Anti-Goals (Inversion Planning)
- Difficulty
- Easy
- Time to result
- ~weeks to results
- Steps
- 5
- Confidence
- —
Instead of guessing what will make you happy, Wilkinson works backwards from what reliably makes you miserable. Borrowing Charlie Munger's inversion habit — 'show me where I'm going to die so I don't go there' — he and his business partner Chris sat down and listed every fear and every thing they wanted to avoid, then deliberately designed a life that dodges those things. The same list-your-fears move is applied to every new commitment: hiring a CEO, signing a deal, buying a building. Each fear is named out loud by both parties, then mitigated up front rather than discovered later. The claim is that people are unreliable predictors of their own happiness but extremely reliable predictors of their own unhappiness, so anti-goals are the cheaper, more accurate input to design around.
Origin
Extracted from Deep Dive with Ali Abdaal
How to run it
- 1
Write the misery list
List everything that reliably drains you — for Wilkinson: owing things to people, an over-scheduled calendar, being trapped in email, feeling like a bad dad. Be specific and personal rather than abstract.
Pro tip Do this with a partner or co-founder so the lists can be compared and overlapped.
- 2
Design the most miserable version of your life
Deliberately imagine the worst-case life: the schedule, the obligations, the people, the work. This exaggerated picture surfaces constraints that a positive goal-setting exercise never reaches.
Watch out Don't sanitise it. A polite list produces polite, non-binding anti-goals.
- 3
Convert each item into an anti-goal
Restate each misery as a rule you will not break — e.g. 'I will not take on work that requires regular travel', 'I will not manage more than one direct report'.
- 4
Run a fear pre-mortem on every new commitment
Before a hire, deal or project, ask the other party directly: what are your fears, how does this go wrong? List them all — mismatched expectations, misaligned strategy, badly structured pay, personal friction.
Pro tip Wilkinson uses this as his favourite question when hiring a CEO.
- 5
Mitigate now, not later
For each named fear, agree the mitigation before starting — restructured pay, clearer strategy, a delegated function. Then re-check the anti-goal list whenever an opportunity tempts you to breach it.
Watch out Expansion is the usual breach point: every new venture, building or partner adds people who can be let down and meetings you must attend.
In the wild
Wilkinson and his partner open CEO hiring conversations by asking the candidate what their fears are and how the arrangement could go wrong. The candidate names things like badly structured pay, an unreachable bonus, mismatched expectations for the business, misalignment on strategy, or simple personal incompatibility. Each one is then mitigated in the agreement before the person starts, rather than surfacing two years later as a dispute.
→ Failure modes are priced into the deal up front instead of becoming expensive surprises.
Wilkinson bought a corner building near his neighbourhood he had eyed for years, excited about redeveloping it into something vibrant for the community. Once the initial excitement wore off, he realised he now had to hire an architect and designers, source tenants, and manage every one of those relationships. Each represented a person who could be let down, a meeting to attend, and a tenant who might not pay rent — precisely the complexity his anti-goals exist to avoid.
→ A purchase that added exactly the kind of obligation and calendar load his anti-goal list was written to prevent.
Common mistakes
Setting goals without setting anti-goals
People are poor at predicting what will make them happy — a bigger house, a better TV — but nearly everyone knows exactly what makes them unhappy. Skipping the inversion means optimising against the less reliable signal.
Treating anti-goals as a rich person's luxury
Wilkinson identified that he hated travel while still running his agency and designed around it immediately rather than waiting until he was wealthy. Delaying the practice until you 'make it' removes its main benefit — shaping the business while it is still shapeable.
Naming fears but never mitigating them
The list only pays off if each item gets a concrete mitigation agreed now. A fear catalogued and left alone is just anxiety with better formatting.
From the transcript
“show me where I'm going to die so I don't go there so the idea would be you want to instruct yourself of all the…”
“we made a list of what are all of our fears what are what are all the things we want to avoid how how if…”
“we'll sit down and we'll say okay how do we mitigate all of those things now instead of later and I find it's an incredibly…”
From the episode
The Pursuit of Wealth: Barista to Billionaire - Andrew Wilkinson
Andrew Wilkinson