You’re the one prepping for your child’s IEP meeting while trying to talk your aging dad out of getting a puppy. You’re booking medical appointments, managing the money, juggling work emails during school pickup and still expected to keep the fridge stocked and know who has practice, rehearsal, or a field trip tomorrow.
Your parents are struggling, but they still insist they’re fine. You see the mobility issues, the memory slips, the unopened mail, but every offer to help feels like an argument. You’re scared to push. You’re scared to wait. And there’s no clear roadmap for how to do any of this without losing your mind or your family.
Hosted by Jill Mastroianni, an estate planning and probate attorney and trusted guide for women holding it all together, this podcast is your space to untangle the mess. With more than a decade of legal experience, Jill brings clarity to the hardest conversations most families avoid until it’s too late.
Each episode offers honest stories, practical tools, and bite-sized steps you can actually take, even if you’re overwhelmed, even if you’re grieving, even if you’re still waiting for your mom to give you the password to the computer. You don’t need a perfect plan. You just need a place to start.
Death readiness isn’t about control. It’s about love and the courage to face what’s next with open eyes and a steady hand.
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Welcome to the very first episode of The Death Readiness Podcast! In this debut, host Jill Mastroianni—an experienced attorney and death readiness advocate—dives into what it truly means to be prepared for the inevitable.
This episode covers:
What is death readiness? A compassionate approach to planning for yourself and the loved ones you leave behind.
A thought exercise: Two contrasting scenarios of how preparation (or the lack thereof) can impact those you care about most.
Practical first steps: Setting up your iPhone's Medical ID and creating an emergency medical information sheet to ensure you're ready for the unexpected.
This isn’t about fear—it’s about empowerment, clarity, and leaving a legacy of love and support. Jill explains how small, manageable steps can make a world of difference and offers insights into what you can expect in future episodes.
This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy.
Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents.
Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.
Trailer
Monday, January 6, 2025 • Duration 02:15
Welcome to The Death Readiness Podcast, hosted by Jill Mastroianni, an attorney with more than a decade of experience specializing in trusts and estates. In this podcast, Jill makes death readiness approachable, understandable, and empowering for individuals and families.
Navigating the legal and emotional complexities of life and death can feel overwhelming. How do you find a trustworthy attorney? How do you ensure your plans stay up to date as life changes? Together, we’ll break down these challenges step by step—no law degree or financial background required.
Each episode will provide practical advice, real stories, and actionable steps to simplify the death readiness process. From avoiding common pitfalls (like outdated beneficiary designations) to revisiting important decisions over time, this podcast will help you gain peace of mind knowing your wishes will be honored and your legacy protected.
Death readiness is about more than just legal documents—it’s about preserving your values, stories, and lessons for future generations. Join us as we take small, manageable steps to prepare for the future, ensuring clarity and confidence for yourself and your loved ones.
Follow us for free on Apple Podcasts, Spotify, YouTube, or wherever you’re listening right now.
Let’s demystify death readiness together!
This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy.
Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents.
: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.
Why Talking About Your Parent's Death Can’t Wait
Episode 12
Friday, May 2, 2025 • Duration 45:17
As a daughter, a sister to a brother with special needs, and a mother herself, Jill Mastroianni knows firsthand what it feels like to carry the weight of future planning. This episode offers an intimate glimpse into her own family’s story—one filled with heartbreak, hesitation, and ultimately, the strength to move forward. Because sometimes death readiness doesn’t feel brave—it just feels necessary.
We explore:
The mental load women carry when they’re the ones holding it all together
The emotional weight of estate planning conversations with aging parents
Planning for a sibling with special needs—and the fear that can paralyze progress
Why legal documents don’t tell the whole story—but they still matter
Why “being the one left behind” demands preparation, not just hope
Real-world estate planning stories that show why “good intentions” aren’t enough:
How to start planning when you’re overwhelmed
Simple first steps for organizing your digital life and essential information
The power of “body doubling” to make estate planning feel doable, not daunting
Start Your Own Family Podcast with these Simple Steps
Episode 11
Friday, April 18, 2025 • Duration 34:10
In this special episode, we step away from legal mechanics and into something deeply personal: the power of capturing family stories. Jill and her daughter April share an episode from their private family podcast, featuring Carmen Mastroianni—Jill’s father and April’s grandfather.
Carmen reflects on his childhood in Schenectady, New York, his unexpected path to college, and his unforgettable experience serving in the Vietnam War. Nicknamed “Macaroni” during basic training, Carmen’s stories are full of humor, heartbreak, and history. Along the way, Jill offers listeners a behind-the-scenes look at how you can create a podcast to preserve your own family legacy.
What We Discussed
The inspiration behind starting a family podcast
Carmen’s early years: riding horses, working in his dad’s bakery, and life at a private Catholic high school
How a last-minute college application changed his life
His friendship with Donnie Brewer and the profound loss that followed
Getting drafted into the Vietnam War and earning the nickname “Macaroni”
His unexpected transfer from infantry to finance—and how it saved his life
The emotional return home from an unpopular war
Life lessons he hopes future generations will remember
April’s choice to honor her grandfather as an “unknown hero” in a school project
Tips, tools, and encouragement for starting your own family podcast
In this heartfelt episode, Jill welcomes Julie Ulrich, founder of Organized Legacy, to explore the importance of preserving family stories and legacies before they're lost. Together, they discuss the challenges and emotional rewards of navigating loss, clearing out a loved one's belongings, and uncovering meaningful treasures—both physical and intangible.
Julie shares her personal journey, including how she found her grandmother’s Pearl Harbor diary while clearing out her father’s home. This discovery sparked an investigation into her family history, revealing unexpected connections. Jill and Julie also emphasize the value of storytelling while loved ones are still here, offering tips on engaging in these conversations now to avoid regret later.
Key takeaways include:
Strategies for clearing and preserving belongings with meaning
Tools like Artifcts and Trustworthy for organizing legacy and estate information
The role of storytelling in passing down family history
Encouraging open conversations about death and preparation
Practical advice for balancing emotional and logistical tasks after a loss
Julie also discusses her nonprofit, SilverTree Seniors, which provides gifts and support to isolated and low-income seniors, and how small actions can make a big impact on a forgotten population.
In this real and relatable episode, Jill explores the often-avoided topic of senior living and long-term care. She’s joined by senior care consultant Mikelle Rappaport, who breaks down the various types of senior living and care options and how to plan for them—both practically and financially. Jill also speaks with Bob Stanton, who shares the journey of moving his wife of 54 years into a skilled nursing facility. Together, they unpack the real challenges families face when navigating aging, caregiving, and the difficult decisions that arise at their intersection.
What We Discuss
What long-term care really means and what types of care are available
Understanding ADLs (Activities of Daily Living) and IADLs (Instrumental ADLs)
Common misconceptions about family caregiving and what's realistically sustainable
How Medicare, Medicaid, VA benefits, and long-term care insurance factor into paying for care
What different types of senior living facilities offer, from independent living to skilled nursing
When it’s time to consider a higher level of care—and how to make peace with that choice
Questions and Suggestions? Email Jill at Jill@DeathReadiness.com.
How to Choose the Right Special Needs Estate Planning Team
Episode 9
Friday, March 21, 2025 • Duration 01:00:09
In this episode, host Jill Mastroianni continues her conversation with Kristen Lewis, a special needs estate planning attorney. They explore how to build the right team of professionals to support your child’s future. From trustees to life care planners, disability care managers, and legal guardians, they discuss who should be on your team and how to choose the right people for these critical roles.
Kristen also shares key mistakes to avoid—such as disinheriting a child with special needs—and explains how tools like special needs trusts and ABLE accounts fit into a well-rounded planning strategy. Whether you're just getting started or refining an existing plan, this episode will give you actionable steps to help you move forward with confidence.
What You’ll Learn in This Episode:
The key professionals to include in your special needs planning team (estate planning attorneys, trustees, life care planners, disability care managers, intimacy counselors, and more)
How to choose a trustee for a special needs trust and why professional trustees are often the best choice
Why disinheriting a child with special needs is a mistake—and what to do instead
The role of ABLE accounts in financial planning and their limitations
How to coordinate assets and beneficiary designations to ensure financial security without jeopardizing government benefits
The importance of family communication and how a well-prepared plan can ease concerns for both parents and siblings
: Estate Planning for Families with Special Needs; Planning Challenges for Families with Special Needs; What Can a Care Manager Do for Me?
A Parents’ Guide to Special Needs Estate Planning
Episode 8
Friday, March 7, 2025 • Duration 01:11:28
In this episode, Jill welcomes Kristen Lewis, a nationally recognized special needs estate planning attorney, to unpack the critical legal and financial steps families should take to secure the future of a loved one with special needs. They explore common misconceptions, how traditional estate planning often fails these families, and why comprehensive special needs planning requires much more than just drafting a trust.
This is Part 1 of a two-part conversation, diving deep into government benefits, asset limits, trust types, and common pitfalls. Whether you’re a parent, grandparent, or caregiver, this episode is packed with essential guidance to help you plan with confidence.
Topics Discussed
Why traditional estate planning is often insufficient for families with a loved one who has a disability
The network of special needs trusts — not just one trust, but several working together
The importance of a coordinated family approach to avoid well-meaning but harmful gifts or inheritances
Government Benefits
SSI (Supplemental Security Income) and Medicaid
SSDI (Social Security Disability Insurance) and Medicare
Essential Trust Types Explained
Third-party special needs trusts (funded by parents, grandparents, etc.)
First-party special needs trusts (funded with the assets of the individual with the disability)
Understanding the Medicaid payback requirement — and how to avoid it when possible
Common Mistakes & Misconceptions
Why disinheriting a child with special needs is NOT the solution
How grandparents’ gifts and bequests can unintentionally disrupt eligibility for government benefits
Host Jill Mastroianni sits down with her father, Carmen Mastroianni, to discuss his journey raising her older brother, Dan, who was born with Down syndrome in 1977. Through personal stories and reflections, Carmen shares the challenges, triumphs, and advocacy efforts that shaped their family’s experience, from navigating early medical uncertainties to ensuring Dan’s inclusion in school, sports, and community life.
Jill and her father discuss how societal attitudes toward children with special needs have evolved over the decades and the crucial role of advocacy in securing opportunities for Dan. They highlight the importance of inclusion, the impact of strong support networks, and the ways Dan’s own resilience shaped his life. You’ll also hear insights from Dan himself, as Jill includes clips from a special interview in which he shares his thoughts on his life, independence, and how he views his Down syndrome diagnosis.
Beyond the personal journey, the conversation also explores long-term planning for individuals with special needs, including Dan’s decision to transition into a group home, the financial and legal considerations of special needs trusts, and how families can prepare for the future of their loved ones.
This episode is a moving and informative discussion on love, advocacy, and the responsibilities that come with ensuring a fulfilling and secure future for family members with special needs. Whether you are a parent, sibling, or community member, this conversation offers valuable lessons on inclusion, resilience, and planning for the road ahead.
Together, Jill and Carmen discuss:
The emotional and logistical challenges of raising a child with special needs in the 1970s
The importance of advocacy in education, community inclusion, and extracurricular activities
How early intervention programs and support networks can make a life-changing impact
Dan’s personal perspective on his life, his independence, and his Down syndrome diagnosis
The decision-making process behind transitioning into a group home
Key financial and legal considerations in planning for the future
The impact of technology on accessibility and communication for individuals with disabilities
What to Know Before Choosing an Executor or Agreeing to Serve as One
Episode 6
Friday, February 14, 2025 • Duration 01:01:39
What happens after someone passes away? Who handles the logistics, financial matters, and legal steps? In this episode, Jill speaks with Mollie Lacher, a leader in the after-loss services industry, about the often-overlooked challenges of estate administration and how professionals can help families navigate these responsibilities.
Mollie shares her personal journey from project management to estate administration, sparked by her own experiences after the deaths of her father and brother-in-law. She explains how after-loss professionals provide essential support to grieving families and executors.
Together, Jill and Mollie discuss:
The critical role of after-loss professionals in estate settlement
Why naming a corporate fiduciary isn’t always the best plan
The common challenges executors face and how to prepare
The importance of professional support in settling estates
How PALS (Professionals of After-Loss Services) is shaping this new industry
Whether you’ve been named an executor or just want to understand what happens after a loss, this episode provides practical advice and insights to help you navigate the process.
Did you enjoy this episode? Share it with someone you care about.
This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy.
Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents.
Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.
This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy.
Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents.
Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.
Start interviewing your loved ones using tools like Otter AI
Click here to download Julie’s wish list template to begin a SilverTree Seniors-inspired initiative in your area.
Support the Podcast: If you found this episode valuable, share it with a loved one and follow The Death Readiness Podcast on Apple Podcasts, Spotify, YouTube or wherever you listened to this episode. Together, let’s make conversations about death readiness empowering and impactful.
This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy.
Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents.
Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.
This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy.
Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents.
Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.
Have Questions about Special Needs Estate Planning?
Special needs estate planning is complicated, and it’s normal to need to hear this information more than once! If you have questions, email me at jill@deathreadiness.com. If enough people ask, Kristen and I may do a follow-up episode to clarify key points.
Subscribe & Share! If this episode was helpful, please share it with someone who could benefit. Follow The Death Readiness Podcast on Apple Podcasts, Spotify, YouTube, or wherever you listen.
This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy.
Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents.
Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.
Programming Note: The Death Readiness Podcast is moving to an every-other-Friday release schedule to bring you thoughtful, high-quality content in a sustainable way.
This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy.
Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents.
Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.
314 South Manning Blvd. Albany, NY 12208 518-437-5700
The Center for Disability Services is a nonprofit organization in New York that provides comprehensive support and services for individuals with disabilities. The Center played a crucial role in securing supportive housing and care for Dan. Through its commitment to inclusion and individualized care, the Center continues to provide essential resources that empower individuals with disabilities to lead fulfilling lives.
Gerald B. Healy, MD, FACS was an ear, nose, and throat specialist at Children’s Hospital in Boston who played a critical role in saving Dan’s life. Dan suffered from severe respiratory issues as a toddler—issues that local doctors were unable to diagnose. Dr. Healy identified that Dan’s airway was dangerously small due to enlarged tonsils and adenoids and recommended immediate surgery.
Kids Like These is a 1987 TV movie that tells the story of a couple who has a baby with Down syndrome. The script was co-written by Emily Perl Kingsley, a well-known advocate for individuals with disabilities, along with Allan Sloane. Kingsley, whose own son, Jason Kingsley, has Down syndrome, infused the film with real-life experiences to highlight the struggles and triumphs of parenting a child with special needs.
One notable detail from the movie was inspired by Dan’s mother, who once shared a story with Emily Perl Kingsley about Dan being denied a library card because he couldn’t sign his name. This real-life event was later referenced in the film, illustrating the systemic barriers faced by individuals with disabilities and the importance of advocacy.
Did you enjoy this episode? Share it with someone you care about.
This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy.
Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents.
Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.
Did you enjoy this episode? Share it with someone you care about.
This podcast provides estate planning guidance for women and discusses real, practical issues, from caregiving, pre-planning a funeral, how to avoid probate using beneficiary designations, planning for individuals with special needs (and special needs trusts), whether you need a professional fiduciary (trustee or executor), how the estate tax works and how to preserve your legacy.
Tuesday Triage episodes answer questions from listeners like you, from powers of attorney, healthcare advance directives (and whether they work when you’re pregnant), what a Last Will and Testament really is, whether you need a trust, how Medicaid works and how to have senior and elder care conversations and how to care for aging parents.
Disclaimer: This podcast and all related content are for educational purposes only and do not constitute legal advice. No attorney-client relationship is established here. Use of this information without careful analysis and review by your attorney, CPA, and/or financial advisor may cause serious adverse consequences. For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.
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