Prepare to Live: Navigating Your Health Like a “Thinking Patient”
with Dana Sherwin
What if you learned to navigate your health before a crisis hits?
Today on Experience Over Expectation, I’m joined by Dana Sherwin, a longtime health system executive who became a stem cell transplant patient and, in the process, discovered a new calling: helping people become “thinking patients” who show up to the doctor’s office prepared, informed, and empowered.
Dana spent 35+ years inside hospitals, health plans, and consulting firms trying to improve patient–physician communication. Then her chronic blood disorder progressed, and she needed a stem cell transplant. Five weeks in the hospital and a long recovery flipped her vantage point from manager to patient.
At one point, Dana realized she was subconsciously “preparing to die.” Then she caught herself and asked: What if I prepare to live instead?
That shift changed everything.
In this episode, we talk about:
The moment her identity shifted from health executive to patient
How daily structure, note-taking, and small habits carried her through recovery
Why every patient needs to become CEO of their own healthcare
The tension between “Dr. Google” and real medical expertise
How to bring AI and online research into the exam room without derailing the visit
The five-part “Thinking Patient” framework:
Preparation – Show up with a clear list of goals, history, and questions
Language – Learn the words for your diagnosis, medicine, and pain
Questions – Use question prompts to deepen understanding
Participation – Be present and engaged in the actual conversation
Courage – Build the confidence to speak up, clarify, and advocate
At the heart of Dana’s story is one simple pivot: stop only preparing for the worst and start consciously preparing to live.
🎧 Listen to the episode:
– On Substack (embed player)
– On Apple, Spotify, and wherever you get your podcasts
▶️ Watch on YouTube:
Reflection Prompt
Before your next appointment, what would it look like to show up as a “thinking patient”?
What are your top 3 questions?
How would you describe your symptoms or pain in clear language?
What information do you want before you leave the room?
📘 Read the book: Experience Over Expectation: Let Go of the Plan, Live on Your Terms
About the Guest
Dana Sherwin is a former health system executive, stem cell transplant survivor, and patient advocate. Through her platform The Thinking Patient, she helps people build the skills, language, and courage to actively participate in their own care.
About the Host
I’m Mary McCorvey, host of Experience Over Expectation and author of Experience Over Expectation: Let Go of the Plan, Live on Your Terms—a book about the beauty of life when it refuses to follow the script.
This conversation is shared for educational purposes and is not medical advice.