After 20 Years in Personal Finance, THIS Is What People Regret Most…

Money regrets hit hard because they're never really just about the dollars. They're about the time you can't get back or the relationships that cracked because of money or the dreams you had to put on hold. You clicked on this because you want to know people's biggest money regrets, and I have spent 20 years listening to them. So I asked people online, what's your biggest money regret? And the answers came flooding in, hundreds of them. The same themes kept popping up: not investing soon enough, Buying too big of a house, crypto FOMO, debt. You've heard those before. But the ones that hit me the hardest were not really about money at all. So stick around. And at the end of this video, I will share the most surprising regret. It's not about crypto. It's not about investing or housing. It's actually something far more personal. People said things like, I should have started earlier. Unfortunately, there's never a perfect time. And the real driver behind this is fear. Fear of losing money, fear of looking dumb, fear of looking at your own expenses and saying, I actually do have $50 or $100 a month that I can put towards investing. A lot of perfectionists will say things like, I'll start when I get all my ducks in a row. Here's what you should do instead. Start small. Start now. Even $50 a month. Compound growth is not built on timing the market. It's built on time in the market. In the market. The best strategy is to stop waiting and get in the game now. But you should be cautious about the next topic. This is one of the biggest regrets that I hear. Here's the truth. Some people did buy a big house and they love it and they can afford it. But a lot of people bought a big house and they now regret it. Remember how this happens? We all hear these phrases. A house is a great investment. You'll make so much in equity. Well, let's take Eric and Elena, a real couple that I spoke to on my podcast. They told me about buying a $770,000 condo in Toronto. Their rent had previously been $2,300 a month. The mortgage was supposed to be $2,600 a month, but once you added in taxes, maintenance fees, and all the phantom costs, the real cost was closer to $3,500 a month. They were making $160K a year combined, very good income, but they were living what they called paycheck to paycheck, losing about $1,000 a month from savings. Their emergency fund was only $354. At this pace, they were 2 years away from running out of money. Elena said something I'll never forget. It's embarrassing to think that we just made a $770,000 mistake. Eric admitted, I'd rather take the hit and the embarrassment than keep doing this. Here's what I told them. Despite homeownership being America's number one religion, it's actually a financial purchase. So treat it accordingly. Run the numbers. And if they don't work, You need to consider your options, including selling. That's not failure. That is taking control. And I want to acknowledge that it's easy to feel embarrassed about a decision like this, especially because all of us are heralded, "Oh, you bought a house. You're so young, so cool." But this is the biggest financial decision of most people's lives, and almost nobody actually runs the numbers. Instead, we just follow these pithy little phrases: owning a home equals success, houses always go up in value. If you don't buy now, you'll miss out forever. No wonder so many people end up stretched thin. Guys, it's not the amount of coffee you're buying, it's that your total housing costs are 36% of gross income. But you don't know that because you never ran the numbers. Here's the lesson: buying a house is a very complex financial decision. You absolutely must run the numbers before buying. And sometimes renting a house can be a better financial decision, as it has been for me for the last 20 years. Speaking of major life decisions, there's another one that is also important, and that's making sure your family is protected financially in case something unexpected happens to you. In that case, you're not able to provide for them anymore. Now, this is morbid. I get these comments saying, stop talking about getting hit by a bus. Why? You're gonna die one day. Look, look in my eyes. You're going to die. And if you have kids, you better make sure you have term life insurance right now. That's where today's sponsor comes in. Fabric by GerberLife is term life insurance you can get done today. It's made for busy parents like you. It's all online. It's on your schedule. You could be covered in under 10 minutes with no health exam required. If you've got kids, and especially if you're young and healthy, it's a great idea to lock in rates now. 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We see someone else get rich quick and we want the same. We're afraid of being left behind. And you will hear people say in one sentence, I know I shouldn't try to get rich quick. Wait for it. 'But' and then everything they say after the word 'but' is about getting rich quick. Speculation is not the same as investing. If you want to take 5 to 10% of your well-diversified portfolio and invest it in speculative assets, whether it be crypto, a buddy's bar, some angel investment, whatever, go for it. I want you to, as long as your other 90, 95% is diversified. The problem is that most people don't do this. They actually scoff at diversification. But building real wealth is boring. It's built on consistent fundamental habits like automating your savings, investing in diversified low-cost funds, and giving it the ultimate blessing. The blessing of time. If you don't understand it, don't put your money in it. And if a crypto bro promises you can get rich with a secret formula, you're probably going to get scammed and rug pulled. But not every regret is about chasing something shiny. Sometimes it's about the weight of choices you've already made, like debt. One couple I spoke with on my podcast was carrying over half a million dollars in student loans. It was so overwhelming that for years they even avoided looking at the numbers. But I talked to them, and once we mapped it out together, they realized they're not doomed. The debt didn't disappear overnight, but the shame started to evaporate as they moved from avoidance to action. Debt is one of the most common regrets I hear from people. A lot of people start off by taking on these gargantuan student loans that they don't understand. Next, it's often mindless spending that puts people into credit card debt, keeps them there. One regret about debt that I wish I heard more was that people in credit card debt keep spending on their credit cards all because they want to earn points. What the hell is wrong with you? It is not worth 26.99% to get these freaking points that are worth less than 1 cent each. Guys, if you are in credit card debt, stop using your credit cards. Another mistake that drives me absolutely insane is going into debt for home renovations. Your home renovation is almost certainly not an investment. It is a luxury. Yes, I'm talking to you American homeowners. Oh, I need my basement done. That's certainly going to add on ROI. No, it's not. It's a fucking luxury. You might as well go out and buy a $25,000 Birkin bag. That would be the same level of expense that you would pay. Sure, you could sell it back and maybe get a little bit of money. But that's not the point of it. You're building a freaking basement so you can enjoy it and brag to your friends on Instagram 3 times a year. Hahaha, simple man. Hashtag man cave. It's a luxury. Now, if you already have debt, the focus should be on paying it off, especially if it is high interest debt and you want to still live your life. You can still eat out if you have debt. It's okay. You just need to have a debt payoff plan and you need to make sure that you are not getting into even more debt. Remember, debt is not a wealth building strategy. I know everybody hears these rich people talking about, oh, I leveraged debt. I'm so cool. You shouldn't even be using the word leverage until you have millions of dollars. Do you understand what the fuck I'm talking about? Leverage? What is leverage? Do you understand that leverage works on the way up and the way down? No. You just thought it was a secret afterburner fuel that makes you get more money magically. Hey everybody, leverage. Where's my money? That's not how it works. If you don't understand how leverage even works, you probably should not be leveraging anything. Leverage a book. Where's my fucking book? Since you can't read it in English, I'm going to show you a different version in a different language. Leverage this. Learn a language, read the book, then follow it. The next regret beyond me spending my life teaching you about money, you not listening to a single thing I say. Let's just get to it. This was actually a surprising regret. People said stuff like, I stressed about my first house because I wasn't prepared. I should have set money aside for that big trip. Not charge it on my credit card. I wish I'd saved more for my wedding instead of going into debt. That's a very common one. All right, so why does this happen? Because a lot of you think you're special snowflakes. Oh, me getting married? I don't believe in marriage. I just want a small, simple wedding. Oh really? You do? That's so novel. I wonder, does your wife or husband want that too? No? They have a family of 80,000 people and they expect a massive wedding? Oh, what are we going to do about this? Extremely predictable event that we knew was going to happen, but we chose not to save because we have an inflated sense of self-importance. Hmm. Stop it. Stop not setting aside money for things that are predictably going to happen to you because you think you're a special snowflake and it will magically work itself out. It won't. Now, why does this happen? Most of us simply don't think ahead. Most of us don't even plan beyond the next month. Most of you don't even know what planet you're on right now. What the fuck am I doing on this video? And therefore, we actually don't know how or why to save for things that are coming up. Like when you talk about savings, a lot of people treat it like flossing. Yeah, yeah, Ramit Sethi, oh, fuck Luddite, I know I should floss, I know I should. I'm not your dentist. I'm not here lecturing you on things you should do. I'm showing you how to use money to have an even more awesome wedding, more awesome vacations, more awesome retirement, kids' activities. But people don't really save. And why would they? Most people still do the things they wanna do They order the food they want. They travel when they want. They have some video game console. They have a roof over their head. It's fine. The way we treat our money is to look backwards at the end of the month and go like this. You all know what I'm talking about. Oh, I was bad. I shouldn't do that. Bad. You fucking love to feel guilty. Whether you were raised religious, whether you simply absorb this guilt, whether you use it as an excuse. If I say I'm bad, then it's okay. This is not confession. This is a YouTube video. And if your way hasn't been working, why don't we just do it my way? In order to be effective with your money, you have to look forward. You got to stop looking backwards and beating yourself up as if that actually accomplishes anything. It doesn't. And you got to look forward and make a plan. What's coming up next month? Oh, I don't know. My life is so chaotic and out of control. Get it in control. What about 6 months? I don't know. Summer. What are we going to do? Make a plan. What's coming up 6 months from now, 12 months from now, 20 years from now? And then set your money up to automatically flow where it needs to go. Guys, this is why I teach the conscious spending plan. This is why I give it away for free. It helps you save automatically and intentionally. So when the big day arrives, whether it's a wedding, a house, a once-in-a-lifetime trip, you can enjoy it fully. Oh, I don't know. Can we get the shrimp? Yeah, you can get the shrimp because you started saving for this trip 7 years ago. Now let's flip this around. What's something you went big on with your money that you actually don't regret. Maybe it was a trip, maybe it was a wedding, maybe starting a business. I want to see your money anti-regrets in the comments below. Missing out on big goals because you didn't save is painful, but I got to tell you, this next regret steals the joy from everyday life. Starts to feel like you can't spend money at all. You ever meet somebody who makes good money but they don't spend it at all? It's easy to call them cheap, but I think that we can go deeper. One of my most eye-opening episodes was episode 63 of the Money for Couples podcast. I talked to over 60 couples by this point about a money issue that holds a lot of people back, and that is spending guilt. People told me, I feel so guilty for getting a $5 drink. I don't know why. It's kind of like a nagging voice. It's just always there, like you shouldn't be buying this. Or even though we set money aside, we just can't enjoy it as much as we want to. Now, this happens with people who have high incomes, even people with millions of dollars in net worth. Why? Let me tell you. Number 1, childhood money scripts. Maybe your parents said, "We can't afford that," even when they could. Number 2, scarcity mindsets. The fear that no matter how much you have, it will run out. And then finally, this one, underdiscussed in the personal finance world, confusing frugality with virtue. Believing that you are a good person if you deny yourself and bad if you spend. Just imagine what we would say if somebody talked about this in regards to their food. It's not a functional, healthy relationship with food. It's not a functional, healthy relationship with money either. And I got to tell you, this is one of the saddest regrets I hear, because money isn't just for saving or investing. I think the purpose of money is to use it to live a rich life. If you've saved and you've invested responsibly, but you still feel guilty about buying a dinner out or taking a trip, you are playing small. And what a tragedy. To live a smaller life than you have to. In order to live a rich life, you have to do two things. Number one, know your numbers. Number two, master your money psychology. Are you tired of playing defense with your money? Of always worrying that you've spent too much, even for something as small as buying a tea? What if we could go on offense with our money? What if we could become so confident that we could feel good about spending on the things we love? That is what my money coaching program is all about. Every single month in the program, I'll show you how to automate your finances, pay off your debt faster, invest your money, and actually spend on the things you love guilt-free. You do not need another budgeting app. What you need is a proven system and coaching and a supportive community that gets you results. You'll find that in my money coaching program. Go to iwt.com/moneycoaching or click the link in the description below to join the program today. I've been hearing this one a lot lately. I never talk to my kids about money, or I feel like we're just repeating the same generational patterns we grew up with. Now, why do you think parents avoid talking about money? Why do you think that so many parents' only discussion about money is to tell their kids, put that back, we can't afford that, money doesn't grow on trees? I'm gonna tell you. Many parents are not comfortable with their own relationship with money. So when it comes to their kids, they unconsciously pass on the same beliefs to them. And when I push them on it and I say, why don't you talk to your kids openly about money? You know what they say? Let kids be kids. I don't want them to worry. What the fuck? From a non-parent to all the parents watching this, what is wrong with you? You know, I don't think you would ever say, I don't want my kids to worry about how to ride a bike. No, you would take them out. You would teach them the skill of riding a bike. And teach them how to do it even when it gets hard. So why don't we do that with money? In my opinion, the secret of effectively teaching kids about money is that it starts with you. Pull out a mirror, pull out that mirror and take a hard look in it because it's not your kid's problem, it's your problem. When you have a healthy relationship with money, when you enjoy money, and when your kids see you talk about trade-offs and how you're using money to make sure the fridge is full of healthy food, then you can teach them effectively what you yourself are modeling. If you want to build a healthy relationship with money and then teach your kids about it, subscribe right now. I share strategies every week to help you learn and pass down those great money habits. Now let's talk about this last regret, and I personally think it's heartbreaking because it's so preventable. I see this on my podcast a lot. People, often men, tell me the following: I'm the money person in our relationship. She stresses out about money a lot, so I tell her it's gonna be okay. You know, this is very common, especially in heterosexual relationships. Men often see themselves as the provider and also as the person it is to stop their wives from worrying. Now, in the same relationship, women will often describe themselves as the ones handling the day-to-day finances, but when I ask them what that means, you know what they say? Making sure all the bills are paid on time. Inevitably, as they start to understand the money day in and day out, they start to worry, especially when they try to engage with their husband and their husband says, "Ah, it's gonna be fine." This makes no sense. The partner who's not even engaged with the money is over here saying it's gonna be fine. How do you know? What are you talking about? Ignorant Reassurer, that's what I call them. Over time, this creates resentment. One partner feels isolated, unheard, the other feels irritated. And this is a fragile dynamic that I see all the time. Guys, it doesn't have to be this way. When I got engaged, I could have very easily been the money person. I decided no. From day one, we are both going to be involved. I made it a priority to get my wife involved in our finances as an equal partner. Why? Again, I'm the money guy. I've been writing about this for over 20 years, but that's not a partnership. If only one person is involved, the other ends up ignorant, often powerless, and that creates stress for people. It also creates a culture where one person has to come and say, "Can I please have money to go to Target?" I don't want that kind of relationship. I want us to both understand how money works, risk, investing, compound interest, be able to make tradeoffs and plan for awesome things like vacations. I didn't want that for my wife. I wanted us to both feel confident and empowered and to be able to talk about all parts of our finances. That is why I made it a priority to make sure we were on the same page with money. And that is why I think you should do the same thing too. Do you notice the patterns with all these regrets? Fear shows up in almost every one. Fear of missing out, fear of losing money, fear of being judged. Even the media knows that fear sells. There's this one site that tried publishing only positive stories. The traffic dropped by two-thirds. Fear grabs our attention, but regret built on fear will not build a rich life. The antidote is building a plan and taking action. If you're ready to stop stressing out and you want to take control of your money right now, click here. I'll show you exactly how to get started today.