How to Avoid the 5 Regrets of the Dying: 3 Simple Words to Live, Age, and Even Die Well

I know I’m a bit odd, yet The 5 Regrets of the Dying list is on my fridge, staring me down daily like a sparring partner in the ring of life:

  1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.
  2. I wish I hadn’t worked so hard.
  3. I wish I’d had the courage to express my feelings.
  4. I wish I had stayed in touch with my friends.
  5. I wish that I had let myself be happier.

I know these regrets firsthand. You probably do too. Yet, my vantage point on life for the past two decades has been death.

In hospice, we never asked,  “What’s wrong with you?” We used three simple words: “What matters most?” This makes sense to most people. For God’s sake, when you’re dying, shouldn’t you be able to finally focus on what matters most?

But why wait until you’re dying?

The Power of Three Simple Words

There are three simple words, one question, that can orient your living, aging, and dying well: What matters most?

It’s Simple, But Not Easy

This question is simple, but not easy, because of all the ways we’ve been taught to believe it’s “selfish” to think about or go for what matters to us:

  • Who do you think you are?
  • What kind of world would it be if we all got what we wanted? (seriously!)
  • Why want what I can’t have?

Questions our monkey minds use to protect us from pain or disappointment. Or so we believe. In my experience, they are simply gatekeepers on the path to living our unique and authentic lives.

Avoiding pain is not the same as experiencing joy. Denying death is not the same as living life. What truly matters most doesn’t come from out mind, but from a different place inside. Some would say their heart, their gut, or their “knowing.” Others, that it comes from their soul or spirit or whatever God they believe in. Whatever its source, for me it resonates more as an inner truth than an external hope.

Living by What Matters Most

Though focusing life on what matters most may sound simple, it’s not always easy. Yet, when it truly matters, it comes with an imbued energy, a magnetism that calls forth its own courage and support.

Real-Life Examples

  • What mattered most to a dying person in the ICU was to see the stars one last time. The care team ‘bent the rules’ and took a left turn to the roof, vs. a right turn to a CT Scan to make his final wish possible, and all were in tears.
  • What mattered most to a respected community leader faced with breast cancer, was not to go it alone. Asking for help in ways she’d never done before, her vast ‘professional network’ became circles of support, enriching her life in ways she never expected.
  • What mattered most to a soon-to-be step-grandma who’d always taken a backseat amidst strained family dynamics, was to love her newborn grandchild. She had a heart-felt conversation with her daughter-in-law and they’re finding new ways between them.
  • What mattered most to a room full of solo-agers was to reconnect to their passions, contribute to their communities, and start conversations about dying well.
  • What mattered most to me when my “dream job” years later began sucking the life out of me, was to stop trying to pretend it was all OK and remember my original dream: supporting people to live and die well. (Which brought me to write this article for you.)

What matters most in the end is what mattered most all along. We don’t need the perfect circumstances to get on with it. But we may need a kick in the pants.

In these crazy, distracting, disconnecting times, there is one question you can be sure will bring you some peace. And if you live into the answers, you may just live without regret: What matters most to you?

Mary Matthiesen is a life coach for mortals, an inspirational speaker, and a consultant to leaders who care. Author of Dying to Make a Difference, and Co-creator of Conversations for Life ™, her passion is living and dying well (both and/not either or). For more, visit

[1] From Bronnie Ware’s terrific book of the same name, The 5 Regrets of the Dying

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