The laws of tax planning that I developed over my writing career that will be expounded in the upcoming Reilly’s Laws of Tax Planning, published by Think Outside the Tax Box, lean a little on the conservative side, as tax planners use the term – conservative versus aggressive, not conservative versus liberal. This results, in large part, from their primary source being court decisions.
The 18th law stands out from the others in this regard. “Honest objective trumps realistic expectation” encourages practitioners to be somewhat more aggressive in claiming losses from activities that seem a little dubious . I still hold that view, even though there have been no encouraging developments in 2023. Here is a roundup on the action last year through December 2, 2023.

The “Busy Season” Myth: Why Accountants Stay Stuck Waiting for Time That Never Comes
If you’re a CPA, you’ve heard it a thousand times. People outside the industry say it like it’s a weather report: “How was busy season?” Firm owners say it to each other, as if it’s a shared badge of honor: “Just get through April 15.” Then it becomes, “After extensions.” Then, “After we rehire.” And after every “busy season,” there’s the crash. The weeks of 60–70 hours. The nights. The lost family time. The feeling that life is on hold until the deadline passes. Here’s the problem: tax deadlines don’t end—they shift. March 15. April 15. September 15. October 15. Year-end planning. 1099s in January. Treating the calendar like the boss means building firms stuck in constant reaction. The truth is, “busy season” isn’t a season. It’s a mindset. And it’s one of the most expensive mindsets we’ve normalized in public accounting.


