Win-Win Weekly #4
October 8, 2025
Hey there ,
You’ve Got to Be in It to Win It… But What If You Can’t Be?
🩺 The Story
The ICU waiting room is one of the most sacred and heartbreaking places I’ve ever been.
Last month, my brother-in-law, in treatment for throat cancer, threw blood clots that sent him into emergency surgery. He died on the operating table for 10 minutes before being revived.
When he returned, he was on machines: intubated, sedated, on dialysis, his heartbeat regulated by drugs.
He could not speak.
He could not negotiate.
He could not even be present for the conversation about his own life.
At his bedside, his three daughters, my two nieces and their step-sister, faced the impossible. The whoosh of the respirator, the beeps of the monitors, the alarms that jolted everyone’s nerves—this was the soundtrack of their vigil.
They were desperate for more time with their father. But all their words circled around their needs: more time, another chance, unfinished business.
His wishes? Unknown. Undocumented. Absent.
💭 Three Possible Futures
As I stood in that room, watching the monitors flicker, I could see three possible futures.
The miracle: he would emerge from the ICU whole, ready to rebuild relationships and resume life.
The goodbye: he would never leave the ICU, and the family would need to begin funeral plans.
The long road: a slow, uncertain recovery, just strong enough to resume treatment for his stage 3 throat cancer.
But the daughters could only see one possibility—the miracle—and they were pouring all their hope and energy into that single thread.
✍️ Giving Him a Voice
That night, I couldn’t sleep. I stayed up until dawn writing a letter—not from me, but from him. A letter to give him a voice in the negotiation he could no longer join.
The next morning, I called a meeting in my cramped hotel room. His daughters came. Their partners came. We sat in a circle, raw with tears, exhausted from the ICU.
And then, with shaking hands, I read the letter aloud.
Here’s just an excerpt:
“My dear girls,
If you’re reading this, it means I cannot speak for myself. Please know first, above everything else: I love you, and I am grateful for the gift of being your father.
I trust you to bring your pieces of me together. Don’t let disagreements drive you apart. Whatever decision you make, I know it will come from love. You have my blessing.”
That was only part of what I wrote. The full letter was longer, deeper, more personal—but even this excerpt brought the room to tears.
Something shifted. They stopped competing in their grief and started collaborating on his behalf. They committed to tackle his affairs. They discussed his directives. They began to stand together.
💡 AGENT at Work (Win-Win Insight)
The turning point was bringing his missing voice into the room.
That’s the heart of AGENT: making sure all voices, even the silent ones, are represented.
AWARE: They realized they were in a negotiation, not just a vigil.
GROUND: Their emotions were real, but they had no clarity about his interests—so the letter grounded the conversation in what was hopefully his perspective.
EMPATHIZE: The daughters could finally imagine what he might want, not just what they wanted.
NEGOTIATE: They shifted from clashing grief to creative problem-solving—who would handle his bills, his car, his medical powers.
TIE: They rallied around unity, carrying his voice as their guide.
👉 The win wasn’t about harmony—it was about clarity and love in action.
🛠 Practice for the Week
With 100% certainty, 100% of us will die someday.
We can’t change that—but we can make it easier for those we love.
Ask yourself: if I couldn’t speak tomorrow, would my loved ones know my wishes?
Take one loving step: write down at least one directive—medical, financial, or personal—and share it with someone you trust.
Put your affairs in order: it’s not morbid—it’s one of the most compassionate gifts you can give.
❤️ Closing Note
The moral of this story is simple: negotiate with your future self.
Envision yourself in that ICU, surrounded by the people you love most.
Do you want them anxious about your finances, your will, or your medical wishes—or free to focus solely on comforting you and each other?
Show them your love now.
Document your wishes.
Make it easy for them to act on your behalf with peace, not panic.
Take action today.
Your loved ones—and your future self—will thank you.
See you in the win-win moments this week,
Sam
✨ Practice with the AGENT chatbot before your next hard conversation.
