Ways I've wasted my money
I removed the "I regret a lot" portion of the title, because I've wasted money, but don't regret any of it. Each time I recognize that I've wasted money, I take it as a lesson for how to spend properly in the future. It's like paying for financial lessons :)
1. Advertising for my books
The best advertising is word of mouth. The money I dropped on advertising books was largely wasted and destroyed any profits I might have had on the books. I still do spend a little bit on advertising (primarily on Amazon), but only in small amounts that I only increase if I see a decent return on the investment.
2. Buying investment newsletters
Most are junk that won't outperform the market. A few may outperform the market, but the price you pay for the newsletters usually makes any margin of outperformance negligible. It's the taxes and fees that cause underperformance, even if you're a skilled investor. The best way to invest I've found so far is just put your money into tax advantaged accounts like 401K or Roth IRA and invest in index funds.
3. My mortgage
I'm a homeowner and I'm grateful for being able to raise my kids in a nice home with a yard for the family pets to enjoy, but I can't help but wonder... is it all worth it? Being raised in Asian culture, I have an aversion to taking on any debts at all, even a mortgage. I bought my house over ten years ago, and so far I've paid about $140,000 in mortgage interest, about $70,000 in taxes, probably over $100,000 in insurance, and probably over $100,000 in maintenance... I don't know, but that sounds kind of like wasting money to me.
4. Trying to get rich fast
I've learned that in general, the faster you try to make money, the more chance you have to lose money. Getting rich is most often a slow and boring process. You can make the road to wealth faster and more exciting (such as with entrepreneurship or taking huge risks), but you will have to sacrifice some important things (like sleep, your youth, your health, your sanity, or your marriage).
5. A custom-made nightguard from my dentist
During a cleaning at my dentist, they persuaded me to get a custom nightguard to protect my teeth from grinding at night. It was so high tech, where they scanned my teeth and created a 3D model, then had nightguards custom made. And it came with a lifetime of replacements and support... for $500. I think you can buy a good nightguard on Amazon for $20, as I learned later.
6. My wedding
My wife and I both agree, our wedding was a waste of money. We were kind of pressured to have a big wedding by my family. But what's the point of blowing all that money on one day to basically buy a hundred people dinner and a round of drinks? We would have been better off having a small private wedding and spending the money on our future together.
7. My camcorder
Speaking of weddings... I spent $500 for a Sony camcorder to film my wedding in 2005. This was just before smartphones became ubiquitous and camcorders became obsolete. Today, I think the camcorder can be sold on eBay for about $10, and I've never watched the video from my wedding (I'm still happily married to the same person by the way, so at least that can be considered a success).
8. Various subscription services
Subscriptions in general area waste of money. I pay for a few, but you really need to monitor them closely to make sure you're getting enough value out of them to justify the costs. One way that helps is whenever I buy into a subscription, I think of the cost as an annual fee. Netflix costs $15.49 per month after a month free? Then I think of it as, Netflix for a year costs $170.39. Is it still worth it? For me personally, Netflix is worth the cost. But I recently canceled my Nintendo Switch Online subscription, which I didn't think was worth $80 for the year.
I've tried a lot of different types of expensive supplements over the years. My conclusion? 95% are a waste of money. Unless you need a specific supplement for a specific purpose, it's probably a waste of money. There are no magic pills.
10. Tourist traps
When I travel these days, I avoid anywhere that's going to be crowded. One specific waste of money that comes to mind is an ice show they have at the National Harbor in Maryland every year. I think it cost us $60 per person (we had 3 adults, 3 kids) to walk through and see ice sculptures. Then there were vendors everywhere selling overpriced food and we had to eat lunch. I think that trip cost us $500 and was underwhelming. So yeah, avoid those crowded tourist traps unless you want to waste money.