The S&P 500 is at an all-time high. The FTSE 100 isn't — it's been flat for years, but that's a different post — but the US index that dominates global market capitalisation is sitting at or near record levels. And if you're looking at your screen wondering whether now is really the right time to invest, you are not alone. This is the single most common question I get from people who are ready to start investing but paralysed by the fear of buying at the top. I understand the fear completely. I've felt it myself, many times. But the data on this question is remarkably clear — and the conclusion is not what your instincts are telling you.
── The Market Is Frequently At All-Time Highs ──
Here's a fact that surprised me when I first learned it and still surprises most people I share it with: the US stock market has been at or near an all-time high roughly 30% of the time over the past century. Not once a decade. Not occasionally. About a third of all trading days. The market trends upward — that's the whole reason we invest in it — and an upward-trending line touches new highs regularly. The chart that looks terrifying when you zoom in on the last six months looks like a gentle slope when you zoom out to 30 years. The all-time highs that feel dangerous in the moment are, with the benefit of hindsight, just points along the path.
From 1950 to the end of 2025, the S&P 500 has hit over 1,200 all-time highs. That's about one every 15 trading days. The market is at a record level, on average, more than once a month. If you waited for a pullback before every investment, you would have spent most of the last 75 years sitting on cash while the market climbed without you.
── The Data: Investing Only At All-Time Highs ──
There's a famous piece of analysis — it's been written up by Ben Carlson, Nick Maggiulli, and others — that asks a deliberately provocative question: what if you were the unluckiest investor in history? What if you only ever invested lump sums at the exact moment the market hit a new all-time high, right before every crash? Surely that would be disastrous, right?
The answer is: it would have been fine. Better than fine, actually. If you had invested $10,000 in the S&P 500 only at all-time highs from 1970 to 2020 — literally picking the worst possible days to invest — and then left the money untouched, you would have ended up with a substantial sum. Not as much as someone who invested regularly at all prices, but far, far more than someone who stayed in cash waiting for the 'right' time. The point is not that all-time highs are the best time to invest. The point is that even the worst possible timing, over a long enough period, is rescued by the market's long-term upward trajectory. Your time horizon matters more than your entry price.
Let me contextualise this for a UK investor. The S&P 500 has been hitting all-time highs regularly throughout 2025 and 2026. If you'd told someone in January 2025 'the market is at an all-time high, you should wait', they would have missed the subsequent gains. If someone had told me in 2016 'don't buy VUAG, the market is near all-time highs and Brexit just happened', I would have missed roughly a decade of extraordinary S&P 500 returns. Every all-time high in history eventually became just a point on the chart. The ones we're looking at now will look the same way in 2036.
── The Story of Bob, The World's Worst Market Timer ──
There's a story that makes the rounds in investing circles — originally from a financial planner named Ben Carlson — about an imaginary investor named Bob. Bob started investing in 1973, right before the 48% bear market that followed the oil crisis and Nixon shock. He invested his entire savings at the market peak and watched it get cut in half. Then Bob did the same thing in 1987 — invested a lump sum right before Black Monday. Then again in 2000, right before the dot-com crash. Then again in 2007, right before the financial crisis. Bob only ever invested at the absolute worst possible moments — the market peaks right before the most famous crashes in modern history.
Bob never sold. He never panicked. He just left the money invested. And by the time he retired, Bob was a millionaire many times over. The original analysis had Bob investing $184,000 total across four perfectly-timed (badly-timed) lump sums over 42 years — and ending up with roughly $1.1 million. The maths is simple: the market recovered from every crash and continued to new highs. Bob's timing was atrocious. His patience was extraordinary. And patience beat timing — as it always does, given enough of it.
The lesson isn't that you should try to be Bob. It's that even if you somehow managed to be the unluckiest investor alive — investing only at peaks — the long-term upward trend of global capitalism would still bail you out. The real catastrophe isn't investing at an all-time high. The real catastrophe is never investing at all because you're waiting for a pullback that might not come, or might not be deep enough, or might arrive after the market has climbed another 30% first.
── What 'Waiting For A Crash' Actually Costs ──
Let's say you have £20,000 to invest today and the S&P 500 is at an all-time high. You decide to wait for a 10% correction — a sensible-sounding, seemingly prudent strategy. The problem is you have no idea when that 10% correction will arrive. It might be next month. It might be in two years, after the market has risen another 35%. If the market rises 20% over the next 18 months and then corrects 10%, you're buying in at a price that's still 8% higher than today's 'all-time high' that scared you off. The correction arrived — and you would have been better off investing immediately and enduring it.
This is not a theoretical scenario. This is exactly what happened to anyone who 'waited for a dip' during the post-COVID recovery. The S&P 500 bottomed in March 2020. By August 2020 it was back at all-time highs. Anyone who thought 'it's come too far too fast, I'll wait for a pullback' watched the market rise another 25% before the next meaningful correction arrived — and that correction didn't even take prices back to August levels. The dip they were waiting for never came. The market moved on without them.
The numbers make this concrete. Between 1928 and 2025, the S&P 500 has experienced 26 bear markets (a decline of 20% or more). That's about one every 3.7 years. But they don't arrive on schedule. The gap between bear markets has been as short as a few months and as long as over a decade. And after every single bear market, the index has recovered to new highs. Every. Single. One. Waiting for a crash is a strategy of indefinite deferral — and indefinite deferral, in investing, is just another name for never getting started.
── What I Actually Do ──
I buy VUAG every single week. Every week. When the S&P 500 is at an all-time high, I buy VUAG. When it's fallen 15% and the news is terrifying, I buy VUAG. When it's climbing relentlessly and feels 'overbought', I buy VUAG. When it's crashing and everyone is panicking, I buy VUAG. The price I pay is whatever Mr Market is offering that day. I do not check whether it's an all-time high before I buy. I do not look at a chart. I do not read any analysis about where the market 'should' be based on valuations or technical indicators or anything else.
This is not because I think all-time highs are irrelevant. They're not — valuations matter, and elevated valuations do historically imply lower forward returns over the medium term. But I cannot predict the timing or magnitude of those returns with any useful accuracy, and neither can anyone else. So I default to the only strategy that doesn't require prediction: buy the index every week, forever, regardless of price. Pound-cost averaging smooths the entry. A long time horizon smooths the volatility. And the weekly discipline removes the paralysing question — 'is now a good time?' — from my decision-making entirely.
If I were investing a very large lump sum — say, £200,000 from an inheritance or a property sale — I might not invest it all on a single day at an all-time high. I'd probably deploy half immediately and DCA the rest over 6-12 months, as I've written about elsewhere. But for the regular, weekly contributions that form the backbone of my investing, the price is the price. I don't think about it. I just execute.
── The Bottom Line ──
All-time highs feel dangerous because our brains are wired to spot patterns, and the pattern of 'things that have gone up a lot' looks like 'things that are about to go down'. Sometimes that pattern is correct — corrections do happen, and they're normal. But the pattern is wrong often enough — and the cost of being wrong is high enough — that waiting for a crash before investing has been, historically, a wealth-destroying strategy. The market spends about a third of its time at or near all-time highs. It recovers from every crash it has ever experienced. And the single most important variable in long-term returns is not entry price — it's time in the market.
If you have money to invest and you're paralysed by the fear of investing at the top: start small. Set up a monthly direct debit. Buy a global tracker or the S&P 500 at whatever price it happens to be. In 20 years, the exact price you paid this week won't matter. What will matter is whether you started. The best time to invest was 20 years ago. The second best time is today — even at an all-time high.
As always: nothing here is financial advice. All investing carries risk — you can lose money, and past performance does not predict future returns. The historical examples and the Bob story describe past market behaviour; future markets may behave differently. The S&P 500 is concentrated in US equities and carries currency risk for UK investors. Do your own research.