Coaching practices for Failure Post Mortem

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Does this sound like the set of challenges you might be facing?

  • I want to look back from the very end of my life and ask honestly what I actually did with my time
  • Lately I keep catching myself aware that my time is running out, and instead of letting it scare me I want to actually sit with it for a few minutes and let it show me what I’d most regret never having done.
  • I know in my head that they’re gone, but it still hasn’t landed
  • There’s so much I never got to say to them, and so much happening now I wish I could tell them
  • When I ask myself "what could go wrong with this plan," I either draw a blank or come up with one vague worry

Practices that may help

  1. The Pre-Mortem: Imagine It Already Failed
    A pre-mortem, developed by psychologist Gary Klein, has a team imagine that a plan has already failed and then work backward to explain why — before any work begins. The technique exploits "prospective hindsight": research found that imagining an outcome as a certainty makes people generate more, and more specific, reasons for it, surfacing risks that ordinary risk assessment misses.
  2. Write a brief final accounting
    Write as if you’re reporting on your life: what did you do with your time?
    Memento Mori: Using Mortality Awareness to Focus What Matters
  3. Memento Mori: Using Mortality Awareness to Focus What Matters
    Memento mori — "remember you will die" — is the Stoic practice of keeping mortality in view as a clarifier: trivial concerns shrink and important ones become urgent when measured against a real deadline. Used well, it sharpens values and action; used badly, it slides into death anxiety. The psychological evidence is genuinely mixed — mortality awareness can produce either defensiveness or value-driven clarity depending on the person and how the awareness is held.
  4. The Regret of the Dying
    Bronnie Ware, an Australian palliative care nurse, documented the most common regrets of dying patients in her book The Top Five Regrets of the Dying. The themes — especially living others’ expectations, working too hard, suppressing feelings, and neglecting friendships — are consistent with broader research on regret and well-being. The evidence is qualitative and self-reported; treat it as wisdom data, not clinical data.
  5. Continuing Bonds in Grief, Made Practical
    Continuing bonds theory, developed by Dennis Klass and colleagues, holds that maintaining an ongoing inner relationship with the deceased — through memory, ritual, and internalised connection — is a normal and often adaptive part of grief, not a sign of pathology. Observational research supports this for many types of connection, though some forms (active searching, idealisation) are associated with poorer outcomes.
  6. Deliberate mortality reflection
    Briefly contemplate your finite lifespan to surface what actually matters to you.
    Terror Management Theory, Made Practical
  7. Task 1: Accept the full reality of the loss
    Move from intellectual acknowledgement to full emotional acceptance that the person is gone.
    Worden’s Tasks of Mourning, Made Practical
  8. Speak or write to the person directly
    Address the deceased in letters, journal entries, or internal dialogue as a form of active continuing connection.
    Continuing Bonds in Grief, Made Practical
  9. Run the basic pre-mortem
    Assume the plan failed, then have everyone write down why.
    The Pre-Mortem: Imagine It Already Failed
  10. Deliberately engage loss-oriented work
    Set aside dedicated time to directly face the grief — the emotions, the absence, the meaning of the loss.
    The Dual Process Model of Grief, Made Practical

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