How to Invest When the Market Feels Too Expensive

Added: 2026-05-30

[00:00:00]I think one of the biggest reasons people never start investing is because the market always feels too expensive.

[00:00:05]Every time you see that the S&P 500 is hitting all-time highs, people tend to say to themselves that like, okay, there's no way this is going to continue. This cannot keep going up. And then they'll think to themselves, oh well, like I already missed the market running up, so I'm just going to wait for the crash or I'm going to buy once things calm down and the market is not on such a crazy, you know, increase and a crazy run. And I think a lot of people are definitely feeling this way right now. I mean, the last crash we had was in 2022, and the market has had a crazy run since then. I mean, sure, we've had little like 5 to 10% dips, like the war earlier this year, the market dropped a little bit, as well as last year, we had the tariff selloff, but nothing really big that was like 20, 25, 30%. And the weird thing that a lot of people don't realize is the market actually spends a lot of its time near all-time highs.

[00:00:49]Like, when we go on a bull run, when we have a couple of consecutive years of the market doing well, it's common for the market to hit all-time highs month in and month out. That's not an unusual thing. And a lot of times those prices that you think are expensive today, once a few years goes out, then you look back at those prices and you start to think, damn, that was cheap. I should have been buying more then. And so that is exactly what we're going to be talking about today is like, how do you invest when the market feels pretty expensive? And I personally think waiting for a market crash, it's not the right move because you could be waiting for a long time and by the time the market crashes, it would have just been better to have just been buying consistently all along. So before we jump into the video, comment down below. Have you ever hesitated to invest because the market felt like too expensive or it just felt too high? I know for me early on I kind of felt that way after the COVID crash because the recovery in 2020 was insane. I mean the market bounced back almost immediately.

[00:01:37]But since then I don't really feel that way anymore cuz I am always buying whether we have a good year, a bad year, an okay year. I am always buying. That is what works for me. So the first thing I want to actually talk about here is why does investing during all-time highs why is it so daunting? Like why is it such a scary feeling? I think one of the first things that we can connect this to is a lot of times people are emotional with their money. And it makes sense why. Like if you invest $10,000 and the market drops 25%, it's not good seeing yourself lose $2,500 in a year. Like you want to make money. That's the whole reason all of us are investing. And I think people associate the market being at all-time highs as a danger thing.

[00:02:12]Like in their mind, it's like, oh well, it has to crash. Something has to come tumbling down. Even though it's pretty normal for the market to hit all-time highs, it's not an unusual thing at all.

[00:02:21]And a lot of times people will say to themselves, "Well, I'm going to start investing after the market crashes." And I do feel like a lot of people just wish that they had been buying more. Like hindsight's always 2020. And whenever you're waiting for a market crash, let's say the market drops 20%. That's the equivalent to maybe 6 months ago prices.

[00:02:36]But you know, let's say 2 years ago you said you were going to wait for the market to crash. You missed out on a lot of gains because of that logic. And what actually happens with a lot of people, like I've even seen this with my friends before, they'll say like, "Oh, I'm not going to invest until the market crashes." then the market will start dropping and then they say, "Well, actually, I'm going to wait for the market to bounce back a little bit and then I'm going to invest." And basically all that's happening is it's just analysis paralysis. Like they never start investing because if the market's doing well, they're going to wait for it to crash. But then if it starts to crash, then they're going to wait for it to start to do well again. And before you know it, they're not investing in years have gone by. And whenever people are investing consistently at all-time highs, your brain is going to sit there and tell you, "Okay, I'm late. I'm about to fall. Something's about to crash.

[00:03:14]Like, I already missed the market running up." And I definitely understand this logic because even if you think about like 2026 for example, the market dropped a little bit because of the war and since then it has ran up a lot. I mean the S&P 500 is up like basically 18% since its lows and that was less than 3 months ago. So nobody's going to feel like a genius buying it right now when they could have bought a couple months ago at a lot cheaper prices. But people tend to connect themselves to the old prices. So, they'll sit there and go, "Okay, well, if the S&P 500 was lower a year ago, current prices feel way more expensive." Even if long-term they're not. And I'm not sitting here saying that the market's going to keep going and keep going up up and away for the next 3 to 5 years. I don't know what's going to happen. I want to be clear about that. I'm not trying to predict the future. And that's kind of the point because trying to predict the future is never going to work. And if you're somebody that is newer to investing or just newer to the stock market, social media does not help this at all. I mean, you can go on to YouTube whether the market is having a good year or a bad year and you can see 20 videos right now that are talking about a huge market crash incoming or a huge bubble or a huge recession. You can find that all over the place. I mean, there are thousands of thumbnails even today that you could look up and you'll see that.

[00:04:20]And so, like I said before, a lot of times people just end up getting trapped in this cycle of saying that they're always going to wait for a good entry point and then that never really comes for them. Therefore, analysis paralysis happens. So, they don't invest at all.

[00:04:31]And so you want to avoid this cycle if you can. And I think one thing people need to understand is that the market is supposed to be hitting all-time highs.

[00:04:39]That is normal for the market. When we see massive companies come out and they have solid earnings and we can see the intrinsic value of these companies are growing, it makes sense that the stock market is going to go up. Especially when the stock market is controlled right now pretty heavily by about 5 to 10 companies. And people like to sit here and treat all-time highs like it's some super dangerous thing and shit's about to, you know, go south. But like I said before, the reality is the markets tend to sit at all-time highs very often. And if you truly believe the market's going to grow for decades, even if you're not investing in the US stock market, let's pretend you own an ETF like VT. Like if even if you think the total world stock market is going to keep growing, then it has to keep hitting new all-time highs. Like that's how it's going to grow for decades. It can't just stay at the same price for 5 years straight. And another thing I really want you to consider and think about is like the all-time highs today might not feel that expensive a couple years from now. Like for example, even if you think about somebody that invested in 2008 before the market like really tanked, if you go look at like the S&P 500, the 2008 peak looks tiny compared to today. I mean, even when we think about the market crashing from like I think it was October of 2021 to October of 2022, it dropped about I think it was like 24%. Even that peak doesn't look that high compared to today. I mean, every time you look at all-time highs, it's going to feel terrifying. But then years later after the market, maybe it does collapse, but even after it bounces back, those new all-time highs will make the previous ones just look small as hell. And like I said before, then hindsight becomes 2020. So you're looking back and going, damn, I should have bought more then.

[00:06:05]That's typically what happens with a lot of people. And a lot of times people will tell themsel like, "Oh, this time is different." It's like, no, we've seen the market be overvived. There are a thousand reasons every single year that the market could crash. It could be high inflation with the Fed increasing interest rates. It could be things like different wars happening. It could be just economic things that happen. Maybe we go into a big recession. Maybe there's some type of, you know, crisis.

[00:06:27]Whatever it could be, there's always tons of reasons why the market can crash. And people love to tell themselves like the market just can't keep going up at this rate. But at the end of the day, like if we have innovation, if we have companies that are growing, if we have a population that is growing and we have technology that's advancing and corporate earnings continue to grow over long periods of time, then the market is going to keep growing. It's just that simple. And sure, it could drop 20 or 30% in a year or two. And I wouldn't mind if it did because then I'm buying things at cheaper prices. It's like hopping in a time machine and going back in time and getting to buy a really high quality asset at a cheaper price. And the thing that's nice is the earnings for most of those companies are going to be even better today than they were a couple years ago. And one important thing I need to point out here is I'm not saying that markets are never going to crash, but I do think that markets will trend up and to the right long term regardless of whether they crash or not. Sure, they could crash for a year or two. Maybe it's a huge crash like a tech bubble crash, but eventually they will bounce back and they typically bounce back within a couple of years anyways. And so I do want to make the point here that waiting for the perfect crash is not a good method. Now a lot of people they feel smart talking about how the market is overpriced. It everybody sounds like a genius when they're talking about how overpriced the market is and how it has to tank. But I really just think market timing is not the move. And this logic tends to collapse because of people's emotions. Because when it comes to timing the market and let's pretend that you are waiting for the market to hit the complete bottom. Let's pretend that right now from the peak wherever that is let's pretend the market drops 30% and you want to buy perfectly at the bottom.

[00:07:54]When it comes to timing the market you have to be correct two times. You have to be correct the first time and that is when you get out. You need to be selling at the peak and then you also need to be correct on when you're buying back in which is at the bottom the trough. And a lot of times people don't realize the second part of that is actually the harder one than the two. Like it's easy to sell out when the market's at all-time highs, but if the market drops 20%, is that the bottom or is 25% the bottom? Maybe 30%'s the bottom and it could keep going another 5 or 10%. You really don't know. And so that's something really important that you want to think about. And also, when you look at a stock market crash, you're going to see a lot of just terrifying headlines.

[00:08:28]You're going to see about recession fears. Maybe we are going into a recession and that could happen. You're going to see a lot of headlines, a lot of news and media just telling you about how bad the economy is. You're going to hear about layoffs and there's just going to be a lot of panic across the board. And when you see all these things, I know for a fact you're not going to sit there thinking, "Oh, wow.

[00:08:45]This must be a great time to be buying."

[00:08:46]Because what most people do is they ask themselves, "Oh, well, what if it drops another 20%, the market's down 20%. What if it goes down another 20%, or what if this time actually is different and the entire stock market is going to collapse?" Or, like I said before, maybe they tell themselves, "I'm going to wait for it to bounce back a little bit and then I'll get back into the market." And what tends to happen is that the markets do not care about your emotions. You cannot be an emotional person and be a good long-term investor. I really do feel that way because the markets will recover way quicker than your emotions will. And by the time people feel safe to start investing again, the price of the stock market is already a lot higher. And another angle that some people might take is they may want to sit in cash. But I do feel like if you just sit there on the sidelines with a bunch of cash, holding cash also has risk because your cash is going down in value every year due to inflation. not only inflation, but you're actually missing out on potential compounding and you're just missing out on the market having a really good run. Like this year is a perfect example that when the market sold off, there were probably so many people sitting there with cash.

[00:09:43]They saw the market drop, they said, "Oh, it's going to drop more." And look where we are today. We're already at all-time highs again pretty quickly. I mean, within a couple of months. And that drop that we saw earlier this year, that was light work. That is a walk in the park compared to a real crash where the market drops 20 or 30% over 1 to two years. That is a very long drawn out crash. that is when you see a lot of the blood in the streets there. And one thing I did just mention is I feel like in order for somebody to be a good investor, you cannot be emotional. That is one thing you want to avoid. And so in order to become an emotionless investor, one thing that helps with that is being very consistent. You don't need to be perfect. You just have to show up and be consistent because long-term investing works best for people that are super consistent. Not the people that are trying to buy into the market every time it dips or it drops. It's the people that are just consistently buying no matter what. A lot of times beginner investors, they obsess way too much over timing the market. Like time in the market is always better than timing the market. There is a huge difference in your total return if you miss out on even the 10 best days in the market.

[00:10:43]Your return gets I think nearly cut in half. And I've shown this graphic before, but I do think it's a really important one that a lot of people need to see. And another thing you have to consider if you're a beginner investor is like what is your time horizon for investing? If you have a 20-year time horizon, you should not be stressing about a little dip that could last 2 years. Because as long as you think the market's going to bounce back pretty steadily over the remaining 18 years, you're going to be fine. Because instead of obsessing about timing the market and trying to buy in on the perfect dip, the main things you need to be focusing on are your savings rate, like your investing rate, how can you save more money or invest more money, how can you do that consistently, and then how can you just stay invested? That matters way more than trying to find the perfect time to get into the market. Most wealthy investors, they don't get rich because they perfectly timed the market.

[00:11:26]They got rich because they stayed invested for a very long time. So, one thing you can do, and this is what I like to do, is just dollar cost average, all that means is that you invest a certain amount every paycheck. So, whether you get paid once a week, bi-weekly, monthly, whatever that looks like, you are trying to invest very consistently. That way, you're just consistently throwing money in regardless of how the market is doing.

[00:11:45]And if you can even automate some of this, it will make it a lot less stressful. Like for example, when you're putting money into your 401k, that money already leaves by the time you get your paycheck. So that's a nice thing. You don't even have to think about it. Or maybe you have an automated system where you get money in your account and then it automatically pulls out 25, $50, $100 and it invests that. Like that is a great way to go about investing. That way it's just like a system and it's super automated for you. And a lot of people don't like to do this because it'll start to feel boring after a while. But boring works, unfortunately.

[00:12:13]And a lot of times people, especially people that are way too into the market news, they overconume it. They let all of these different news outlets just get in their head and it makes them more emotional. And the more that you sit there and move your money around, first of all, the more that you're going to be getting taxed because every time you sell a stock at a gain, you're getting taxed for that. And if you don't hold the stock for longer than a year, it's a short-term capital tax rate, which is even higher than long-term capital gains. And not only that, but now you're playing the timing game where you have to be right twice, like what I just talked about. And so I do feel like dollar cost averaging and just having a system that works for you is going to make you a lot less emotional when it comes to investing. And that is how you can build a lot of wealth over a long period of time. And like I said before, if your investing timeline is 15, 20, 30, 40 years, today's prices are not going to matter at all in the grand scheme of things. Like like I said before, you can go look at the prices from 2005, 2007. You can look at it at the peaks of the 2000 in the dot bubble or you know in 2008 before the market crashed. Like those peaks look like absolutely nothing compared to today's prices. And so like I said before what I personally do is I dollar cost average every single time I get paid. I put money consistently into the market.

[00:13:20]Whether I'm going to put a lot of money or a little bit less money doesn't really matter for me. I just need to be investing consistently because nobody's sitting there with the magic eightball knowing exactly what the market's going to do. And if somebody does know exactly what the market's going to do, they're not going to tell a bunch of people online. Why would they do that? But the truth is, nobody exactly knows. So don't try to pretend like you do. Could the market completely tank the back half of 2026? Sure. But it also could be way higher 3 to 5 years from now. And so you need to focus on the things you can control, which is your income and trying to find ways to increase your income.

[00:13:51]Whether that is side hustles, maybe you job hop, maybe you put in a little bit more effort and get that promotion, whatever you need to do to increase your income, try to do that. And then on top of that, you can also control your savings rate or your investing rate. So out of the income that you get today, how much of that is being saved or invested? And so that's basically looking at your expenses. That's living beneath your means. And the better that investing rate is. And then the more income you get later on, the more money you're going to be saving and investing, which is great. And so that's another thing you can control. And then in case this was not clear, you want to avoid bad debt. Please do not get yourself into a bunch of super high interest debt. You don't need to run up your credit cards. It's like focus on high interest debt before you do any of this stuff. But these are the things I'm just mainly talking about that you can control and you want to focus on because market crashes are normal, but history tells us that the market tends to go up more than it crashes. So even if it drops 30 or 40% over the next 2 years, you got to tell yourself, hey, this is a good time to be buying on a discount. I know the market's going to bounce back within a couple years. In 3, 5, 7 years after the market crashes, you're going to be regretting not buying more during that time. So, try to tell yourself that if we did go into a market crash, but if we didn't, the peaks that we're seeing today are going to be pretty small long term because every single long-term investor is going to be mentally tested when the market does crash. So, just be aware of that because for me, I would rather spend decades participating in the market, even if I'm not perfect and the market has its ups and downs, than to sit there and spend years and decades waiting for the perfect time to invest.

[00:15:15]That is just not a winning strategy. And that is how I would approach investing in the stock market at all-time highs.

[00:15:20]So, that is it for me. I hope you guys enjoyed this video. If you did, drop a like down below. Hit that subscribe button. I'll see you in the next one.