Missing the Best Days is (Still) a Myth – and Why it Matters for Your Retirement

By: Adam D. Koós, CFP®, CMT®, CFTe, CEPA

Every time the market gets bumpy, Wall Street pulls the same old chart out of the drawer… the one warning investors that if they “miss the best days,” their long-term returns will collapse.

I’ve been seeing this for more than 24 years now… and somehow, the concept refuses to die.

The problem isn’t the chart itself.  Rather, it’s what the chart doesn’t show you.

Because when you expand the lens (when you zoom out, add context, and look at the market through a grown-up statistical microscope) a very different picture starts to emerge.

And after another decade of fresh data (and an enormous amount of work from Vince Randazzo, CMT®, along with Ryan Gorman, CMT®, CFA, and Shawn Keel, CMT®, CFA, who graciously permitted me to reuse portions of their research), the truth behind “the best days” myth is even clearer than it was back when I first wrote about it in 2015, which, at the time, was a redux of the original white paper written by Paul Gire in 2005.

Let’s dig in… because once you see the full picture, the old narrative falls apart fast.

The Myth: You Must Stay Fully Invested or You’ll Miss the Best Days

Here’s the sales pitch most people have seen:

“If you miss just the 10 best days in the market over the last 20–30 years, your long-term return drops dramatically… so you should always stay invested.”

This message is usually surrounded by mountain charts, pie charts, and a gentle nudge to keep your money exactly where it is, often in whatever mutual fund, annuity, or managed account generated the chart in the first place.

What they don’t mention is where these “best days” come from…or what else is happening around them.

The Reality: The Best Days Happen During the Worst Market Environments

When Randazzo re-ran the numbers all the way through 2024, the results weren’t just interesting… they were damning for the old narrative.

Here’s what the data shows for the S&P 500 over the past 30 years:

📊 TABLE 1 — Where the 20 Best and 20 Worst Days Actually Occurred

Summary:
The biggest up-days and the biggest down-days almost all occur during the same chaotic, high-volatility periods, not during calm, healthy uptrends.

📈 FIGURE 1 — S&P 500 Price with Best/Worst Days Highlighted

Summary:
The chart looks like someone splattered red and green paint all over the ugliest parts of the bear markets. Times during high drama, high tension, and virtually zero stability.

So, this is the point that Wall Street sales literature quietly skips:

You only experience the “best days” if you’re willing to sit through the worst days wrapped around them.

And those worst days matter a lot more than most people realize.

Volatility Isn’t Just Uncomfortable — It’s Mathematically Devastating

Let’s slow down and talk about the math for a second.

• If your portfolio drops 10%, you need an 11.1% gain to get back to even.
• If it drops 20%, you need 25%.
• A 50% drop? …now you need 100% to break-even

…and heaven forbid you’re taking withdrawals from your portfolio to supplement your retirement income, but I digress.

This isn’t pessimism… it’s arithmetic.

And the more volatile your portfolio becomes, the more those asymmetries start to eat away at the long-term compounding value of your retirement portfolio.

Randazzo visualized this beautifully in a Monte Carlo simulation.

📈 FIGURE 2 — Same Average Return, Different Volatility (30-Year Outcomes)

Summary:

• At low volatility, the outcomes cluster tightly around the median.
• At high volatility, outcomes explode… some great, many disastrous.
• Even with the SAME average return, volatility alone determines your fate.

This is why retirees feel blindsided by sequence-of-return risk.  It’s not the averages that inflict the pain, it’s the sequence of returns.

The Most Important Chart Wall Street Never Shows

People love talking about missing the 10 best days… but you never see a chart about missing the worst days.

Thankfully, we’ve once again, re-created one of the cleanest versions the public has ever seen.

📊 FIGURE 3 — Terminal Value of $100 (1988–2023)

Effect of Missing Best Months, Worst Months, or Both

Source: Bloomberg and Norgate data, 1988 – 2023

Summary:

Said another way, avoiding the worst periods is more than 3x more powerful than capturing the best periods.

This is the death blow to the old, stale, sales-ridden talking point.

Because if you’re already showing people how much they “lose” by missing the best days…
you owe them the honesty of showing what happens when they miss the worst days too.

So Why Does Wall Street Keep Pushing the Best-Day Narrative?

As my dad used to say when I was a kid: “Follow the money.”

Buy & Hold is easy.  It’s scalable.  It’s profitable.

And it’s very comfortable (not to mention “convenient”) for:

• Mutual fund companies
• Insurance carriers
• Asset-gatherers, as well as
• The financial advisors and brokers that big Wall Street firms train

But here’s the quiet truth:

No investment product manufacturer benefits when you sell or reduce your exposure to their investments during high-risk periods.

That doesn’t necessarily make them villains.

It just means you’ve gotta’ look out for yourself… because the industry’s incentives won’t.

A More Honest, More Complete Understanding of Market History

When you step back and look at the full 30-year dataset, here’s what jumps off the page:

1. Market returns are path-dependent.

• The order of returns matters enormously, and averages hide this.

2. Extreme volatility clusters during major downtrends.

• The “best days” and “worst days” are fraternal twins.

3. Drawdowns dictate long-term financial outcomes.

• Not annual returns.
• Not averages.
• Drawdowns.

4. Investors don’t need to perfectly time anything.

• They just need to avoid the worst market regimes and times of extremely high market volatility, especially during downtrends, not chase the best days.

So… What Should Investors Take Away From This?

• No, this isn’t a call to day-trade.
• No, you don’t need to predict market peaks or bottoms. and
• No, you don’t need A.I., a palm reader, or any sort of clairvoyance.

You simply need to manage risk with the same seriousness that you manage returns.

Because the old narrative (the “don’t miss the best days in the market” warning) is only half the story… and half-stories create bad decisions.

The full story says something very different:

• The best days almost always occur in terrible markets
• Missing the worst days (not capturing the best) is what transforms outcomes
• Volatility isn’t just uncomfortable… it’s corrosive
• It’s impossible to miss either the best or the worst days in the market, but
• It is possible to miss both the best and worst days in the market by avoiding these prolonged, extreme volatile times when the market is in a downtrend, and
• Risk management isn’t market timing.  It’s stewardship of your hard-earned life savings

At the end of the day, investors deserve more than a sales slogan.

They deserve the truth… the whole truth.  And a framework that respects both sides of the volatility coin.

If there’s one thing the last 30 years of data screams loudest, it’s this:

Your long-term success, especially near or in retirement, depends more on avoiding deep drawdowns than on obsessing over capturing the best days in the market.

And that’s a message worth repeating… even a decade later.

Adam Koos, CFP^®, CMT, CFTe, CEPA is a CERTIFIED FINANCIAL PLANNER^TM, one of approximately 3,000 active Chartered Market Technicians (CMT) worldwide, as well as a Certified Financial Technician (CFTe^®) through the International Federation of Technical Analysts (IFTA), and a Certified Exit Planning Advisor (CEPA) via the Exit Planning Institute.  In July, 2014, he was named by Columbus Business First as one of their 20 People to Know in Finance for 2014, was a recipient of the Forty Under 40 award in November of 2011, was ranked by Investopedia in July of 2017 as one of the Top-100 Most Influential Financial Advisers in the U.S. for 2017, his company is a 7-time winner of Columbus CEO Magazine’s “Best of Business” Awards for “Best Private Wealth Management Firm” (2010-2014, 2019, and 2024), a winner of Columbus Business First’s “Fast 50,” representing the fastest growing companies in central Ohio (2025), and is still the only financial planning and investment management firm in central Ohio to ever win the coveted Better Business Bureau Torch Award for Ethics and Trust (2011).  Adam serves his clients as the president and portfolio manager at Libertas Wealth Management Group, Inc., a NAPFA-affiliated, Fee-Only Fiduciary and Registered Investment Advisory (RIA) firm, located in Columbus, Ohio.