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A Can of Worms

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AUTHOR: Dan Smith on 7/17/2026

I’m not making this up. I once overheard a conversation in a bar by a couple guys who were planning something nefarious. They were discussing what was essentially the same kind of risk/reward conversation we think about when making allocation decisions; the major difference was that they were weighing time in prison should they be caught. 

I don’t know how things worked out for the pair, but at least they were considering the can-of-worms they were about to open. 

Another fella, Dennis, also a customer at one of the bars I used to service, was clean cut and friendly. At some point, I didn’t see him around for quite a while, and I assumed he moved away. A few years went by, and I finally ran into him having lunch at the neighborhood diner. I asked where he’d been, and he explained that he was arrested after he robbed the bank just down the street. 

Dennis explained that he was at his wits end and desperate; not an unusual predicament for folks in that neighborhood. Dennis did not give much thought, or did not care about his can-of-worms. His record had been clean, no weapon was used in the great bank holdup, and he was remorseful. He got off pretty darned easy. 

Our shelves are lined with cans of worms to be opened when we don’t consider the consequences. 

  • Bad eating habits and not considering poor health down the road.
  • Buying a sports car, or any car for that matter, without first considering the insurance premium, reliability, resale, or gas mileage. 
  • Leaving a job without realizing that the loan from your 401k just became an early distribution with tax consequences, until a 1099R shows up in your mailbox in January.
  • Not saving and not considering how you will retire some day.
  • Taking large distributions without considering you may run out of money before you run out of time. 
  • Taking an adjustable rate mortgage and not considering how much your payment might rise.
  • Taking a capital gain on the 365th day without considering taxes.
  • Skipping a Required Minimum Distribution without considering the penalty.

I bet you can add a can or two of worms to my list.

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Edmund Marsh
17 days ago

Dan, I’ve tried to suppress those painful memories, and many of the bad decisions I do remember highlight bad behavior I’d rather not air in public. But here’s one:

During my years in the employment wilderness, when I was still trying to find my way to a steady career, I contracted with a startup package delivery service who was trying to compete with UPS (Ha!). I borrowed money to buy a van and ran a long route for nine months, leaving home at 5:00 a.m. and returning after 9:00 p.m. No one made money in that venture, but I carried away a few lessons that helped me in subsequent years.

DAN SMITH
17 days ago
Reply to  Edmund Marsh

Edmund, isn’t there a country song about a young guy asking an old guy how he learned to make good decisions. The old fella’s answer was “by making bad ones first”. There’s always a lesson to take away.

DrLefty
18 days ago

OK, we bought a sports car in 2018, but we still have it, it has low mileage, and we’ll be driving it until we’re too old and feeble to climb in and out of it. The amount of enjoyment we’ve already received from it is worth a lot to us. A convertible in California is a beautiful thing.

Other than that, I don’t think I’ve opened any other of your cans of worms! ✅

Ormode
18 days ago
Reply to  DrLefty

The big issue in any luxury purchase is simple: can you afford it? There are wealthy retirees who can afford all the stuff that the retirement videos tell you not to buy. Yes, if you have $20 million, you can buy a new Corvette….if you wish to do so.

1PF
17 days ago
Reply to  Ormode

Ah, Corvette — as I used to hear, the car that passes everything except a gas station. 😉

Dave Melick
17 days ago
Reply to  1PF

Won’t pass my GT350!

DrLefty
17 days ago
Reply to  Ormode

We have neither $20M nor a Corvette! There are sports cars and there are sports cars.

Mark Crothers
19 days ago

I once opened a youthful can of worms — appropriately enough, it was all about fishing.
As young teenagers, we were into beach casting, which meant we needed heavy lead weights on our lines. Being resourceful (and not remotely sensible), we decided the lead flashing on a derelict house’s roof would make excellent raw material. All we had to do was strip it off and melt it down.

Simple plan. Fatal flaw: getting up there was a lot easier than getting back down. We got stuck on the roof.

Then the fire service arrived. Then the police arrived. Then our parents arrived.

I’ll leave the rest to your imagination.

DAN SMITH
18 days ago
Reply to  Mark Crothers

My friend and I thought it funny  to throw crab-apples at passing cars. After one of the drivers turned around and chased us down, we ceased that pastime.

DavidHLancaster
19 days ago
Reply to  Mark Crothers

In jr high school my twin brother and a few of our classmates had a french teacher we didn’t like. At Halloween the teacher said he wasn’t going to be home. We told him if he wasn’t and didn’t give us candy we would egg and shave cream his house. Well like stupid teenagers we did. At about 2 am we got a wake-up call from our father, and formed a cleaning brigade.

Nick Politakis
19 days ago

I haven’t gone to a bar in years but just from hanging around friends and family I’ve heard some doozies. Like I have this 4 year old car that runs great but I’m trading it in because they gave me $12000 and I got to jump on it before the value goes down further. I said how much do you owe? $18000as the answer.

DAN SMITH
19 days ago
Reply to  Nick Politakis

Oh, you must have talked to my friend Bubba, Nick. He’s been hit in the head one too many times with a beer bottle.

Mike inLA
19 days ago

Got it. Eat well, drive safely, rob more banks!

DAN SMITH
19 days ago
Reply to  Mike inLA

Sure, Mike inLA, whatever floats your boat, brother.

greg_j_tomamichel
20 days ago

Thanks Dan. The things you hear in bars!

Like lots of things in life, I think that there is a “sweet spot” for considering future consequences. Considering what might happen is certainly prudent, and a pretty good way to navigate most of your life.

But there is also a place to take a “leap of faith” and forge on, despite the rationale suggesting it’s not a good idea. The failure rate of small businesses is so high that it really doesn’t make sense to start a new venture. But despite that, people still feel compelled to give it a go, and the businesses that do survive are an enormously important part of any economy.

Andrew Clements
20 days ago

Dan, this is a great reminder that every decision comes with consequences, some immediate, others that may not show up for years. I think many of life’s biggest regrets aren’t the result of bad luck but of failing to ask, “What happens next?” Your examples are all financial, but the same principle applies to relationships, health, and even the words we choose. As Jonathan often wrote, good decisions compound over time and unfortunately, so do bad ones. Thanks for another thought-provoking article.

DavidHLancaster
19 days ago

We were pretty laid back about the decisions my children made once they became teenagers. But we did teach them to consider the consequences, both good and bad, before they decided. We also reminded them they have to live with the consequences. Luckily they kept their noses clean and have turned out to be good young(ish) members of society.

DavidHLancaster
16 days ago
Reply to  Dan Smith

Dan,

I think children turning out well is primarily due to parents with good values passing them on to their children, and demonstrating proper behavior. I’m sure there are exceptions to this such as significant mental health issues.

DAN SMITH
16 days ago

David, I sure think that’s true most of the time, still, I’ve seen some exceptions that just leave me scratching my head.

George Counihan
17 days ago
Reply to  Dan Smith

Certainly a combination of the two Dan … When I look at my kids and see very successful adults I never discount luck!

DAN SMITH
17 days ago

I agree, George, luck is a recurring theme in many HumbleDollar stories.

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