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It was some time in the 2000s, and I was at the outlets in Flemington, New Jersey. I stumbled upon a pair of black leather Cole Haan shoes priced at $75, marked down from $300. It was the only pair left, and the shoes happened to be my size. How could I possibly resist?
I hated those shoes. No matter how many times I wore the darned things—and, trust me, I didn’t give up easily—my feet screamed. The stiff leather never got any softer, and the shoes ended up languishing at the back of my closet for years until I finally stuffed them in the charity bin at the local supermarket.
The lesson: Just because something is on sale doesn’t mean it’s a bargain.
So, what purchase do you most regret?
I don’t really regret my purchases. I was thoughtful when I made them and I’ve really learned from them, even the bad ones. That was all a part of life.
(Like what a sunk cost? That would be funny except for the fact my wife and I were once led to invest in a small submarine for tourists to see underwater fish, rays and other wildlife. It was a fun operating business in Hawaii that wanted to expand to the Virgin Islands. And we were young and impressionable. It was a limited partnership investment in the very low five figures. Now THAT was a “sunk” cost. It went bad, but we actually got more than 50% of our money back in the end, so I’m not ashamed to tell the story.)
But I do greatly regret not exercising options and diversifying a big chunk of my portfolio when the company I worked for was sold. I later took a big hit when the new managers stumbled, and that was on me. That was a “non-purchase”. Cie la vie.
It was the late 70’s and runaway inflation. I was snookered into buying – of all things – “investment grade” collectible tax stamps. Based on the sincerity of the stamp broker and his evidence of the stamp’s rapid growth in value, it was certain to be a sweet deal… until it turned sour. Once I became disenchanted with the speculative returns, it quickly became apparent that I didn’t have a clue what I was investing in, and that I failed to consider ease of liquidation and transaction fees.
The loss on that sure-thing-investment still smarts. But, it taught me to be a whole lot more Humble with my Dollar!
My sister was going to make a killing collecting Beenie Babies.
Something I’ve heard people commonly purchase and then regret is expensive exercise equipment. We’ve bought several that we’ve gotten great use out of, but the one I’m thinking of was used a few times and never again. We ended up selling it back to the store as used for a lot less.
Worst by far was shorting orange juice futures a week before a significant snap freeze in Florida in the early 80s. Couldn’t get out for 5 sleepless nights!
Yep, it was stocks. I should have learned, at age 18 bought $500 worth of my Dad’s good friend’s stock, it did not pan out. Luckily after that friend died, his wife offered the buying price some 15 years later, good for me, but you think I would have learned. My best friend, of 50 years, talked me into purchasing a bank stock, he was on the Board. I had $100,000 worth after a $50,000 investment, all looked good. Something about a government investigation, and changes in regulations, and the stock tumbled to $0. Yes, after that, no more purchases for stocks from a Friend’s suggestion in 2005. I now invest in the S&P 500, other indexes, and Berkshire, all good after 60 years investing. Generally speaking no magic in stocks! I have a general rule and for individual stocks, only about 2% of my portfolio. It took some time but all good at age 78.
My first and last Prada bag. I got talked into it while traveling Europe ten years ago, given the VAT tax advantage. I never went into a single business meeting or a non-business occasion with it. It is still sitting in the back of my closet, and I have had to move with it three times. I am keeping it as a reminder of my mistake.
i had one recently. Bought a used car and the dealer offered me a chance to buy an extended warranty. The warranty covered everything (except consumable type things). On my other car that had 50K miles on it, I recently had to replace the front facing camera that controls the collision avoidance and other things. The repair was $1,400. So, for a $20K used car, I spent almost $4,000 for the warranty. I am now regretting that decision and will be canceling the warranty. Moral of the story is to understand your risk tolerance. (i.e., how much am i willing to spend on any given repair and what are my chances for a loss). Also, don’t make split second purchases.
I have bought 2: 1983 SAAB 900, but if I didn’t use it for any of the covered repairs, it was refunded to me, less the interest I could have earned. Worked out, got the refund. A kitchen stove, because of all the new electronics, I bought an extended warranty of up to 5 years. 2 months before expiration wiring harnesses burned out. Got the repairs done and works like new, but we learned not to use the self cleaning function. So, I got lucky twice.
Somehow I made some calculations and read a lot about warranties, and learned they were highly profitable, and they were. One reason why you see them all the time, like on Amazon. Truly, real money maker. So I made the decision to never buy warranties, no matter how good they looked, from age 22 when we got married. Now at age 78, out of many major ones, like cars, appliances it has worked out well. It takes discipline but does pay off. Remember you get one or two years from the manufacturer, plenty of time to have something go wrong and get it repaired or replaced. Yes, you have to remember to buy from a quality company. Same for insurance, and after talking to a few reps, I could see what they wanted me to buy, rather than what I needed. Stay aware.
People aren’t good at taking a portfolio approach to risk. If you always lose on everything then by all means insure for everything but many people leave money on the table through over insuring for things that they can easily afford to bear. Even taking high deductibles can be sensible – sure a $3000 hit might smart but you are really insuring your car for the total loss not a bit of minor bodywork repair.
I’ve made many frugal, bargain purchases which have served me well, and a few which have not. But one financial DECISION we made which gave us repeated headaches and cost us hugely as well was to HIRE A PROPERTY MANAGER for a rental home. It was our first “home purchase” and we thought we would live there forever in our humble, yet dearly love 1600 sq ft home with one acre. Things changed and we had to move hundreds of miles away with only 7 weeks to prepare for the move with a new job. We didn’t have time to prepare the house and make the arrangements necessary to sell the house, plus we had dreams of returning to OUR DREAM HOME one day. SOOO—we decided to rent it and secure a property manager (recommended by our tax preparer whom we loved and trusted) to oversee collection of rent and manage necessary repairs. WHAT A MISTAKE! We LOVED our home and wanted it to be care for as WE would do. IT was NOT, so our grief was huge each time we saw the damages to our home. The hired one would call us rather than handling repairs so WE ended up arranging for the work at a distance anyway. She made the practice of accepting rent payments late WITHOUT CHARGING A LATE FEE! And when we asked her to get estimates and have the renters pay for the repair when they crashed into our storage building, she told us the building wasn’t worth it (it was later appraised at 14k by our insurance company). We sold the house after a few years and lots of headaches and lots of money in repairs to prepare it for the market.
Purchasing a Variable Universal Life insurance policy, sold to me by a “friend” I knew from church. I “invested” solely in this for the first 6-7 years of my career, i.e., the earliest dollars that would have most gone up in value if I’d invested more smartly. After 7 years of it, I wisened up and surrendered the policy, and went with “term life plus invest the rest” in a simple 3-fund Bogleheads-style portfolio.
Big regret (wasted time) and best learning:
Just after getting married in my early 20s, my wife and I got lured into a timeshare presentation for a free gift. After 3 hours of our time, they wanted us to sign a contract for an $8000 timeshare at Ocean City, MD (1987).
I was considering it – but was smart enough to say I wanted to take the contract home and read it over with my Dad. The sweet smiles quickly turned to urgent requests that “this great deal” won’t last and then snarls and put downs. They would not give me a copy of the contract to review. No sale from me. Years later I understood what a trap they were.
I learned
1) Never be in a hurry
2) Other opportunities will come (years later made some great money on an investment at Bethany Beach)
3) Seek advice from people you trust
4) Don’t be bullied into anything
Maybe that 3 hours wasn’t a waste after all.
Everyone needs to read your comment, excellent info. I had the same situation a couple of times, but resisted by saying I have to think about it, I have to read about it, and boy they wanted a decision, then I just said NO!
My response is less about a purchase I most regretted. It’s about how I react once I make such a decision. Like you, Jonathan, I would have these poor decisions hanging around for years. And for years the objects would haunt me.
More recently, when I make such a decision, and it’s too late to return it (if indeed it ever was returnable), I get rid of it. Donate it, give it to a family member, toss it, or sell it. Out of sight. Out of mind.
I’ve learned that once the mistake is made, I don’t want it around me any longer. I have enough aggravation in my life.
P.S. While I would need to think about it, one such large regret was a very expensive fountain pen that I rarely used before sticking it in a drawer.
Bought a used 1962 Rambler for $350, what a piece of junk. The end came quickly, about eight months, when the transmission which had buttons by the dashboard would no longer respond in reverse. Forward only and definitely no parallel parking, this was American Motors quality…poor.
I’ve made a number of small purchases that I’ve regretted, until I finally wised-up.,
I’m just old enough to remember when much of the regular stock sold in a variety of retail stores was manufactured with an eye toward quality. But at some point, price apparently became the primary objective, with sellers cutting deep into quality to keep prices low. From clothes to tools, products just didn’t perform or last like they used to.
These days, I’m loathe to make any purchase without shopping around for acceptable quality. And it’s not easy. For footwear, my wife and I take advantage of “free returns” from online sellers by ordering half a dozen pairs–sometime twice that many–looking for one to keep.
The enemy is us. We accept less for our money. I once read an article by a wholesale grocer lamenting the quality of fruit sold. He said it would continue until folks finally refused to buy green peaches and plums.
I always drove Toyota’s (and loved them) but always wanted the luxury version-a Lexus. In my 50’s I paid cash for a Lexus RX350. Hated that car because my head ended up hitting every time I got in/out. Still drove it for 8 yrs before giving to a family member. Now I am a Hyundai Palisade guy and MUCH happier.
I heard the siren call of buying a luxury sedan just last fall. Thought about buying a BMW or a Mercedes. Then I read consumer reports reviews of these cars and was shocked at the low percentage of buyers who thought the purchase was a good value. Didn’t even go to the dealers. Have been a Toyota owner almost exclusively for 30+ years and ended up buying a Toyota Crown Signia.
That’s actually a funny story to me. Back in 2010 or 2011, my wife and I visited Sevierville, TN/Gatlinburg. I bought a pair of Cole Hahn Black and Brown Tasseled loafers, on sale for $60-70.
I finally tossed them last year, the they just couldn’t be resoled again. I polished and treated them religiously, for all those years.
The absolute MOST comfortable shoes I have ever owned.
One reason for my mistake was that I’d previously owned a super-comfortable pair of Cole Haan shoes. But the leather was much softer.
Absolutely! They make great shoes.
Most regretted was probably a pair of boots that didn’t quite fit. Spent a bit more to try to stretch them. Ultimately decided they weren’t for me and donated them, almost new.
But …. My most regretted purchase was almost a house. Fortunately we realized this was a dumb idea in time to back out of the deal, so it only cost us a few hundred dollars and some embarrassment with our realtor.
A condo! Sold it one month later. I still get panic attacks thinking about that stupid purchase.
On a very weak moment, I took the advice from a wall street broker.
Luckily, I had enough sense to never, ever, do that again.
It seemed like a good idea and with the best of intentions, I got a NordicTrack. Enough said…
My wife wanted one in the worst way. Bought it for Christmas that year. We called it the NordicTrack clothes hanger.
Yup, done that.
My most disappointing purchase was as a child when I saved up to buy those “Sea Monkeys” that I saw at the back of comic books. Does anyone remember them? I expected to just add water and have instant, though tiny, friends.
I’m pretty sure I remember them. Were they sponges that ballooned up after being in water? My brother in law got in a lot of trouble but also thoroughly enjoyed himself by buying a lot of those items from comic books, like whoopie cushions that farted when his dad sat on them. And the other two boys and mom had to try not to laugh when the dad blew his stack. I’m sure my brother in law felt these items were well worth what he paid.
At least you didn’t buy the lots in Florida advertised right next to the sea monkeys (yeah, I bought them too). I DID always want to go to Palisades Park, NJ because of those ads.
They were actually brine shrimp! The pictures showed a little family smiling and waving. I was pretty gullible — or wishful. And I, too, remember all of those other things marketed to kids, Linda!
It’s odd how powerful that disappointment was that I still remember it some 55 years later.
Ditto! Johnson & Murphy black wingtip. Even took them to a shoe guy to soften the leather and stretch them. Finally went to goodwill.
My first new car. A gorgeous ’85 Cougar XR-7 turbo. Five turbo failures in the six years I owned the car.
And then there were a few ridiculous stock purchases…
American made cars. First, an Oldsmobile Cutlass Ciera. Ordered from the factory. My head turned every time one went by due to the styling. When we went to pick it up the emblem on the inside passenger door was missing. That was the warning. This was our first new car. Multiple problems. The worst was replacing the steering rack twice (once under warranty). They were trying to copy the Japanese front wheel drive and obviously the engineers didn’t have a clue. A Plymouth Voyager. Had a bubble in the dash. Told by dealer it wasn’t a big deal to replace. What a nightmare rattled forever. When first picked up and driving it and smelled exhaust, they finally discovered it had something to do with radiator fluid and the heating system. Then the AC compressor failed at three years. Basically bought both cars and got rid of them soon after the 3 years, 60,000 mile warranty expired. After that only Japanese cars, mostly Toyotas (one Subaru). First a Camry. I remember saying to my wife it was more than I wanted to spend, but bought it due to the reputation for quality. Never got rid of one due to frustration with repairs. All well over 100K. One lost due to being totaled in an accident, another due to starting to burn oil (12-15 years old 150K), another owned for 18 years, sold to brother, now coming up on 23 years old and sill going.
We bought a house in 1990 that made us “house poor”. I didn’t know this term until some years after we had moved locations. As I have mentioned many times, we were not educated in finances and didn’t understand that just b/c the bank says you can afford it, doesn’t mean you really can. All I knew was that things were tight financially and we couldn’t get ahead. Moving locations for a job transfer helped immensely, and by then I was checking out books from the library to learn what I was doing wrong. Chris
Told my son and daughter in law when they started looking to buy a home to not pay more than 75% of approved amount.
In my finance course that I taught, I always told my students the banker is not your friend, the broker is not your friend, the insurance agent is not your friend. You are the only friend you have so learn something 😆
Back in the eighties, we bought a used brown Ford Pinto for $300 that drove like a tin can but lasted for 3 years. We thought we were experts at purchasing used cars when we fell for a pretty, red Ford Taurus for about $500. Exactly one week later, the engine seized on I 95 in Philly and we had to shell out another hundred bucks to get it towed. So much for our bargain-hunting used car expertise!
My first car a Pinto Runabout (yeah the explosion mobile that old folks remember). However it was my best value ever. Bought for 1K, drove for four years. Sold it when we moved from graduate school and had decide on which of our two cars to keep as was driving a U-Haul and didn’t want a trailer.
Yeah, I watched a friend buy several cars in the less-than-a-thousand dollar range. None lasted very long, and she could never afford the repair.
Literally “buying the farm” – or really, moving into it after my 102-year-old grandmother passed. She needed cash in her final years and, at the time, we were briefly flush. She became our tenant her last two years. By that time, our circumstances had changed. Instead of selling the farm, we sold our primary home in Queens and moved to the farm. I think our kids enjoyed the eight years of country life, but for city-born and bred parents, it wasn’t a good fit. The finances worked out badly – we had to hire people for the many needed renovations and the property didn’t appreciate enough to compensate. We never tallied up how we came out at the end – it would have been too discouraging. It didn’t ruin us, and we certainly had some wonderful experiences while there. I won’t talk about the long winters and record-breaking snowfalls during six of the eight years.
I bought a slightly used 1998 Toyota Previa minivan. Recommended by the Car Guys on NPR. Great seating, but designed in California, it was without a doubt the worst car I’ve ever owned. Dangerous in inclement weather and deadly on snow. Even with 140 lbs of sand and better tires it still mishandled. After an oil change at the dealer in which a nylon gasket hadn’t been replaced it lost most of the engine oil within 10 miles. I pulled into a Wal Mart parking lot and bought several quarts to limp the final 2 miles home. I got it back to the dealer who apologized. My spouse hated it and I sold it at a loss. On the flip side I bought a Subaru WRX and G loved it. Ya win some and you lose some. After two Toyotas since 1995 both which did not live up to expectations I’m cautious with that brand.
We also owned a Previa… Best family van we ever. Likely because it was designed in California. 🙂
I have been sitting here for a half hour trying to think of something.There have been little things like a souvenir that I should never have bought, but I have yet to come up with anything significant. It may be I’m too cheap.
US Mint proof and uncirculated sets (for decades), which are now worth a quarter of what I paid the mint.
Same here. I bought sets for my kids for years. My Dad bought them, too. Now they’re all in a box in the attic.
I’m organizing the 1/3 of my father in law’s collection that I’ve acquired. It’s a big job despite some being in their original packaging. Many are loose but I’m making progress and want to do the best I can for his grands and great-grands as he intended.
Here’s a regrettable purchase that I bet nobody else has made– antique Chinese ceramics. Bought several thousand dollars worth in the mid-1980’s while working in the Philippines. Re-couped some of the funds when I sold some pieces before moving back to the US. Some were “lost” during shipment and the rest are on my bookshelf downstairs. If only I’d put those funds into Berkshire Hathaway stock….
Your comment literally made me cringe. In 2003 I weighed two choices – buy a 100th Anniversary Harley Davidson Road King Classic, or Berkshire Hathaway stock. I went with the Harley. Absolutely beautiful bike, which I quickly sunk another $3000 into making it more beautiful. Total Cost = $25,000. Sold it in 2008 (with only 3000 miles), thankfully right before the GFC really kicked in and the market for used Harleys plummeted. All-in investment with storage, maintenance, insurance, taxes, etc = $28K. Sold it for $14K. I did buy BRKB with the $14K, but I maintain a spreadsheet that calculates the loss on the difference in shares purchased. It is titled “Stupidity Knows No Boundaries”, in honor of one of my father’s favorite sayings… “Even genius has it’s limits, but stupidity knows no boundaries”.
Purchasing shares in a Real Estate Investment Trust when didn’t understand what one was.
Ouch!
I learned NOT to make an investment in something I don’t understand.
Where have we heard that before? Ha! The exact reason I am not a Bit Coin buyer.
An expensive pair of Oakley sunglasses to replace a lost pair of Foster Grants when on vacation sometime in the 1990s. Crappiest shades I ever owned. Lenses glared in direct sun, and lines formed on the lenses. The retailer said it was something I did: it wasn’t.
Funny thing is, some time later I came across an identical looking knock off pair at one of my inner city beer customers. I paid 5 bucks for those and they were much better than the real thing.
Great story, Dan!
It’s still the timeshare.
Amen Brother. I had mine for 6 years and finally hired a law firm and got the contract cancelled. Cost me $4,000 but worth it, just to be rid of it.
Never had openings when I wanted to go, always had excuses, and always increasing the annual fees and costs.
I got suckered in 1979 with the promise of a camera. After making a 5 hour drive, my husband and I were put in a hot room with a promo video featuring George Kennedy. It was $3,000 and I paid $56 a month for YEARS. Along with the RCI membership.
My husband joked about the $3000 camera for all the years of our marriage. But there is a silver lining—I actually used it to trade in 1986 and every year thereafter. Its existence forced me to take vacations I may never have taken. To Florida, to Hawaii, England, the Caribbean, Spain.
Finally in 2019, I went to the actual timeshare I bought (I had never even seen it since I bought it) with my brother as he is a big skier. We went again the next year. He enjoyed the week so much, I gifted it to him. 40 years of shame—SOLVED!
.
Been there. Done that. Got the t-shirt.
When I was a young hard working guy in Austin, Texas, I thought investing in rent houses during one of Austin’s booming real estate cycles was the sure-fire way to make money.
Then a bust cycle hit, the rent houses were underwater, and I had to work harder than ever just to pay the mortgages. I was stuck with the properties for years and learned a never forgotten lesson: Real estate can be very “illiquid”.
And that’s not even taking into account a few tenants-from-hell experiences….
Andrew I have been there and had the same results
Dan, I still remember a “Cosmic Cowboy” tenant from maybe 40 years ago. He wasn’t happy after I promptly got his overflowing commode fixed. He wanted to know what I was gonna do about his Nocona boots that were damaged in the flood.
Stocks in permian basin shell oil company leases that were “safely” hedged—until they plummeted into bankruptcy. One CEO drove into a freeway overpass as a method of suicide—I just learned an investment lesson.
Sounds like Chesapeake Energy.
What purchase do you most regret? I first posted that question more than four years ago. I decided to revive the question today, prompted in part by memories of those (expletive deleted) Cole Haan shoes.
Should have glued one to a canvas like a banksy work of art and hung it on the wall somewhere.
I didn’t notice the timestamp on some of the replies until I saw this. That’s when I understood why I didn’t recognize the names associated with some of the posts.
Enron in the Summer of 2001.
I bought a very large John Deere snowblower. Actually it was a John Deere tractor with a heated cab, overhead lights, and a huge rotating snow thrower on the front. 100% overkill.
I bought this because my little Honda snowblower was overwhelmed given a big driveway and I ended up shoveling so much.
Now I’m much smarter and I hire a reliable snow blowing service to clear my driveway and walks.
A commercial quality elliptical when I was bored with my job and on the job market. Six months later, I accepted a new job halfway across the country at a considerably better salary and with membership to the gym next door. I sold the elliptical at a significant loss after I looked at what it would cost to move it halfway across the country.
Three months before I started my first big girl job after college, I bought a Toyota Celica, it was beautiful. But it came with two loans-one was a 5 year note and the second was a one year note for the down payment I should have had. Those payments totaled over 1/3 of the paycheck I would start receiving in three months. UGH. But I paid off the down payment loan in four months and paid the car off in three years. That took frugality in every other aspect of my life.
The lesson learned was worth the price, that stupid (but awesome) car put me on the path to financial independence. Saving and investing became my primary priorities and I was able to retire at 51.
I bought a Hot Tub a couple of years ago and have only been it in a couple of times. The purchase is an embarrassment, I have to clean it all the time and spend money on expensive chemicals. I might make a flower planter out of it!
A couple years after college and still on my first job, I bought a condo without knowing/asking myself if I woud be settling down in that part of the country.
I bought a cabin on land leased from the State…. so really …just a cabin. It made 0 sense. I regret that I purchased it without really thinking it through. That said, we learned so much and had many good experiences there. We sold it at a loss just before the pandemic… but I could of lost that money in the stock Market just as easily, and not had the life experience. So a financial regret, but wiser for it.
I once bought put options on a stock that I was (temporarily) worried about. The stock price today is about 7 times higher than the strike price on those options.
A timeshare 6000 miles from our home. I feel lucky I got out of it with only a ~75% loss.
My first marriage was crumbling so I signed a lease agreement for a hot red sports car to make myself feel better. The marriage ended, finances shattered, and I was still trapped in an expensive long-term car lease.
Sailboat when my wife was pregnant. What was I thinking?!
For many of us, our mistakes are serendipitous. Investing through the wrong company just made me determined to never allow that to happen again. Some lessons are worth the cost.
It’s not the money I regret or the object. It’s defying that voice inside that said “this is a bad idea”. Making stupid purchases and knowing before I made the purchase that it was a stupid purchase is what I regret.
Brilliant answer. Sometimes we feel carried along by certain emotions or assumptions or relationships, regardless of our knowledge, and it is necessary to swim against the tide.
My first house. We weren’t as financially prepared as we should have been.
My second biggest regret was my second house. Buying high and selling low is a poor strategy for building wealth.
A pair of ATV’s. It was a purchase made as a last ditch effort to save a failing marriage.
Sports cars. I’ve bought flashy -unreliable-sports cars that caused aggravation and expense. The next bounceback vehicle is always a Toyota or a Honda. My lesson is to trust Consumer Reports and not be swayed by the sex appeal of the car.
Yes but Consumer Reports loves the Mazda Miata 😁 – that was the gift to ourselves once our kids were fully educated and gainfully employed. Ragtop, stick shift, and no regrets so far!
Any kid who sunk every dollar they earned in the late 80s and 90s into baseball cards knows the answer to this question. Sigh.
John –
Hopefully you’ve saved them because trading cards are absolutely on fire. Not kidding.
I took mine in to be appraised two weeks ago, and I somehow have managed to not own the cards that sell. I bought cheap mass produced stuff, not the rare cards that have gone stratospheric, but it’s a great life lesson learned for me on supply and demand that I’ve never forgotten!