Decision-making•March 24, 2026
When NOT to use a random tool to decide
This is going to sound strange coming from a site that builds random decision tools: please don't use them for everything. Misapplied, they cause harm. Here's where the line is.
The three-question test
Before you let a random tool decide, ask:
- Are the options actually equivalent? If one is genuinely better and you know it, randomness just costs you the better outcome.
- Are the stakes low enough that 'wrong' is fine? Random tools assume that any outcome on the wheel is acceptable. If some outcomes aren't acceptable, they shouldn't be on the wheel.
- Is the decision reversible? A random pick of takeout is reversible — you can pick differently tomorrow. A random pick of a tattoo design is not.
If you can't say yes to all three, the wheel is the wrong tool.
Decisions that should NEVER be randomized
- Medical choices. Don't flip a coin on whether to take a medication, follow a treatment, or see a specialist. The cost of being wrong is too high and asymmetric.
- Major financial decisions. Investments, large purchases, signing leases, taking on debt — these need analysis, not chance. The randomness of the outcome will dwarf any randomness of the decision.
- Anything involving someone else's wellbeing. Whether to break up with someone, whether to discipline a child, whether to fire an employee. Other people deserve a considered choice, not a coin flip.
- Ethical questions. 'Should I lie to my friend?' is not a coin flip question. Even if you're genuinely uncertain about the right answer, the deliberation is the work, not the outcome.
- Any decision you're avoiding by randomizing. If you find yourself reaching for the wheel because you don't want to face a hard call, the wheel is letting you off the hook in a way that isn't doing you any favours.
Decisions where randomness is genuinely useful
- Trivial recurring choices. Lunch, what to do tonight, which podcast to listen to.
- Tie-breakers between equally good options. When you've already done the analysis and the options are within a hair's breadth, spin and move on.
- Fairness situations. Who goes first, who has to do the unwanted task, how to split a finite resource. Visible randomness is the most defensible form of fairness when there's no reason any individual deserves the better outcome.
- Creative prompts and games. Writing exercises, party games, role-playing — randomness here is a feature, not a workaround.
- Decisions where the deliberation is costing more than the outcome. If you've spent 20 minutes choosing between two restaurants, the marginal joy of the better choice is already gone.
The honest principle
Random tools are leverage for decisions you've decided don't deserve more thought. They're not a substitute for thought. Used right, they free up your attention for the decisions that genuinely matter.