You describe a life dilemma or decision you are facing and direct the depth of analysis by selecting specific questions. The analysis takes a systematic approach: identifies potential outcomes of each path, analyzes risks and gains, maps the impact on key life areas (relationships, career, finances, health) and compiles a strategic plan with concrete steps. A worst-case / best-case scenario analysis is also included.

Where it comes from

Thinking through a road not taken has a name in psychology: counterfactual thinking. Research on it began in earnest with Kahneman and Tversky in 1982, who showed that people generate alternative versions of events automatically and that the ease of imagining an alternative drives how strongly they feel about what actually happened. Later work separated upward counterfactuals, which imagine a better outcome and produce regret, from downward ones, which imagine a worse outcome and produce relief. Both turn out to be useful when they lead to a plan and corrosive when they only repeat.

How the method works

A structured what-if reading takes one decision point and changes a single variable, then follows the consequences forward rather than stopping at the first fork. The discipline is in changing only one thing: most regret comes from imagining an alternative in which everything else also went right. Working through it properly usually shows how much of the outcome was outside the decision altogether.

What a reading covers

The reading takes the decision you name, builds out the alternative branch step by step, and marks where the branch would have run into the same constraints anyway. It ends with what is still open now, which is the part that can actually be acted on.

Common questions

Does this not just feed regret?: It can, if it stops at the comparison. The research finding is that counterfactuals are useful when they end in a rule for next time and harmful when they only replay the loss.
Can it say what would have happened?: No. Nothing can. It can say which constraints were inside your decision and which were not, and that is the part worth having.
Which decisions are worth examining?: The ones you are still arguing with yourself about. A decision you have genuinely closed rarely repays the effort.