Enlarging or Diminishing Decision Test
Choose the path that expands your life rather than shrinking it
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 5
- Confidence
- 94%
Oliver Burkeman borrows a question from psychotherapist James Hollis: does a choice or life path enlarge you or diminish you? The test distinguishes meaning from immediate enjoyment. Some experiences are unpleasant yet still feel growth-producing and deeply right, while enjoyable experiences can feel as though they miss the point. Apply the question to each available path, notice the direction of growth or contraction, and use that signal alongside the practical facts. Burkeman illustrates the mechanism through helping friends in a crisis: doing their dry cleaning was not fun or inherently glamorous, but it carried a clear sense that there was nowhere else he ought to be. The test is a reflective decision aid, not a claim that intuition alone settles every choice.
Origin
Burkeman attributes the central question to psychotherapist James Hollis. Extracted from The Diary of a CEO.
Core principles
- 01Meaning is not identical to enjoyment
- 02A difficult choice can still support growth
- 03A pleasant choice can still feel empty
- 04Intuitive direction can be useful when rigid labels fail
How to run it
- 1
Define the real choice
State the paths in concrete terms rather than asking whether life as a whole feels meaningful.
Pro tip Compare the next honest move on each path, not idealised futures.
- 2
Test for enlargement
Ask whether each path develops, deepens, or opens you despite any immediate difficulty.
Watch out Do not equate discomfort automatically with growth.
- 3
Test for diminishment
Notice whether an option feels narrowing, stagnant, or disconnected even if it is enjoyable or socially rewarded.
- 4
Check the felt direction
Ask which option creates the grounded sense that this is where you ought to be now.
Pro tip Use the signal as one input alongside consequences and evidence.
- 5
Take the next step
Act on the better-supported direction without waiting for a perfectly rigid category or complete certainty.
Watch out Seek qualified advice where the decision carries specialist risk.
In the wild
Burkeman recalls doing dry cleaning for friends facing an awful situation. The errand was not enjoyable or impressive, but helping gave him the clear feeling that he was in the right place and there was nothing else he ought to be doing.
→ A mundane task registered as meaningful because it served people who needed him.
Common mistakes
Confusing meaning with fun
Immediate enjoyment does not prove that a path is enlarging, and temporary difficulty does not prove that it is wrong.
Treating intuition as proof
The question reveals direction, not every practical consequence. Keep factual and specialist checks in the decision.
Is it for you?
Best for
It is best for people comparing plausible life, work, or relationship paths that carry different kinds of discomfort.
Not ideal for
It is not sufficient for decisions that require legal, medical, financial, or safety evidence beyond personal reflection.
From the transcript
“whether it's enlarging you or diminishing you”
“there isn't something else i ought to be doing now”
From the episode
How To Finally Stop Procrastinating: Oliver Burkeman