The Currency of Grief
Death and money are two of the most taboo topics in our society yet they are inevitable for all of us. So why don’t we talk about death and money more? The fact is, we’re all going to have to face our mortality and the mortality of the people we love. During the toughest times in our life, we will also be faced with an overwhelming amount of financial and logistical decisions. These decisions have the power to bring people together or tear families apart. That’s why our mission is so important! Here on The Currency of Grief, we bring death and money to the forefront of the conversation. We’ll feature real life stories from real life people who have navigated the intersection of grief and money. Our guests are not celebrities, they are normal people just like you and me. My name is Justin Weidenfeld, and I’m going to serve as your Grief Financial Officer on the journey that is The Currency of Grief Podcast. My purpose for this podcast is to normalize conversations around death and money, inspire you to have deeper conversations with your loved ones (while you can), act as a resource for people currently navigating a grief and money journey, and encourage listeners to approach their own legacy head on. Whether you’re in the midst of your own grief and money journey or need a reality check about planning for the inevitable, this podcast is for you. Each episode provides heartfelt insights, logistical nuances and practical advice that will help you navigate financial and emotional adversity WHEN you are faced with loss. The Currency of Grief Podcast will air biweekly on Fridays and can be listened to on Spotify and Apple Podcasts. I am grateful that you’ve decided to join me on this journey!
Episodes

Jul 17, 2026
Jul 17, 2026
59 min
Nobody prepares you to grieve a parent and manage their affairs at the same time. On The Currency of Grief, host Justin Weidenfeld sits down with Michael Lodato, a Brooklyn-based writer and owner of LiquorPermit.com, who became a co-executor of his mother’s estate in his early thirties after she passed away from melanoma just days before Christmas.
Michael and his sister stepped in as co-executors and got a crash course in everything no one talks about. A death certificate needs a raised seal or the DMV turns you away. A lender can repossess a car from the driveway as the estate paperwork sits in limbo. And a one-person consultancy can hold more value than anyone expects.
Michael shares what losing a parent at a young age taught him about support systems, from grief groups created for people in their twenties and thirties to the friend who dropped off bruschetta on a hard night. He also tells the story of inheriting a business that many people would have walked away from. Rather than selling his mother's domain and closing her files, he digitized her archive and continued building on the specialized work she had developed throughout her career.
Every estate executor faces choices that no checklist can fully cover. This conversation looks at those decisions through the experience of someone who made mistakes, kept the lessons, and found a way to carry his mother’s work forward. For anyone dealing with grief and financial responsibilities at the same time, Michael’s story offers an honest look at finding a way through.
Episode Breakdown:
00:00 Meet Michael Lodato and His Mother's Story
03:24 Melanoma Diagnosis and the Rush to Hospice
04:42 Family and Friends Rally During Hospice Care
06:44 How Friends Show Up During Grief
10:42 Therapy and Grief Groups for Young Adults
13:28 Writing a Eulogy for a Beloved Mother
19:02 Taking On the Estate Executor Role
21:37 Gathering Death Certificates and DMV Roadblocks
25:03 The Car Repossession Ordeal
28:47 Inheriting His Mother's Liquor Permit Business
34:31 How Grief Reshaped Michael's Career Path
37:35 Financial Inheritance and Selling the House
40:45 Conversations Left Unspoken With His Mother
47:00 How Loss Changed His Approach to Planning
50:01 Inheriting a Dress Shop and Finding Humor in Grief
52:26 Advice for Anyone Facing a Similar Loss
55:56 Honoring His Mother's Legacy With a Park Bench
Connect with Michael Lodato:
Visit Mike's website
Follow Michael on Instagram
Visit the Liquor Permit website
Connect with Justin Weidenfeld:
Connect with Justin on LinkedIn
Follow The Currency of Grief on LinkedIn
Follow The Currency of Grief on Instagram
Follow The Currency of Grief on TikTok
Subscribe to The Currency of Grief on YouTube
Visit Justin’s website bio
Podcast production and show notes provided by HiveCast.fm

Jul 3, 2026
Jul 3, 2026
1hr 4 min
When your spouse dies abroad, nobody warns you that the paperwork battle might outlast the worst of the grief.
Nikki Sherman was living in the UK with her husband Scott and their daughter when Scott died suddenly at 52 from a pulmonary embolism. Settling an estate after a spouse dies is hard enough. Doing it across two countries, during a pandemic, while raising a teenager, is another thing entirely.
On The Currency of Grief, host Justin Weidenfeld talks with Nikki about the side of widowhood that nobody prepares you for. Not the sadness, but the bureaucracy. The phone calls where you tell the same story over and over. The financial institutions with different requirements. The Medallion Signature Guarantee rabbit hole that took years to resolve. The guilt of not being able to work, while quietly being relieved you didn't have to.
Nikki's experience with death overseas and probate in two countries lasted nearly three years. What got her through it was life insurance that paid out immediately, joint accounts that transferred without a fight, and a will that was recognized on both sides of the Atlantic.
Her story is one of grief and growth in equal measure. She stayed in the UK, raised her daughter through it, built a new life, and came out the other side with hard-won clarity about what it really takes when a spouse dies abroad and leaves you holding everything.
Episode Breakdown:
00:00 When a Spouse Dies Abroad: Nikki Sherman's Story
04:01 Scott Sherman: Life, Love, and 20 Years in the UK
09:31 What Is a Pulmonary Embolism and Why It's So Deadly
13:51 Making Decisions While Drowning in Grief
14:17 Funeral Planning Overseas and Celebrating a Life Well Lived
23:27 Traveling With Human Remains on an Airplane
25:46 Settling an Estate After Spouse Dies: The Financial Reality
27:45 UK vs. US Assets and How Joint Accounts Saved the Day
31:34 Why Having a Will Across Two Countries Matters
36:09 Life Insurance After Spouse Dies: The Emotional and Financial Truth
37:17 When Grief Makes It Impossible to Go Back to Work
41:37 Life Insurance as a Financial Lifeline for Widows
46:53 Probate in Two Countries: UK First, Then the US
47:23 The Medallion Signature Guarantee Nightmare for Expats
53:19 What Nikki Wishes She Had Done Differently
55:36 How This Experience Changed Her Relationship With Money
58:11 Honoring Scott's Legacy and Finding Life After Loss
Links:
Visit the Widowed and Young website
Apply to the Experience Camps programs
Connect with Justin Weidenfeld:
Connect with Justin on LinkedIn
Follow The Currency of Grief on LinkedIn
Follow The Currency of Grief on Instagram
Follow The Currency of Grief on TikTok
Subscribe to The Currency of Grief on YouTube
Visit Justin’s website bio
Podcast production and show notes provided by HiveCast.fm

Jun 19, 2026
Jun 19, 2026
1hr 8 min
Losing a parent at 14 does not just change your childhood. It changes every version of you that comes after.
On The Currency of Grief, host Justin Weidenfeld sits down with Emily Bouchard, family dynamics expert, TEDx speaker, and host of the Wealth Coherence podcast. Emily was 14 when her mother died suddenly at 44 from a brain aneurysm. What followed was decades of grief that kept showing up, in new relationships, in major decisions, and in a single year that changed everything.
That year was the death year. The age Emily turned 44, the same age her mother was when she died. She did not see it coming, but her body did. It stopped her, reoriented her, and ultimately freed her to live by her values in a way she never had before.
Emily also shares her concept of “the slinky of grief”, and why loss does not arrive once and leave. It comes back around, hitting you at different points across your life, sometimes when you least expect it.
The conversation turns to families and the weight of what goes unsaid. What does it cost when parents and children never talk about the purpose of our wealth, about wishes, values, and what they want their legacy to mean? Emily has seen those costs up close, and she knows how to help families start talking before it is too late.
She leaves with two words that have carried her through it all. Grace and gratitude. Not as platitudes, but as a real practice.
If any of this feels familiar, this episode is for you.
Find Emily at emilybouchard.com or trustmoneyfamilies.com
Episode Breakdown:
00:00 Meet Emily Bouchard: Family Dynamics Expert and TEDx Speaker
04:28 Losing Her Mother at 14: Emily's Story of Grief
09:50 Who Was Joan: Remembering a Mother's Kindness and Legacy
13:11 Finding Support After Loss: The Grief Cliff and Who Shows Up
16:14 Family Dynamics After Sudden Loss: Remarriage and Rebuilding
19:13 The Slinky of Grief: How Loss Resurfaces at Every Life Stage
23:00 The Death Year: What Happens When You Reach the Age Your Parent Died
29:26 No Plan, No Will, No Conversation: What Happened After the Funeral
33:32 How Families Fight Over Belongings and How to Prevent It
40:27 The Cost of Silence: Why Families Avoid Talking About Inheritance
46:52 Legacy Versus Estate Plans: Knowing What to Do With What You Inherit
49:15 How to Start Inheritance Conversations Without Talking About Numbers
57:35 Aligning Values and Purpose Before Making Estate Decisions
58:22 How Loss Changed Emily's Approach to Planning and Giving
1:02:50 Grace and Gratitude: Words of Wisdom for Anyone Carrying Grief
Connect with Emily Bouchard
Visit Emily's website
Get a copy of The Little Book of Trust and Money
Listen to The Wealth Coherence Podcast
Watch Emily's TEDx talk about inheritance
Visit the Enlightened Philanthropy website
Connect with Justin Weidenfeld:
Connect with Justin on LinkedIn
Follow The Currency of Grief on LinkedIn
Follow The Currency of Grief on Instagram
Follow The Currency of Grief on TikTok
Subscribe to The Currency of Grief on YouTube
Visit Justin’s website bio
Podcast production and show notes provided by HiveCast.fm

Jun 5, 2026
Jun 5, 2026
1hr 12 min
He was trying to be present for his father’s final weeks while carrying the legal and financial responsibility of what would come next.
That's the reality Vincent Valeri faced in the winter of 2022, and on this episode of The Currency of Grief, host Justin Weidenfeld gives him the space to tell it honestly. When Vincent's father Vincenzo was diagnosed with stage four bile duct cancer in December of that year and given six to eight weeks to live, Vincent had to hold two roles at once. He was the grieving son and the person legally responsible for closing out a complex, imperfectly planned estate.
Executor responsibilities after death don't wait for grief to pass. Vincent learned that quickly. In the weeks that followed, he was simultaneously updating beneficiaries, getting the matrimonial home properly titled, meeting with accountants about holding companies and crossing fiscal years, and making legal decisions on a timeline no one plans for. By the time his father passed in February 2023, Vincent was facing multiple tax filings and what became a 26-month probate process.
What makes this conversation so valuable is Vincent's candor about grief and estate planning from the inside. He talks about the invisible wall of cultural respect that made hard family conversations about death nearly impossible, the loneliness of being an executor, and the painful gap between what he knew professionally and what his father had actually put in place.
The practical lessons here are real. Update beneficiary designations. Get both names on accounts before it's too late. Know what a bank will and won't let you do when someone can't come in to sign. Understand that executor responsibilities after death include decisions you'll be making without the person who should have made them.
Vincent closes with something simple and true: It's going to be okay. Not as a platitude, but as something he had to find his way back to.
Episode Breakdown:
00:00 Welcome to The Currency of Grief with Vincent Valeri
03:30 Vincenzo Valeri: An Italian Immigrant Who Built a Life in Canada
06:25 Getting a Terminal Diagnosis and Knowing the Estate Wasn't Ready
10:21 How Italian and Canadian Culture Shapes Family Conversations About Death
20:34 Executor Responsibilities After Death: What No One Tells You
30:16 The First Financial Steps to Take After a Terminal Diagnosis
34:36 Holding Companies, Blended Families, and Complex Estate Situations
47:15 When Siblings Have Unequal Information About the Estate
58:12 Why Family Meetings Are the Foundation of Good Legacy Planning
1:09:33 Words of Wisdom for Anyone Facing a Parent's Terminal Illness
Connect with Vincent Valeri:
Visit the Valeri Associates website
Connect with Vincent on LinkedIn
Connect with Justin Weidenfeld:
Connect with Justin on LinkedIn
Follow The Currency of Grief on LinkedIn
Follow The Currency of Grief on Instagram
Follow The Currency of Grief on TikTok
Subscribe to The Currency of Grief on YouTube
Visit Justin’s website bio
Podcast production and show notes provided by HiveCast.fm

May 22, 2026
May 22, 2026
58 min
Grief after losing a child doesn't follow a script, and no one knows that better than Richard Wood.
Nearly 20 years ago, Richard's 22-year-old son Spencer died in a sudden unexpected loss that changed everything. There was no warning, no goodbye, and no roadmap for what came next. In this episode of The Currency of Grief, host Justin Weidenfeld sits down with Richard to talk about how a father carries that kind of loss forward, through marriage, through raising daughters, and into a season of life where seven grandchildren now grow up hearing Spencer stories.
Richard is a father who held his family together while quietly falling apart. His wife grieved through anger. Each of his daughters found their own painful path. Richard himself never went a single day without telling someone a Spencer story. He didn't move through the stages of grief in any tidy order, and he's honest about why that is. Grief after losing a child is shaped by the relationship you had, and no two relationships are the same.
The conversation gets into what people get wrong when supporting someone who is grieving. Richard has heard every well-meaning platitude and he handles them with patience. His advice is straightforward. Show up. Say you're sorry. Then stop talking and listen. Not just in the first week, but for months afterward when everyone else has moved on and the person grieving is left alone with it.
Faith played a quiet but significant role in Richard's journey. He didn't expect to find it the way he did, but losing Spencer revealed a depth of belief he hadn't known was there. It didn't erase the pain. It gave him somewhere to put it.
A fraternity brother once said that Spencer was not just someone people knew. He was someone who changed the way life felt when he was around. That comment became the foundation for something Richard has kept alive for two decades. Every year at Cal Poly, a student is anonymously nominated by peers for how they live and how they treat others. They never apply for it. They simply get chosen because of their kindness. Richard has watched that scholarship outlive an entire generation of Spencer's college friends because it stopped being about Spencer specifically and became about everything he represented.
This episode is for anyone who has experienced losing a son, a daughter, or any person they weren't ready to live without.
Episode Breakdown:
00:00 Welcome to The Currency of Grief
02:22 Richard Wood's Story and Why He Shares It
06:40 Who Spencer Was and the Family He Left Behind
08:59 Grief After Losing a Child and Why Time Does Not Heal
16:23 How Every Family Member Grieves Differently
19:05 What Not to Say to Someone Who Is Grieving
22:28 The Grief Cliff and What Happens When Support Disappears
23:32 The Lifestyle Scholarship and Honoring Spencer's Memory
42:14 Financial and Practical Advice for the First Year of Grief
47:28 Faith, Hope, and Love as Pillars of the Grief Journey
Connect with Richard Wood:
Visit The Compassionate Friends Org Website
Connect with Justin Weidenfeld:
Connect with Justin on LinkedIn
Follow The Currency of Grief on LinkedIn
Follow The Currency of Grief on Instagram
Follow The Currency of Grief on TikTok
Subscribe to The Currency of Grief on YouTube
Visit Justin’s website bio
Podcast production and show notes provided by HiveCast.fm

May 8, 2026
May 8, 2026
1hr 3 min
Estate settlement after death is one of the most overlooked burdens grieving families face, and on this episode of The Currency of Grief, host Justin Weidenfeld sits down with Davis Wilkinson, CEO and founder of Heirloom, to talk about why that burden exists and what it actually costs families to carry it alone.
Davis's story starts with sibling loss and grief. His older brother Adam died of a methadone overdose in 2009, when Davis was just 14. He spent the next decade in emotional repression, not out of indifference but out of sheer incapacity. It wasn't until his mid-twenties, after leaving the Mormon church and losing the theological certainty that he'd see Adam again, that the grief finally caught up with him. What followed was years of intensive therapy and a hard-won understanding of what it means to grieve on your own timeline.
The conversation moves naturally into grief and money when Davis describes watching his mother navigate the estate administration process after Adam's passing. That experience became the foundation for Heirloom, a platform designed to support executors through one of the most logistically overwhelming roles a person can be asked to fill while also managing loss.
Davis talks about asset discovery, the staggering volume of unclaimed assets in the United States, and the systemic gaps that leave families without clear guidance at the worst possible time. Right now, there are no enforced standards for how banks treat executors during estate settlement after death, and he makes a clear case that this gap is costing grieving families more than just time.
This episode is for anyone who has ever wondered why handling a loved one's affairs feels so impossible, and for anyone who needs to know they are not alone in finding it that way.
Episode Breakdown:
00:00 Introduction to The Currency of Grief
02:02 Davis Wilkinson and the Story Behind Heirloom
03:45 Sibling Loss Grief: Losing a Brother to Drug Overdose
09:54 Childhood Grief and Emotional Repression
17:29 Finding Support and Coping After Loss
19:55 Leaving the Mormon Church and Facing Grief for the First Time
21:57 Estate Settlement After Death: What Davis's Mother Faced
45:04 How to Fix the Estate Administration System
49:16 Unclaimed Assets and What Families Are Missing
51:44 What Executors Need and How Heirloom Helps
55:50 How Loss Changes Your Approach to Life and Planning
58:35 Words of Wisdom for Anyone Navigating Grief
Connect with Davis Wilkinson:
Visit the Heirloom website
Connect with Davis on LinkedIn
Connect with Justin Weidenfeld:
Connect with Justin on LinkedIn
Follow The Currency of Grief on LinkedIn
Follow The Currency of Grief on Instagram
Follow The Currency of Grief on TikTok
Subscribe to The Currency of Grief on YouTube
Visit Justin’s website bio
Podcast production and show notes provided by HiveCast.fm

Apr 24, 2026
Apr 24, 2026
57 min
Most people spend more time planning a vacation than choosing who will manage their estate.
In this solo episode of The Currency of Grief, host Justin Weidenfeld, your grief financial officer, walks through the roles that shape what happens to your estate, your medical and financial decisions, and your family dynamics when life changes without warning. This episode is about the people you put in charge and what saying yes to that role means.
Justin breaks down each role on your planning team. The executor who carries out your wishes after death. The trustee who manages assets over time. The POA who steps in during incapacity. He is also clear about something people often avoid. The right person for each role is rarely the person you love most.
You will hear why naming co-executors often creates delays and conflict, why emotional closeness does not always mean someone is equipped to make hard decisions, and why putting every role on one person can lead to burnout. Understanding the difference between an executor, a trustee, and a POA can change the way you think about estate planning.
Justin also gets into the part people do not talk about enough. How to start the conversation. Whether you are a parent trying to prepare your heirs or an adult child trying to bring this up without making it feel threatening, he shares practical language you can use.
These roles do not fill themselves after loss. The people who love you deserve more than guesswork. If you want your estate plan to feel clear, thoughtful, and easier for the people you love, this episode is a strong place to start.
Episode Breakdown:
00:00 Estate Planning Basics and Why Roles Matter After Loss
02:21 Medical Power of Attorney and End-of-Life Healthcare Decisions
04:48 Financial Power of Attorney, POA Types, and Incapacity Planning
07:08 Executor Responsibilities in Estate Administration After Death
09:29 Trustee Duties, Successor Trustee Roles, and Trust Management
16:43 Guardian Selection and Estate Planning for Minor Children
21:34 Common Estate Planning Mistakes That Create Family Conflict
31:10 Why Families Avoid Estate Planning Conversations
35:46 How to Talk to Heirs About Estate Roles and Wishes
45:05 How Adult Children Can Ask Parents About an Estate Plan
Connect with Justin Weidenfeld:
Connect with Justin on LinkedIn
Follow The Currency of Grief on LinkedIn
Follow The Currency of Grief on Instagram
Follow The Currency of Grief on TikTok
Subscribe to The Currency of Grief on YouTube
Visit Justin’s website bio
Podcast production and show notes provided by HiveCast.fm

Mar 27, 2026
Mar 27, 2026
1hr 8 min
Please note this episode discusses drug use and domestic violence.
Sibling inheritance conflict rarely starts with money. It often begins in the space where grief, silence, and unspoken expectations live. On The Currency of Grief, host Justin Weidenfeld sits down with Peter Johnson to share what unfolded after his mother’s brain cancer loss and how that experience shaped his work at the intersection of grief and money and the human side of legacy.
This conversation challenges a common belief that family estate planning will keep families aligned. Peter explains why documents alone are not enough. Without shared understanding and trust, sibling inheritance conflict can still surface, even in families that believe they are prepared. His story brings attention to the real gap, which is the absence of family legacy conversations that clarify values, expectations, and how decisions are meant to be understood.
Peter introduces the idea that connection after loss is something people can actively build, not something that happens on its own. That shift matters for anyone dealing with caregiving, inheritance decisions, or strained relationships. If you want a clearer perspective on what helps families stay connected, this episode offers a place to start. It also reinforces that preventing sibling inheritance conflict begins well before any legal plan is put in place.
Episode Breakdown:
00:00 Welcome to The Currency of Grief With Justin Weidenfeld and Peter Johnson
03:22 Why Connection Is the Real Currency in Grief
08:58 Grief Anxiety, Panic Attacks, and Emotional Survival After Loss
11:16 Men’s Groups, Therapy, and Finding Support After Grief
17:30 The Three Turning Points That Shaped Peter Johnson’s Legacy Work
23:18 Brain Cancer Loss, Estate Administration, and Sibling Inheritance Conflict
30:21 Receiving Inheritance at 21 and the Emotional Side of Money
34:28 Why Family Estate Planning Fails Without Mentoring and Communication
43:30 Family Legacy Conversations That Could Prevent Estrangement
49:38 The Human Side of Estate Planning and How Families Avoid Court
1:04:21 Grief Advice for Sibling Conflict, Loss, and Connection After Loss
Connect with Peter Johnson:
Get a copy of “The Little Book of Family Treasure”
Visit Peter's website
Visit the Family Nature Treats website
Visit the Collaborative Practice website
Connect with Justin Weidenfeld:
Connect with Justin on LinkedIn
Follow The Currency of Grief on LinkedIn
Follow The Currency of Grief on Instagram
Follow The Currency of Grief on TikTok
Subscribe to The Currency of Grief on YouTube
Visit Justin’s website bio
Podcast production and show notes provided by HiveCast.fm

Mar 13, 2026
Mar 13, 2026
1hr 15 min
Loss can place unexpected responsibility on someone overnight, especially when legacy and family wealth are part of the story.
Justin Weidenfeld sits down with Kristen Heaney, founder of In3Generations and host of The Family Wealth Edge Podcast, to talk about the reality of navigating grief and inheritance at a young age. When Kristen lost her father during college, she suddenly faced young inheritor responsibility while still trying to figure out her path. The experience created a powerful identity shift as she moved from student to someone responsible for decisions tied to legacy and family wealth.
Kristen reflects on the challenge of stepping into legacy and family wealth before feeling ready. The responsibility extends far beyond financial decisions. It raises questions about purpose, relationships, and how to carry forward the values behind the wealth. Those early experiences shaped the work she does today helping families prepare for next-generation wealth stewardship so future inheritors have guidance and community.
The conversation also touches on something people rarely discuss openly. Even during loss, there can be beauty in grief when families create space for connection, reflection, and support. Kristen explains how those moments influenced her outlook on leadership, family responsibility, and the meaning behind legacy and family wealth.
For anyone navigating grief and inheritance, building a family legacy, or preparing the next generation to carry responsibility well, this episode offers a perspective on how loss can reshape identity and deepen the understanding of stewardship.
Episode Breakdown:
00:00 Money and Mortality, The Mission of The Currency of Grief
01:05 Meet Kristen Heaney and the Reality of Grief and Inheritance
03:58 Losing a Father at 21 and the Start of Young Inheritor Responsibility
08:33 The Beauty in Grief and What Community Support Can Look Like
13:52 Anticipatory Grief and Alzheimer’s Caregiving Trauma
19:10 Identity Shift After Inheritance and Finding Purpose in Work
25:21 Legacy and Family Wealth, Stewardship, Foundations, and Values
38:46 Next-Generation Wealth Stewardship and Teaching Kids Money and Loss
53:22 Marriage and Inheritance, Communication and Power Dynamics
01:08:29 “You’ve Got This” and the Mountain Metaphor for Grief Recovery
Connect with Kristen Heane:
Connect with Legacy Consultant on LinkedIn
Visit the In3Generations website
Listen to The Family Wealth Edge Podcast
Connect with Justin Weidenfeld:
Connect with Justin on LinkedIn
Follow The Currency of Grief on LinkedIn
Follow The Currency of Grief on Instagram
Follow The Currency of Grief on TikTok
Subscribe to The Currency of Grief on YouTube
Visit Justin’s website bio
Podcast production and show notes provided by HiveCast.fm

Feb 27, 2026
Feb 27, 2026
1hr 28 min
Money and grief have a way of colliding when you are least equipped to handle either. In this episode of The Currency of Grief, Justin Weidenfeld sits down with financial advisor Kay Pfleghardt to unpack what happens when money and grief stretch across years of illness, responsibility, and complicated family dynamics.
Kay lived through eleven years of her father’s decline from diabetes, navigating anticipatory grief long before his death. She speaks candidly about caregiver guilt, the emotional whiplash of hospital calls, and the regret that can linger after the process is over. If you have ever wondered whether you did enough, showed up enough, or handled it the right way, this episode will resonate with you.
Justin and Kay dig into the reality of sibling estate decisions and how even close families can feel strained when assets, timelines, and expectations collide. They openly say conflict is usually not about greed. It is often about exhaustion, old roles, and the emotional weight attached to small financial details. You will hear how Kay’s family protected their relationships and what she sees differently now as a financial advisor guiding others through similar moments.
They also delve into a topic rarely discussed, a breakup during a time of loss and the unexpected clarity that can arise when the parent you once sought guidance from transforms into an internal guide. Kay shares how money and grief reshaped her career decisions, her boundaries, and the way she counsels clients today.
If money and grief are showing up in your life, whether through illness, estate questions, or family tension, this episode offers perspective based on lived experience. Money and grief are powerful forces. With the right conversations, they can shape growth instead of division.
Episode Breakdown:
00:00 Grief and Money: Why Grief and Finances Collide
03:41 Estate Chaos and a $347,000 Tax Lien Lesson
07:28 Type 2 Diabetes, Denial, and a Slow Medical Decline
17:04 Caregiver Guilt and Anticipatory Grief During Dialysis
18:22 Choosing to Stop Dialysis and the Hospice Goodbye
32:40 What Actually Needs to Happen Financially After a Death
38:33 Sibling Estate Decisions, Disclaimers, and Protecting Family Relationships
49:12 How Money Changes People During Estate Settlements
01:03:21 Regret, Isolation, and What She Wishes She Had Done Differently
01:22:44 “It Gets Better”: Growth, Legacy, and Life After Loss
Links:
Listen to Leaving Behind a Legacy with Kay Pfleghardt
Listen to Terrible Thanks for Asking
Get the No Longer Awkward book
Connect with Justin Weidenfeld:
Connect with Justin on LinkedIn
Follow The Currency of Grief on LinkedIn
Follow The Currency of Grief on Instagram
Follow The Currency of Grief on TikTok
Subscribe to The Currency of Grief on YouTube
Visit Justin’s website bio
Podcast production and show notes provided by HiveCast.fm







