Life insurance is such a great income tax deal that it really disturbs me when people manage to create income tax nightmares with it. The build-up in value of a whole life policy is not currently taxed if the policy is properly structured. And even better, except for the insured, the proceeds are totally income tax free when paid because of the death either actual or clearly coming soon of the insured. Of course one of the greatest pieces of marketing genius ever was calling it life insurance, as it is in its pure form, actually death insurance. Here are some stories of life insurance tax nightmares and we’ll see if we can draw a moral from them.

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.


