End-of-Life Planning Made Simple: Insights from Funeral & Financial Expert

In a recent conversation on The Digital Legacy Podcast, Niki Weiss, founder of ENDevo, sat down with Greg Barnsdale, funeral director, financial planner, and author of Do Not Ignore Your Mortality, to talk about what it means to plan for the end of life with clarity and compassion. It all starts with one truth: planning for death is not giving up. It’s showing up for the people who will one day have to carry on.

About This Blog

Most of us don’t want to talk about death.

We don’t want to think about it, plan for it, or make space for conversations that feel heavy or uncertain. And yet, if you’re reading this, chances are you’ve felt that quiet pull. Maybe after a diagnosis, a loss, or simply a growing awareness that someday, this will matter. Because it always does.

In a recent conversation on The Digital Legacy Podcast, Niki Weiss, founder of ENDevo, sat down with Greg Barnsdale, funeral director, financial planner, and author of Do Not Ignore Your Mortality, to talk about what it means to plan for the end of life with clarity and compassion.

It all starts with one truth: planning for death is not giving up. It’s showing up for the people who will one day have to carry on.


Avoidance is Normal. But It’s Not Helpful.

Greg has worked on both sides of the “mortality coin,” as it were. First as a funeral director, then as a financial advisor. In both roles, he’s seen a pattern: families caught off-guard, overwhelmed, and unsure what to do because no one had “the talk.”

He calls it deathbed estate planning: those panicked moments in the hospital hallway, when loved ones whisper, “Did anyone ask what they wanted?”

This isn't rare. It's common. And it's preventable.

It’s not always fear that keeps us from planning. Sometimes it’s superstition, believing that talking about death might invite it closer. Other times, it’s cultural conditioning. Topics like money, death, and even serious illness are often treated as taboo in Western societies.

But the truth is, death will happen, and it will happen on its own schedule. Waiting to address it doesn’t prevent it. It just makes it harder for the people we love.


Planning Is an Act of Care

Greg shares his own story openly. Two months after publishing his book, he was diagnosed with a brain tumor. It turned out to be benign, but he underwent radiation and faced real uncertainty. What gave him peace? Knowing his affairs were in order.

He had a will, powers of attorney, medical directives, and because of that, his energy could go toward healing; instead of scrambling to put pieces in place under pressure.

End-of-life planning doesn’t just ease legal or financial burdens. It offers emotional relief—for both you and those who love you.


Your Legacy Is More Than Money

One of the most powerful points Greg makes is that end-of-life planning isn’t just about who gets what. It’s about protecting relationships, creating clarity, and reducing conflict.

A thoughtful estate plan:

  • Minimizes family disputes

  • Keeps the courts out of your business

  • Protects your values and wishes

  • Allows for charitable giving and tax benefits

  • Strengthens the economy by reducing unclaimed assets

Think of it as relational wealth, not just financial wealth.


Where Digital Meets Deathcare

In today’s world, planning for death includes managing your digital estate: your passwords, online accounts, and personal data. Greg uses a simple binder and pencil to stay organized, but the key is this: make sure someone you trust knows where everything is.

That means:

  • Keeping login info updated

  • Assigning a digital executor

  • Making a list of key assets (bank accounts, subscriptions, social media)

  • Stating what you want done with your online presence

As more of our lives move online, organizing this aspect of your legacy is becoming just as important as drafting a will.


Not Sure Where to Start? Start Small.

Greg’s book offers practical tools to begin. On his website, you’ll find:

  • A short Living Legacy Quiz to assess your preparedness

  • 30 curated questions—15 for starters, 15 more advanced—to spark conversation with loved ones

These tools are designed to be approachable. You don’t need to know all the answers. You just need to begin the conversation. They can be found on DoNotIgnoreYourMortality.com.


Death Positivity Isn’t Morbid. It’s Empowering.

The death positive movement, which Greg and Niki both champion, isn’t about celebrating death. It’s about embracing life more fully by removing the fear and shame around its inevitable end.

It’s about saying:

  • “This is hard, and I’m doing it anyway.”

  • “I want to make this easier for the people I love.”

  • “I want to have a say in how I leave this world.”

And sometimes, it’s just about being curious: What would a good death look like—for me?


Let Planning Be a Gift, Not a Burden

You don’t have to do it all at once. You don’t even need to do it perfectly. But every step you take—writing down a password, having a conversation, drafting a will—is a powerful act of love.

And here’s the thing: these aren’t just end-of-life decisions. They’re life decisions.

They help us live more fully, love more clearly, and rest a little easier knowing that when the time comes, we won’t leave chaos behind.


If You’re Ready to Take the First Step:
Take Greg’s quiz or talk to a loved one about just one question from his list. Perhaps check in on your will—do you have one? Is it up to date?


Want to hear more?
Watch the full conversation with Greg Barnsdale on The Digital Legacy Podcast on YouTube. It’s thoughtful, honest, and might just give you the encouragement you’ve been waiting for.

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How AI Technology is Reshaping Our Relationship with Mortality

In a time when our lives are increasingly intertwined with technology, the collision of death and digital innovation presents opportunities and challenges previous generations couldn’t foresee happening. Dr. Sarah Parker Ward, an end-of-life futurist and professor at Rensselaer Polytechnic Institute, brings her perspective to this new frontier. With a background in digital advertising and a PhD from Boston University, Dr. Parker Ward's journey into death technology began with a profound personal experience during her grandfather's end-of-life journey. This experience, combined with her academic exploration of how industrialization has transformed both birth and death mindsets, highlights her voice in understanding how technology is reshaping our relationship with mortality. Game Changes in Death Technology The concept of death technology, or "death tech," encompasses innovations that span the entire spectrum of end-of-life experiences, from aging and hospice through post-mortem care. This evolving field is being driven partly by demographic shifts, like baby boomers, with approximately 11,000 individuals turning 65 each day. This demographic has geared entrepreneurs and private equity firms who recognize the significant market potential to develop technological solutions for end-of-life needs. On the one hand, there's a movement toward what Tony Walter termed "The Revival of Death" in the mid-1990s, where people are seeking to return to more personalized, less industrialized approaches to post-mortem care, similar to practices from the mid-1800s. On the other hand, there's a surge in technological innovations aimed at enhancing and personalizing the end-of-life experience through digital means. The crossed paths of these trends have led to the development of various digital tools and platforms that aim to make end-of-life planning more easy and accessible. One of the more popular innovations to come from this include pre-planning platforms that generate personalized letters explaining funeral arrangements and applications designed to help parents create legacy messages for their children, demonstrating how technology can be used to maintain meaningful connections even after death. Digital Legacies and Virtual Immortality The management of our digital legacy is crucial for end-of-life planning. Our digital footprints are vast and complex, encompassing everything from social media accounts and email to digital subscriptions and online banking. Our digital presence raises important questions about data management and privacy that extend after we have passed on. One of the most controversial developments in this space is the emergence of "grief bots" - artificial intelligence systems designed to simulate conversation with deceased individuals based on their digital communication patterns. While these technologies offer the alluring possibility of maintaining a connection with lost loved ones, they also raise significant ethical concerns about the authenticity of these interactions and their impact on the natural grieving process and the person experiencing loss. Advanced planning for digital assets has become a new field, requiring careful consideration of how our online presence will be managed after death. This includes decisions about account closure, data deletion, and the preservation or removal of social media profiles. The complexity of these decisions has led to the development of digital legacy advance directives, documents that specify how digital assets should be handled posthumously. The Transformation of Death Care The evolution of death care (during the passing of loved ones and after) practices reflects broader societal changes in how we approach mortality. Historical shifts in death care parallel similar changes in birth practices, with both experiencing waves of industrialization and medicalization, followed by movements toward a more empathetic outreach. Modern death care is becoming increasingly automated and personalized, with individuals seeking greater control over their end-of-life experiences. We have prepared a list of various planning tools and resources that help people articulate their wishes for both physical and digital assets. Essential considerations for modern end-of-life planning include: Advanced care directives for medical decisions Digital legacy planning for online accounts and assets Designation of legacy contacts for digital platforms Instructions for data privacy and management Preferences for memorial and remembrance practices Guidelines for executors regarding digital asset management Your Data Privacy Data privacy concerns extend beyond death, with current regulations offering limited guidance on posthumous data management. Common issues include unwanted social media reminders of deceased individuals, continued account suggestions, and questions about data ownership after death. The ability to effectively manage and potentially remove digital information after death remains a big and often overlooked question. The role of executors has expanded to include the management of digital assets, requiring not just emotional capacity but also technological competence. This new responsibility highlights the need for a careful selection of executors who can navigate both traditional and digital aspects of estate management. What will you do to protect your digital data when you pass? Planning for the Digital End As we navigate this new frontier of death in a digital age, proactive planning is important. With less than 40% of people engaging in advanced care planning, there's significant room for improvement in how we prepare for end-of-life matters. The ubiquity of smartphone technology, even among baby boomers with a 90% adoption rate, provides an accessible starting point for digital legacy planning. Try taking simple steps such as assigning legacy contacts on your devices and social media accounts. Consider creating a comprehensive digital inventory of your online presence and developing clear instructions for how you want your assets to be managed after death. Most importantly, engage in conversations with loved ones about your digital legacy preferences and ensure your wishes are documented in a way that provides clear guidance for survivors. By taking proactive steps to manage our digital legacies, we can help ensure our online presence aligns with our values and preferences, even after we're gone. If something happened to you, would the people in your life know what to do? Don't leave your loved ones in the dark. Start developing your end-of-life and digital legacy plan. Download My Final Playbook App on the App Store and Google Play to get started. Through this app, you'll be able to start and learn how to organize your legal, financial, physical, and digital assets today. Until then, keep your password safe and your playbook up to date.
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