Nobody warns you that the most clarifying conversations of a person’s life happen in the last weeks of it. Not in the therapist’s office, not in a particularly honest argument, not on the long drive home from a holiday that went sideways. At the very end, when there is nothing left to perform and no version of the future to protect, people say exactly what they mean. And what they mean, almost universally, is that they wish they’d paid attention sooner.
The dying people regret this more than almost anything else: not the big failures, not the professional disasters, not the money they didn’t make. What guts them, in those final weeks, is the smaller, quieter account of their own life – the relationships they let calcify, the words they circled around for decades, the passions they filed under “someday.” By the time the truth arrives, the window for acting on it has mostly closed. What Diane Button has spent nearly two decades doing is holding that window open a little longer, and asking the rest of us to climb through it while we still can.
Button has spent close to 20 years guiding people through the emotional, spiritual, and practical realities of dying. She practices in the San Francisco Bay area, holds a master’s degree in counseling psychology, and is a breast cancer survivor herself – a detail that gives her work a particular texture, because she hasn’t just watched people face the end. She’s been somewhere adjacent to it. What she did with that proximity was build a six-question framework she calls the Final Checklist, designed not for the hospice bedside alone, but for everyone living their ordinary life right now.
The Doula
According to a 2025 report from Today.com, Button practices in the San Francisco Bay area, holds a master’s degree in counseling psychology, and is a breast cancer survivor. The checklist centers on six questions: who matters most, what truly matters, what causes worry, what brings joy, what remains unsaid, and what has been left undone. As Button describes it in her work featured at Integrative Touch, these are “six powerful questions” she designed to open meaningful conversations about who and what truly matters – not only for people at end of life, but for anyone who wants to stay in tune with what matters most. Answering them honestly, she argues, can prompt meaningful change.
1. Who Matters Most to You?
This is the question that sounds almost too obvious to be useful, until you actually sit down and answer it – really answer it, not the version you’d recite at a dinner party. Button says it all comes down to a few special relationships: the ones whose hands you want to hold when you take your final breath. That image is stark, and it’s meant to be. It asks you to strip away the people you’re obligated to and find the ones you’re drawn to.
What’s striking about this question is how often the answer surprises people. We spend enormous amounts of time maintaining relationships that feel important mostly because they’re familiar, or because abandoning them would require a conversation nobody wants to have. The person you’d want in the room at the end is not always the person you’re actually investing in right now. That gap, between who matters and who you’re spending your time on, is one of the most common sources of end-of-life grief that Button witnesses.
The practical move here isn’t dramatic. It doesn’t require an overhaul of your social calendar. It’s just honest attention. Who are the three or four people whose presence in your life makes it feel like a life? And are you treating that like the priority it is?
2. What Truly Matters to You?
Possessions and titles fade, Button says. What rises in their place is spirituality, connection, and contribution. If life were short, where would you focus your time and energy? The follow-up question she uses with clients is a version of this: she asks them to confront what’s been robbing them of peace.
Most of us already know the answer. We know whether we’re spending our days on things that matter to us or on things that have accumulated around us by accident. The problem isn’t ignorance, it’s inertia. The job that made sense at 28 doesn’t have to define 45, but changing it requires a level of disruption that most people keep deferring until the disruption is no longer optional.
People often tell Button they worked too many hours and missed out on time with loved ones. They’re sorry they didn’t heal relationships earlier, or held a grudge for years or perhaps decades. The grudge is a particularly interesting detail. What’s interesting about it isn’t the anger, but the energy. A decades-long grudge requires active maintenance. It takes up room. The question “what truly matters” is partly asking: is this what you want to spend that room on?
3. What Keeps You Awake at Night?
This is where the checklist gets more uncomfortable, because it’s the one that asks you to look at what you’ve been actively avoiding. What happens at night, once the mind is free, is that the unresolved things surface. Button tells the story of a client who couldn’t die in peace until she saw the chaplain, who came and prayed with her – her nighttime worry had been about the afterlife, a fear she’d carried for years without ever addressing it directly.
Pay attention to what’s worrying you, Button advises. Regrets, fears, broken relationships – these are the things that rob us of peace. Face them now. Resolve what you can. Free your mind and heart to live more fully. That’s not a platitude when it comes from someone who has sat with people in their final hours. She’s seen, firsthand, what an unresolved worry costs a person.
The word “resolve” is doing real work in that advice. Not “fix.” Not “make disappear.” Resolve – which might mean having the conversation you’ve been putting off, or accepting that some things won’t be tidy, or finding the chaplain, or writing the letter. The shape of the resolution matters less than the act of no longer turning away from it.
4. What Brings You Joy?
Although her clients are dying, Button says, they are often the most joyful people she knows – because they are taking in the moments and living in the present. One of the stranger paradoxes of end-of-life work is how often the dying seem more alive than the living. They’re not doomscrolling. They’re not fretting about the next performance review. They have, finally, the thing most of us spend years trying to manufacture: a clear sense of what’s actually good.
One client told her: “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.” That’s not cynicism or surrender – it’s a kind of ruthless clarity about where joy actually lives. It lives in specific, ordinary things. The Tuesday night dinner. The friend who makes you laugh until something embarrassing happens. The book you’ve been meaning to re-read. The hobby you keep saying you’ll get back to.
Button recommends taking one minute every day to look at something beautiful, whatever is in front of you. “We’re so busy trying to get to the next moment,” she says, “that we’re actually missing the moment we’re living in.” For people who process joy intellectually rather than experience it in the body, that one minute is harder than it sounds.
5. What Have You Left Unsaid?
This might be the question with the longest shadow. Many people die with words unspoken, Button emphasizes – and one call or note can change a life, including your own. Say it now. Don’t let your words go unspoken. She’s seen people carry sentences for thirty years: love they never said out loud, apologies they let harden into silence, gratitude that always felt unnecessary to speak because surely the other person knew. Surely they knew.
For a piece on what terminally ill mothers taught their families about living, the pattern that surfaces most consistently is this one – not the grand gestures left unfinished, but the ordinary words left unsaid. The “I love you” offered freely. The “I’m sorry” that didn’t require the other person to apologize first. The “you changed my life” that people assume is too dramatic to say out loud.
People who are dying are often haunted by moments when they were unkind, Button notes. “It’s so amazing to me,” she says, “that you can carry something for 30 or 40 or 50 years that you might’ve done when you were a teenager and you’re still feeling badly about it.” The repair, she argues, is far easier than a lifetime of carrying the weight. An apology sent to someone you treated badly in 1994 costs you one uncomfortable hour. Not sending it can cost you decades.
6. What Have You Left Undone?
Button created this checklist after working with hundreds of clients, many of whom had regrets not because of what they’d done but because of what they never got around to. Like all of us, they thought they’d have more time.
One client, Nathan, was diagnosed with ALS in his early 50s. He could no longer speak or walk, yet his mind and heart were wide awake, with so much left unsaid. He typed out his thoughts one knuckle at a time, a single message taking him all night. In one very long letter, he wrote: “I always thought I would have more time.” As Next Big Idea Club reports, Button is a founding partner of the Bay Area End-of-Life Doula Alliance, and Nathan’s story is one of the most striking in her body of work.
That sentence – “I always thought I would have more time” – has a way of landing differently depending on how old you are when you read it. Button has 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. The invitation isn’t to quit your job and move to Italy, though if that’s the thing, it’s the thing. The invitation is to take the first step toward whatever you have been continuously setting aside for a future version of yourself who will apparently have more bandwidth. That version isn’t coming. You’re the one with the bandwidth. It’s just currently aimed elsewhere.
This is also where the checklist intersects with what former palliative care worker Bronnie Ware documented in her own years at the bedside: the most common regret she heard was “I wish I’d had the courage to live a life true to myself, not the life others expected of me.” When people realize their life is almost over and look back clearly, she found, it is easy to see how many dreams have gone unfulfilled – and how many people had to die knowing it was due to choices they made, or didn’t make. What’s left undone is almost never the ambitions that were genuinely impossible. It’s the ones that were entirely possible and simply never started.
Read More: 8 Things I Learned from Watching My Mom Die
The Archive Never Gets Smaller, Only Larger
Button doesn’t just give these questions to her clients – she asks them of herself every month, writing down her answers, revisiting them, and adjusting as her life evolves. “Again and again,” she says, “I’ve heard the same aching words: ‘I wish I had lived my life differently.'” The practical instruction is blunt: don’t wait.
What makes these six questions different from every inspirational poster you’ve ever seen in a waiting room is the source. They didn’t come from a motivational speaker or a self-help framework built from surveys. They came from a woman who sat with people at the very end and understood that healing is not about fixing or curing – it’s about acceptance of all that was, all that is, and all that will be. Once people talk about their regrets and fears and unfinished business, she found, they can start focusing on something else. A person might still be dying, yet feel more whole, more complete, more honest than they’ve ever been.
You don’t have to be dying to answer these questions. You don’t have to set an afternoon aside or buy a journal or make it into a project. You just need to be willing to sit with the question long enough to hear what your honest answer actually is, not the answer you’d give at a dinner party. The gap between those two answers is where most of the interesting work of a life happens – and most of the regret, if you’re not paying attention.
AI Disclaimer: This article was created with the assistance of AI tools and reviewed by a human editor.