Individual Strategies

The Cohan rule is named for George M. Cohan. George Michael Cohan (1878 – 1942) was a theatrical producer. In the decade before World War I, he was called the “man who owned Broadway” and is considered the father of American musical comedy. In 1940 he was awarded the Congressional Gold Medal for his contribution to morale during World War I with his songs “You’re a Grand Old Flag” and “Over There,” the first time the medal was awarded to someone in an artistic field. But his most enduring legacy may be the tax rule that shared its name.

Why aren’t more veterans using the benefits they’ve earned? Part of the problem is awareness, and part of it is discomfort (for both veterans and advisors). After all, veteran benefits are rooted in service-connected health and trauma, placing them in a category that often feels more personal than financial. That alone can deter veterans from discussing their disability compensation and keep advisors from broaching the subject altogether. The result is financial plans that look optimized on paper but are built on incomplete assumptions and missed opportunities – opportunities that have been more than earned.

Part of preparing to leave a high state tax is facing up to the fact that the tax collectors of high-tax states can be kind of clingy. There is more to changing your residence for tax purposes than simple steps like a new driver’s license and a change in voter registration.

Captive insurance remains one of the most closely examined tax planning strategies in use today, not because it is inherently flawed, but because small missteps can carry outsized consequences. Many taxpayers assume that careful formation and proper documentation are enough to protect the intended tax outcome. A recent Tax Court decision, Kadau v. Commissioner, serves as a reminder that those assumptions deserve closer scrutiny. The court’s analysis did not hinge on whether captive insurance can work, but on how a specific arrangement actually functioned in practice. For tax professionals advising clients who rely on micro-captives, the case raises important questions about where structures tend to break down, why some arrangements attract IRS attention while others do not, and what really separates a defensible captive from one that invites challenge.

One of my greatest frustrations as a tax writer is that I just don’t have the time to cover everything that I notice. Early in my blogging career, when I was younger and had more energy, I set myself on a Monday, Wednesday, Friday schedule like the college professors I envied. Even that did not keep up with everything I noticed, so periodically I would do a post that had short blurbs about interesting things I didn’t dig further on. Here is an example from 2010 of a post that covers an entity not considered a church by the IRS, S corp shareholder basis issues, definition of alimony and two Chief Counsel Advices on TEFRA issues. So here are some things for 2025, that I opened a file on but never managed to make an article with.

So as I did last year, I have reviewed a multitude of year-end tax tips articles. One of them is a real standout that you should be sure to check out. If you missed it, you should definitely roll back to the November 15 edition and go over Dominique Molina’s piece, which focuses on what you need to do sooner rather than later in response to OBBBA. It provides more detailed, relevant, actionable advice that you won’t see anywhere else than any of the multitude of pieces I have reviewed. As for the rest, I will give you a basic rundown of what I call the SOSO (same old, same old) and a few suggestions that stand out as different that I will get into a little more along with some thoughts of my own.

Jessica, a self-employed consultant, was thrilled when she found a viral TikTok video promising a “little-known” tax trick. The video claimed she could get a huge refund by claiming a special Fuel Tax Credit and even writing off her family’s beach vacation as a business expense. Following the advice, Jessica filed an amended tax return and waited eagerly for a windfall. A few months later, instead of a refund check, Jessica received a stern IRS notice. Her so-called credits were disallowed, her refund was denied, and she now faced penalties. Jessica isn’t alone. Every tax season, well-intentioned taxpayers get lured by false tax advice on social media, only to end up in trouble. As tax professionals, we often meet panicked clients like Jessica who need our help to untangle the mess.

There is a great scene in the movie On The Basis Of Sex. The actors portraying Ruth Bader Ginsburg and her husband, Martin Ginsberg, a very high-level tax attorney, early in their careers are reading in separate rooms. He comes in with something he wants her to read and she snaps that she doesn’t read Tax Court cases. In that moment she showed her future as a Supreme Court Justice. Not many Tax Court cases reach the Supreme Court. So when one does it’s exciting. And, as it happens, Commissioner of Internal Revenue v Zuch contains some practical lessons worth considering.