You’ve probably heard it before:
“If you miss the 10 best days in the market, your returns will be crushed.”
It’s one of the most repeated stats in investment brochures. And on the surface, it makes a compelling case for staying fully invested all the time. But here’s the part they rarely tell you:
Those ‘best days’? They almost always happen during the worst markets.
If you’re in or near retirement, that detail changes everything.
The Myth: “Stay Invested or Lose Out”
The “missing the best 10 days” myth has long been used to promote a passive, buy-and-hold strategy. The logic is simple: since it’s impossible to predict when the market will jump, you should always stay in just in case.
But this logic hides a hard truth:
To catch the market’s best days, you almost always have to live through its worst ones too.
The Reality of Volatility Clusters
Markets don’t move randomly. They move emotionally. And when fear hits, volatility spikes in both directions. This is what researchers call “volatility clustering.”
In other words, the best and worst days often happen side by side, usually during bear markets.
Take a look at this chart showing S&P 500 movements from 2000–2013:
Green dots represent the 10 best days in the S&P 500 over a 13-year period.
Red dots are the 10 worst days during that same time.
The yellow rectangles highlight three major downturns:
- The Dot-Com Crash (2001–2003)
- The Global Financial Crisis (2008–2009)
- The sharp 2011 market correction
Here’s what’s striking: 19 out of the 20 best and worst days occurred during those three bear markets.
And when you expand the view to the top 50 best and worst days, the pattern gets even clearer: 92% of the best days (46 out of 50) happened during market crashes. So did 88% of the worst days (44 out of 50).
If your retirement plan can’t absorb a 30–50% drawdown just to capture a handful of up days, “just staying invested” isn’t a strategy. It’s a risk.
Why This Matters More in Retirement
When you’re still in your earning years, market volatility is easier to stomach. You’ve got time to recover from downturns, and you’re still contributing to your portfolio—buying more at lower prices.
But once retirement is in sight or already here, timing risk becomes everything.
You’re no longer just growing your nest egg. You’re protecting it. You’re depending on it. You’re drawing income from it.
This makes timing risk, particularly the risk of early losses, devastating.
If you withdraw money during a major drawdown (aka sequence risk), your portfolio has to work much harder just to break even. And if your strategy is “stay the course no matter what,” you could be exposing decades of savings to a market event that reshapes your retirement timeline.
So, if the best and worst days come bundled during bear markets, what should retirees actually do?
The Smarter Approach: Align, Don’t Predict
Forget trying to time every market top and bottom.
Forget staying fully exposed no matter what.
There’s a middle path—alignment.
At Retiresure, we use what’s called a Relative Strength approach.
Rather than guessing what the market might do, we track what it is doing right now.
It’s a rules-based, unemotional strategy that follows actual money flows across sectors and asset classes.
Think of it as your financial weather radar, showing where capital is strengthening and where risk is building.
This allows us to:
- Increase exposure when trends are strong
- Reduce exposure when risks are elevated
- Help clients grow their assets and protect their income during downturns
No predictions. No crystal balls. Just data and discipline.
The Bottom Line
You don’t need to chase the market’s “best days” if you can sidestep the worst periods, especially when retirement security is on the line. Outperformance doesn’t come from catching every up day. It comes from avoiding the worst ones.
We believe in strategies built for real life, not investment theory. Let’s see how we can align your portfolio with the market, not ride its every wave.
Get in touch with us today to explore whether your current strategy is protecting your future or just hoping for the best.