In this powerful and deeply personal conversation, Lucinda sits down with caregiving expert and author Jennifer A. O’Brien to explore what it really means to lead—at home, in crisis, and in the quiet, unseen moments of caregiving.

From navigating communication with caregivers to redefining what “good leadership” looks like in parenting and grief, this episode reframes caregiving as one of the most complex and demanding leadership roles a person can hold.

Jennifer shares how Lucinda’s message—“you are the CEO of your situation”—inspired her book Care Boss, and why caregiving is often harder than being an actual CEO.

Together, they unpack:

How to set communication boundaries with caregivers and professionals
The difference between urgent vs. important (and why it matters)
The power of pinpointed positive feedback in parenting and leadership
The emotional complexity of caregiving, grief, and identity
Why “okay” is sometimes the highest form of success
And how to survive—not just care for others—through it all

Key Takeaways

1. You are the CEO of your caregiving experience

Whether you’re parenting, supporting a partner, or caring for a loved one—you are leading. That means setting expectations, defining communication norms, and making decisions with intention.

2. Not everything is urgent (even if it feels like it)

Using a framework inspired by Dwight D. Eisenhower, Jennifer explains how to distinguish:

Urgent & important (true emergencies)
Important but not urgent (most caregiving moments)
Urgent but not important (distractions or noise)

3. Feedback shapes behavior—especially positive feedback

Instead of only correcting what’s wrong, highlight what’s working. Specific, positive reinforcement builds trust, confidence, and better outcomes—whether with kids, caregivers, or teams.

4. Caregiving is often harder than leadership in business

Jennifer, a seasoned healthcare executive, shares that caregiving is more demanding than being a CEO—because it’s constant, emotional, and deeply personal.

5. “I am surviving while they are dying”

One of the most profound distinctions in caregiving:

You and your loved one are on two different paths—and holding both realities at once is one of the hardest parts.

6. Grief doesn’t follow a timeline

There is no “how long.” Instead, healing happens in moments—sometimes even just making it through the next hour.

7. Flip the narrative: measure backward, not forward

Instead of asking “How will I get through tomorrow?”

Ask: “I made it through today. That counts.”

Powerful Quotes

“Caregiving is by far the harder job—even compared to being a CEO.”
“You are always speaking to the most sensitive person in the room.”
“He is dying. I am surviving.”
“Okay is rock solid.”
“At the end of the day, congratulate yourself—you did another day.”

About the Guest

Jennifer A. O’Brien is a healthcare executive, caregiver advocate, and author of The Hospice Doctor’s Widow and Care Boss. With decades of leadership experience and firsthand caregiving for her husband and parents, she brings a rare blend of strategy and humanity to the conversation.