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The 6 questions all dying people regret not answering, and why you should ask them yourself now
Nathan was just 52 when his life changed forever.
One day he noticed a slight tremor in his left hand. Within four years, ALS had locked him in his body.
He could no longer walk, feed himself, or even speak. His hands were twisted into claws. The only way he could communicate was by resting one hand on the other and slowly tapping words on a phone with a single knuckle.
Tap… pause… tap… pause. Letter by letter, agonizingly slow.
The problem wasn’t only the speed. Nathan had so much left to say. Friends he wanted to thank. Relationships to repair. Feelings buried too long. But time was running out.
Late at night, unable to sleep, he often wrote to his end-of-life doula, my colleague Dr Virginia Chang. One night he sent a four-page letter to her that began: ‘Dear Virginia, I feel like I’m dying too young. I always thought I would have more time… I never had a great love in my life… I presumed I’d live easily into my seventies or eighties. So, to have all those hopes and dreams ripped out from under me has been hard… I’m seeking a sense of acceptance.’
Nathan was desperate to heal old wounds and share the words locked in his heart. But typing with one knuckle was a race he couldn’t win. Sadly, Nathan ran out of time.
I’ve seen this before in my work as a death doula, guiding people and their families through the emotional, spiritual, and practical realities of dying.
For two decades, I’ve sat with people as they took their final breaths, witnessed final moments and heard heartfelt words most people never get to hear - conversations that aren’t about money, status, or success. They’re about love and gratitude… and just as often, about regret.
Again and again, I’ve heard the same aching words: ‘I wish I had lived my life differently.’
The greatest lesson? You can’t wait until you’re dying to discover what matters most… to you.
That’s why I created what I call The Final Checklist - six deceptively simple questions I ask all my clients. They uncover regrets, mend relationships, and bring peace in the final days.
But they aren’t only for the dying. They are for you, now, while there’s still time to act.
1. Who matters most?
We meet many people who we love and care about over the course of a lifetime, but at the end of life it’s those few special relationships that matter most, those whose hands you want to hold when you take your final breath.
Once I had a client hang on for two days just waiting for her brother to fly in from across the country for one last goodbye. When he stepped into her room, they locked eyes and then just held each other for a long time.
My client died within hours of seeing her brother.
If this were your last week of life, who would you want to spend it with? These are your people. Have you told them they matter? Have you shown them? Strengthen those bonds today.
2. What matters most?
One of the most common experiences when one is dying is the process of letting go of what doesn’t matter and holding tightly to what does.
I’ve had countless clients spending their final months of life cleaning out sheds, storage units, garages and getting rid of material possessions that they didn’t even remember they had.
At the end, possessions and titles fade. What rises instead is spirituality, connection, and contribution. If life were short, where would you focus your time and energy? Don’t wait - redirect it now.
3. What keeps you awake at night?
Knowing what someone is worrying about helps me understand what is keeping them from feeling comfort, peace, and a sense of calm in their final days.
I ask them a very direct question: ‘What are you worrying about when you lay awake in bed at night?’
Their answer always guides me.
One client was raised in a very religious home, then left the church as an adult, abandoning her childhood faith for what she called ‘a lifelong quest for something more’.
She never found that ‘something more’ and regretted leaving the church all those years ago.
For her, the worry was about the afterlife. She couldn’t die in peace without seeing the chaplain, who came and prayed with her.
When we know what’s hurting our hearts, we can address it. So pay attention to what’s worrying you.
Regrets, fears, broken relationships - these are the things that rob us of peace. Face them today. Resolve what you can. Free your mind and heart to live more fully.
4. What brings you joy in the daytime?
Although my clients are dying, they are often the most joyful people I know. Why? Because they are taking in the moments and living in the present.
One client said: ‘I used to care about everything. Now, I don’t care about politics, the news, or what deals I can get on that super sale on Amazon. I just want to cuddle with my kids and my cats.’
The outside world fades and what is left is the simplicity of everyday life.
Joy is hidden in the ordinary: morning coffee, sunlight on your skin, a shared laugh. Name your joys. Protect them. Nurture them. Let them guide your days.
5. What is left unsaid?
Sharing unexpressed words can become an urgent need at the end of life. Clients have lamented never saying ‘I’m sorry,’ ‘thank you,’ or ‘I forgive you.’
One parent raised his children in a loving home, but somehow never used the words ‘I love you.’ Sometimes healing takes place in life’s final hours.
Love, gratitude, forgiveness - unsaid words can weigh heavily on our hearts. One call or note can change a life, including your own. Say it now. Don’t let your words go unspoken.
6. What is left undone?
Regrets also weigh heavy at the end of life, but often it’s too late to do anything more than find a way to let them go.
If you can, follow your passions. After all, we are still living until our very last day.
I’ve had clients take art classes, read poetry at an open mic night, and ask someone to move in with them even when time was short.
Big dreams or small promises - both matter. Take one step toward them today. Even a small act brings relief, purpose, and peace.
I don’t just give these questions to clients - I ask them of myself every single month.
I write down my answers, revisit them, and adjust as life shifts.
This practice has deepened my relationships, clarified my priorities, and stripped away much regret.
When you answer these questions honestly, you see clearly and can stop postponing what matters most. You mend relationships. You savor joy. You move toward dreams that can’t wait.
You begin to live with the clarity the dying already know.
In the end, and with Virginia’s support, Nathan managed to type many letters.
They weren’t about adventure or accolades. They were about simple reconnection. His deepest wish was to send this message to his friends: ‘Thank you for being a part of my life.’
That’s it. No grand declarations. Just gratitude, offered too late.
What about you? What would you write in the middle of the night with just one knuckle?
Ask yourself these six questions today. Write down your answers. Revisit them often. Let them guide how you spend your time, the words you say, and the people you hold close.
Nathan couldn’t rewrite his past. But his story can change yours.
Don’t wait for ‘someday.’ Say it. Do it. Live it. Now.
Diane Button is a death doula and author of What Matters Most: Lessons the Dying Teach Us About Living, published September 16 by Open Field
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