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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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greg_j_tomamichel
58 minutes 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
2 hours 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.

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