Why All-Time Highs Don’t Mean It’s Time to Sell

If you’ve been following the markets lately, you’ve probably seen a lot of headlines about “new all-time highs.”

For many investors, that phrase triggers fear: “If the market is at record levels, doesn’t that mean it has nowhere to go but down?”

It feels logical, but the reality is that selling every time the market sets a new high is one of the most expensive mistakes an investor can make.

The History of All-Time Highs

Markets are supposed to hit new highs. That’s how compounding works.

If you zoom out on the S&P 500 over decades, you’ll notice something important: the index spends a surprising amount of time at or near all-time highs. Since 1950, more than 7% of all trading days have been record-setting closes. That may not sound like much, but it means that new highs are a feature of long-term investing, not a bug.

If you sold out every time stocks hit a new peak, you would’ve missed the bulk of history’s compounding.

Consider the decade from 2013 to 2023:

• The market set over 300 new highs.

• Investors who stayed invested saw their portfolios more than double.

• Investors who tried to sell at highs and “wait for a pullback” often missed the next leg up.

The point? Records don’t signal danger — they reflect progress.

Why Investors Fear Highs

The fear is psychological. People anchor to recent prices. If the S&P was at 3,800 last year and now it’s 5,500, it feels “expensive.”

But “expensive” relative to what? The economy is bigger, corporate earnings are higher, and interest rate expectations shift over time. A new high doesn’t mean the market is overpriced — it means that businesses are growing and investors are recognizing that growth.

The Cost of Market Timing

Plenty of investors think they’ll be the exception. “I’ll sell now, wait for a 10% drop, and buy back in.”

Here’s the problem: markets don’t cooperate.

Study after study shows that the biggest gains often come in short bursts — days when sentiment flips and stocks rip higher. And those days are usually right after periods of volatility, when most people are least likely to be invested.

Missing just the 10 best days in a 20-year span can cut your returns by nearly half. Missing the 20 best days? Your returns collapse even further.

The market punishes hesitation.

What You Should Do Instead

The better approach is boring but effective:

1. Stay invested in quality. Focus on companies with real earnings power, durable advantages, and long-term tailwinds.

2. Dollar-cost average. Add steadily, and add more aggressively when markets give you discounts.

3. Let compounding do its work. The magic only happens when you give it time.

The investors who build real wealth aren’t the ones who “call the top” — they’re the ones who don’t flinch when others do.

The Bottom Line

All-time highs aren’t warning signs. They’re proof the system is working. Businesses are growing, markets are rewarding them, and compounding is doing its job.

Selling out at highs might feel safe in the moment, but over the long run it usually means missing the very returns you’re investing for in the first place.

Surmount

For investors who don’t want to constantly second-guess when to buy or sell, tools like Surmount are worth a look. Their platform runs automated, backtested strategies directly in your brokerage account — so you don’t have to stress over timing or emotions.

It’s simple, beginner-friendly, and built on logic instead of headlines.

I’ll be launching my own strategy on Surmount soon, so if you’re wanting to check it out here it is: https://surmount.ai/strategies?utm_source=newsletter&utm_medium=promo&utm_campaign=ashton