Coaching practices for Is it Normal to Grieve Your Younger Self at Midlife

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

  • I’ve hit the goals I set and they feel strangely empty now, and what I quietly want is to pour what I’ve learned into someone coming up behind me
  • 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
  • Something I built my life around has ended
  • It’s been a few months and everyone around me clearly expects me to be over it by now, and I’ve half-swallowed that timeline myself
  • I keep telling myself I shouldn’t be this wrecked when other people have lost so much more

Practices that may help

  1. Engage generativity — the natural work of midlife and later seasons
    Midlife and later seasons are calling for contribution, mentorship, and transmission — not just personal achievement.
    Seasons of Life
  2. 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
  3. 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
  4. Identify how cultural norms shape your grief
    Examine whether cultural scripts about how long and how much to grieve are shaping your experience.
    The Dual Process Model of Grief, Made Practical
  5. Validate your own grief without waiting for external permission
    Give yourself the recognition that society has withheld — your loss is real because it matters to you.
    Disenfranchised Grief, Made Practical
  6. The eulogy exercise: working backward from the life you want
    Write a brief eulogy for yourself that describes who you were and how you lived — then work backward to what that requires today.
    Values-Based Action (ACT), Made Practical
  7. 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
  8. Identify your natural grieving style and adjust for it
    Know whether you tend toward more loss or more restoration orientation — and compensate accordingly.
    The Dual Process Model of Grief, Made Practical
  9. Look honestly for what has grown or changed for the better
    Without minimising the loss, notice any growth, change, or perspective that has emerged from it.
    Meaning Reconstruction in Grief, Made Practical
  10. Navigate season transitions — the gap is normal and necessary
    The confusion and loss of meaning between seasons is structural, not personal failure.
    Seasons of Life

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