The Regret-Proof Retirement Plan

Dear Friends -

Last weekend, I visited my only living aunt. My parents have both passed, and I’m an only child—so this visit wasn’t just overdue, it felt essential.

It struck me how easy it is to assume we have all the time in the world. But we don’t. And that realization isn’t meant to be morbid—it’s meant to be motivating.

In my work with clients, we often talk about retirement planning. Not the financial kind (though that’s important), but something much deeper: the emotional blueprint for a life well lived.

We work through something I call the No Regrets Retirement Plan. It’s a simple but powerful tool that helps clients imagine their future from three vantage points:

1. With all the time and health in the world

2. With just five years left to live

3. With just 48 hours

The goal? Clarity.
To spot the things you don’t want to miss.
To notice what you’ve been postponing.
To stop letting life’s “somedays” slip away.

So today, I want to offer you a few ways to think about living with intention—and without regret.

Three Reflective Prompts to Journal or Discuss:

🌀 The 20-Year Mirror
Imagine yourself 20 years from now. What advice would your older self give you today? What are they most grateful you did? What are they still aching for you to do?

🌀 The Sliding Door Moment
Think of a decision you’ve delayed—big or small. What would change if you made that decision today? What might you regret if you never made it?

🌀 The Regret Reversal
Finish this sentence: “If I knew my time was limited, I’d stop ______ and start ______.”
What’s holding you back from starting now?

Book + Podcast Recommendations to Go Deeper

📚 The Top Five Regrets of the Dying by Bronnie Ware
A life-changing perspective from a palliative care nurse who listened deeply to what people wish they'd done differently.

🎧 The Diary of a CEO: “The Real Trick to Long Term Motivation” with Daniel Pink
Author of The Power of Regret, Pink redefines regret as a compass, not a weight.

📚 The Second Mountain by David Brooks
A reflection on meaning, purpose, and what we climb toward after we’ve achieved success.

AI Prompt of the Week
Open ChatGPT or another AI tool and type:

Let the conversation guide you somewhere surprising.

This week, I invite you to pause and take stock. Not just of your calendar or your to-do list, but of your life’s direction.

You still have time.
To reach out.
To let go.
To begin again.

Warm regards,

Cara Gray
Third Act Consultant, CPRC, CEPA™️

P.S. If you want to start planning your third act, set up a time on my calendar for a chat: Schedule a Chat with Cara