Those sorts of thought experiments are usually relegated to the private worlds of our own minds… usually. Sometimes we find them appearing in the oddest places in the real world. An imaginary number cannot at first glance exist except as a mathematical construct, and yet we find it popping up in fields like electrical engineering and finance to represent very real and concrete things.

We also find them on 5500s.

Wait, what?

I'm talking specifically about the 5500 Short Form – the wildly condensed form that was introduced in 2009 for small retirement plans. There are a number of requirements you need to meet in order to file it: the plan size, obviously, but also certain regulations regarding eligible assets, exemptions from examination and report by an IQPA, etc.

What's interesting is that the Short Form has two questions on it (6a and 6b for the curious) that ask the filer whether they meet the requirements for filing the Short Form. What's even more interesting is that, of the 487,863 short forms that were filed last year, 19 of them actually checked off the box that said, "I'm not supposed to file the Short Form."

Why would the DOL include this as a question? Does it come from a darkly sardonic place where they want to laugh at filers who are being willfully and knowingly noncompliant? How many people get to work filling out the Short Form, hit that question, and toss it into the wastebasket before printing off a more proper full 5500? And what's wrong with the 19 who pressed on in spite of overwhelming red flags?

This 5500 Short Form cannot be filed on a 5500 Short Form.

What happens if Pinocchio says, "my nose will grow now"?

A student of Zen approached his sifu and asked, "Master, can a 5500 Short Form be filed that has 6a and 6b checked off?" The sifu replied, "mu."