The Market Is at an All-Time High. Should You Sell?
It’s the question landing in our inbox more than any other right now. Nearly every major index is sitting at or near a record, and after a run like this, the instinct is almost reflexive: buy low, sell high — well, we’re at the high, so… sell?
This week on Money On Tap, Ben Brayshaw and Dan Michelon take that question apart — with a lot of history, a few statistics that genuinely surprised us, and a clear-eyed look at what a record high actually means for you, depending on where you sit in life.
Fear and Greed Are Both in the Room
When someone opens a statement and sees the biggest number they’ve ever seen, there are really only two reactions.
The first is fear: This is the most I’ve ever had. I don’t want to lose any of it. How do I lock it in? The second is greed: This is going so well — how do I get more?
Almost no one is purely one or the other. We all carry some blend of the two, and that blend — not the headline — is what quietly drives most investment decisions. Understanding which one is talking when you look at your account is the first real step.
The Statistic That Breaks Everyone’s Intuition
Here’s the data point that stops people cold.
Fidelity looked at investors going all the way back to 1950 and compared people who invested specifically at an all-time high against people who invested on any random day. The all-time-high investors didn’t do worse. They did about a tenth of a percent better.
A separate study found that buying at all-time highs generated roughly 14.6% average one-year returns, versus 11.7% for buying on a random trading day.
Read that again, because it runs against every instinct. You would expect a penalty for buying at the top. The history says the opposite. A record high is usually a signal of a healthy economy — and healthy economies tend to keep being healthy for a while.
A Quick Walk Through History
The fear of buying high is old, and history keeps embarrassing it. A few stops on the tour from the show:
1982 — the bull begins. Coming out of the late-’70s oil shocks and stagflation, the S&P sat around 102 in August 1982. Twelve months later it was near 166 — a 63% one-year gain. Five years in, it was near 273, a 168% five-year gain. Anyone who said “I missed the boat” in 1983 then watched the boat sail for the better part of 18 years.
1987 — Black Monday. In October, the S&P fell roughly 33% and the Dow dropped 22% in a single day. People declared the bull dead. Instead, the S&P rose 17% over the next 12 months and 53% over the next three years — and the bull ran another 13 years. A brutal day is not always a harbinger.
1995–1999 — the internet era. The S&P rose 34% in 1995, then 20%, 31%, 27%, and 20% — five straight years above 20%, a cumulative gain of roughly 250%. Each year, plenty of people decided it had “gone too far.” Each year, it went further.
2000 — the dot-com peak. This is the one that was different. Companies with no profits and little revenue carried billion-dollar valuations. When it broke, the S&P was down about 10% twelve months later and the Nasdaq was down roughly 60% within two years. Innovation drove an 18-year bull — but innovation alone, with no earnings underneath it, wasn’t enough.
2009 and 2020 — the crashes that recovered fast. In the 2009 financial crisis the market lost 38–40%; twelve months later the S&P had gained 76%, and five years later it was up 200%. In the 2020 COVID crash the market fell about 34% in just over a month — and was up 74% twelve months later, sitting more than 50% above its pre-pandemic high within three years.
Why Today Looks More Like 1995 Than 2000
The easy, knee-jerk comparison is the dot-com bubble: tech is tech, so this must be the same. We think that’s lazy, and the difference matters.
In 1999, the high-flyers were often pure speculation — a couple of people, an idea, and a “.com” at the end of the name. There was no meat on the bone. When earnings never showed up, the companies simply vanished.
The AI leaders are the opposite. They’re Google, Amazon, Apple, Meta, Nvidia — mature giants with real, profitable businesses that exist with or without the AI build-out. They aren’t raising your capital to get off the ground; they’re spending their own war chests, which means real skin in the game and real scrutiny on every dollar of return.
The parallels to 1995 are striking: an infrastructure boom, massive technology spending, and real productivity gains. If anything, on the AI timeline we’re closer to discovering the internet than to washing out its failures. We haven’t even reached the stage of sorting what works from what doesn’t.
Timing the Market Is a Loser’s Game
The thread running through every one of those eras is the same: the people who jumped out to avoid the next drop usually missed the next several gains. Miss just a handful of the market’s best days — and they cluster right after the scary ones — and your long-term return falls off a cliff. You have to be in it to win it.
That is not the same as saying never take a profit. We trim positions all the time — we did exactly that in our value portfolio recently — but not out of fear. We trim because a winner has grown into an oversized slice of the pie, and rebalancing it back into line is simply good discipline. Put a chip down, win, take your original chip back, and keep playing with the house’s money. That chip in your pocket is called diversification.
If You’re Near or In Retirement, This Is Different
Everything above assumes you have time. If you’re 25 with three decades ahead, the honest advice is usually simple: be in the market and ride the waves.
But if you’re five years from retirement — or already in it and drawing income — a record high carries a different weight, and the math changes. This is where sequence-of-returns risk lives.
We have a short video on the Brayshaw Financial website that shows it better than any paragraph can: a brother and sister who retire just three years apart. The brother starts drawing income into a rising market and ends up a millionaire. The sister retires three years later into a downturn, draws less income than he did — and still runs out of money. Same family, same idea, wildly different outcomes, all driven by what the market did in the first few years of withdrawals. (If you’ve never watched it, it’s about three minutes and genuinely worth it.)
The lesson we’ve seen play out in real lives: the person who stared at a 38% loss in 2008–2009, panicked, and pulled their money out often didn’t reinvest for three, four, five years — and missed the entire recovery. Avoiding that mistake is worth more than catching any single rally.
Tools That Let You Stay In Without the Full Risk
If you want market participation but can’t stomach a 2009-style hit this close to retirement, you have more options than most people realize.
- Buffered ETFs. These have gained real mainstream traction recently. The trade is straightforward: you accept a cap on the upside (say, 18% for the year) in exchange for downside protection. If the market drops 10% and you have a 10% buffer, you lose nothing for the year. You give up the home-run year to put guardrails under the bad one.
- Annuities with lifetime income riders. Used selectively, these can turn “I don’t have enough to retire” into a real, guaranteed paycheck. Some prioritize preservation, some maximize distribution, and some attach long-term-care riders that boost your income if a care event hits.
These instruments are relatively new to mainstream planning, the field of options changes almost daily, and the competition among product designers is fierce. That’s exactly why this is a conversation to have with someone who lives in this end of the market — the gap between what exists and what actually fits you is enormous.
The Bottom Line
A record high is not a sell signal, and it’s not a green light either. It’s a moment that asks a better question: given my time horizon, my income needs, and my temperament, what’s suitable for me right now?
If a 20% pullback wouldn’t surprise us, neither would a 30–40% upswing. Both are on the table. The point isn’t to predict which — it’s to build a portfolio that can weather either and still deliver the income you need.
Don’t be afraid to ask, and don’t be afraid the market won’t deliver. Answers exist. Solutions are out there. The hard part is knowing which ones fit your story — and that part you don’t have to do alone.
Be informed. Be intentional. Be a good steward of what you’ve been entrusted with.
Next Steps
If you’d like a real look at how your portfolio is positioned for this market — including a sequence-of-returns stress test, a downside-protection review, and a look at whether buffered or guaranteed-income tools fit your plan — we invite you to schedule a conversation with our team.
Call: 855-226-8551
Email: info@yourmoneyontap.com
Frequently Asked Question
Is it a bad idea to invest when the stock market is at an all-time high?
Historically, no. Research from Fidelity covering investors since 1950 found that money invested at an all-time high performed about a tenth of a percent better than money invested on a random day, and a separate study found all-time-high investing produced roughly 14.6% average one-year returns versus 11.7% for a random trading day. The reason is that record highs typically reflect a healthy, expanding economy, and healthy economies tend to continue. A record high should prompt a suitability question based on your time horizon, income needs, and risk tolerance — not an automatic decision to sell. For investors near or in retirement, the more important issue is sequence-of-returns risk, which can be managed with diversification, downside-protection tools like buffered ETFs, and guaranteed-income strategies.
Money on Tap is your trusted resource for investing, retirement planning, and building long-term financial confidence.