1. List out:
    • Situation & Context
    • Goals + “5 Whys”
    • Challenges, blockers, concerns
      • Assumptions –> Open Questions -> Who can answer?
    • Costs: Time, money, attention
    • People / Who’s involved
    • Important Dates
    • Choices
      • Ask someone - maybe there are other choices
      • Reduce to 3 choices
  2. Evaluate Choices. For each choice:
    • Pros / Benefits
      • Satisficing vs Maximizing
    • Cons / Drawbacks
    • Nth-order thinking
      • “and then…”, “results in…”
    • Outcomes
      • What’s the impact for different time ranges
        • Tomorrow
        • Next week
        • Next month
        • Next year
        • 5 years
        • Looking back on death bed
      • How does this affect other people you care about in your life?
        • Partner, family, friends, colleagues
    • Emotions
      • Which choice / outcome would be the most satisfying looking back?
  3. Decide
    • Quick
      • Time-box to 10 min or 1 hour
      • Involve 3 trusted people
    • Slow
      • Sleep on it. Journal at the beginning & end of a day to catch different moves
      • “Wear the hat” for a day – Mentally commit to choice for a day, and fully imagine it. Plan it out. Picture the process. Write down all the actions, people, resources invoved. The next day, mentally commit to the other choice.
    • Emotions: Evaluate your emotions & subconscious honestly. How do you FEEL about the choice and why?
  4. Review
  • Schedule retrospective on calendar.
    • Event title: “Decision review: (YYYY-MM-DD)”
    • Event Date: Create events for 1 week, 1 month, 1 year
    • Event Notes:


- Situation, decision, dates
- What did we learn?


  • Have I done this before? If not, can I learn something from it?
  • Can I spend only a little time on it before committing further?
  • Can I meet interesting people by doing this activity?
  • Is this something most people like me would say no to? Going against the “crowd wisdom” is an underrated way to gain novel insights.
  • Can I stop doing it if I don’t like it? Avoids committing long-term to things that don’t work out.


  • When in doubt, Rock-paper-scissors for it. It’s fun!

business decisions, ask yourself how important parts of the ecosystem are likely to respond. How will employees deal with this? What will my competitors likely do? What about my suppliers? What about the regulators?

Some decisions are consequential and irreversible or nearly irreversible – one-way doors – and these decisions must be made methodically, carefully, slowly, with great deliberation and consultation. If you walk through and don’t like what you see on the other side, you can’t get back to where you were before. We can call these Type 1 decisions. But most decisions aren’t like that – they are changeable, reversible – they’re two-way doors. If you’ve made a suboptimal Type 2 decision, you don’t have to live with the consequences for that long. You can reopen the door and go back through. Type 2 decisions can and should be made quickly by high judgment individuals or small groups.


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