The Enlarge-or-Diminish Question
Judge every big life choice by whether it will enlarge you or diminish you, not whether it will make you happy
- Difficulty
- Easy
- Time to result
- ~ongoing to results
- Steps
- 4
- Confidence
- 79%
Faced with a big life decision, most people ask whether the option will make them happy: will this job, this relationship, this move increase my happiness? Jungian analyst James Hollis proposes a sharper test: ask instead whether the choice will enlarge you or diminish you. This works because it captures something the happiness question misses, that worthwhile paths often involve real stress and difficulty. The enlarge-or-diminish frame lets you distinguish the difficulties worth sticking with, the ones making you a bigger person, from the ones that make your soul shrivel and signal genuine incompatibility. Crucially, it connects to an intuition people usually already hold about a path they're on; when they get quiet, they tend to know which kind of difficulty they're facing. It applies not just to relationships but across career and other major domains.
Origin
Burkeman attributes the question to Jungian analyst and writer James Hollis, and returns to it as a favourite tool for approaching big life questions.
Core principles
- 01Will-this-make-me-happy is the wrong question because it can't see growth-through-difficulty
- 02Some worthwhile stresses enlarge you; some diminish you, and you usually already sense which
- 03Enlargement connects to intuition most people already hold about their own path
- 04Growth-worthy difficulty and soul-shrivelling difficulty feel different from the inside
- 05The frame applies across relationships, work, and other major domains
How to run it
- 1
Frame the big question
Isolate the major decision at hand, such as staying in a relationship, taking a job, or changing direction.
- 2
Swap the happiness test for the size test
Replace 'will this make me happy?' with 'will this enlarge me or diminish me?'
Pro tip It can feel kooky at first; sit with it rather than dismissing it.
- 3
Classify the difficulty
Distinguish stresses that grow you and are worth the payoff from stresses that make your soul shrivel.
Pro tip Growth-worthy difficulty and dead-end difficulty genuinely feel different from the inside.
- 4
Trust the intuition and choose
Check the answer against what you quietly already sense about the path, and pick the enlarging option even if it's hard.
Watch out Do not confuse discomfort with a signal to avoid; enlarging paths are often uncomfortable.
In the wild
Rather than asking whether leaving would make them happier, a person asks whether the relationship's stresses are enlarging or diminishing. They recognise the difficulties as the kind that make them a bigger person and are worth sticking with for the growth, versus the kind that signal fundamental incompatibility and a shrivelling soul, a distinction the happiness question left blurry.
→ A decision grounded in growth and intuition rather than a vague forecast of future happiness.
Common mistakes
Defaulting to the happiness question
Asking only whether something will make you happy hides the fact that many worthwhile paths involve real, growth-producing difficulty.
Reading all discomfort as a stop sign
Enlarging choices are frequently uncomfortable, so treating difficulty itself as disqualifying steers you away from growth.
Is it for you?
Best for
Anyone weighing a major decision about a relationship, job, or life direction.
Not ideal for
Small, low-stakes, reversible choices where deep introspection is overkill.
From the transcript
“this question that comes from james hollis the jungian analyst and writer which is to ask of every big life question ... whether it will…”
“they know whether the stresses and difficulties that they encounter in say a relationship are the kind that are making them a bigger person and…”
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