Rich but Restless: Why Your $5M Portfolio Isn’t Buying Retirement Confidence
I took a deep dive into what actually builds retirement confidence. The answers had less to do with the amount saved than I expected.
Americans are worried about the future. Inflation, market swings, the rising cost of healthcare, the long-term fate of Social Security… the list of things keeping people up at night seems only to grow.
Eleanor Roosevelt, who lived through her own share of national anxiety as first lady during the Great Depression and World War II, offered a piece of advice that still applies: "You gain strength, courage and confidence by every experience in which you really stop to look fear in the face."
There’s plenty of fear to look at right now. A new Allianz Life study found that 67% of Americans worry more about running out of money than about death. It’s a record high. Nearly half don't have a written financial plan, 57% feel anxious when markets drop and shockingly, 34% say they pull money out of investments during downturns.
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Retirement confidence has taken a similar hit. The 2026 EBRI Retirement Confidence Survey found that confidence among American workers and retirees has fallen to its lowest level since 2017. Just 64% of Americans say they feel confident they’ll have enough money to live comfortably throughout retirement, as financial strain, rising costs, and growing concerns about the future of Social Security and Medicare weigh on workers and retirees alike.
The good news, financial advisers say, is that you’re far from powerless. With the right steps, it’s possible to build the resources — and the confidence — to move forward.
"I’ve worked with households who have $5 million and feel uncertain, and others with less who feel fully in control." — Preston Cherry
Confidence isn't about the size of your nest egg
Americans believe they need $1.46 million to retire comfortably, according to Northwestern Mutual's 2026 Planning & Progress Study. But hitting that number doesn't necessarily buy peace of mind.
"I’ve worked with households who have $5 million and feel uncertain, and others with less who feel fully in control," says Preston Cherry, CFP® and founder of Concurrent Wealth Management. "The difference is structure, clarity, and lived experience, not just assets."
Melissa Caro, CFP® and founder of My Retirement Network, sees the same pattern. "Two individuals with the same balance sheet can feel completely different levels of security depending on their past experiences, their tolerance for uncertainty, and how they interpret risk. That psychological layer is often more important than the raw dollar amount."
In other words, if you’re feeling shaky about retirement, the instinct is usually to save more. But that may be only part of the answer. Without addressing the concerns underneath, no amount will feel like enough.
Build a guaranteed income floor
Perhaps the single biggest confidence builder comes down to one word: guaranteed. Social Security, pensions and, in some cases, simple income annuities can help cover essential bills no matter what the market does.
Workers seem to agree. According to the EBRI, more than four in five workers say they’re interested in purchasing a guaranteed monthly income product with retirement savings, and two-thirds are interested in a Social Security "bridge" annuity that would provide income until age 70 to maximize Social Security benefits.
"When clients know the essentials are covered for life, their anxiety drops dramatically," says Patrick Huey, CFP® and founder of Victory Independent Planning.
He calls delayed Social Security the most underrated tool retirees have at their disposal: “Delaying Social Security, where health and circumstances allow, is often the single best ‘annuity’ most retirees can buy. It’s inflation-adjusted, government-backed and lasts as long as you do.”
The psychological effect of guaranteed income may be bigger than the dollars suggest. Caro explains why: “One of the hardest transitions in retirement is behavioral — people are conditioned to rely on a paycheck while their savings grow in the background, and retirement flips that dynamic overnight.” Pensions, delayed Social Security or annuities, she says, can act as “a stabilizer” during that shift.
Morningstar research backs up the case for layering in guaranteed income, finding that allocating a portion of a portfolio to an immediate annuity could meaningfully increase lifetime spending and help mitigate sequence-of-returns risk.
Keep a cash reserve to weather downturns
Once your essentials are covered, the next layer of confidence comes from liquidity. A meaningful cash reserve can help you ignore short-term market noise.
Eric Nelson, CFP® and founder of Independence Wealth, recommends two to three years of living expenses in cash or short-term fixed income.
"If the market drops 25%, a client with two to three years of expenses sitting in cash or short-term fixed income doesn’t need to sell anything," Nelson says. "They can wait it out. That’s what separates a temporary decline from a permanent loss of capital."
Another way of putting it: cash reserves don’t just fund spending, they buy time, which can turn a scary downturn into a manageable one.
Have a written withdrawal plan
Knowing you have money is one thing. Knowing exactly how you’re going to spend it and how you'll adjust if conditions change is another.
Consider that Americans with a financial plan in place are more than twice as likely as their peers (83% vs. 38%) to feel confident about their retirement prospects, according to Fidelity’s 2026 State of Retirement Planning study.
"When clients have a written plan, the anxiety around ‘am I doing this right?’ largely disappears," Nelson says. "They know what they’re spending, where it’s coming from and what the guardrails are if something changes."
Huey adds that a real plan goes beyond rules of thumb like the 4% rule. It should spell out which accounts you’ll draw from first, how you’ll respond in bad market years and when you’ll refill your cash bucket.
"A written plan is what keeps people from making sleep-robbing decisions in the middle of a downturn," he says.
Cherry emphasizes flexibility: "Confidence comes from having a written, flexible withdrawal strategy. Not just a rule of thumb, but a plan that adjusts based on markets, taxes and life events."
Look beyond the numbers
The financial scaffolding matters, but advisers are nearly unanimous that some of the biggest factors in retirement confidence aren’t financial at all.
Amy Mullen, CFP® and president of Money Quotient, suggests that low confidence is often misdiagnosed as a planning problem. "Even the most well-crafted financial plan can’t fully resolve uncertainty or fear. When confidence is low, the issue usually isn’t a lack of strategy, but a lack of clarity around what truly matters and what the plan is meant to support."
That clarity, she says, comes from the non-financial side of the ledger: purpose, health and relationships.
"Retirement is an identity transition," Cherry says. "When people retire from something without clarity on what they’re retiring to, confidence often erodes regardless of wealth."
Lived experience matters, too. Someone who watched their parents lose everything in a downturn may carry that fear long after their own balance sheet has made it irrelevant.
Huey says naming that history is part of the work: "The goal isn’t to eliminate emotion; it’s to build a plan sturdy enough that you don't have to rely on willpower in the worst week of the worst year."
Doubts about the future may feel uncomfortable, but as Roosevelt suggested, they can also be valuable. It’s an opportunity to look fear in the face and find the strength, courage and confidence on the other side.
Next Steps to Feel More Confident in Retirement
- Put a guaranteed income in place.
- Mind your mental and physical health.
- Face the expense of long-term care head-on.
