In this episode, Maddy Roche sits down with Zeena Regis, MDiv, Director of Priority Populations at Compassion and Choices, to explore one of the most requested, and most avoided, conversations in the Childfree community: medical aid in dying.

Zeena brings nearly 20 years of end-of-life experience, beginning as a hospice chaplain and evolving into a national advocate for equitable access to end-of-life options. She and Maddy unpack what medical aid in dying actually is, who it's for, and why having open conversations about death leads to better care for everyone, whether or not medical aid in dying is ever something you'd personally choose.

In This Episode, You'll Learn:

• Why medical aid in dying is one option within a broader spectrum of end-of-life care, and what the legal safeguards around it actually look like
• How Childfree adults face unique risks when no healthcare proxy or estate documents are in place.
• How community, storytelling, and even art can open the door to death planning conversations that feel impossible to start alone
• Why having a healthcare proxy who truly knows you and is prepared to advocate for your wishes makes a difference in the quality of your final chapter

Join a Live Q&A with Zeena Regis:

Title: Designing Your End-of-Life: A Live Q&A with Zeena Regis, MDiv

Date: 4/1/2026 Time: 5 PM Eastern

Registration Link: https://us02web.zoom.us/webinar/register/WN_g-AYE_5GR1O2nRM-7l9tCg

Episode Host:

Maddy Roche: Chief Growth Officer at Childfree Trust® and responsible for all sales and marketing initiatives.

Episode Guest:

Zeena Regis, MDiv serves as the Director of Faith Engagement and Priority Populations at Compassion & Choices, improving care, expanding options, and empowering everyone to chart their end-of-life journey. Prior to her role with Compassion & Choices, Zeena served as a chaplain and grief care specialist for over a decade. Zeena also serves on the faculty of Columbia Theological Seminary's Older Adult Ministry Certification program and was selected as a 2024 American Society on Aging Fellow. Zeena is also a playwright, and her latest work, A Free Black Woman's Guide to Death & Dying, was selected for the Synchronicity Theatre's arts incubator project.

Learn more about Compassion and Choices: https://compassionandchoices.org/

About Childfree Insights

Childfree Insights is a trusted resource for life planning without children. It explores financial planning, estate planning, relationships, and long-term decisions for adults building a future without kids. Home of Childfree Wealth® and Childfree Trust®.

Connect with Us:

Ready to work on building better financial habits? Connect with our financial planning team at childfreewealth.com or learn more about estate planning at childfreetrust.com.

Follow Childfree Life by Design on your favorite podcast platform and join the conversation on social media:

Instagram: https://www.instagram.com/childfreeinsights
Facebook: https://www.facebook.com/ChildfreeInsights/
LinkedIn: https://www.linkedin.com/company/childfreeinsights
YouTube: https://www.youtube.com/@ChildfreeInsights

Disclaimer: This podcast is for educational & entertainment purposes. Please consult your advisor before implementing any ideas heard on this podcast.

In this episode, Maddy Roche sits down with Chris Dale, CFP®, CeFT®, founder of Life After Grief Financial Planning, to share the real-life story of helping a client navigate aging, medical emergencies, and end-of-life decisions.

From hospice-informed insights to a sudden car accident just weeks after estate documents were signed, Chris walks through what actually happens when someone declines, and why having the right team and paperwork in place makes all the difference.

This conversation is honest, practical, and grounded in lived experience. If you’ve ever wondered what planning for emergencies and end-of-life truly looks like without traditional next of kin, this episode will give you clarity.

In This Episode, You’ll Learn:

• Why Childfree individuals need both estate planning documents and a coordinated financial services team before a medical emergency occurs
• How powers of attorney and professional fiduciaries protect your healthcare decisions, financial accounts, and long-term care options
• What can go wrong when there is no clear next of kin, and how the state may become involved in decision-making
• How a financial advisor acting as a fiduciary helps manage insurance claims, hospital bills, and long-term care costs during crisis
• Why building your aging plan early preserves autonomy, protects assets, and ensures your end-of-life wishes are honored.

Episode Host:

Maddy Roche - Chief Growth Officer at Childfree Trust® and responsible for all sales & marketing initiatives.

Episode Guest:

Chris Dale, CFP®, CeFT® is a financial advisor with 21 years of experience and the founder of Life After Grief Financial Planning™. As a CERTIFIED FINANCIAL PLANNER™ and Certified Financial Transitionist®, he specializes in guiding clients through the financial and emotional complexities of loss. His approach integrates technical planning with psychological insight rooted in his significant personal experience and 200+ hours of hospice volunteering.

A five-time "Top Financial Advisor" in Orlando (2019–2023), Christopher is a prominent speaker, author, and host of the podcast Real Talk With Life After Grief Chris. Beyond his clinical expertise, he is a dedicated advocate for addressing how racism and discrimination intersect with grief. Through Life After Grief Consulting™, he provides CE-approved training, earning the reputation of the "Advisor's Advisor."

He lives in Orlando with his wife and two sons.

Learn more about Chris: Lifeaftergrieffp.com

About Childfree Insights

Childfree Insights focuses on planning for solo aging and later life without children. It offers trusted education on financial planning, estate planning, and building support systems for people aging independently. Home of Childfree Wealth® and Childfree Trust®.

Connect with Us:

Ready to work on building better financial habits? Connect with our financial planning team at childfreewealth.com or learn more about estate planning at childfreetrust.com.

Follow Childfree Life by Design on your favorite podcast platform and join the conversation on social media:

Instagram: https://www.instagram.com/childfreeinsights
Facebook: https://www.facebook.com/ChildfreeInsights/
LinkedIn: https://www.linkedin.com/company/childfreeinsights
YouTube: https://www.youtube.com/@ChildfreeInsights

Disclaimer: This podcast is for educational & entertainment purposes. Please consult your advisor before implementing any ideas heard on this podcast.

In this episode, Maddy Roche and Bri Conn, CFP®, explain why legal documents alone aren’t enough. Estate plans grant authority. Care plans provide direction. They spell out the details that make real-world care possible: where to find your mailbox key, your alarm code, how to feed your pets, what medical history your doctors should know, and what living with dignity truly means to you.

They also discuss documenting cultural or religious preferences and why these plans should be treated as living documents, updated as your life, relationships, and values evolve.

Key Takeaways:

• Estate plans give the who, care plans give the how. Legal documents grant someone the power to make decisions. Care plans outline what those decisions should actually look like, from daily routines to end-of-life wishes.
• Document the everyday details others wouldn't know. Alarm codes, mailbox locations, pet feeding routines, storage facilities, and where to find important items are all critical for someone stepping into your life.
• Define what life with dignity means to you. Cultural preferences, religious practices, LGBTQ+ identity, and personal boundaries should be clearly stated so your wishes are honored, not someone else's assumptions.
• Build a team to support you as you age. Financial planners, doctors, and aging care managers all play a role in ensuring your care plan can actually be executed when you need it.
• Treat your care plan as a living document. Update it as your life changes. New pet, new home, new diagnosis, new preferences. The goal is to keep it current so it reflects who you are now.

Episode Hosts:

Maddy Roche - Chief Growth Officer at Childfree Trust® and responsible for all sales & marketing initiatives.

Bri Conn, CFP® - Customer Experience Manager at Childfree Trust®. Bri coaches clients through estate planning and care plan development, helping them document their wishes and build support teams.

About Childfree Insights

Childfree Insights is a trusted resource for life planning without children. It explores financial planning, estate planning, relationships, and long-term decisions for adults building a future without kids. Home of Childfree Wealth® and Childfree Trust®.

Connect with Us:

Ready to work on building better financial habits? Connect with our financial planning team at childfreewealth.com or learn more about estate planning at childfreetrust.com.

Follow Childfree Life by Design on your favorite podcast platform and join the conversation on social media:

Instagram: https://www.instagram.com/childfreeinsights
Facebook: https://www.facebook.com/ChildfreeInsights/
LinkedIn: https://www.linkedin.com/company/childfreeinsights
YouTube: https://www.youtube.com/@ChildfreeInsights

Disclaimer: This podcast is for educational & entertainment purposes. Please consult your advisor before implementing any ideas heard on this podcast.