Top Five Regrets of the Dying—Lessons for Financial Independence (FI)
What are the most common regrets during the sunset of life? Photo by Tadej Skofic on Unsplash.
Reading time: 8 minutes
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Top 5 Regrets of the Dying: What They Teach Us About Life and FI
Author Bronnie Ware spent years as a palliative care nurse, caring for patients in the final weeks of their lives. Her role gave her a unique vantage point to hear their life reflections—when all the noise of ambition and appearances had started to fade away.
People at the end of their lives rarely regret not having worked more—in fact, they regret having worked too much, neglecting relationships and failing to live authentically.
In this article, we’ll break down Bronnie Ware’s book The Top Five Regrets of the Dying and explore what these regrets mean for our careers, money, and Financial Independence (FI) journey. You’ll learn the five most common regrets people face at the end of life, and how pursuing FI can help you avoid them now.
Introduction: Deathbed Wisdom Meets Financial Independence
One key theme throughout Ware’s book is the realization of how much denial of death shapes the way most of us live. Western society has pushed death out of sight and out of mind, leaving people completely unprepared when it inevitably arrives. That denial often keeps us stuck in the wrong priorities—sometimes obsessing over status, money, or appearances instead of focusing on what really matters.
In this sense, there are strong parallelisms to be found with some of the ancient Stoics’ wisdom. It’s important to acknowledge and reflect on the brevity of our lives—and how that should at least partially determine our paths forward. The regrets Ware documents show us what happens when we ignore this reality.
It sounds cliché but no one on their deathbed ever said they wished they had worked more hours or stayed longer days in the office. Instead, they regret the complete opposite—the years wasted on careers that swallowed up their energy and stole time away from their family, friendships, and interests.
Under this lens, Financial Independence can be a tool that helps us reclaim those healthy years before they’re gone. It’s not only about compounding returns of our portfolio, it’s about having more time to spend with the people we love, have the experiences that matter, and making the choices that align with our values and lifestyle preferences. I think the author’s message will align well with most folks on their FI journey.
That said, and before jumping into the five regrets of the dying, a quick critique of the book itself. The ideas found in it are powerful, but the delivery is not—I did not find this an easy book to finish. The structure was very predictable—introduce patient, introduce insight, and long wanderings where the author shared mistakes or lessons learned from her past. In the end, the nearly 300 pages felt very stretched. In my view, a 100-page book would have worked much better.
Regardless of the style, though, the core messages from the dying are timeless. And that’s what I want to focus on in this post—the regrets themselves, paired with the lessons for those of us pursuing Financial Independence.
It takes courage to walk your own path and not conform to the path of others. Photo by Zoltan Fekeshazy on Unsplash.
Regret #1: Living an Inauthentic Life
According to the author, this is one of the most repeated regrets. Bronnie Ware heard that people wished they had lived a life true to themselves instead of conforming to the expectations of others. Her clients spoke of dreams left untouched, passions never fully pursued, and decades playing roles that they didn’t truly fit into. The outcome was often experiencing extreme anguish in the last weeks of life. This regret—of living an inauthentic life—is one of the most common things dying people regret.
The tragedy was that the realization usually came too late when illness or age made it simply impossible to do anything about it. In the end, they suffered not only from the loss of opportunity, but also from the anguish of having betrayed themselves for so long.
Behind this regret lies a simple truth: fear often keeps us conforming to others’ expectations. People worried about ridicule from friends, family, or society if they somehow step outside of the mold and walk away from their network’s expectations. By conforming, they silenced their dreams rather than risk disapproval.
Unfortunately, their deathbeds end up catching up with this decision. At that point, the opinions of others no longer matter—only the years they wasted during their one chance at life. Pursuing Financial Independence in itself can be an act of courage—it means ignoring cultural scripts of climbing corporate ladders, buying bigger houses, and engaging in lifestyle creep.
It means implicitly saying you choose to live differently, because you are designing the life you truly want. For me, this came into play when I recently quit my conventional job before reaching FI—choosing freedom over status or pay. I’m now a part-time consultant, part-time influencer.
Another aspect the author points out is the important role of our environment. The people and surroundings in our lives end up shaping our life decisions. If your circle is focused on status, debt, or consumption, it’s much harder to stay true to yourself. On the other hand, surrounding yourself with people who are aligned with your values makes it easier to live courageously.
This first regret reminds us that we can take steps to create an environment that supports the life we want, rather than feel trapped by the one we happen to inherit. Building that environment—where we live, the community and friendships we develop, the habits we practice, or the financial choices we make—isn’t only about minimizing regret later. It’s also about giving ourselves permission to live true to ourselves right now.
Of course, some may argue it’s irresponsible to ignore obligations or family duties in the name of authenticity. But the point isn’t selfishness or to stop providing for your family—it’s about balancing obligations with your true self, so duty doesn’t erase your identity.
“I just wish I’d spent more time in the office”. Did anyone ever say that on their deathbed? Photo by Arlington Research on Unsplash.
Regret #2: Working Too Hard Instead of Living
This second regret hits particularly hard for anyone grinding away in a demanding career. The author’s patients consistently looked back at decades of long hours, commutes, and missed moments with their loved ones and found little arguments for justifying it.
They realized too late that work had stolen what was most valuable in life—the time to be present every day with loved ones, the time to travel, and the time-freedom to enjoy the simple things in life. Many dying patients admitted they didn’t even love the work itself, but that they clung to it as a source of status or for the paycheck it provided.
But by the time they were dying, though, status no longer mattered. This is a reminder that what people regret most on their deathbed isn’t working too little—but spending their best years on work they didn’t truly value.
What they longed for instead was balance. There’s nothing inherently wrong with hard work or enjoying one’s career, but it shouldn’t come at the cost of health, family, or joy. One man in the book described how the thrill of closing deals had become addictive, but ultimately hollow—his wife passed away before they could share the retirement they had dreamed about. Since they didn’t need the money, she had been begging him to retire for over a decade to spend more time with her and travel. Now it was too late.
When work dominates your life, there is little room for anything else. Pursuing Financial Independence offers us a framework to take a step back, place boundaries on work, and re-design a lifestyle that doesn’t mean sacrifying your healthiest decades for a paycheck or status.
This lesson also applies to parenting. The author recalls patients saying that they valued time with their parents as kids far more than any material thing. Our kids don’t need us to buy them more presents—they need us to be more present for them. Practicing frugality on different levels and pursuing FI grants you that option.
Aligning with one of the messages from Bill Perken’s Die With Zero, in the end, it's not only making sure children inherit more money, but that they inherit more memories. Reducing work hours, prioritizing parenting time, or designing a more flexible working lifestyle are different ways that pursuing FI addresses this regret before it’s too late.
If overwork steals our time, unspoken feelings steal our connection—leading to the next regret.
* Further Reading – Article continues below *
Regret #3: Not Expressing Feelings or Emotions
Another common regret was the pain of unspoken feelings. Dying patients admitted to having held back their emotions for years, keeping family and friends at arm’s length. Some even confessed that their children didn’t even truly know who they were, because they had spent far too long suppressing affection, vulnerability, or tricky conversations.
But the cost of this emotional distance was devastating—both to the dying but also to those left behind. The author emphasized how expressing feelings can be difficult at first until it becomes a habit—eventually bringing peace. Those who had the courage to share their emotions reported fewer regrets and enjoyed more authentic relationships, while those who kept silent often carried their loneliness and guilt to the grave.
The lesson should be clear: silence may avoid short-term conflict, but in the long run it brings more pain and regret.
We can find a strong parallel here to financial honesty. Hiding from your financial numbers—ignoring spending or debt issues, or procrastinating when it comes to setting financial goals—usually makes the problems worse. Facing your finances head-on—just like expressing your feelings—is scary at first, but it’s the only path to real financial freedom.
A top regret of the dying is not having expressed their feelings to others. Photo by Courtney Cook on Unsplash.
Regret #4: Losing Touch With Friends and Loved Ones
Unsurprisingly, loneliness was another major theme throughout the book. Dying patients had left their friendships drift over time, often too busy with careers or family responsibilities. By the end of their lives, though, they felt isolated, with no one who truly understood them or knew about their story. Some of the stories in the book are heartbreaking. They realized too late that friends were not a luxury to have in life—but essential to feeling understood and connected.
Friends also served as anchors for identity. While family roles and careers can shift over time, friendships remind us of who we are at our core—and of the journey we’ve taken to get there. They provide acceptance, laughter, and perspective that can’t be replicated otherwise, and the blessing of not taking ourselves too seriously.
On their deathbeds, patients regretted having lost touch with those who knew them best—rebuilding those connections was no longer possible, either because they no longer were there or too much time had passed. This regret reminds us not to let the busyness of daily life crowd out what is truly irreplaceable.
From a Financial Independence perspective, again, time-freedom isn’t just about quitting your career early. It’s also about having more time and headspace to nurture existing and new friendships. When your calendar isn’t fixed by your employer, you can prioritize dinners, trips, and chats with the people who make your life meaningful.
Staying in touch with your friends isn’t just about avoiding loneliness at the end of your life—but about enriching every step of it now.
Even when friendships and family are present, another regret remains: not giving ourselves permission to embrace happiness.
Keep in touch with your friends and loved ones. Photo by Vidar Nordli-Mathisen on Unsplash.
Regret #5: Not Allowing Yourself to Be Happier
We finally arrive at the final regret—wishing we’d chosen to be happy. The author documents dying patients realizing too late that happiness was often a choice that they didn’t allow themselves to make. They often confessed living under self-imposed limits, convinced they didn’t deserve happiness or that they needed permission to enjoy life.
They realized too late that joy had always been available, but they had actively blocked themselves from embracing it. Too often, we fall into the trap of believing happiness depends on others—on society fixing itself, on politicians delivering on some promise, on our boss changing, or on some circumstance lining up just right. But the dying remind us this is a mirage. As Stoic philosophers argued, peace, tranquility, and contentment come from within, not from waiting for external factors to align.
Sometimes fear and ego were the culprits. People stayed in jobs, relationships, or lifestyles that didn’t really serve them because they were worried, again, about status, appearances, and other people’s opinions. By chasing recognition from others, they sacrificed their own happiness. At the end of their lives, those fears were meaningless, but what remained was the regret and sorrow of not having laughed more, relaxed more, and chosen to enjoy the simple day-to-day pleasures.
Pursuing Financial Independence also ties well to this lesson. Achieving FI doesn’t guarantee happiness, but it does remove many external constraints. What matters even more, though, is the internal work—learning to let go of comparison, giving yourself permission to enjoy life as it is (not as you’d like it to be), and recognizing that salaries, possessions, or approvals from others won’t create lasting joy.
There’s also a subtle but important distinction here: the word “happiness” is thrown around a lot and means different things to each person. But remember that, as most people understand it, happiness itself is fleeting—an unexpected burst of emotion, not a permanent state of being.
What endures, though, is a life well-lived—a life of meaning, integrity, and balance. The Stoics encouraged focusing not on chasing “happiness” but on cultivating tranquility and virtue instead. Ironically, in the end, those momentary bursts of joy will show up more often when you’re living that kind of life. That’s the real takeaway from the top five regrets of the dying: happiness isn’t handed to us—it’s built through our daily choices.Skeptics may say not everyone can choose happiness in hard circumstances. That’s true—but even in hardship, focusing on what we can control—our responses and our outlook—gives us more peace than waiting for the world to change.
Give yourself permission to be happy and enjoy life. Happiness is much less dependent on external factors than most of us think. Photo by Sherise Van Dyk on Unsplash.
Conclusion: Using Regrets as a Guide for FI
Bronnie Ware’s book may not be perfect in its delivery, but the core regrets she highlights are timeless. They can serve as a mirror for anyone wanting to take an honest look at their own life—how are we faring in regards to these 5 regrets?
Sometimes, it can be hard to know what we want out of life, but focusing on regret minimization can be a good starting point—a philosophy also shared by Perkin’s Die With Zero.
For those of us on the path to FI, these regrets can provide an even sharper focus. Pursuing Financial Independence isn’t just about money, but about avoiding those regrets by realigning how we decide to spend our days. It’s also a reminder that we shouldn’t wait until we reach some magical FI number to implement these—we can start reflecting on these ideas and regrets now.
The biggest takeaway for me is that these regrets are preventable. By Stoically facing our own mortality—something we are not very good at collectively—and by admitting we simply don’t have unlimited time, we can shift our priorities now rather than experience regret and anguish later. We can choose to live authentically and follow our own path, to find a good work-life balance, to share our feelings, nurture friendships, and be open to happiness.
These are not abstract concepts—but daily choices we can choose to make or not to make.
So let’s not wait until we are in the deathbed next to Bronnie. Let’s use some of this knowledge as guardrails on our FI journey. If the dying could speak, most would likely say the same thing—live fully now, before it’s too late. And that’s the real gift Financial Independence offers—not just early retirement, but a life free from the most common regrets of the dying.
💬 Which of these five regrets resonates the most with you? Have you already made changes in your career, finances, or lifestyle to avoid any of them—or do you feel pulled by the same societal pressures Ware’s patients described? Please share your thoughts in the comments below!
👉 New to Financial Independence? Check out our Start Here guide—the best place to begin your FI journey. Subscribe below to follow our journey.
🌿 Thanks for reading The Good Life Journey. I share weekly insights on money, purpose, and health, to help you build a life that compounds meaning over time. If this resonates, join readers from over 100 countries and subscribe to access our free FI tools and newsletter.
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Frequently Asked Questions (FAQs)
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The five most common regrets documented by Bronnie Ware are: not living true to oneself, working too hard, not expressing feelings, losing touch with friends, and not allowing oneself to be happier.
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The biggest regret is not having lived authentically. Many people conformed to others’ expectations and ignored their own dreams until it was too late.
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Many regret working too hard. They sacrificed time with family and health for careers that brought little meaning once they faced death.
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The core takeaway is that people regret time wasted on inauthentic choices. By listening to these regrets, we can prioritize relationships, meaning, and freedom.
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Often we regret not expressing our feelings or not staying in touch. Ware’s patients emphasized that relationships matter more than possessions.
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Happiness is often blocked by fear, ego, or waiting for external approval. Regret comes from realizing too late that happiness was always an internal choice.
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FI allows you to reduce work, spend more time with family, nurture friendships, and design a life aligned with your values before it’s too late.
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They often admit they could have chosen to laugh more, relax, and enjoy life—but didn’t give themselves permission to be happy.
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Focus on authenticity, balance work and relationships, express your feelings, nurture friendships, and cultivate tranquility instead of chasing fleeting happiness.
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Bronnie Ware, an Australian nurse who spent years caring for dying patients, wrote the book after documenting their most common reflections.
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