• Schedule a Free Retirement Strategy Session​
• Fidelity’s 2026 State of Retirement Planning Study
• 72% of Americans Say They Will Retire on Their Own Terms as They Embrace a New Playbook
• Fidelity’s 2025 Retiree Health Care Cost Estimate
• Even Rich Retirees Fear Outliving Their Money
• Schroders’ Retirement Study Reveals 62% Don’t Know How Long Their Money Will Last
• Financial Anxiety and Stress Among U.S. Adults (FINRA and GFLEC)
• Schwab’s 2025 Modern Wealth Survey

A few months ago, we met with a couple who shared something most of you can likely relate to. They were in their sixties and both retired with a healthy seven-figure retirement portfolio, a pension, social security, and no debt. 

By every objective measure, they had won the retirement game.

And yet the husband expressed that he had been losing sleep ever since he read a single news article predicting trouble was ahead for the stock market. He just couldn’t shake the feeling that one bad downturn could potentially undo everything.

Now, plenty of clients walk in asking the question you’d expect: “Do I have enough money to retire?” But after almost two decades of doing this work, I’ve learned that’s not always the question actually keeping them up at night. When you get to the root of it, the real question is often some version of: “Why doesn’t this feel like enough?”

That gap — between having enough and feeling like you have enough — is one of the most underdiscussed problems in retirement planning.

And a recently published research report helps explain why that gap exists, and points to what actually drives confidence in retirement.

So, today, I’m sharing those findings. And then I’m walking you through the four things I see consistently in the retirees who actually feel secure — the ones who don’t check their accounts every morning, who don’t panic when the headlines turn ugly, who sleep through the night. And spoiler alert: not one of the four has anything to do with the size of your account.

Welcome to another episode of the Stay Wealthy Retirement Show. I’m your host, Taylor Schulte, and every week I cover the most important financial topics to help you stay wealthy in retirement. Ok, onto today’s episode.

The Real Reason Wealthy Retirees Still Wake Up Anxious (And the 4 Pillars That Fix It)

The FINRA Investor Education Foundation, working with the Global Financial Literacy Excellence Center, found that roughly 60 percent of American adults are financially anxious. And about half of those people are not just anxious — they describe themselves as financially stressed.

These feelings aren’t limited to those living paycheck to paycheck. As a recent Wall Street Journal article put it, “Even Rich Retirees Fear Outliving Their Money.” The piece highlighted research from a handful of retirement academics and real stories from high-net-worth retirees who, despite having more than enough, still struggle with the fear of running out.

So if you have been quietly assuming that the anxiety would lift once you hit a certain account balance — once the 401(k) crossed a million, or two, or five — I want to gently push back on that. The data does not support it.

What the data does support is something else entirely. The most recent example is Fidelity’s recently published 2026 State of Retirement Planning Study. To conduct the study, they surveyed Americans either approaching retirement or already in it, and for one piece of it they split the group in two: those with a written financial plan, and those without one.

And what they found was that those who had a financial plan in place were more than twice as likely as their peers to feel confident about their retirement prospects. 83 percent versus 38 percent to be exact. 

Fidelity then looked specifically at people who are already retired. Among that group, 81 percent of retirees with a plan say they have enough money to last the rest of their life. Among retirees without a plan, only 45 percent say the same.

Same generation. Same economy. Same Social Security rules. The plan, as boring as it may sound, is a key differentiator.

But this is where we need to be careful. Because, “having a plan” can mean very different things. For some people, it means a folder full of statements, a retirement calculator printout, or a monte carlo projection they looked at once and never touched again.

That is not what creates lasting confidence. The kind of confidence Fidelity is pointing to comes from something more complete. Yes, it starts with a written plan. But the retirees I see who feel most secure usually have four things working together: a plan they can reference, numbers they understand, a life they are retiring into, and a second set of eyes to help them make decisions when conditions change.

So let’s walk through each one, starting with pillar number one which is what Fidelity’s data highlights most directly, a real plan, written down.

Pillar 1: A real plan, written down

And the reason this matters so much is that a written plan does something your account balance can’t do: it gives your brain a place to put all the uncertainty.

On the surface, that may sound almost too simple. Of course retirees with a written plan feel more confident. But I don’t think the value is just in the document itself. The value is in what the document does for your brain.

Cognitive psychologists have a concept called cognitive offloading. The basic idea is that your brain has limited working memory. In other words, it can only hold so much at one time before it starts to get overwhelmed.

And retirement has a lot to hold. Multiple income sources. Social Security decisions. Medicare premiums. Tax brackets. Required minimum distributions. Portfolio withdrawals. Market volatility. Healthcare costs. Long-term care concerns. Legacy goals. Spending decisions.

When you try to hold too many moving parts in your head at once, the system gets overloaded. And when working memory is overloaded, two things happen consistently in the research. Your decision quality drops. And your anxiety goes up.

Think about it this way. Picture a chef trying to run a complicated dinner service without writing anything down. No prep list. No tickets. Everything held in their head. Even a great chef will start to feel the panic creep in by the second seating, not because they aren’t skilled, but because the human brain is not built for that kind of load. Now picture the same chef with a system — a board, a ticket rail, a written prep list. Same kitchen. Same chef. Completely different nervous system.

Your retirement is the same way. When the plan lives in your head, every market dip, every news headline, every offhand comment from a friend about long-term care can trigger fight-or-flight. There is nothing to anchor to. When you have a living, breathing plan that is regularly updated, you can review it and say:

“Right. We already thought about this.”

“Here’s where income is coming from.”

“Here’s how much we can spend.”

“Here’s what changes if markets fall.”

“Here’s what we’ll do if taxes rise.”

“Here’s what happens if one of us needs care.”

This is the primary reason why Charles Schwab’s most recent Modern Wealth Survey found that only about 36 percent of Americans have a written plan — but among those who do, 96 percent say they feel confident they will reach their goals. That isn’t because writing things down magically creates wealth. It’s because writing things down creates clarity, and clarity is the antidote to anxiety.

So what does “written plan” actually mean? At a minimum, it should include your income sources, projected expenses, withdrawal strategy, tax plan over time, healthcare assumptions, Social Security strategy, long-term care considerations, and contingencies. 

In other words, not just: “Here’s our goal.” More like: “Here’s how the pieces fit together.” If markets fall, here’s where we’ll draw income from. If one spouse dies first, here’s what changes. If healthcare costs rise, here’s how we’ll adjust. If we want to spend more in our go-go years, here’s what that means later. If tax laws change, here’s what we’ll revisit. 

That’s a plan. If the only documents you currently have are a 401(k) statement, a Social Security estimate, and a few notes buried in a spreadsheet somewhere, you don’t really have a retirement plan yet. You have inputs.

And I want to say this gently, because most listeners on this show are very smart, well-read, financially literate people. The reason you don’t have a written plan probably isn’t laziness. It’s that retirement is genuinely complicated, and writing it down forces you to confront things you’ve been able to keep abstract. That’s the whole point. The abstraction is what’s keeping you up at night.

Pillar 2: Knowing your actual numbers

And once you’re willing to move the plan out of your head and onto paper, the next step is where the real clarity starts to show up. Pillar number two is knowing your actual numbers.

You have to put numbers to it. Because abstract retirement fears almost always sound bigger than they really are. “Healthcare is going to be expensive.” “Taxes might go up.” “What if markets fall?” “What if I spend too much too soon?”

Those are all legitimate concerns. But until they’re attached to actual numbers, they remain open loops your brain keeps trying to solve. And that’s what separates retirees who feel generally okay from retirees who feel truly grounded.

Confident retirees don’t just have a plan. They know their numbers.

In fact, the Employee Benefit Research Institute runs an annual Retirement Confidence Survey that I quote constantly because it is so revealing. 

More recently, their survey found that only about 52 percent of pre-retirement workers have actually estimated how much monthly income they will need in retirement. Only 44 percent have thought through how much they should withdraw from their portfolio each year. And only 41 percent have calculated their likely healthcare costs.

Less than half. Right before the most important financial transition of their lives.

And it isn’t just pre-retirees. The Fidelity 2026 study found that even among people who say they have a plan, nearly 1 in 3 admit they don’t actually know how much they’ll have saved by the time they retire. 

Here’s the thing—you cannot feel secure about a number you have not run. You can feel optimistic. You can feel hopeful. But security — the kind that lets you sleep well at night — requires that you have seen the math. And nowhere is this more important than healthcare.

Let me put some numbers to this. Fidelity’s latest retiree health care estimate says a 65-year-old retiring today can expect to spend an average of $172,00 on health care throughout retirement. A couple is double that amount. And, by the way, those numbers do not include long-term care, which is its own line item.

In someone’s head, those numbers can all blur together into one big source of stress. Documented in a living and breathing plan, they become a series of solvable problems. Large Medicare premiums in your seventies. Supplemental coverage. A long-term care strategy that fits your specific risk tolerance, family situation, and balance sheet. An HSA you’ve been funding for years. The same dollar amount, depending on whether you’ve modeled it, can either dominate your retirement or be a manageable line item.

Really quick, I want to make a small but important, and hopefully, obvious point here. When I encourage people to “know their numbers,” I do not mean memorize them. I mean see them, in context, in writing, and update them when life changes. The retiree who knows their numbers is not the one with the best memory, it’s the one who built a system they can look at when they need to.

And by the way, this is one of the reasons I’m skeptical of the one-page online retirement calculators and one-page financial plans that have become so popular. They give you a binary answer — green light, red light, “you’re on track” — without showing you the math. That can produce false confidence. Worse, it can produce false panic. A real plan looks at the actual interaction between your Social Security claiming strategy, your tax brackets, your asset location, your healthcare projections, and your withdrawal sequence, and it shows you how the whole thing moves together. Once you can see that, you can stop catastrophizing. You can also stop being unrealistically optimistic, which I’d argue is the more dangerous of the two.

Pillar 3: Knowing what you’re retiring to

And once you can see the numbers clearly, it becomes easier to recognize what the numbers can and cannot answer.

They can tell you whether the plan works.

They can show you how much you can spend, where income will come from, how taxes might be managed, and what happens if markets or healthcare costs surprise you.

But they cannot tell you what your life is going to feel like when work is no longer at the center of it.

That’s the third pillar: Knowing what you’re retiring to.

The American Psychological Association has been publishing on retirement transitions for decades, and the finding holds up consistently. The people who report the highest satisfaction in retirement are not necessarily the wealthiest, they’re the people who planned for identity, purpose, relationships, and the daily structure of their time.

I’ve covered this in prior episodes — including a recent one on the signs you might be closer to retirement than you think — where I told the story of a wealthy executive who hired us a few years after retiring. On paper he was more than fine. But what he said to me was something I’ve heard, in some form, dozens of times since: “I left as soon as I could, and now I don’t know what to do with myself.” His health declined. His marriage got tense. And the money in his account — which was substantial — did not help, because the problem was never financial.

Here is the version of this I want you to hold on to: a spreadsheet can tell you that you can afford to retire. A spreadsheet cannot tell you why you would want to.

I had a different client a few years ago — an extraordinarily disciplined saver, sharp engineer, sold his small company in his late fifties — who came in with what he called his “retirement readiness checklist.” He had ticked off the financial items meticulously. What he hadn’t done was answer the question of what his ordinary weeks would actually look like. Within a year of retiring, he was back consulting part time, not because he needed the money, but because he hadn’t built any structure into his post-work life. He’s one of the success stories. He course-corrected, eventually landed in a part-time teaching role at a local community college that energizes him, and has settled into what he calls his “second act.” But it took some painful months in between.

And by the way, his path is becoming far more common than the traditional cliff-edge version of retirement. Fidelity’s 2026 study found that 6 in 10 Americans now have a plan to transition into retirement — and most of those transitions are not “Friday night farewell party, Monday morning sleeping in.” About 1 in 3 plan to reduce their hours before fully retiring. Another 3 in 10 plan to take on fewer responsibilities. And nearly 1 in 5 plan to transition into freelance or contract work. 

Surprisingly, only about a third plan to continue working as normal right up until a fixed retirement date. The path itself is being redesigned right in front of our eyes, which means the what are you retiring to question is no longer optional…you have to actively design the next phase.

So as part of your plan — and I mean this literally, write it down — answer the question: what does a great Monday in February look like for you? Not a vacation. Not a special occasion. A regular Monday. Who are you spending it with? What are you working on? What community are you part of? What problem do you care about, paid or unpaid?

If that question feels hard, that’s actually useful information. It tells you where there is more planning to do. And ignoring it is one of the most common, and most expensive, mistakes I see otherwise well-prepared retirees make.

The retirees who feel secure are not the ones with the largest balance. They are the ones who can answer the Monday question.

Pillar 4: A second set of eyes

And this brings us to the fourth pillar, “a second set of eyes.” Retirement planning touches almost every emotional and financial part of your life — your spending, taxes, investments, spouse, kids, health, identity, legacy, and your fear of making a mistake you can’t undo. That’s a lot to process alone.

And I’ll admit, this is a pillar I’m always self-conscious about including. As most know, I own a retirement planning firm, so it can sound self-serving. But I strongly believe I’d be leaving something important out if I skipped it.

Retirees who feel secure tend to have a second set of eyes — a financial advisor, a trusted CPA, a thoughtful spouse, or a friend who understands the moving parts. 

The point isn’t that everyone needs to hire and pay someone an ongoing fee forever. It’s that confident retirees almost never make major financial planning decisions alone or in isolation.

In fact, several studies have found that Americans who work with a financial advisor save roughly twice as much for retirement as those who don’t. To be clear, that’s correlation, not causation — people who hire advisors are often already taking their finances seriously, so I don’t want to overstate it.

But Fidelity’s data finds something perhaps more interesting: people who work regularly with a financial professional report meaningfully lower worry. But the reason isn’t what most people assume. It isn’t the investment selection or the tax strategy—it’s that when the market drops 25 percent — and at some point, it will — you are not alone with the question of what it means for you.

Picture the difference. The market sells off 7 percent in a single day. The unplanned retiree wakes up at 6 a.m., refreshes the news, and starts running scenarios — what if this is the start of something worse, what if I have to go back to work, what if my plan is broken. 

The retiree with a a financial professional in their life, makes coffee, picks up the phone: “What does this mean for me?” Gets a specific answer rooted in their numbers. Even more common, in my personal experience, the client doesn’t pick up the phone at all. They’ve done the hard work, they trust the plan we put together, and they know we will proactively reach out if something needs to be discussed or updated. 

The first person is in fight-or-flight for weeks. The second resolves it in twenty minutes, or in many cases, 20 seconds.

There’s one more dimension that doesn’t get talked about enough that surfaced in the Fidelity 2026 study that I want to quickly touch on, which is that 3 out of 4 people who work with a financial professional said they value that relationship for family conversations about retirement wishes. Not portfolio performance. Not Roth conversions. Family conversations. In other words, how to handle an aging parent who needs care. How to talk to your adult kids about what they should and shouldn’t expect to inherit. What happens if one spouse passes first. Families avoid these conversations for years and then have to handle them at the worst possible moment. A thinking partner who has been part of them and their life from the start can be more valuable than anything we do with the portfolio.

Before I close, I want to share two more data points that, I think, side by side, capture the whole picture.

The first is from the Schroders 2025 US Retirement Survey, which looked specifically at Americans who are already retired — not pre-retirees, but actual retirees living off their portfolios right now. And the study revealed that 62 percent said they had no idea how long their savings will last. Sixty-two percent. They crossed the finish line. They’re spending the money. And they’re flying blind.

The second is from the Fidelity 2026 study we’ve been referencing throughout this episode which stated that 90 percent of Americans agree that planning is still necessary even after you retire.

Put those side by side and you have the entire problem in one sentence. Nine out of ten people know planning matters in retirement. Yet, more than six out of ten retirees are doing it without one.

We all know a plan doesn’t eliminate risk. Nothing does. What a plan does is take that big, undifferentiated shape looming over your future and break it into specific, measurable, plannable pieces. 

Which brings me back to the couple from the top of the episode—the husband losing sleep over a single news article. By every objective measure, they were fine. What they couldn’t yet do was see their own situation clearly. Once we walked them through an integrated, comprehensive plan, the whole picture finally came together, and those articles stopped landing the way they had. The anxiety they’d been carrying lived entirely in the gap between what they had and what they could see.

And, I think, that really sums up today’s episode: Confidence in retirement doesn’t come from the size of your nest egg. It comes from the quality and clarity of your plan.

This is why we built what we call the Total Retirement System. Not a portfolio. Not a software output. A highly personalized, regularly updated, coordinated plan that brings your income, taxes, healthcare, investments, and estate planning into one place — modeled, stress-tested, and revisited as life evolves. You’ve already done the hardest part: decades of saving, learning, and paying attention. Our job is to coordinate every piece of it so no decision happens in isolation, nothing falls through the cracks, and you can finally stop carrying it all in your head.

If today’s episode landed close to home, you can schedule a free Retirement Strategy Session through the link in the episode description, or visit youstaywealthy.com and click the “work with me” button.

Thank you, as always, for listening. And to view today’s research and resources, just head over to youstaywealthy.com/283.

Disclaimer

This podcast is for informational and entertainment purposes only, and should not be relied upon as a basis for investment decisions. This podcast is not engaged in rendering legal, financial, or other professional services.