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@OversimplyLLC.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.

In this heartfelt episode of The Death Readiness Podcast, 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: OversimplyLLC.com
• Email: jill@oversimplyllc.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: OversimplyLLC.com
• Email: jill@oversimplyllc.com
• Subscribe to receive news and updates.

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

Taxes can be confusing, but they don’t have to be terrifying. In this solo episode, Jill Mastroianni breaks down estate, inheritance, and gift taxes, helping you separate fact from fiction. Will estate taxes impact your family? Probably not. And what’s the deal with gifting limits? Jill walks you through the history, the myths, and what really matters when it comes to taxes and death readiness.

What You’ll Learn in This Episode:

• The history of estate taxes and how they came to be
• What the federal estate tax exemption means for you in 2025 (and how it’s scheduled to change)
• Which states still have estate and inheritance taxes
• How the step-up in tax basis at death can save loved ones from major tax bills
• The truth about gift taxes and why most people will never owe them
• Practical tips to minimize tax burdens when passing on assets

Show Notes & Resources:

• State-Level Estate & Inheritance Tax Info: https://taxfoundation.org/data/all/state/estate-inheritance-taxes/
• Jill's cousin, Trusts & Estates Attorney in New Jersey, Stephen Pagano: https://riker.com/attorneys/stephen-j-pagano/

Taxes might not be fun, but knowledge is power. Listen in as Jill simplifies these complex topics and helps you remove one more worry from your list.

Connect with Jill & Oversimply

• Website: https://www.oversimplyllc.com/
• Email Jill: jill@oversimplyllc.com
• Subscribe to receive news and updates: https://www.oversimplyllc.com/subscribe

Support the Podcast

• Follow us on Apple Podcasts, Spotify, YouTube or wherever you listened to this episode.
• Share this episode with someone you care about.

Podcast editing provided by JAG in Detroit Podcasts

• Website: www.JAGinDetroit.com
• Email: jag@jagindetroit.com

In this episode of The Death Readiness Podcast, Jill is joined by Megan Malick, founder of A New Path, grief and after-loss educator, speaker, and author. Megan shares insights on navigating the complexities of loss, discussing why conversations about death readiness are so difficult, and offering practical steps to approach these conversations with loved ones. She also introduces her new book, A New Path: A Practical Workbook and Planner for the First Year of Grief and Settling Your Person’s Affairs, which serves as a compassionate guide through the emotional and logistical challenges of administering a loved one’s estate after a loss.

What You'll Learn in This Episode:

• Why talking about death is so difficult—and how societal shifts have contributed to this avoidance.
• The emotional weight of grief and estate administration – the “double whammy.”
• Five small steps to begin a conversation about end-of-life planning:
• The different types of support people we may need after a loss, which Megan categorizes as:
• The importance of pre-planning and how having essential documents in place can ease the burden on loved ones.
• How Megan’s personal experience of losing both parents unexpectedly shaped her approach to after-loss planning.

Practical Takeaways

• Start conversations about estate planning and death readiness with small, approachable topics.
• Don’t pressure loved ones into sharing more than they’re comfortable with—any information is better than none.
• If you’re grieving, don’t hesitate to ask for help. Megan provides scripts in her book to make reaching out easier.
• Prepare in advance for emergencies. See the downloadable resources below.

Resources Mentioned

• Megan Malick’s Book: A New Path: A Practical Workbook and Planner for the First Year of Grief and Settling Your Person’s Affairs
• Downloadable Resources:
  • Home Important Information Sheet: https://www.oversimplyllc.com/home-important-info-sheet
  • Pet Important Information Sheet: https://www.oversimplyllc.com/pet-important-info-sheet
  • Child's Important Information Sheet: https://www.oversimplyllc.com/childs-important-info-sheet

Connect with Megan Malick

• Website: https://a-new-path.com/
• Email Megan: megan@a-new-path.com

Connect with Jill & Oversimply

• Website: https://www.oversimplyllc.com/
• Email Jill: jill@oversimplyllc.com

Support the Podcast

• Follow us on Apple Podcasts, Spotify, YouTube or wherever you listened to this episode.
• Share this episode with someone you care about.

Podcast editing provided by JAG in Detroit Podcasts

• Website: www.JAGinDetroit.com
• Email: jag@jagindetroit.com

In this episode, we discuss:

• A real-life probate issue and why it’s more common than you think
• What probate is and why it matters for your estate
• The role of an executor and the challenges an executor may face
• The importance of proper estate planning and using professionals
• Common misconceptions about wills and probate court
• How different assets pass through (or avoid) probate
• Steps you can take today to make probate easier for your loved ones

Resources Mentioned:

• 1MillionCups Metro Detroit:
• After Loss Professionals: afterlosspros.com
• Oversimply, LLC Resources: oversimplyllc.com/podcast
• iPad Will: https://actecfoundation.org/podcasts/holographic-will-ewill-ipad/
• Free Personal Balance Sheet Download: https://www.oversimplyllc.com/balancesheet

Contact the host, Jill Mastroianni:

• Visit www.oversimplyllc.com
• Email Jill: jill@oversimplyllc.com

Contact today’s co-host, Jon Gay:

• Visit www.jagindetroit.com for information on how Jon can help with your podcast.
• Email Jon: jag@jagindetroit.com

Practical Takeaway:
Start small—gather information about your assets and how they are titled. Even filling in partial details can make a big difference for your loved ones in the future.

Stay Connected:

• Follow us on Apple Podcasts, Spotify, YouTube or wherever you listened to this episode.
• Share this episode with someone you care about.

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: afterlosspros.com
• Organized Legacy: organizedlegacy.com
• Trustworthy for digital organization: trustworthy.com
• Artifcts for legacy preservation: artifcts.com
• Carmen Mastroianni Vietnam artifct: https://artifcts.com/a/9e0CkLto/carmen-mastroianni-vietnam-finance-department
• Julie Ulrich Japanese fishing float artifct: https://artifcts.com/a/czylvWEl/grandma-gs-japanese-fishing-float
• Start interviewing your loved ones using tools like Otter AI (https://otter.ai/)
• Visit oversimplyllc.com/podcast to download Julie’s wish list template to begin a SilverTree Seniors-inspired initiative in your area.
• SilverTree Seniors Facebook page: https://www.facebook.com/silvertreesenior

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.

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: https://youtu.be/Q6UKwApjj-o

Emergency Medical Information Form: https://www.oversimplyllc.com/medical-information-form