One More Year — Issue #10
46% of Retirees Didn't Get to Choose Their Date
ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK
Issue #10 - One More Year
“One more year.” It is the most reasonable thing a senior professional ever says. The bonus vests in the spring. The reorganization needs a steady hand to complete it. And the successor, everyone agrees, is not quite ready. Each reason is valid. Each year is defensible on its own.
That is exactly what makes it dangerous.
The cost of waiting was never about any single year. It is in all of them, stacked one sensible decision at a time. The stack stays invisible until you turn around one day and it is five years tall.
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.
He had built a company over 30 years and was ready, on paper, to step back. He was more than ready, really. He had hit his financial comfort number twice over.
He came to coaching after he finally sold his business, expecting to feel relief. Instead he felt something he could not identify, and it was bothering him more than any quarter’s results ever had.
We traced it back. Three times over the last decade he had set a date to step away. Three times he had moved it. Once, he stayed for an acquisition he wanted to see through. Another time, the market was good, and one more year of growth would pad the sale. Most recently, he didn't know who he'd be on the other side of selling and retiring, and another year of work let him avoid finding out.
Each delay made sense. He would make the same calls again with the same information.
But while he was heads-down hitting the number, the things he had been saving for had quietly changed. The long treks he and his wife had planned now bothered his knees. His appetite for big, ambitious travel had cooled into a preference for the familiar. The friends he pictured doing all this with had scattered, or slowed or were managing their own health.
He had not failed. He had retired exactly as planned, with more than enough financial resources. He was just late. Not tragically late, just late enough that the chapter of life he thought he'd bought began after the version of him who could fully enjoy it had started to disappear.
That is the quiet grief of an on-time retirement. The money was there. The life it was meant to enable was no longer feasible. The retirement he'd once envisioned was out of reach.
The Changing World of Work
📊 A key data point and my insights about what it means to the changing world of work around us.
The retirement plan has one part almost everyone gets wrong.
“One more year” assumes the choice will still be yours next year. For nearly half of people, that assumption would be wrong. 46% of workers who retired in 2025 left earlier than they had planned, and more than three-quarters of those early exits were driven by unexpected circumstances: health problems, a disability, a layoff, a parent who needed care. (EBRI, 2025 Retirement Confidence Survey)
Consider that fact in your decision process. If you’ve set a date, you likely assume you will arrive in that moment on your terms, in the shape you are in now. Almost half the time, life has a different plan.
Waiting feels like the safe, responsible move. It is actually the gamble. Every “one more year” decision is a bet that the future you are counting on will still be available when you finally decide to claim it.
Sometimes people win that bet. Often, they don’t.
This Week’s Resource
⚙️ A framework, tool, tip, AI prompt or skill that you can save and put to use immediately.
The Cost-of-Waiting Audit
Most senior professionals can tell you the exact date or financial goal they are waiting for. Very few have said out loud what they are assuming will still be true when it comes.
This is a short, uncomfortable exercise. Do it on paper.
1. Name the milestone. The vesting cliff, the birthday, the milestone, the “after the reorg.” Write down the specific thing you are waiting for. Be honest about whether it is one date or a date that keeps moving.
2. Name what you are assuming. Write down what you are quietly counting on still being true when that milestone arrives. Your health. Your energy. Your spouse’s health. The friends you pictured in this chapter of your life. The appetite to do the thing, not just pay for it.
3. Ask one question of each assumption. Is this guaranteed, or am I treating a hope as a fact?
That is the whole exercise. It is not meant to scare you out of waiting, because sometimes waiting is right. The point is to acknowledge the bet you are making, so that if you choose to wait, you are choosing it with your eyes wide open.
Your very next action: write down the milestone. Just the milestone. Most people have never actually put it on paper.
A Powerful Coaching Question
🤔 This week’s high-value coaching question for you to consider in whatever way you like to reflect.
If you were sitting across from me, this is what I’d ask:
Name the milestone you've been waiting for. Now acknowledge what you're assuming will still be true about you when it arrives.
Most people have never said the second part out loud.
Inspiration for the Week
“It is not that we have a short time to live, but that we waste much of it.”
— Seneca, On the Shortness of Life (c. 49 CE)
2,000 years later this wisdom still resonates, because the trap of a finite life has not changed. We do not lose the time in one dramatic stroke. We spend it, one reasonable year at a time, always counting on more time to come.
Before You Go
So what does one more year actually cost you, specifically, in your situation? That is the real question, and it deserves a real number. Next week, we put one on it.
Until next week,
I was given some excellent advice by my US-based boss when I went to work in Brazil in my early thirties. He suggested I use some of my excellent salary to travel around South America. He told me a story of another professional employed by our company, who never did anything because he was saving to buy a farm. The end of the story? He bought the farm, as they say, before he could retire and actually buy a farm. That advice stuck with me the rest of my career.