The Cost That Isn't Money — Issue #08
She calculated the cost of leaving down to the decimal. The number that actually mattered was one her financial planner never asked her to find.
ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK
Issue #08 - The Cost That Isn’t Money
Careers move in cycles. We are taught to see a career as one long climb, but it runs more like a series of chapters, each with a beginning, a productive middle, and an end that arrives whether or not we are ready to acknowledge it.
At the senior stage of career, the riskiest move is rarely leaving too soon. It is staying long past the end of a cycle, for reasons that look like prudence from the outside.
Staying too long carries a cost, and it’s not the one your financial planner models. It’s a quieter cost, measured in years rather than dollars, and almost no one is taught to count it.
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 was a senior executive at a company she had helped build, in her early sixties, with the kind of compensation package that makes leaving feel irresponsible. A vesting cliff that was 18 months out. A title that still opened every door. By every external measure, staying was the only sane choice.
She arrived at our session with a spreadsheet. She had modeled the cost of leaving down to the decimal: the unvested equity she would forfeit, the bonus she would miss, the months of income between this role and whatever came next. She knew exactly what walking away would cost her. She wanted me to tell her the number was too big to argue with.
I asked her a question her financial planner never had. It wasn’t about the cost of leaving. It was this:
What does staying cost you?
She started to answer in dollars again. I stopped her.
Not in dollars.
She went quiet. Then she told me her husband had been asking for two years to take a long trip, the kind that needs working knees and real stamina, while they both still had that capacity. Every time, she had said to him:
After the next milestone.
But the milestone kept moving. Last year, it was a reorganization. This year, the vesting cliff. Next year, there would be something else, because there is always something else.
There was another figure that mattered, but it wasn’t on her spreadsheet. It was the number of good years she was spending to earn money, when she already had enough.
She was not being reckless, and she was not being sentimental. She was the most rigorous person in every room she walked into. That was exactly the problem. The most rigorous people run the numbers they were trained to run. They don’t always stop to ask which other numbers they should be tracking.
What she had been calling discipline was a career cycle that had ended some time ago and stayed open because the only ledger she trusted was the financial one. The cost of staying was never going to show up there. That cost was being tallied somewhere her training had never taught her to look.
The Changing World of Work
📊 A key data point and my insights about what it means to the changing world of work around us.
Nearly a quarter of workers over 50 planned to change jobs in 2025, up from 14% the year before. [AARP, More Americans 50-Plus Seek to Make a Job Change in 2025, 2025 — https://www.aarp.org/pri/topics/work-finances-retirement/employers-workforce/older-job-seekers-age-discrimination-artificial-intelligence/]
That is a 71% jump in a single year. The people around you are not winding down. They are making moves.
The next chapter is promising, meaningful, and rich in the ways that matter most. And people your age are stepping into it right now. The thing standing between most senior professionals and that chapter is rarely money. It is the assumption that there will be time later, and the energy to enjoy that time when it comes.
That assumption is the most expensive one a senior professional makes. The executive with the spreadsheet had modeled every dollar and none of the years. The chapter she kept deferring has a waiting room, and the cost of delay is paid in vitality she is spending somewhere else.
This Week’s Resource
⚙️ A framework, tool, tip, AI prompt, or skill that you can put to use immediately.
Last issue, I named the concept of Regret Risk, the slow cost of staying in a role past the point where it is still building the life you want next. This week, you can score your own Regret Risk.
The Career Cycle Diagnostic is the tool I use with senior clients who arrive at coaching with some version of should I stay or retire? The tool has four steps, and it takes about 15 minutes to complete.
You start by placing yourself on a four-quadrant grid based on whether you are still gaining or growth has plateaued, and whether your enthusiasm for the work is high or fading.
Then you rate yourself on four measures of whether this chapter is still giving something back to you. Those four add up to a Regret Risk Score. A fifth measure, Forward Pull, is scored separately, because wanting what comes next is different from being done with what you have.
The Regret Risk Category (determined by your Regret Risk Score, and adjusted if needed by the Forward Pull) tells you where you stand: low, moderate, high, or critical levels of Regret Risk. Then the tool turns the question around and asks what staying is costing you. Then it ends by asking you to name what you will do with this information.
There is one question inside this tool that I ask every senior client. It stops them cold, every time. I am not going to spoil it by sharing it here. It works best when you meet it on your own.
The score and category show you where you are. Calculating the full cost of a cycle that has run its course takes more than a newsletter, but this tool will point you toward what comes next.
A Powerful Coaching Question
🤔 This week’s high-value coaching question for you to consider in whatever way you like to reflect.
Here is the question I would put to you if you were sitting across from me:
You know almost to the dollar what one more year in your current role pays you. Have you ever once calculated what it costs you, in years and vitality that you will not get back?
Inspiration for the Week
“How we spend our days is, of course, how we spend our lives.”
— Annie Dillard, The Writing Life (1989)
We treat our days as if they are a rehearsal for some later, more real chapter. They are not. The chapter you are in is your life. The only question is whether you are spending it on a cycle that is still giving something back to you, or one you have simply not gotten around to closing.
Before You Go
If the cost that isn’t money named something you have been avoiding, hit reply and tell me what surfaced. I read every response. They shape what comes next.
Until next week,
