Coaching practices for The Regret of the Dying During a Big Change

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

  • I look at the big shape of my life
  • I’m stuck on a real decision and lost in the noise of it, and I want to step back and ask how the version of me at the very end of life would see this
  • A big change is coming and I’m so focused on what’s next that I’m treating the last weeks of this chapter as a waiting room
  • I’m stuck at the edge of a huge life decision and the fear right now is so loud it’s drowning everything else out
  • A few big regrets keep circling back because they never got an ending

Practices that may help

  1. 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.
  2. Audit whether you are living your life or someone else’s
    Identify the places where your choices reflect others’ expectations rather than your own values.
    The Regret of the Dying
  3. Use mortality salience to clarify what actually matters
    Regularly reflect on finitude — not to produce dread, but to sharpen the signal-to-noise ratio of your choices.
    The Regret of the Dying
  4. The last chance before a transition
    Before a major life change, fully inhabit what is ending, rather than only anticipating what comes next.
    The Last Time Meditation
  5. Project to age 80 and look back
    Ask which choice your 80-year-old self will least regret.
    The Regret-Minimization Framework
  6. Revisit and reconcile your significant regrets
    Name your regrets explicitly and work through them toward acceptance — not suppression or rumination.
    Life Review and Reminiscence Therapy
  7. Apply the regret minimization frame
    Ask “Which choice will I regret more at 80?” — people consistently underestimate regret for inactions.
    Status Quo Bias — Why We Stick with the Default
  8. Apply the deathbed test to current decisions
    When facing a trade-off, ask which option the future you will wish you had chosen.
    The Bucket List Method
  9. Reframing loss as transformation
    When something ends or is lost, practise asking what it is becoming rather than only mourning what it was.
    Zhuangzi and the Practice of Perspective Shift
  10. Audit work hours against your stated priorities
    Compare how you actually spend your time this week against what you say matters most.
    The Regret of the Dying

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