The Death Readiness Podcast: Not your dad’s estate planning podcast – Details, episodes & analysis

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.

Actionable Takeaway: Don’t wait! Take your first step toward readiness by setting up your Medical ID or downloading Jill’s free emergency medical information form. 

Let’s normalize the conversation around death, reduce fear, and make life better for ourselves and those we love.

Don’t forget to follow for free on Apple podcasts, Spotify, YouTube or wherever you're listening right now.

iPhone Medical ID Tutorial

Emergency Medical Information Form

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 From avoiding common pitfalls (like outdated beneficiary designations) to revisiting important decisions over time, this podcast will help you gain peace of mind knowing your wishes will be honored and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!

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

Resources & Links:

• Aretha Franklin Probate
  • Detroit Free Press article: Aretha Franklin's handwritten wills reveal window into her private world: Read them here, dated May 21, 2019
  • May 20, 2019, petition re: purported holographic wills
  • Purported holographic Wills, dated
    • June 21, 2010
    • October 20, 2010
    • March 31, 2014
• Estate of Frankford Michigan Court of Appeals decision, dated February 18, 2025
• Estate of Jesse L. Beck Montana Supreme Court decision, dated October 29, 2024
• New York Times article: They Caught the Flu, and Never Came Home, dated April 24, 2025
• Set up your legacy contacts for online accounts:
  • Google – Set up your Inactive Account Manager
  • Apple – Add a Legacy Contact to your Apple Account
  • Facebook – Add, change or remove your Legacy Contact on Facebook
• Download information sheets:
  • Personal Important Information Sheet
  • Key People Information Sheet
  • Home Information Sheet
  • Password Tracker
    • Find your saved Google passwords with Google’s password manager

Connect with Jill:

• Book a free 15-minute consultation
• Website: DeathReadiness.com
• Email: jill@deathreadiness.com
• Subscribe to receive news and updates.

Did you enjoy this episode? Share it with someone you care about.

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

Resources & Links

Podcasting Tools Mentioned:

• Microphone:ATR-2100X (~$50)
• Foam Windscreen (~$5)
• Recording Software: Riverside.fm (~$30/month)
• Podcast Hosting: Simplecast (~$15/month)
• In-Person Recording: Zoom PodTrak P4 (~$170)
• Cover Art Creation: Canva (free and paid options)
• Family Podcast Starter Checklist
• Family Podcast - Questions to Start Real Stories

Podcast Editing Support:

Jon Gay – JAG in Detroit Podcasts

Connect with Jill:

• Website: DeathReadiness.com
• Email: jill@deathreadiness.com
• Subscribe to receive news and updates

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.

Mentioned in this Episode:

• PALS - Professionals of After Loss Services
• Organized Legacy
• Trustworthy for digital organization
• Artifcts for legacy preservation
• Carmen Mastroianni Vietnam Artifct
• Julie Ulrich Japanese fishing float Artifct
• 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.
• SilverTree Seniors Facebook page

Connect with Julie Ulrich: organizedlegacy.com

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.

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

Resources and Links

• Golden Lifestyle Partners – Learn more about Mikelle’s services: goldenlifestylepartners.com
• Contact Mikelle directly at: mikelle@goldenlifestylepartners.com
• VA Aid & Attendance Info: U.S. Department of Veterans Affairs – Aid and Attendance
• HASCA: Home Aide Service of the Central Adirondacks, Inc
• Masonic Care Community: Skilled Nursing Care

Questions and Suggestions? Email Jill at Jill@DeathReadiness.com.

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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

Resources & Links:

Find a Special Needs Estate Planning Attorney: Special Needs Alliance
ABLE Account Information: ABLE National Resource Center

Kristen Lewis’ Resources: Estate Planning for Families with Special Needs; Planning Challenges for Families with Special Needs; What Can a Care Manager Do for Me?

Caregiver Important Information Sheet

Contact Kristen Lewis: klewis@harrisonllp.com

Connect with Jill:

• Website: DeathReadiness.com
• Email: jill@deathreadiness.com
• Subscribe to receive news and updates.

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.

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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.

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

Articles & References

• The Case for Updating SSI Asset Limits – Center on Budget and Policy Priorities
• Georgia Council on Developmental Disabilities - Georgia’s NOW/COMP Waiver Waitlist: The Time is Now
• Bobby Dodd Institute - How to Get Approved for a Medicaid Waiver by Only Following This Simple Checklist
• Transcripts for The Death Readiness Podcast

Questions about special needs estate planning?

Email Jill at Jill@deathreadiness.com 

If she notices a lot of the same questions, she and Kristen will record a follow-up episode to answer these popular questions.

Subscribe to receive news and updates.

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.

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

Resources & Links:

Center for Disability Services: Residential Services

Center for Disability Services

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.

Connect with Jill:

• Website: DeathReadiness.com
• Email: jill@deathreadiness.com
• Subscribe to receive news and updates.

Did you enjoy this episode? Share it with someone you care about.

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.

Resources & Links:

• Learn more about After-Loss Professionals
• Connect with Mollie Lacher & Sunny Care Services
• Listen to The Move In Senior Living Marketing podcast: Smooth Transitions: Happy Futures, with Maureen, Lisa and Matt
• Learn about LivNow Relocation’s services
• Check out Matt Paxton’s Clutter Cleaner business
• Watch Matt Paxton’s appearance on Jimmy Kimmel

Connect with Jill:

• Website: DeathReadiness.com
• Email: jill@deathreadiness.com
• Subscribe to receive news and updates.

Did you enjoy this episode? Share it with someone you care about.