Coaching practices for The Regret of the Dying for My Teenager

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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 keep telling myself family comes first, but when I actually look at where my hours went this week it’s almost all work
  • 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
  • I can almost hear my older self looking back at the choices I’m making right now, and I’m scared it’s with regret
  • 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

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. 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
  4. 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
  5. Write a letter from your future self to your present self
    Ask your 70-year-old self to write back to you now — with gratitude or regret.
    Future Self Continuity, Made Practical
  6. Project to age 80 and look back
    Ask which choice your 80-year-old self will least regret.
    The Regret-Minimization Framework
  7. 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
  8. 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
  9. Use the 10-year horizon as a regret test
    Ask: in 10 years, will I regret not doing this more than doing it?
    The 10-10-10 Rule
  10. Deliberate mortality reflection
    Briefly contemplate your finite lifespan to surface what actually matters to you.
    Terror Management Theory, Made Practical

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