The Dumbest Purchases I’ve Made In My 20’s


The Dumbest Purchases I’ve Made In My 20’s Blog Image

I want to begin by pointing out that everybody has different ideas of what qualifies as a “dumb” purchase. Some influencers drop thousands on ads that only land them a few sales or conversions, and I consider that a dumb way to spend money. A lot of people also look at the value of things based on their personal preferences.


For instance, Brazilian footballer Neymar Jr. spent more than $13 million on a Batman-themed helicopter. He wanted it, and he’s a highly successful athlete, so he bought it. Would I make the same purchase? No. But that’s because I don’t want a Batman-themed helicopter. Just because it’s a wrong choice for some people doesn’t mean it’s a bad choice for everybody. 


But if you’re an entrepreneur or an aspiring entrepreneur, you can’t always compare your purchases to someone who’s not actively trying to build businesses and develop sustainable passive income for themselves. You have to think about what makes sense for you as a person and an entrepreneur.


More often than not, this will make you realize that a LOT of the purchases you make are not all that smart. From the $8 coffee you bought this morning to the $50,000 sports car you financed to look cool on Instagram, it’s all about setting priorities and making informed decisions.


But again, I am not in a place to judge anybody. I’ve made a lot of mistakes with money, and fortunately, I’ve been able to learn from those mistakes. Now, I want to share some of these embarrassing purchases with you, and hopefully, you can avoid making the same mistakes I did.


I’m sure that many of you will have had similar experiences, too, because your 20s are a time when you tend to make the worst choices with your money. But by watching videos like this, you can learn how to make better decisions and skip out on the stuff you don’t really need.



The first dumb thing I bought in my 20s was a thousand-dollar Citizen-brand watch. Now, don’t get me wrong, Citizen is a great brand, and there are way more expensive watches out there. What made this purchase dumb wasn’t the watch itself but the reasoning behind my purchase.


You know that feeling you get when you want to make impulsive purchases at checkout? It’s the reason so many stores place a bunch of overpriced things you don’t need right behind the counter. Well, that’s basically what happened to me. I saw somebody wearing a nice watch, and I thought, “I work hard. I want to look good. I deserve a nice watch, too.” 


So, I asked a friend for advice, and they recommended Citizen. As I searched through their online store, I kept getting caught up in all the great features. First, I wanted a classic-looking watch that had a solar-powered battery. Then, I noticed that I could get a watch with GPS features. Then, it was atomic timekeeping. And then super titanium. Before I knew it, I had bought a watch that was way more than I wanted to spend, with a bunch of features I didn’t really need.


When my watch arrived and I tried it on, I liked how it looked, but I quickly realized that all the bells and whistles were totally unnecessary. My phone could do all the same things as the watch and much more. What’s worse, I ended up losing the watch during a business trip, so I only got about one year of use out of it, but it taught me not to get sucked into the cycle of never-ending upgrades. 


The second dumb purchase on this list didn’t happen all at once. It was spread out over several years. Just about every person in their 20s goes through the “party” phase. You know what I’m talking about. You turn 21 or 18 where I’m from, and you can legally drink alcohol, so you go absolutely wild with your friends. At first, it seemed great. You drink, you party, you meet new people, and you have fun. But many mornings during that time in my life, I woke up, checked my phone, and was horrified when I saw my bank account.


Party culture doesn’t just hurt your wallet. About 20% of college students develop a substance abuse disorder because of trying to keep up with the party lifestyle and culture. I was lucky enough to avoid this problem, but partying hard takes a huge toll on your physical and mental health. We humans simply are not designed to get drunk every night and wake up the next day to start the process all over again. If I could go back in time and dial down my partying to just the weekends, I could have saved thousands and thousands of dollars.


And this doesn’t mean you have to be a complete saint in your 20s. You can still have fun, but moderation is the key. And always remember: alcohol lowers your inhibitions, which makes you much more willing to reach for your wallet, especially in situations where you would call it a night. So try to play it safe and put your money toward more rewarding experiences.


Like, even though it may sound absolutely crazy, you can still party and have a good time without spending $100 a night at the bar. It’s true. I’ve done it. The best part was that I could wake up the following day without a terrible hangover or a feeling that I had wasted too much money.


Another big purchase I made in my 20s was a luxury apartment. Now, keep in mind that it was a rental. I didn’t buy it outright, but it was still 3x more than I should have been paying for housing as someone in their early 20s. Today, I would feel more comfortable spending that much on a nice place to live, but at the time, it was totally unnecessary.


I wanted a jacuzzi, vaulted ceilings, a private bar, marble countertops, and all the other stuff you would expect in a high-end bachelor pad. The only problem was that I couldn’t really afford it. And while it felt great living there for about three weeks, once those past-due notices started hitting my mailbox, I knew that I was in trouble.


I ended up working days and nights to make ends meet when I could have just downsized, simplified my housing, and saved a fortune. My advice: don’t try to upgrade your lifestyle until you’re making at least 2 to 3 times more than you need to afford the upgrade comfortably.


If you’re currently in your 20s or even your early 30s, you also need to think about how your housing needs will change with age. You really don’t need a luxury pad when you’re 21 years old. You just don’t. You can get something nice, but make sure it’s within your budget. Then, as you build your income and have greater financial stability, you can invest in better properties and even start doing your real estate work for you. But until then, don’t be afraid to settle for a basic studio apartment. There is absolutely nothing wrong with saving money on housing. In fact, it’s one of the smartest things you can do now to ensure a better financial future for yourself.


I know you watch all these 20-year-old billionaires on Instagram and TikTok like I do. You see their fancy clothes, apartments, cars, and all the trappings that come with wealth. And because they look so happy and cool you tell yourself you need those things to be happy, even if not consciously. But I’m going, to be honest with you, the fact is you don’t need that much money to be happy and buying luxury goods doesn’t really add to your happiness.


I’ve had all of the experiences and things; they’re cool, don’t get me wrong, but you really don’t need those things to feel the way you want. You can have the life you dreamed of, a life you’re truly happy with for much less. Most need to get to the point where you have all those things to realize. But I’ve seen super-wealthy people very unhappy with their lives and vice versa. The goal isn’t just to be rich. It’s to live the life you want and make the money necessary to live that way.


If you’re starting to judge me at this point, I don’t blame you. Just remember that I was in my 20s, and everybody makes mistakes when they’re young. But this next one probably won’t make you think any better of me. Most people want to live the luxurious jet-setter lifestyle, but unless you’re one of the lucky few people who has already built a hugely successful business in their 20s, you’re not going to be able to afford it yet. Even if you CAN afford it, it doesn’t mean that you should spend ten times more money for a little bit more comfort and luxury.


That’s exactly what I did when I started traveling the world. I realized that having a successful online business meant I wasn’t chained to a desk anymore. It was great. I could travel and work from literally anywhere on the planet. The problem? I wanted to travel in style. I was dropping tens of thousands of dollars on first-class flights, the best resorts, and dinners at 5-star restaurants. It was insane. While it’s nice to have a bit of comfort, you should be spending your money on great experiences, not unnecessary amenities. 


For example, you can spend $300 to go to a music festival and have the time of your life. Or you could be like me and pay more than $3,000 on an overnight trip to Tokyo, where I spent the whole time working and barely got to enjoy the city. Don’t do that. I still can’t believe I did that. It makes me cringe to this day and has taught me the value of balancing value and comfort when I travel anywhere.


And if you can’t enjoy your travels without paying for all the extra amenities, then put in the work for it. You don’t have to live like a monk, but if you want to live like a king, you have to put in the hours and make sure you have the income to back it up. Otherwise, you’re going to dig yourself into debt really quickly. 


The last and probably dumbest purchase I made in my 20s is something that I’ve talked about a lot before. But it’s important to understand that this is not a purchase that I regret. I wouldn’t be where I am today without it, but it was still dumb. Why? Because I dropped $5,000, I didn’t have a course to help me learn how to start my own business.


The course was not terrible, but it only taught me pretty basic stuff. I came out with some helpful information, and it helped lead me toward my future building Drop Servicing Blueprint. But was it worth $5,000? Absolutely not. If I had just done a little more research, I could have found a course that offered 10x more information for a fraction of the cost. 


But you live, and you learn. Without all of these mistakes, I wouldn’t be the person or the entrepreneur I am today. Each one taught me different lessons about the value of my time and money. Do I look back and regret some of them? Yes and no. You can’t change the past. You can learn from it. And that’s what I’ve been doing. As I said before, just making this video has helped remind me of some of the dumb financial decisions I’ve made and how I still managed to find success in spite of mistakes. 


I hope these 5 dumb purchases can help you avoid making the same mistakes I did. That way, you can use your money more wisely, invest, and build a more stable future for yourself. It’s all about separating what you need from what you want. You don’t have to deprive yourself of all pleasure, but you should absolutely think about how purchases, both big and small, can affect your future and your overall well-being.