Draft three genuinely different five-year plans

Sketch three distinct five-year lives — not variations on the same theme, but genuinely different directions.

Why it works

Holding alternatives in parallel prevents premature closure, the cognitive bias toward committing to the first plausible option. Decision research shows that generating multiple alternatives before evaluating reduces anchoring and reveals assumptions embedded in a single-path plan. The three-plan format also separates "planning" from "committing," lowering the anxiety that blocks honest exploration.

How to do it

1. Plan A: your current trajectory — what the next five years look like if you continue as-is, with honest ambition but no pivot.
2. Plan B: what you would do if Plan A became unavailable — the alternative you might pursue if forced to shift.
3. Plan C: the life you would plan if reputation, money, and others’ expectations were irrelevant — the thing you would do if no one was watching.
4. Make each plan specific: role, location, relationships, financial picture, a day-in-the-life sketch.

Evidence

Generating multiple alternatives before choosing is a core decision-quality technique supported by research on debiasing: people who consider alternatives make better-calibrated decisions. The odyssey-plan format applies this to life design. (observational)

The odyssey plans format itself has not been subjected to a controlled trial; its rationale is drawn from decision-quality and design-thinking research, plus practitioner experience.

Sources

• Heath & Heath (2013), Decisive, summarizing research on considering alternatives in decision-making

Common mistake

Making Plan B and Plan C minor variations on Plan A — "Plan A but in a different city" — rather than genuinely different lives. The exercise has no value if the plans are effectively the same.