Caregiving is Leadership: A Conversation with Jennifer O’Brien, Author of Care Boss
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Caregiving isn’t just emotional labor – it’s leadership.
At Funeralocity, we understand that end-of-life planning is more than a logistical task—it’s a deeply personal journey, often led by a devoted family member navigating the complex terrain of caregiving and loss. In many families, that person—frequently the eldest daughter—emerges as what Jennifer O’Brien calls the “Care Boss.”
A thought leader in caregiving, end-of-life preparation, and grief, O’Brien brings both professional expertise and personal experience to this role. She is the author of Care Boss: Leadership Strategies & Resources for Family Caregiving and two editions of the acclaimed The Hospice Doctor’s Widow: An Art Journal of Caregiving and Grief. Drawing from her background as both a healthcare executive and the spouse of a hospice physician, she has become a leading voice on what it truly means to care for someone at the end of life—and to survive it.
In this conversation with Funeralocity, she shares practical insights, hard-won wisdom, and powerful tools for those caring for loved ones at the end of life.
“Family caregivers are leaders – whether they see it or not.”
FUNERALOCITY: You frame family caregivers as “Care Bosses”—a powerful redefinition. What inspired you to apply a leadership lens to the caregiving experience?
O’BRIEN: A few years ago, Lucinda Koza, then a caregiver for her father, posted to her followers: “Remember, you are the CEO of the situation.” That line stayed with me. Most caregivers haven’t been CEOs, but I’ve been both—a serial CEO and a serial family caregiver. That combination inspired me to write Care Boss, applying leadership tools to caregiving.
FUNERALOCITY: Many caregivers feel overwhelmed and invisible. How can seeing themselves as leaders help them cope?
O’BRIEN: I don’t think it’s a reimagination—I think it’s reality. Family caregivers are leaders. Caring for the person you love most is a higher calling than leading any Fortune 500 company. I hope the book helps caregivers feel more empowered and less alone.
FUNERALOCITY: You’ve been both a healthcare executive and a caregiver. What did you learn from switching roles?
O’BRIEN: Caring for my late husband gave me a better understanding of patients, families, and the system’s failures. It also helped me better support my employees who were quietly managing caregiving at home—many fear divulging their caregiving responsibilities will hurt their careers. Caregivers bring invaluable leadership skills to any workplace.
FUNERALOCITY: What self-care advice do you offer for caregivers who feel they have no time?
O’BRIEN: Some days, self-care might be just a few deep breaths. My book offers strategies for delegation, prioritization, and problem-solving—all of which ultimately make more space for self-care.
FUNERALOCITY: Your book includes planning tools. Which do you consider most vital?
O’BRIEN: The At Peace Toolkit. Since most caregiving ends with the death of the care recipient, it helps ensure the caregiver knows and can honor end-of-life wishes. That provides peace for both the recipient and the caregiver. Other key tools are the Medical Record and the Go-Bag.
FUNERALOCITY: What communication breakdowns most often occur between caregivers and the medical system?
O’BRIEN: The system often overlooks caregivers as key partners. Only palliative care seems to consistently value them. Also, many doctors confuse palliative care with hospice. Palliative care is not the end—it’s about symptom relief and support, and it can begin early in serious illness alongside curative or life prolonging treatment.
FUNERALOCITY: End-of-life conversations are difficult. How can caregivers begin them?
O’BRIEN: Start with your own planning. When caregivers prepare their own documents, it naturally sparks conversation with their loved one. You can also gently ask, “Who would you want the doctor to talk to if you couldn’t speak?” or even, “Who should take care of Buster [the pet] when you’re gone?”
FUNERALOCITY: If readers take away just one lesson from Care Boss, what should it be?
O’BRIEN: The power of vision. I share a caregiver’s vision statement:
“A comfortable, dignified end of life for my care recipient; a smooth transition from caregiver to griever; and an emotionally, mentally, spiritually and physically healthy future for me, the family caregiver.”
Leaders set a vision and work toward it. Caregivers must do the same.
Jennifer O’Brien reminds us that caregiving is not just an act of service — it’s an act of leadership. The Care Boss is the steward of a loved one’s comfort, dignity, and final wishes. Often, this same person steps up to plan the funeral, carrying their devotion across the threshold of loss.
At Funeralocity, we honor these unsung leaders. We hope this interview brings support, recognition, and reassurance to all who walk this path of caregiving and remembrance.
“Start the conversation by planning your own documents. That opens the door.”
After years of caring for people with serious illness as a physician, Jennifer’s husband, Bob Lehmberg, was diagnosed with a stage IV, metastatic cancer. But caregiving for the man who had made a 40-year career of caregiving as a physician was not easy.
Now Jennifer works to help family caregivers feel supported while caring for others and taking care of themselves.
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