Client Alert
I Sell Feet Pics on the Internet, Can I Deduct My Pedicure? (And Other Questions of the Gig Economy)
“I’m going to get a pedicure later,” my wife said to me one Saturday morning. I quickly replied, “You should start an OnlyFans so you can deduct it.” (Everything has a tax angle when you’re married to a tax person.) “Is that really a thing?” she inquired. “Well…” I said, “It depends...” (Nothing is certain when you’re married to a tax person.) “...ordinarily I would say no, but in this case, it might be necessary.” (Everything is a tax pun when you’re married to a tax person.) In the “post” covid era, many taxpayers have turned to the gig economy. (Aside from the number of companies paying workers as contractors when they should actually be employees, but that’s a different topic for a different time.) Many of these gig workers are new to being self- employed and wonder what exactly they can “write off.”
Read MoreInnocent Spouse Relief
"I knew he was a crook when I married him." Come again? And you still married him? That's what I said in my head as it took every muscle in my face to keep my forehead from scowling. But instead, I said, "What do you mean?" "We always had good money and nice things, but we never paid taxes. I always owed when I was single. But when we got married, I stopped working and we never owed." Let me take a moment to rewind and get you up to speed. This taxpayer, let's call her Mrs. Bonnie for the purposes of this story, reached out because she needed to file last year's tax return. She was recently widowed, and her husband typically handled the tax filing. So, she was already feeling overwhelmed and lost when it happened. She went to the mailbox and pulled out mail from the IRS. It was a CP3219A , notifying her that credits claimed on a previous tax return were being disallowed by the IRS. Not only did she owe taxes, but she also owed accuracy related penalties. She only had 90 days to respond if she disagreed and didn't know what to do. When she reached out to me, she inquired about whether I could review previous year returns. Mrs. Bonnie wanted to make sure that they were "done right". This isn't a strange request. I told her that I would review the prior year to have a baseline and if I saw anything fishy, I'd bring it to her attention and perhaps look at another year. I didn't even make it to the signatures before the fishiness leaped off the page. I set up a meeting with her via Zoom to review my findings. As I begin to ask about some of the credits claimed and her husband's business her answers did not match what was on the return. That's when she let me know that she knew her husband, Mr. Clyde, was a crook when she married him. Mrs. Bonnie didn't know much about taxes, but she did a bit of research. She read about something called Innocent Spouse Relief and thought she may be eligible. Let's look at what Innocent Spouse Relief is and why Mrs. Bonnie was not eligible, but your client may be.
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Tax Tales I Let Slip in 2025: From Whistleblowers to Easement Woes and Beyond
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.

The IRS in 2025: A Snapshot of Reality
The IRS is not the same agency we dealt with a decade ago, or even three years ago. The pandemic accelerated operational strain, exposing long-standing infrastructure weaknesses while also prompting overdue investment and modernization. Some areas have improved meaningfully, including digital tools, faster account updates, and improved phone service during filing season. Other areas, however, feel frozen in time. Correspondence units remain slow, backlogs persist, and automated notices often fail to reflect what is actually happening on a taxpayer’s account. This article outlines the practical realities of working with the IRS in 2025, what strategies are working, what remains broken, and how to set clear, healthy expectations so you can deliver results without burning out.

The IRS in 2026: A Strategic Field Guide for Tax Professionals
As we head into the 2026 filing season, tax professionals are operating in an environment unlike any we have seen in recent memory: a smaller and more automated IRS, the new OBBBA, and rapid experimentation with AI-enabled tools inside the Service. This field guide is designed to separate what we know for sure from where the IRS is likely to move next, and to translate both into practical planning moves. It does not predict the future; instead, it offers a structured way to think about enforcement, documentation, and client strategy when the rules, the technology, and the politics are all in motion.


