The Plan You Don't Have — Issue #15
Across 125 studies and 78,632 people, the best predictor of a good retirement was not the money.
ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK
Issue 15 - The Plan You Don’t Have
Today’s issue begins The Meaning Plan series — five-articles on what you build inside your Golden Window, once you've seen it.

Somewhere in a drawer or a portal, you have a document that describes your retirement in detail. It has a date on it, and numbers, and someone has probably stress-tested it. What you almost certainly do not have is a different document entirely, one describing the life those years will contain. Most people never notice the gap, because the financial plan is so thorough that it feels like the whole plan.
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.
I worked recently with a couple who had done everything right.
She chairs a department at a large university in the Midwest and holds a national leadership role in her field. He was a financial advisor and has been retired for two years. Between them, they have a retirement financial strategy in better shape than most: modeled, stress-tested, and revisited on a schedule. He built it himself, the way he built them for other people his whole career.
When I asked what they could afford, the answer arrived fast and with numbers attached. They can live comfortably. The withdrawal rate is set, and there are contingencies for the contingencies.
When I asked what an ordinary Wednesday would look like the first spring after she steps down, something shifted.
She said she wants to stay engaged professionally and hold onto her national role. He said he wants to travel and see the grandchildren. Both answers were true and reasonable, yet neither had ever been articulated in quite those words. And neither of them could say what their answer really meant. What would “staying engaged” actually consist of, on a calendar? Which weeks would the travel take, and who would be in the house the rest of the time?
They had never built a detailed spending budget for retirement, and the reason was not carelessness. You cannot budget for a life you have not yet defined.
So we walked through the architecture of a week. Hobbies: neither of them has one they have kept up. Friends: their professional networks ran on separate tracks for most of their careers, and the two close couple-friends they have are consumed right now by serious health issues, so they are largely unavailable. The two of them are originally from the East Coast, and they live in a midwestern city they moved to for her job. Their children are bicoastal.
Every decision they’d made for their future had been a sound one. They were simply all focused on the money. They had given almost no thought to their daily life in their next phase.
(De-identified composite story does not represent the experience of any one person or organization.)
The Changing World of Work
📊 A key data point and my insights about what it means to the changing world of work around us.
Their situation is a common one. Only 11% of couples retire at the same time, and nearly two-thirds stagger their exits by a year or more. (Ameriprise Financial, “Couples, Money & Retirement,” 2024) Very few couples plan for that stretch of years, because on paper it reads as one person’s date moving rather than as a gap at all.
He saw the problem before she did, because he used to sit on the other side of that desk.
Among Americans in their 50s and 60s who work with a financial professional, 87% have discussed an investment strategy for retirement. Only 53% have discussed a budget for the activities they say they want to do. (Lincoln Financial Group, “The Action Plan,” 2024) Same client, same office, same hour. One half of that conversation is standard practice, and the other half of the planning is optional.
Here is what I did not expect. The largest study of its kind pooled 125 reports and data from 78,632 people. Of the five things it analyzed, social participation was the strongest predictor of how well people adjust after leaving work, and it outperformed finances by a statistically significant margin. Financial preparedness had a correlation coefficient of .07 and did not reach statistical significance at all. (La Rue, Haslam and Steffens, “A meta-analysis of retirement adjustment predictors,” Journal of Vocational Behavior, 2022)
Income and net worth were important, so let me be careful here: having enough money is real, and it matters. It was the planning — the part everyone dutifully does — that failed to predict how the years, and the satisfaction with life, would actually go.
And social participation, the study’s strongest predictor of adjusting well to retirement, is exactly what this couple has the least of. People rightly worry about purpose after retirement, but it’s the easier piece to rebuild, because a person can go looking for purpose alone. A life with people in it is the hard part. It requires other people, and at this stage of life they have to be recruited.
Work friendships are largely the reason. They run on passive contact: the same building, the same meetings, a shared project that supplies the conversation so neither person has to actively drive it. Take away that scaffolding, and many friendships do not survive the transition. In addition, the couple’s professional networks were never joined, so there is even less to build on.
This Week’s Resource
⚙️ A framework, tool, tip, AI prompt or skill that you can save and put to use immediately.
Take one page and draw a line down the middle.
On the left, write what your financial plan specifies. Be exact, because it should be exact. The date. The withdrawal rate. The accounts, the sequence, the tax treatment, the long-term care assumption, and the number the whole plan is built to protect.
On the right, write what a plan for what life will look like in those same years, and hold it to the same standard as the left column. Where you will be. What a typical week contains. Who is in the calendar, by name. What you must build that has not existed during your working years. What you would need to start now to ensure it’s ready when you are.
That last item has a price you can actually estimate. Research on how friendships form puts it at roughly 50 hours of shared leisure time to turn an acquaintance into a casual friend, and upward of 200 to make a close one. (Jeffrey A. Hall, “How many hours does it take to make a friend?”, Journal of Social and Personal Relationships, 2019) Those are hours of chosen time, not hours logged in the same building. If your right-hand column involves three of those friendships, you are looking at a multi-year build, and it has to start well before the date sitting in the left column.
Now, read the two columns side by side and notice how much of the right one you can fill in with the same confidence as the left.
That right column has a name. I call it your Meaning Plan. Almost no one has one, and the people with the best financial plans are often the furthest behind on it — because a good financial plan feels so much like readiness.
A Powerful Coaching Question
🤔 This week’s high-value coaching question for you to consider in whatever way you like to reflect.
What does your first ordinary Wednesday of retirement look like, and who else is in that week's calendar?
Inspiration for the Week
Traveler, there is no path. The path is made by walking.
— Antonio Machado
Machado is describing how a path actually comes into being. Your path through retirement will not automatically be spelled out for you the way your portfolio will be. You have to create it, one step at a time.
Before You Go
This couple already had an excellent financial plan. What they were missing was a plan for the life that money was going to pay for. And they had no idea how much they needed it.
That gap is where this season is going. Over the next four issues, we are going to build the right-hand column I described in this week’s resource, one question at a time. Next week we start with the question that unlocks the rest, the one underneath the question everybody asks: what would you do if the money questions and concerns were already handled?
Before then, write me the one sentence your financial plan cannot answer. I am collecting them, and they will shape what I write for the rest of this season.
Until next week,





