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I’ve met with dozens of people in the past year who fit the same criteria. Saved and invested properly for 40 years (or more). Paid off debt and overcame mistakes. Sacrificed current enjoyment for future enjoyment to get to the finish line and enjoy the golden years.
Only now, fear appears to be creeping in. And all that hard work is in question.
We see it in sports all the time when a team does everything correctly for the first three quarters, only to play overly conservative in the last frame. And they lose.
The people who have shielded themselves the most effectively are the ones who now have the most to lose. So that’s how they play retirement. They don’t play to win, they play not to lose.
The most interesting part in this is that the numbers work, and it would take a catastrophic event (or several) in retirement for things to go wrong. But it doesn’t matter.
These people are Wealthy Worriers and must overcome something bigger than the numbers.
The #1 Problem Wealthy Worriers Have
This is a nearly universal problem for retirees who have funded their retirement:
How do I spend money I have been saving for 40 years?
It’s distressing to have managed a savings plan over 40 years, riding the ups and downs of the market. Saying no to so many temptations through the years, saving while peers were out spending. Buying cars that were practical, not luxurious. Telling your children “we have ___ at home” every time they’d ask for something new (as a newer father, I can officially relate – and publicly apologize to my parents for this).
But now? The wealth is there. Yet the worry is holding you back.
This is a Real Phenomenon
Morgan Housel explores this tension in one of my favorite books, The Psychology of Money. He points out that for many high achievers, the drive to accumulate never comes with an off switch. The same disciplined, saver’s mentality that built the wealth makes it nearly impossible to recognize when enough is actually enough.
For retirees, that is the trap. You crossed the finish line, but you are still running.
Frankly, the math isn’t overly complicated for many Wealthy Worriers. The mindset shift, however, can feel like steering the Titanic.
“I Don’t Know What To Do – I’ve Worked Since I Was 14”
Saving for retirement requires real discipline. You deferred gratification, resisted lifestyle inflation as your income grew, and kept feeding accounts that were numbers on a page for most of your career.
While you were working, your bills got paid and your life got funded by your paycheck. The retirement savings were (and are) definitely real, but not felt in the way your direct deposit was real.
When you retire, that changes entirely. Your money does the work. You stop working.
Housel makes a point worth sitting with here: getting wealthy and staying wealthy require fundamentally different skills.
Getting there demanded optimism, risk-taking, and the belief that more was always possible.
Staying there, and actually living off what you built, requires a completely different posture. More humility, patience, and willingness to let the portfolio do the work while you step back.
That transition from earner to owner is harder than most people expect. You have to delegate a task you’ve done at a high level to your savings. And almost nothing prepares you for how that feels.
But What If It Goes Wrong?
Perhaps the spending fear wouldn’t be there if not for everything that can go wrong. The biggest culprit is that the market does not stop moving just because you stopped working.
Market corrections are normal. They happen almost every year. When you were employed, you may have noticed them, but you didn’t feel them. A bad quarter showed up in your statement, maybe caused a few sleepless nights, but your paycheck kept coming. You could earn your way through it.
In retirement, corrections become crashes and they are felt, not just noticed. It raises a specific, uncomfortable question: can my money recover faster than I am spending it?
That fear, if left unchecked, can lead you to spend less than you should. To sit on a pile of savings while skipping the vacation, the renovation, the experiences you worked for.
Shifting from Worrier to Warrior
The good news is this is a solvable problem.
And any great warrior will tell you preparation is key prior to going into battle. While the stakes may not be life or death as it is for someone going into war, the concept is the same.
You must be prepared for the things that can and will go wrong. And plenty in retirement can and will go wrong.
Here are four things that I think will help.
#1: Build the Buffer Before You Need It
The market will correct and have its share of losses. Rather than be surprised and upset it’s here, it’s better to accept the fact that it will take place.
Housel has a concept he calls room for error. The idea is that the most important part of any financial plan is not the projected return. It is how much margin you have built in for when the projection is wrong. Because at some point, something will go wrong.
For retirees, room for error looks like this: you should never have to sell stocks at a loss because you need grocery money. If you have enough stable, accessible assets to cover several years of expenses, a market correction becomes an inconvenience instead of a crisis.
Build the safe haven before you need it, not after. A well-structured retirement portfolio has different jobs. Equities give you long-term growth. Fixed income, alternatives, and cash give you stability and a place to draw from when equities are down.
The biggest failure point for retirees is selling low during one because they panicked. Build the buffer first, and that problem is one you can work around.
#2: Study History and Use It as a Guide
Investment legend Nick Murray has called one phrase the most dangerous in a retiree’s vocabulary: “This time it’s different.”
He is right to call it dangerous. It almost never is.
Since 1990, the S&P 500 has experienced over a dozen corrections of 10% or more. Recessions, rate crises, geopolitical shocks, pandemics. Every single one of them felt catastrophic in the moment. Though the timing differed in each circumstance, each of these corrections eventually saw the market recover and hit new all-time highs.
The ‘Why” behind each correction is different. The “What” is remarkably consistent: markets fall, then they rise, then they reach new highs.
When you are in the middle of a downturn and everything in you wants to move to cash, pull up a long-term S&P 500 chart. Find the scariest drop you can remember living through. Then look at where the chart went afterward.
That is your permission slip to stay invested.
If you had retired in 2008, right before the financial crisis, and stayed the course, you would have participated in one of the longest bull markets in American history. The retirees who panicked and moved to cash locked in those losses permanently.
History will not tell you exactly when the next recovery starts. But it tells you, pretty clearly, that it comes.
#3: Tune Out the Noise
This is probably the most underrated item on the list.
Financial news exists to get you to watch, read, and keep watching. Alarm sells better than reassurance. “Markets Are Steady” does not generate clicks. “Is This the Next Crash?” does.
The problem for retirees is that your account balances now feel personal in a way they did not when you were accumulating. A headline about a market correction hits differently when you are drawing down instead of adding in.
Housel addresses this directly. He argues that being reasonable is more important than being perfectly rational. You do not need the optimal portfolio on paper. You need a strategy you can actually stick to when things get scary. A plan you abandon in a panic is worse than a slightly imperfect plan you hold through the noise.
A good question to ask is: will this matter five years from now?
If the answer is yes, it probably deserves your attention. If it will not matter in five weeks, you might be better served by a walk outside than another hour of financial news.
Reacting to short-term noise is one of the fastest ways to make a long-term mistake.
#4: Work With a Professional You Can Actually Trust
I think trust is the most important factor in any relationship. We put trust in nearly everything we do. When we go on the road, we trust our brakes, and those of others, are working properly.
We trust (or perhaps, people put their trust in us), to watch and babysit our children and pets.
We trust our doctors and dentists with personal health information and for them to guide us.
Working with someone who is managing your assets is no different. And their job is to get you to and through retirement.
Housel writes that the highest dividend money pays is not found in a brokerage account. It is the ability to wake up and do what you want, with who you want, for as long as you want. Otherwise known as financial freedom.
But a lot of retirees never get there because they never gave themselves permission to use it. You can become a servant to your account rather than your account serving you.
The right advisor helps you close that gap. By giving you a framework for spending confidently, without the constant fear that you are about to run out.
That means having the occasional uncomfortable conversations. Not just about asset allocation and withdrawal rates, but about what you actually want your retirement to look like. What you want to do. What you are afraid of. What success actually means to you.
When you have that kind of relationship with an advisor, a market correction hits and you get a phone call instead of a panic. Someone who knows your plan, your numbers, and your goals tells you whether this is a fire drill or something worth acting on.
Finding The Warrior Within
Play the game to win. Don’t play the game not to lose. In baseball, having a starter who constantly mows down hitters in the first 7 innings is such a value. They get paid big bucks.
But in the 9th inning, everything changes. It’s a different feel, different energy, and the stakes become much higher.
Elite closers have a different mindset. Retirees must adopt the closer’s mindset after being an innings eating starter their whole life.
The math of retirement is solvable. The fear of spending what you saved is solvable too. We all have a time where we will have to make the mindset shift if we’re interested in enjoying ourselves in retirement.