How to Succeed in the Caregiving Role No One Trained You For

Caregiving isn’t side work - it’s a leadership position. Host Jill Mastroianni talks with Jennifer O’Brien, author of Care Boss and The Hospice Doctor’s Widow, about the emotional labor, strategic thinking, and societal blind spots surrounding caregiving. Drawing from her experience leading healthcare organizations as well as caring for her husband and parents, Jennifer challenges the notion of caregiving as “soft” work and offers real-world tools to do it well. We cover everything from palliative care to “go bags” to how not to offer help to a caregiver.

If you're juggling caregiving responsibilities, this episode is for you. And if you're not a caregiver (yet), it’s a window into what your friends, family, or future self may need.

What We Discuss

• Why caregiving is leadership. Caregivers are decision-makers, advocates, and strategists. They're doing CEO-level work without the pay or recognition.
• Jennifer’s caregiving story. Caring for her husband Bob, a palliative care and hospice physician, Jennifer learned the hard way how lonely and demanding caregiving can be.
• The vision and purpose of caregiving. Why it’s essential to align on a shared goal, usually a peaceful, dignified death, and use it as a guidepost through tough decisions.
• Starting the conversation early. How Jennifer and her husband talked about end-of-life preferences before illness and clarified end-of-life wishes after a terminal diagnosis.
• The At Peace Toolkit. A free, “jarringly practical” resource Jennifer created to help people get their documents and wishes in order before a crisis.
• How to ask for help (and offer it). Strategies for delegating, examples of pinpointed positive feedback, and how to support caregivers without creating more work for them.
• The Death Deck. A conversation-starting card game that can bring reluctant partners on board.
• Hospice vs. Palliative Care. What these terms mean, how they differ, and how to advocate for the care your loved one needs.
• Why you need a “Go Bag.” It’s not just for caregivers. Medical information, power cords, dentures—what to pack and why it matters.
• Home design and end-of-life care. From slippery marble floors to six-inch shower curbs, we talk about how your environment can make, or break, caregiving.
• Self-care vs. self-management. Why “get a pedicure” doesn’t cut it and what real self-management looks like for caregivers.
• Precious time. The term Jennifer’s husband used to signal the end of life was near. Why it matters, and how to recognize it when it comes.

Resources & Links

• Subscribe to the Death Readiness newsletter. Get bonus episodes, tools, and straight talk in your inbox.
• Books by Jennifer O’Brien
• At Peace Toolkit. Jennifer O’Brien’s guide to being at peace with end of life. This packet walks you through setting up the medical ID on your smartphone, establishing your advance healthcare directives, organizing administrative details, and starting conversations with loved ones.
• Video – How to create a Medical ID on your iPhone
• The Death Deck. 112 cards with a mix of multiple choice and open-ended questions designed to spark lively discussion around the topic of death.
• State Advance Directive Forms provided by the National Alliance for Care at Home
• Caregiver Important Information Sheet
• Medical Information Sheet
• Precious Time Implementation Guide. Guides healthcare professionals in communicating the reality of the end-of-life situation to patients and their families.

Connect with Jennifer:

• Website: jenniferaobrien.com
• Send a message to Jennifer

Connect with Jill:

• Book a free 15-minute consultation
• Website: DeathReadiness.com
• Email: [email protected]
• Subscribe to the Death Readiness email newsletter.

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.