Health: Six questions dying people often regret not asking—and how to ask them now

Six questions that dying people often wish they had asked sooner are being promoted as a practical guide to living with intention, even for those not facing an imminent death. The approach comes from Diane Button, a death doula who has spent two decades beside patients as they near life’s end, helping them translate last days into clarity, connection and peace. The case of Nathan, a 52-year-old man who started with a subtle tremor in his left hand and later faced an ALS diagnosis that left him unable to walk, feed himself or speak, underscores the urgency. As the disease progressed, Nathan’s only reliable means of communication became tapping words on a phone with a single knuckle, letter by painstaking letter. In the months before his death, he wrote a four-page letter to his end-of-life doula, Dr. Virginia Chang, seeking a sense of acceptance and reconciliation that time was running out to secure. That experience, among others, framed Button’s later work and public attention to the six-question framework.

Button, who has guided families and patients through the emotional, spiritual and practical realities of dying for 20 years, describes The Final Checklist as a simple yet powerful prompt designed to uncover regrets, mend relationships and bring peace in the final days. She emphasizes that the questions are not just for those near death; they can be asked now, while there is time to act and to change how one lives each day. The six questions are presented as a way to expose what truly matters and to steer daily choices toward those values.

The six questions, in short, are designed to surface what matters most when time is limited. They are framed as follows: Who matters most? What matters most? What keeps you awake at night? What brings you joy in the daytime? What is left unsaid? What is left undone? While they may sound simple, Button argues that answering them honestly can reveal deep insights that guide how a person spends their last days and their relationships with others.

In practice, the questions tend to surface stories, regrets and aspirations that people have carried for years. One client who believed his most important ties were with a distant sibling found that those bonds could be repaired, sometimes with a single conversation or a shared moment. Another client, after years of pursuing material goals, began to prioritize spirituality, connection and contribution as the end of life approached. The process often helps people shed clutter—literally and figuratively—and redirect energy toward meaning rather than accumulation.

The questions are not punitive; they are designed to help people examine fear, forgives, gratitude and love. For example, identifying what keeps someone awake at night can reveal fears about the afterlife, doubts about faith, or unresolved obligations that prevent rest. Naming what brings daytime joy can anchor daily routines in small, tangible moments—holding a grandchild, enjoying a morning coffee, feeling sunlight on the skin. Untold words—“I’m sorry,” “thank you,” or “I forgive you”—often emerge as healing acts when spoken or written in the final days. And letting go of unfinished dreams, while painful, can also bring relief by enabling focus on achievable, meaningful steps in the remaining time.

Button notes that the practice has produced measurable shifts for many families: improved communication, more heartfelt goodbyes and a sense of closure that can lessen the burden of regret. She also stresses that the exercise is ongoing; she revisits her own answers every month as life evolves, and she encourages others to do the same in order to live with greater clarity and purpose.

The story of Nathan also offers a poignant illustration of how the six questions can function in real time. In his final correspondence, he sought to reconnect with friends and express gratitude for the relationships that shaped his life. His effort did not culminate in grand declarations or adventures; rather, it crystallized into simple, sincere thanks—an acknowledgment that even years of missed chances can be forgiven when time is scarce. Nathan’s letters, written with the aid of a single-knuckle tap, emphasize the core message Button wants readers to hear: you cannot rewrite the past, but you can choose how to show up now.

For readers who want to apply the approach themselves, Button offers a practical invitation: write down your answers, revisit them regularly, and use them to guide conversations, decisions and daily conduct. The aim is not to frighten people with end-of-life thoughts but to empower them to live more intentionally by identifying what truly matters and acting on it today. The six questions have been shared in various media outlets as part of a broader conversation about end-of-life planning and emotional well-being, including reporting on how one man’s life was touched by ALS and how a death doula’s framework can help people address regrets before they become regrets for good.

The six questions are a starting point for reflection, but Button cautions that real progress comes from consistent effort. She says that asking these questions monthly—along with honest self-reflection and open communication with loved ones—can transform how people relate to time, relationships and their own ambitions. The goal is not to wait for a crisis to prompt change but to live with the awareness that time matters and that meaningful action today can diminish tomorrow’s regrets.

What is left undone—whether a promise to pursue a passion, a request to move closer to family, or a decision to seek reconciliation—will often remain a weight on the heart unless addressed. Button’s message is clear: the questions are not a prescription for fear or doom; they are a doorway to clarity, resilience and deeper connection. And while the stories invoked by Nathan’s struggle highlight the urgency, the guidance is meant to be universal—relevant to parents, workers, friends and anyone who wants to live with fewer regrets and more meaning.

If readers take the six questions to heart, the hope is that they will begin conversations with loved ones, set priorities that align with their deepest values, and pursue small, practical steps toward long-held dreams. The approach is not a universal cure for life’s anxieties, but it is a conscious framework that can curtail the kind of regret that too often accompanies the end of life. And for those who fear that talking about mortality accelerates fear, Button offers a counter-narrative: facing hard truths now can actually relieve fear later by providing clarity, connection and purpose in the days that remain. The ultimate takeaway is straightforward: don’t wait for someday. Say it. Do it. Live it now.