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The Spreadsheet That Never Sleeps
Over the years, I’ve noticed a pattern among a certain kind of client. Often — though not always — an engineer by training. Methodical. The kind of person who built a savings spreadsheet sometime in their thirties, updated it faithfully every year since, and can tell you their net worth to the dollar without opening the file.
That discipline is exactly why they’re sitting across from us with $1 million or more saved. It worked. In fact, it worked for twenty-five or thirty years.
And then retirement arrives, and the same discipline that built their nest egg becomes a sort of trap standing between them and their money. The income faucet gets turned off, and their spreadsheet can’t accommodate all the risks, assumptions, and factors they may face over the next 30-40 years of retirement. They also have a hard time distributing from their fortified nest egg.
The Real Question Isn’t Math
Here’s the part that surprised me the first few times I saw it, but doesn’t surprise me anymore: the hardest conversation in retirement planning usually isn’t about returns, fees, risk, or asset allocation. It’s about permission.
Somewhere along the way, “save more” became identity, not just strategy. Disciplined people form habits. But in a twist of irony, breaking that habit of saving is difficult to break. Flipping that switch — going from accumulate to spend — isn’t a math problem. The math can say yes. The spreadsheet can be airtight. And the person who built it can still feel like they’re doing something wrong every time they book a flight to visit their grandchildren.
I want to be fair, because the instinct isn’t irrational. It’s the same discipline that got them to where they are. Nobody accidentally saves a million dollars. The caution that feels like an obstacle in retirement is the same caution that made retirement possible in the first place. They were faithful in spending less than they earned for years.
But a plan that doesn’t account for spending in retirement isn’t a plan. The downside is that it trades real experiences with family while you can, for a bigger legacy that your kids may not be prepared for mentally.
Three Phases, Not One Long Retirement
J.P. Morgan has a useful way of thinking about this that I like: retirement isn’t one flat period. It tends to move through three phases.
- The go-go years — roughly the first decade after retirement, when health and energy are highest and travel and activity tend to be at their peak.
- The slow-go years — the following decade or so, when the pace naturally eases.
- And the no-go years — the final phase, when travel becomes limited and priorities shift toward health, care, and often a very different kind of budget.
The reason this framework matters isn’t the labels. It’s the reminder that the money saved for “retirement” isn’t meant to be spent evenly across thirty flat years. The go-go years are often the only years where a certain kind of spending — travel, in particular — is even physically possible. I spoke to a gentleman recently who had been on over 50 cruises, and he said, “I do it because one day, I may not be physically able to do it.” A dollar not spent in the go-go years doesn’t necessarily get spent later. Sometimes it just goes unused. During the no-go years, spending shifts dramatically toward healthcare and away from travel.
What “Probability of Success” Is Actually For
This is where stress testing earns its keep, and it’s also where I think a lot of retirees get more comfort than they expect.
One of the things we’re able to show clients through the planning software we use is a probability of success number — a way of asking, given everything we know today, how sound this plan looks if spending increases, if travel goes up, or if the market has a rough few years right after retirement — a risk retirees carry that’s sometimes called sequence of return risk: the danger of a downturn landing early in retirement, when withdrawals are happening at the same time the portfolio has less time to recover.
Even though we can’t predict the future, what we can do is run your financial plan through different scenarios. We stress test the plan. We revisit your Intelligrations® plan every year, because markets change, health changes, and your spending will change. A plan built on this year’s assumptions is worth updating with next year’s facts.
In fact, our software gives clients access to their financial plan and lets them, in a “sandbox playground” sort of way, modify their assumptions and goals without touching the official plan. This gives them the psychological freedom to see whether buying that dream car they always wanted will harm their plan. That freedom is valuable. We often see clients’ faces light up when they realize, mathematically, that they have permission to follow their dreams.
The goal isn’t a guarantee. It’s a written plan a client can actually look at and ask, “given everything we know, is this still solid?” — and get an honest answer, updated annually, instead of guessing once and hoping for the best.
When One Spouse Wants to Go and the Other Wants to Wait
There’s a second version of this same tension, and it shows up almost as often: one spouse ready to spend and enjoy the years they worked for, the other nervous every time a big trip gets booked.
Neither position is wrong. One partner is usually thinking about experiences while there’s still health and energy to enjoy them. The other is usually thinking about what happens if the money runs short later, or if something unexpected — health, family, a market downturn — changes the picture. Both concerns are legitimate. They’re just aimed at different points on the same timeline.
What I’ve found helps most isn’t persuading one spouse to think like the other. It’s putting real numbers in front of both of them — the same plan, the same stress test, the same probability of success — so the conversation moves from a disagreement about feelings to a shared look at facts. Often, that’s enough to get two people who’ve been talking past each other for years back on the same page.
Before the Ink Dries
No plan survives contact with reality unchanged. Markets move. Health changes. Priorities shift once the grandchildren show up or the knees stop cooperating. That’s not a flaw in planning — it’s the reason a plan gets revisited every year instead of filed away once and forgotten.
If any of this sounds familiar — a spreadsheet that’s hard to stop feeding, or a spouse who’s ready to go while the other one hesitates — it might be worth putting real numbers behind the conversation instead of having it in the abstract.
We’d love to demo our proprietary Intelligrations® and show you what a sample Intelligrations® report looks like.
We love to minimize your financial stress, so you can focus on maximizing your life.
Is Your Current Plan Flexible enough to survive retirement changes?
We want to have a complimentary call or coffee with you, if any of the above is what you are struggling with. We love helping couples figure this stuff out in a casual, pressure-free meeting where we can listen to your needs. Reach out and let us know how we can help. Don’t try and do it alone, as you only get one chance to get it right.
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