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New tax reduction strategies carefully explained and exhaustively researched every two weeks. Receive breaking news updates on tax law changes. Members only monthly AMA with TOTTB.tax.

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The Tax Lives of Performing Artists

Performing artists are everywhere. Whether you’re a fan or indifferent, they’re tough to ignore. They color our world with print, broadcast, and social media coverage. We have actors, musicians, newscasters, and podcasters performing live, streaming online, captured on film/radio/television, and just about everywhere in an expanding online universe. We celebrate their triumphs, empathize with their trials, feel shocked at their gaffes, and grieve for and with them. We may not think we have much in common with performers, but we do have one commonality: We’re all taxpayers! A performer’s life may seem glamorous, but it’s hard work and not always financially predictable. The tax lives of performers are complicated. They have income and expenses, but with many twists and peculiarities. Twists and peculiarities can make it both interesting and complex when navigating the Tax Code, but performing artists need tax reduction, too. Tony Nitti said, “It has to suck to make your living as an artist.” But paying taxes as an artist doesn’t have to suck when you have a great tax plan. To read more about the unique tax planning opportunities available to performing artists, continue reading.

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CURRENT EDITION

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.

The Tips Deduction and the Self-Employed: Potholes Everywhere

By now, tax professionals and taxpayers are familiar with the fact that the One Big Beautiful Bill (OBBBA) created a new tax deduction for tips received. What we want to look at in this article is — how do self-employed taxpayers handle this deduction?

The Succession Plan You Keep Meaning to Write

I have a friend who has been retiring “in about two years” for the last five years. He is 67, runs a successful practice with about 400 returns, and specializes in tax planning. He has never had the practice valued. He also has no succession plan in the event he does not come back from his next fishing trip. This is not unusual. This is typical. The 2020 American Institute of Certified Public Accountants (AICPA) firm succession survey found that only 6% of solo and sole practitioners had a practice continuation agreement in place. Nearly half of those surveyed said they knew they needed one and had no idea how to start. That second figure is the one that gets me, because it is not denial. Our colleagues know exactly what is at stake and are stuck. Let us get unstuck.

SIMPLIFIED TAX STRATEGIES &
PRACTICAL IMPLEMENTATION

Think Outside the Tax Box provides tax reduction strategies along with practical
implementation advice in order to reduce your clients’ federal tax bill with ease.

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