How to Waste Money and Not Regret it

Just shy of $20,000 to go to Antarctica travelling solo (small cruise ship). More than I've spent on every other vacation I've taken combined.

Was one of the best trips of my life. It also gave me enough space and clarity to realize how toxic my ex was to me so that I could find the strength to leave not long after I got back.

I'll always want to go back to Antarctica. The inner peace I found there changed my life.

A quick 7 day trip to Maui in February a couple years ago with one of my teenage daughters, who happened to be free the same week I had off. Work was grinding me down and I needed a break.

My wife and the rest of the family couldn't go, they were working or in school. The tickets were expensive, $850 each for bare-bones economy narrow rock hard seats, it was a 12 hour flight that was packed to the brim - I was getting bedsores by the time we arrived.

We rented snorkeling gear and a car, and spent every day from dawn to dusk snorkeling, sitting on the beaches and hiking in the mountains; we did the Hana road, the Seven Sacred Pools and the Haleakalā volcano national park at sunset, and took tons of photos. We ate spam musubi for breakfast, poke and somen noodles for lunch and loco moko for supper. Slept like babies with the windows open wide in the cool nighttime breezes.

The best way to blow $5,000 EVER. So much what I needed at that point in my life.

My grandfather absolutely loves the Beatles. He listens to their music every day. He doesn't speak English, but he always tries his best to sing along. It's so endearing. I had heard that Paul McCartney was coming to town for a concert. When I checked the ticket availability, there were only a few left and they were quite pricey. Especially for me, a high school student at the time.

But I was determined to get him a ticket. And I did! I decided to present the ticket to him on my birthday since the concert would be just a few days afterwards. When I gave my grandfather the ticket, he had broken into tears and hugged me so hard. I had never seen him so happy. The smile didn't leave his face for the rest of the day. Leading up to the concert, he would talk to everyone about how he was going to see Paul McCartney and that he had the most thoughtful granddaughter in the world. :')

I spent $300 on a mule. An actual living, 4 hooved, long-eared mule. We raise cattle, so a protection mule was a good excuse. But, really, I just fell in love with him. He's huge and sassy. He'll steal your hat and run away. He's got a Ninja mode where he can sneak up on you, just to breathe down your neck or startle you.

He does keep the coyotes away. However, he has proved himself priceless because he eats thistle. When we got the lease on the land for our cattle the pastures had been neglected and were in bad shape. Thistle is a spiky plant that spreads across the pasture, choking out grasses. Cow's won't eat it. It's really hard to get rid of. To our surprise, the mule cleared out nearly all the thistle in a matter of months. He would eat the flowers out of the center. He saved us an enormous amount of money and labor. We were able to avoid using chemical weed killers, which we really didn't want to do.

Probably the best investment in our whole cattle raising experience.

My fiancé and I dropped close to three grand on a kitchen table and coffee table from Carolina Game Tables. The kind where you can take the top off and have a board game space underneath. They’re comparatively plain compared to some you see online, no lights or USB ports, no cubbies, drawers or cup holders. Just really solidly build solid wood tables where the top comes off. But hot damn they’ve been awesome!! We use them all the time. One unexpected use was legos. I got a Lego set and started building it on the coffee table and when I needed to stop for the night I just put the lid on until I was ready to continue.

Don’t regret a cent.

I went to a Renaissance Fair with my husband and some friends. It was his first time, and he’s a pretty introverted person, so while he has fun watching everyone else dress up and act all goofy and old-timey, he doesn’t really participate. When we went to buy our first beer, the wench tried to sell him on one of those big mugs that looks like it’s carved out of wood but it’s just plastic. It cost $100. Yes, you get free refills, but we were not planning on drinking $100 worth of beer that day. I could tell by the look on his face that he wanted it- he looked like a little kid at Disney World. Without thinking, I whipped out my credit card and dropped $100 on a shitty plastic mug.

All day, he walked around proudly with his mug. He even took some big gulps and cheered “huzzah” once or twice. This might not seem like much but for my quiet, gentle giant, it is huge. I manage the finances in our relationship and I am CONSTANTLY cracking down on wasteful spending, so I think we were both amazed I made such a dumb purchase. Four years later, we still have that mug. He gets a big grin every time he sees it and teases me about my irresponsible impulse. And every time I see it, I just think about how much I love that big galoot...

I moved out of my mom’s house last year (2019 so no covid) and I always wanted a good couch. I tested so much. I went to so many furniture stores. Looked at so many different models. And then choose mine. It’s actually from Ikea. Three seats and long enough to let someone sleep on it. In a grey but I saw they were also having a black cover so I am thinking about getting that one.

Extremely comfortable. I wanted a couch where you could chill out and love how fluffy it is without losing the ability to sit on it. In some couches, you are not able to lean on the back and still have a straight back. You can sit on the backboard and the armrests. They are flat so you can also put a cup of tea on them. It’s also not too low so you don’t feel like sitting on the ground (which I do strangely often compared to my love for this couch) but you can let yourself fall onto that damn thing! It also looks easy and simple.

I got into a stupid fight with my brother, so I found a game he had pledged on kickstarter (Space Haven) and saw that for 360 dollars I could write a premade character bio that would randomly show up. So I pledged it and wrote a character bio with his name and made him a flaming ahole. I have never played this game and don't want to.

I’ve been a fat guy all my life. Like, really fat. Dressing comfortably was always my preference because being stylish just isn’t an option at my size. This was always a source of anxiety at any social event that required dressing up. When I realized I had 4 weddings of close friends all coming up within the year, I decided to bite the bullet and get some decent “formal” clothes. I spent $800 on a suit jacket, $250 on two pairs of dress pants, a little over $300 for 3 shirts and 3 silk ties that were between $70 and $100 each.

I stood for all my measurements and had everything tailored to my exact specifications. Did a fitting and had a second round of alterations on the pants so they actually looked decent, even though I wore them under my gut. People were floored when I showed up at the first wedding. I received so many compliments and actual double-takes. Being introduced to new people felt completely different. I felt impressive. Some of those weddings were the best times of my life and it was due, in no small part, to how those clothes looked and made me feel.

Some of those friends have big pictures from their weddings hanging on their walls, and I don’t cringe in embarrassment when I see myself in them. Those clothes cost more than I had/have ever spent on clothing in any ten-year period, and they were worth every penny.

Finally found the motorcycle I wanted years ago but could not get. It was not running, but after around dumping $3,500 into it and doing a full frame-up restoration and custom job on it. I have the bike I wanted years ago, but better. Yes, I did everything myself, full paint job Tank frame fenders everything. I also did a full engine rebuild, remade the wiring harness, everything was all done in-house. So I put a touch over 3K into a bike that is only worth about $1,500. on a good day, but hell it is mine and I built it.

I spent $3000 for my wife to meet the backstreet boys and get front-row seats. It is the best thing that has ever happened to her and the smile on her face after the show and look of pure bliss in someone who suffers often from anxiety was worth every cent.

My wife and I were on our honeymoon in London in 2016. We had just gotten an influx of cash from friends and family, and we went out to dinner at the Savoy Grille. They had an absurdly overpriced tasting menu with the option of overpriced wine pairings. We ended up dropping about $600, and it was honestly the best meal I've ever had. The service was off the charts, with little stories about each course and its accompanying wine, and they had the timing down perfectly. Just a fantastic experience from top to bottom, and if we didn't do it then (on our honeymoon with a bunch of free money), we were never going to do it.

Back in 2017 my family went on a road trip to Minnesota to visit my nana shortly before she passed. During our stay, me and my little sister went to the Mall of America and bought whatever the fk we wanted. Big ice cream cones? Lego store souvenirs? Tickets to the aquarium? Fare for every indoor amusement park ride? A doll from the American Girl Store and eating an expensive lunch in the Store with your new doll sitting at the table with us? Fk yeah little sis it's all yours. I dropped over $300 in that one mall trip but damn was it was one of our best shopping days ever, we still talk about it to this day.

When I was younger I came into a sum of about $15k. I wasn’t very careful with the money and other than putting $5k down on car, I blew the money here and there. But what I put the largest amounts toward were friends in need. I paid one friend's power bill just before it got shut off. I helped another friend keep her water on. I never could keep my hands on money for long but I don't regret having "wasted" it helping friends.

Due to poor insulation and distance from the water heater, my shower is never properly warm in winter. I just bought a single end-point tankless water heater for just my shower. Best hundred and fifty bucks I ever spent. Could I really afford it? No. Did I need it? No. Do I love it? You bet your sweet bippy I do!

The summer after graduating high school, I won a decent amount of money playing online poker. Since I wasn’t going off to college and all of my friends were, I decided to buy them all ridiculous going away gifts. A carpet, mailbox, toilet seat etc. were among the gifts. The most expensive and ridiculous gift I bought on a whim was a massive wheel of cheese, somewhere between $200-300. Little did I know at the time, that cheese wheel would set off a yearly event called “Cheesegiving” where our entire (much larger now with spouses and kids) friend group gets together to celebrate and partake in cheesy goodness. This year was our 17th (unfortunately all virtual due to covid) and I genuinely hope it never ends!

Just bought a treadmill. There is a perfectly good street outside I could run on, or I could pay for a gym membership for years and years. BUT now I can get a run in during my daughter's naptime, or when it's cold, or when I only have 30 minutes free and driving to and from the gym would eat up half of my time. I certainly could have made it work without this expense, but I really love it.

I got $27k and spent it on a solo cross-country road trip that led to me moving on the completely opposite side of the country from everyone I've ever known. I was in a dark place in my head, the original plan was to find a nice place to end my story, but the trip itself helped me reconsider, so absolutely no regrets to speak of.

When my mom was diagnosed with cancer (a year after my dad died unexpectedly...from cancer) I went to the animal aid thrift shop, bought a bunch of odd dishes, put down a drop cloth, and threw them at my house while screaming bloody murder. I don't regret one second of that temper tantrum or one dime I spent to make it happen. I eventually made a couple of beautiful mosaics out of the pieces. And my mom is 6 months cancer free.

Visiting the NBA finals while being an intern in the US (I’m from Germany originally). Tickets were 300$ each, had to drive back the 3 hours from Cleveland to Detroit at night to show up at work the next day but damn, I’ll never forget KD hitting the 3-pointer 45 seconds before the end.

Right at the end/after college, I had a decent paying job (for a 23-year-old) and as much as I liked having money to spend on myself after being a broke college student, I enjoyed more spending it on others. Spoiled my little sisters, bought a bunch of gifts for an adopt a family Christmas program, took my friends out for nice meals, etc. Is was fun. Then the student loans came due...

Back in high school, I was about to go on my first ever date and I made extra money to make sure I had enough (around $600 I had) the day before our date she gave me a letter and she basically broke up with me. Being a teenager I had no control over my emotions as being brought up in my family would say guys shouldn’t cry over anything but I had no way to process it. So after school I went to 7 eleven bought 2 large Slurpees, 6 hotdogs and got a pre-paid card and bought a bunch of NECA action figures. I actually had a good weekend because I honestly splurged on that money and got into action figure collecting as well-practiced stop motion which ended up helping me to pursue an animation career and I’m about to finish and ready to apply to stop motion studios

This may not feel like much to some but it was important for me. I got divorced in my late 20s and I bought an eHarmony subscription to help me date again. This was before free apps were a thing. It was way more money than I could afford at the time, but it helped me realize that I was wanted and people would be happy to get to know me and date me. It helped me move on from an emotionally abusive situation to repair my sense of self-worth.

I spent $56,000 on college for a degree I don't use, but I met my husband there so I really can't complain. If I divide that over the nearly 25 years we've been married and consider that he's the best of dudes it is a pretty good deal.

I just paid our full $8k health care deductible to send my wife to rehab. We're getting divorced and my lawyer told me I didn't have to pay for it, but she wouldn't have been able to do it otherwise. 8k is a small price to pay for her (hopeful) sobriety and treatment of her mental health issues.

This may not seem like a lot of money to some but I weighed 287 lbs. I lost 100 lbs and my reward was a 300.00 pair of Frye boots. I had been drooling over them for years and finally scrimped and saved to buy them. I told my husband it was my food money. Lol. It was actually my cigarette money. I had quit smoking a year before that but still faithfully put away 7.00 a day. I figured that I could always find cigarette money when I smoked so I will keep finding it to save. I bought a Nintendo Wii that way too. I have never regretted using those boots. I love them.

My first university degree (but it was really my parents’ money that I wasted). I don’t do anything related to it now. I went back to get the degree that I wanted and everyone told me would be a waste of my potential afterward. I now work in that field and love it.

Moving away from home was one of the best things that happened to me because it allowed me to grow a lot as a person.

And also my road bike. 4 grand, but I love every second on it.

Paying the adoption fee for the oldest/longest resident cat at shelters, cat rescues. I think I am up to about 8k in adoption fees.

For a bit of background, my job allows me to travel an insane amount (usually about 200 days a year) and one of my hobbies is going to cat cafes - I've been to 56 around the world. Because I was making stupid amounts of money, on top of getting a per diem, access to catering 3 times a day AND living very frugally I had a lot of extra cash. So I would visit cat cafes which are usually partnered by rescue groups or go to local shelters. I would spend time with the cats and anonymously pay for the adoption fee of the cat who was the oldest or been there the longest. A few times I paid for transportation arrangements for cats from high kill shelters as well.

Also, sometimes when we would stay in hotels of tiny little towns that were clearly low-income I would leave $100 at whatever small restaurant I ate at. I always made sure to slip out before they noticed.

I was engaged to my high school sweetheart when I was in the military. She had about 5k in credit card debt that had been hanging over her so I took care of it for her during my first tour in Iraq. I had no bills or obligations, why not?

Well, I spent another 4 or 5k coming home on leave mid-tour and furnished our apartment (her) before going back downrange. When my deployment tour ended, I came home and had to find out from my sister that some other dude(s) were seeing my fiancé and one had been living in the apartment with her the better part of 6 months.

When she found out I was back she ghosted me. Changed locks, etc. Her mother apologized to me in the neighborhood grocery store.

I regretted it for a long time. Mostly being angry. But I don’t regret it anymore. It was a far less painful lesson than the ones I’ve seen men in their 40s come to terms with. At least I got my medicine in my 20s.

My first paycheck I bought a $900 wedding cake. Me and my brother had no way to get it home since it didn't fit on our skateboards. We just had a cake fight in the parking lot.

My brother passed away shortly after that. I still think about that day whenever I'm sad.

If you were wondering, I worked as a window cleaner. I'd rappel down the side of 30+ story buildings.