt is expensive or irreversible, or where early failures carry genuine signal that the strategy is wrong
From the transcript
“I've got it on a post- a note that I right behind my my camera and it's measure in hundreds”
“if your mental model is to measure in hundreds if I measure in hundreds the five times that you failed at something youve failed tried…”
“if you don't try enough times like you're never going to be successful at it”
From the episode
Inside OpenAI
Logan Kilpatrick (head of developer relations)