Regret Risk — Issue #07
The most successful people I coach are the ones most at risk. By the time they feel the cost, they've already spent the years they needed for what comes next.
ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK
Issue #07 - REGRET RISK
A client sat across from me last month. Accomplished, well-compensated, three years from the retirement he had been planning since his forties. We had cleared the morning for our session, and a few minutes in he said, very quietly, “I don’t know if I’ll still want this when I get there.”
He didn’t tell me what “this” meant. He didn’t need to.
Forty percent of C-suite leaders considered leaving their roles in the past 12 months. Almost none of them actually did. That gap, between the thought and the action, is where Regret Risk lives.
It is the most expensive quadrant on the grid I draw for clients. And from the outside, the people who are there look like the most successful people you know.
A Coaching Story
💬 A de-identified composite scenario based on my coaching experiences. This story does not reflect the experience of any particular individual or organization in any way.
She is a senior physician executive. Mid-sixties. Chief of a clinical service line at a large health system. Compensation excellent, board seat lined up for the post-retirement chapter. By every external measure, she is the picture of late-career success.
She arrived for our session and forgot why she’d booked it.
Her question for me was the one she’d been bringing to her CFO and her financial planner for years. When should she retire?
The real issue took longer to surface. She had been answering the retirement question by saying, “in three years,” for five years. Every January, her years to retirement reset. She wasn’t lying to anyone, not even herself. She was treating “in three years” the way she’d been trained to treat every clinical decision: as a position to defend, not a question to keep open.
I drew the Stay/Go Grid on a piece of paper and turned it toward her.
She placed herself in Stay & Survive within 90 seconds. The placement was easier than the year of conversation it took to get there.
I asked her to walk me through the Four Es of her current role. Education had gone quiet two years ago. She could not remember the last clinical or leadership concept that had genuinely changed her thinking. Experience was still abundant on paper, but she had stopped gaining meaningful benefit. Exposure was at a ceiling: everyone who needed to know her name already knew it. Enthusiasm was the tell. When I asked her for a number out of 10, she said “a four,” then sat back as if saying it out loud had cost her something.
Then I asked the question we really needed to explore.
“If you knew this was the last good year you’d have — the stamina, the clinical acumen, the love of the work — what would you spend it doing?”
She didn’t have an answer. That was the answer.
What she had been calling discipline now had a name. Regret Risk is the cost of staying past the point where the work is still helping you build the life you want next. And the people most at risk are the ones whose careers look, from the outside, the most enviable.
The Changing World of Work
📊 A key data point and my insights about what it means to the changing world of work around us.
Forty percent of C-suite leaders said they considered leaving their roles in the past year, and half of them said they think about it “very often.” [HR Dive, March 2025] CEO turnover hit an eight-year high in 2025, with 234 chief executives exiting their roles globally. [Russell Reynolds, Global CEO Turnover Index 2025]
The story those numbers tell is not a labor market story. It is a finite-life-energy story.
Senior leaders are doing math their advisors never asked them to do. They are calculating in years and in capacities, not in dollars. They are looking at the trajectory of the next chapter and asking whether one more year at this level is worth the year of life they will spend to get it.
The financial plan was built the way most of them were taught. It assumed time was infinite and identity was portable. Both of those assumptions are wrong, and the cost of the second one is what no one is teaching them to count.
This Week’s Resource
⚙️ A framework, tool, tip, AI prompt or skill that you can save and put to use immediately.
The Stay/Go Grid is the tool I use with every senior client who comes to coaching with a “should I stay?” question. Two axes. Four quadrants.
Stay & Thrive — high enthusiasm, still gaining at least one of the Four Es. Stay as long as that’s true.
Stay & Survive — biding time for a financial milestone; growth has ceased. This is a dangerous quadrant. It looks like discipline. It costs like delay. This is where Regret Risk compounds quietly.
Go & Thrive — actively designing the next chapter with intention. The healthy exit.
Go & Survive — leaving without a thoughtful plan. Identity-loss risk runs highest here.
Before you decide which quadrant you’re in, run the diagnostic that goes with it.
📋 The Four Es — Senior Career Self-Assessment
Rate yourself 1–10 on each.
Education — Am I still learning new skills, concepts, or domains in this role?
Experience — Am I still gaining value from the leadership work itself, not just the title?
Exposure — Am I still being seen and known by the people who will matter to my next chapter?
Enthusiasm — When I picture doing this for another three years, how much of me leans in?
How to read it: Enthusiasm is the pivot point. If Enthusiasm is below a 6 and at least one other E is below 7, what you are calling strategy is stalling. That is Stay & Survive.
The executive in the story above placed herself within 90 seconds. So can you.
⬇ Go deeper — download the Stay/Go Grid
If those four numbers got your attention, the full Stay/Go Grid walks you through what to do with them next. It is the same tool I use in coaching, formatted for self-guided use.
A Powerful Coaching Question
🤔 This week’s high-value coaching question for you to consider in whatever way you like to reflect.
If you knew this was the last year you would be at full strength — same energy, same clarity, same capacity — would you spend it the way you are spending it now?
Inspiration for the Week
“Tell me, what is it you plan to do with your one wild and precious life?”
— Mary Oliver, The Summer Day (1990)
That line of poetry is overused for a reason. At a certain career stage it stops being inspiring and starts functioning as a deadline. The question itself is the asset. What you do with it, this season, is the test.
Before You Go
If "Regret Risk" named something for you, hit reply and tell me what surfaced. I read every comment. They shape what comes next.
Until next week,
