The S&P 500 just closed at another all-time high.

Cue the headlines. Cue the opinions.

And for many investors? Cue the hesitation.

When markets are setting records, it can feel like the worst possible time to invest new money.

After all, nobody wants to buy at the top.

But here's the thing: All-time highs are not rare.

In today's email, I'm sharing why all-time highs are more like mile markers on a long journey.

3 Overlooked Threats to a Fulfilling Retirement In this episode, I’m revealing 3 retirement regrets that many people overlook until it’s too late. I’m also sharing how to avoid the same mistakes so YOUR retirement is fulfilling rather than filled with regret. 🎙️ Listen now on ​Apple​, ​Spotify​, or ​YouTube​.

(📚 Reminder: Don't miss the "What I've Been Reading" section included at the end of every newsletter.)

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All-Time Highs: What Should You Do?

From 1950 to 2024, the S&P 500 has reached over 1,250 record highs.

That’s over 16 new highs per year, on average.

So if you’re thinking, “Maybe I’ll wait for a better entry point,” you’re definitely not alone.

But let’s break it down…

Investing at all-time highs has actually produced solid results, often not much different from investing at any random time.

More specifically, here’s how those returns compare:

• 1-year holding period: 11.2% after all-time highs vs. 12.6% for ALL periods
• 3-year holding period: 10.9% vs. 11.5%
• 5-year holding period: 10.3% vs. 11.3%2

In other words, investing at a market high has been just slightly below average… still solid, and far from concerning.

There’s more.

Since 1950, the market has dropped more than 10% in the year following an all-time high only 9% of the time. 🤯

Look out 10 years, and the S&P 500 has never ended that period more than 10% down after any of its record highs.

That’s a powerful reminder for long-term investors.

Waiting to invest because prices are high is like waiting to fill your gas tank until prices drop.

You might save a little.

Or you might make the road trip take longer than planned.

Yes, the market could pull back. But it might not.

And sitting on the sidelines while prices climb can be more costly than it seems.

Bottom Line

I’m not saying to chase the highs.

I’m not saying you should try to time the market.

And I’m definitely not saying these historical returns will play out the same way in the future.

But I am saying this:

History shows that investing at all-time highs has not been as risky as many investors assume.

It’s been, at least historically, a reasonable time to invest. And for long-term investors, it has often worked out just fine.

📚 What I've Been Reading

• America Has Become Vastly Richer Than Europe (Yascha Mounk)
• Even God Would Get Fired as an Active Investor (Alpha Architect)
• Social Security's 2025 Financial Outlook (Center for Retirement Research)
• Want a Better Relationship With Your Children? Exercise With Them (WSJ)
• Are You Examining the Emotional Costs In Your Life? (Justin Welsh)
• You Better Start Moving If You Want to Live Longer (Outside.com)

Thank you for reading!

Please reply to this email with comments, questions, and/or feedback.

Stay wealthy,

Taylor Schulte, CFP®