Why the First 5 Years of Retirement Are the Most Dangerous for Your Portfolio

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By David Beren Updated Published

Quick Read

  • Why the timing of one bad year matters more than thirty years of average returns

  • What the 4% rule doesn’t account for when your first five years go wrong

  • Why 2026 specifically sets the stage for sequence risk to do its worst damage

  • The analyst who called NVIDIA in 2010 just named his top 10 AI stocks. Get them here FREE.

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Why the First 5 Years of Retirement Are the Most Dangerous for Your Portfolio

© 24/7 Wall St.

Two retirees, $1 million each, same withdrawal schedule, same average return over thirty years. Schwab’s Center for Financial Research ran this exact scenario. One portfolio lasted three decades; the other was gone by year eighteen. The only variable separating those two outcomes was the timing of a single 15% decline.
 
If you retired this year — or plan to within the next few years — this isn’t a hypothetical. Morningstar’s 2026 State of Retirement Income research found that roughly 70% of simulated portfolio failures trace directly back to losses taken in the first five years.
 
Your withdrawal strategy, your fund selection, your fee structure — none of those variables changed the outcome as much as the one variable most retirement plans don’t directly address: when a down year arrives.
 

Timing, not returns.

Morningstar’s 2026 research and Schwab’s modeling point to the same mechanics — specific, counterintuitive, and largely absent from standard retirement planning tools. Here is what the data actually shows:
 

Why Early Losses Hit Harder Than Late Ones

During the accumulation phase, a market decline is an opportunity, and as prices drop, you keep contributing, and you buy more shares at lower prices. The math works in your favor, but the moment you start withdrawing, the dynamic reverses completely. When you sell into a declining market, you lock in losses and reduce the number of shares available to participate in any recovery. A 20% decline in year one of retirement, combined with a $50,000 withdrawal, doesn’t just cost you the decline itself. This decline can also cost you every dollar those sold shares would have compounded over the next 20 to 25 years. This is why a 10% drop at age 30 and a 10% drop at age 63 are not even remotely close to the same event. 

The Math That Makes It Irreversible

Schwab’s Center for Financial Research has modeled what happens to two identical $1 million portfolios when one takes a 15% hit in the first two years, and another takes the same hit a decade later. Assume that both withdrew $50,000 initially and adjusted 2% for inflation, and earned 6% in all other years. The early-loss portfolio was fully depleted by year 18, while the late-loss portfolio lasted the full 30 years. 

This is the part of the argument that catches most people off guard, as the average return over the full period was identical in both cases, and the total return was also identical. The thing that changed was timing, and it’s the only variable that can make all the difference between financial security and running out of money. 

Morningstar’s 2026 research puts the current safe withdrawal rate for a 30-year retirement at 39%, but even this number assumes that early years don’t deliver a significant downturn. 

Why the 4% Rule Doesn’t Account for This Scenario

During the accumulation phase, a market decline is an opportunity, and as prices drop, you can keep contributing, and you buy more shares at lower prices. Ultimately, the math works out in your favor, but the moment you start withdrawing, this dynamic reverses completely. 

When you sell into a declining market, you lock in losses and reduce the number of shares available to participate in any recovery. Hypothetically, a 10% decline in year one of retirement, combined with a $50,000 withdrawal, doesn’t just cost you the decline itself. Instead, it costs you every dollar those sold shares would have compounded over the next 20 to 25 years, and this is why the same 10% or 15% drop at age 35 isn’t the same as a similar drop at age 63. 

How Retirees Can Protect the Early Years

The most effective defense here is usually the most basic, in that you just shouldn’t sell during a downtown. Schwab recommends holding at least one year of anticipated withdrawals in cash, with another two to four years in short-term bonds or Treasuries. The logic here is that the average bear market recovery time from peak to peak has historically been about three and a half years, so a four-year cushion should (emphasis on “should”) cover most scenarios without forcing you to liquidate equities at the worst possible time. 

Beyond the cash buffer, flexibility matters more than most retirees realize, as Morningstar’s research indicates that every flexible spending strategy it tested supported a higher initial withdrawal rate than the fixed-withdrawal approach. Even small adjustments, like skipping an inflation increase in a down year or trimming discretionary spending by 10%, can meaningfully extend portfolio longevity. The retirees who survive the first five years aren’t necessarily the ones with the biggest portfolios, they are just the people who are most willing to adapt. 

Why This Matters More in 2026

Heading into 2026, retirees are facing an environment where this risk definitely deserves extra attention. After strong equity returns in late 2025, portfolio balances are elevated, which means the potential dollar impact of a correction is larger than it would have been two years ago. At the same time, inflation has moderated but hasn’t disappeared, all while healthcare costs are rising faster than general prices, and bond yields, while improved, are trending lower as rate cuts continue. 

None of this means that a downturn is guaranteed to arrive soon, just that the conditions are set for a sequence risk to do the most damage if one does arrive. For anyone retiring this year or in the next few years, the priority isn’t predicting what the market will do. It’s about building a portfolio that doesn’t require the market to cooperate in order to pay your bills. Cash reserves, flexible spending rules, and a diversified income strategy aren’t just nice to have, but in the first five years of not working, they’re the difference between a retirement that works and one that does not. 

 

Photo of David Beren
About the Author David Beren →

David Beren has been a Flywheel Publishing contributor since 2022. Writing for 24/7 Wall St. since 2023, David loves to write about topics of all shapes and sizes. As a technology expert, David focuses heavily on consumer electronics brands, automobiles, and general technology. He has previously written for LifeWire, formerly About.com. As a part-time freelance writer, David’s “day job” has been working on and leading social media for multiple Fortune 100 brands. David loves the flexibility of this field and its ability to reach customers exactly where they like to spend their time. Additionally, David previously published his own blog, TmoNews.com, which reached 3 million readers in its first year. In addition to freelance and social media work, David loves to spend time with his family and children and relive the glory days of video game consoles by playing any retro game console he can get his hands on.

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