If you're waiting for a crash to buy in, you probably won't

I have friends who have been sitting out of the market for over a decade. Every time I bring up investing, the answer is the same: “I’m waiting for a drop.”

Fair enough. Sounds reasonable. Buy low, sell high. Wait for things to go on sale. It’s the kind of logic that works at every store in the world.

Except the stock market isn’t a store. And in the ten years they’ve been waiting, we’ve had plenty of drops. A nasty correction in late 2018. The fastest crash in history in March 2020. A brutal 2022 where the S&P 500 fell over 25%. Tariff-driven chaos in early 2025 that wiped out months of gains in a week.

Those same friends didn’t buy during any of them.

The problem with waiting for a sale

When people say they’re waiting for a crash, they’re imagining a very specific scenario. The market drops, they calmly step in, buy everything at a discount, and ride it back up. It’s a clean, rational picture.

But that picture leaves out the most important part: what the world looks like during that drop.

A crash isn’t a markdown sticker on a stock price. It arrives with layoffs and hiring freezes. With headlines about recessions and bank failures. With your group chat full of people panicking about their own portfolios. Sometimes with a global pandemic that shuts down the entire economy.

The crash my friends were waiting for did happen. More than once. But it never felt like a buying opportunity. It felt like the worst possible time to put money at risk.

You’re already experiencing it in real time

This is the part I think gets missed the most. People imagine a crash as something they’ll observe from a distance and act on rationally. But you don’t observe a crash. You live through it.

In March 2020, I wasn’t sitting at my desk thinking “what a great time to invest.” I was watching the NYSE halt trading because stocks were falling too fast. Canadian banks, the safest stocks most people can name, were dropping 15% in a single day. Airlines fell 40%. Oil prices literally went negative.

My own portfolio was deep in the red. I didn’t know if my industry would survive the pandemic. Nobody knew how long the world would be locked down, or what the economy would look like on the other side of it.

I stayed invested. I even bought more. But I want to be honest about that: it didn’t feel smart at the time. It felt uncomfortable. Almost reckless. The only reason I did it was because I’d been investing long enough to have a framework for these moments, and I trusted the framework more than I trusted my nerves. Even then, it was hard.

If that’s how it felt for someone already in the market, imagine how it feels for someone who’s been cautious with money their whole life. Someone who’s been waiting years for “the right time.” You think that person is going to look at a world that feels like it’s falling apart and suddenly go all in? That’s not how caution works.

The ten-year cost of waiting

Let’s make this concrete. Say someone had $50,000 to invest in 2016 and decided to wait for a crash. They wanted at least a 20% drop before they’d get in.

We got that drop in 2020. But let’s say they didn’t invest then either, because it didn’t feel safe. So the money sat in a savings account for ten years.

If they’d invested that $50,000 in a broad market index fund in 2016, even with all the crashes in between, they’d be looking at a portfolio worth well over $100,000 by now. Some estimates put it closer to $120,000, depending on reinvested dividends. Instead, their savings account earned them maybe 2% per year. That $50,000 became roughly $60,000.

The difference is $50,000 to $60,000 in “safe” returns. That’s the cost of waiting. Not because the crashes didn’t happen, but because the growth between the crashes dwarfed the drops.

Why cautious people don’t suddenly become bold

There’s a specific type of person who says they’re waiting for a crash. They’re usually careful with money. Risk-averse. They think things through, maybe overthink them. That caution is exactly why they haven’t invested yet.

Here’s the contradiction: a market crash is the single most stressful financial environment possible. Everything that makes a cautious person cautious gets amplified during a crash. The uncertainty is higher. The stakes feel bigger. The fear is everywhere.

If you can’t bring yourself to invest when things are calm and the market is going up, you’re not going to flip a switch and buy stocks while the news is telling you the financial system might be collapsing. That’s not a criticism. It’s just how people work. Caution doesn’t evaporate because prices are lower. If anything, it gets louder.

The crashes keep proving this

I’ve watched the same pattern repeat across every downturn I’ve been alive for.

In late 2018, the S&P 500 dropped about 20% in three months. Friends who’d been “waiting for a dip” didn’t buy. “It could go lower.”

In March 2020, the market dropped 34% in five weeks. That was the sale of a lifetime. Those same friends didn’t buy. “Nobody knows how bad this pandemic will get.”

In 2022, a slow, grinding bear market dragged on for months. Stocks were meaningfully cheaper than they’d been the year before. Still nothing. “Interest rates are going up, it’s not the right time.”

In early 2025, tariff announcements sent stocks tumbling. “Too much uncertainty right now.”

There’s always a reason not to. That’s the entire point. If there were no reason to worry, prices wouldn’t be down. The discount and the fear are the same thing.

What actually works instead

I understand the instinct to wait. And I should be clear: this article is about people who have money to invest but keep putting it off. If you’re still building savings or don’t have the financial room yet, that’s a completely different situation, and none of this is aimed at you.

For the people who do have the room but keep waiting for the right moment: nobody wants to invest at the top. Nobody wants to watch their money go down right after they put it in. That fear is real and it makes sense.

But here’s what I’ve learned: the alternative to timing the market isn’t recklessness. It’s consistency.

The people I know who’ve built real wealth through investing didn’t do it by catching a crash at the bottom. They did it by starting and not stopping. They invested a little every paycheque, whether the market was up, down, or sideways. Some months they bought at a high. Some months they bought at a low. Over years, it averaged out, and the direction was up.

That approach doesn’t require courage. It doesn’t require timing. It doesn’t require you to make a big, bold move during the scariest financial moment of the decade. It just requires showing up regularly.

The friend who finally started

One of those friends I mentioned at the beginning did eventually start investing. Not during a crash. Just on a random Tuesday after we’d talked about it one too many times. He set up automatic contributions and stopped trying to find the perfect entry point.

He told me later that the thing that changed his mind wasn’t any particular market event. It was doing the math on what his savings account had earned him over the last seven years and realizing he’d been optimizing for a moment that was never going to feel right. The “right time” wasn’t a price level. It was whenever he stopped waiting.

If this sounds like you

If you’ve been sitting on the sidelines waiting for a drop, I’d ask you this honestly: what would the crash actually need to look like for you to invest?

Think about it specifically. How far would markets need to fall? What would the headlines say? What would your friends be doing? What would your own job security look like?

If the answer is “I’d need prices to be low but everything else to feel fine,” that’s not a crash. That’s a fantasy. Prices are low precisely because everything else doesn’t feel fine. That’s how markets work.

The crash you’re waiting for isn’t going to feel like an opportunity. It’s going to feel like a reason to keep waiting. And if you keep waiting for it to feel right, you might never start. The best time to invest was years ago. The second best is whenever you stop waiting for the perfect moment.

This isn’t financial advice. It’s just what I’ve seen happen to people I care about, and what I’ve learned from my own experience sitting through the moments they were waiting for.