17 Purchases I Regret Buying

One of my favorite Frank Sinatra songs is “My Way.” In that song, he says, “Regrets, I’ve had a few, but then again, too few to mention.”

Well, I regret a lot of my bad buying decisions. I want to tell you about them so you can avoid making the same mistakes and know you’re not alone if you’ve done the same thing.

Regretful purchases and lessons learned

1. Uncomfortable when trying on. I loved the sweater when I saw it at Suit Supply. It’s sort of fuzzy and chunky. I thought it looked cool. When I tried it on I thought it was itchy, made of mohair and silk. I discovered it was the itchiest thing ever, and I’ve not worn it. The lesson is if you put something on and it doesn’t feel good immediately, don’t buy it. It’s not going to break in, and it won’t get more comfortable.
2. Not utilizing a collection. My rose gold Yacht-Master on the oyster flex strap was my grail watch. I get obsessive about things, and I’m not proud to say that. Well I got this watch, and then I liked another one better. The lesson is that you need to know yourself. I shouldn’t collect watches because I don’t rotate them. I get a favorite, and I wear it all the time. It’s a massive waste of money.
3. Loving the ‘idea’. I love REI and the idea of being outdoorsy. I saw these Blundstone boots and thought they were rugged, but I’ve worn them zero times. I should have known better. As you will see on this list, I regret many of the boots I have purchased.
4. Not listening to yourself. I love my black plastic $50 pair of Birkenstocks that I wear all summer. So, I thought I’d get a proper pair of leather Birkenstock sandals. I thought I wouldn’t wear them and regret it because I don’t.
5. Vacation purchases. For instance, I bought some boots in Aspen with my wife. A lesson is to be careful when you’re in the spirit of the moment.
6. Thinking it will break in. Again, this purchase was about the experience. I was with Ryan Masters and my buddy Antonio Centeno in downtown Austin. I saw these Helm boots and liked the soles’ ruggedness. I dug the cap toe. Even though they weren’t super comfortable, I thought they’d break in. They didn’t.
7. Buying in multiples. I have an incredible collection of black and white T-shirts. What a waste of money! How many days are in the week? Seven. How many T-shirts do I own? 39. It’s a waste. Never in a million years will I wear all my T-shirts. I didn’t spend much on them because most came from an outlet store, but that’s another story.
8. Discount shopping. I’ve wasted a lot of money on outlet clothing. It’s about endorphins and the rush of purchasing items at the outlets. The problem is that they shrink when you wash them, and you look like Britney Spears.
9. Buying with ego. When I finally had money, I bought a car with my ego. Perhaps I needed to prove something to somebody, but I don’t know who. That’s one of the problems when we buy based on how we think it will make us look or feel or based on others’ perceptions. It’s a recipe for disaster. I ended up with cars I hated, and the car payments were astronomical.
10. Going overboard. Remember when I told you that I get obsessed with things? In my YouTube career’s earlier days, I dressed up in my videos. I wore suits daily, so I found Suit Supply and went overboard. I bought 12 suits in a year. When I got them, I was about 10 to 15 lb lighter than I am now.
11. Buying during weight flux. Presently, I look like a sausage in those Suit Supply suits. I can’t wear them. Don’t shop after dieting down for your extra lean. Also, don’t buy clothes that you aspire to fit into. They need to fit you well when you buy them.
12. Buying trendy. I became obsessed with All Saints jackets and purchased 12 or so. I never wore them, which was a massive waste of money. I don’t wear them because they’re not exactly my style. Buying trendy items is not a good investment.
13. Not being sensible. You know yourself, so don’t buy far outside of that. For example, I now wear all black and white. I used to think I’d wear various colors, and I was wrong. Those purchases were a waste as I didn’t wear them.
14. Impractical. I regret buying both of my e-scooters about five years ago. I thought I’d zip around with my wife, but we’ve never used them. We’d rather walk or ride a bike.
15. Impulse buy. This bike was an impulse buy, which my wife thought would also be awesome. It’s been used about three times.
16. Cheap cardio equipment. When you buy fitness equipment, it’s essential to purchase high-quality equipment. If you buy something cheap from Dick’s Sporting Goods, Walmart, or Target, it’s crap and will not last. It will be rickety and funky, and you’ll not use it. Or it will break down. Invest in higher-quality fitness equipment that lasts longer.
17. Because it’s cheap or on sale. Just because it’s cheaper or on sale does not mean you should buy it; if you never wear it, it’s a complete waste of money.