The Pre-Mortem (Obstacle-Based Planning)
Before you start, imagine the goal has failed and name every reason why — then plan around each.
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 4
- Confidence
- 88%
Milkman argues the power of negative thinking is that anticipating obstacles beats simply adopting a positive mindset. You still need to believe in yourself, but if you don't plan for what can go wrong you forfeit the benefit of every behavior-change strategy. Gabriele Oettingen's research shows that identifying what could get in your way and pre-deciding how to overcome it improves results. Milkman frames this as a pre-mortem: before pursuing a goal, imagine it has completely fallen apart and list the most obvious reasons. Engineers do this naturally with structures; people fail to apply it to their personal lives and productivity.
Origin
Milkman draws on NYU psychologist Gabriele Oettingen's work on obstacle-based planning and reframes it as a pre-mortem — the inverse of the familiar post-mortem — applied before a goal is pursued.
Core principles
- 01Blind positive thinking and overconfidence leave you unprepared for what goes wrong.
- 02Anticipating obstacles and pre-deciding how to overcome them improves results.
- 03A pre-mortem does before the fact what a post-mortem does after: surface likely failure modes.
How to run it
- 1
Keep some self-belief
Retain positive belief that you can succeed — it matters — but don't rely on it alone.
- 2
Imagine total failure
Picture the goal has already fallen apart and gone completely wrong.
- 3
List the obvious causes
Name the most obvious reasons the goal failed — the obstacles most likely to derail you.
Pro tip Engineers do this instinctively for structures; apply the same rigor to personal goals.
- 4
Plan a response to each
For every anticipated obstacle, pre-decide how you'll overcome it — constraints, social support, or a commitment device.
Watch out Skipping the planning leaves you at the mercy of predictable, foreseeable setbacks.
In the wild
NYU psychologist Gabriele Oettingen studied planning where people ask what could go wrong and how they'll overcome it.
→ This obstacle-based planning measurably improves goal outcomes over positive thinking alone.
Engineers naturally anticipate the forces that could make a structure fail, but people rarely do the same for their personal productivity.
→ Applying pre-mortem thinking to personal goals surfaces the setbacks that would otherwise blindside them.
Common mistakes
Relying on positive thinking alone
Over-optimism blinds you and breeds overconfidence, so you never build the constraints and support that prevent failure.
Only doing post-mortems
Analyzing failure after it happens misses the chance to foresee and neutralize the same obstacles beforehand.
Is it for you?
Best for
Any meaningful goal or project where predictable obstacles can be anticipated in advance.
Not ideal for
Situations that need pure confidence and self-belief with no room for planning paralysis.
From the transcript
“if you don't plan for what can go wrong if you aren't thinking negatively and anticipating obstacles ... then you are much less likely to…”
“it can be really useful to do the same thing before you pursue a goal and to sit down and say imagine this all falls…”
From the episode
Katy Milkman: The Science of Change
Katy Milkman