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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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Retirement Tax Planning – Work for All Seasons of Life
The single best skincare tip for avoiding wrinkles is to stay out of the sun. What does this have to do with retirement tax planning? Well, much as skincare shouldn’t stop when the first wrinkle appears, tax planning for retirement shouldn’t stop at retirement. Tax planning for retirement is an ongoing balancing act that, in a perfect world, begins with the first earned income and continues for the remainder of the taxpayer’s life. The trick is to balance tax strategies that help while a client is working with tax strategies that are going to benefit the client once they retire all without having a crystal ball as to how tax laws may change in the short- or long-term future. This article is the first in a four-part series that explores tax planning strategies both before and during retirement and discusses the importance of pro-active planning before and during retirement. Keep reading to learn more…
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Remember, Influencers, the IRS Follows You Too!
The influencer marketing industry was able to grow during Covid as many advertisers had to adjust or cancel their marketing campaigns. This was because more people were sitting at home consuming content on social media. This new opportunity for smaller influencers has created a new group of taxpayers who need to know their new filing obligations. They’ll also be open to tax planning strategies that you have to help them reduce their tax liability.

Hobby Loss Regulations And Loper Bright
For me, the most exciting Tax Court opinion of 2025 was Judge Joseph Goeke’s supplement to his 2024 opinion in the case of Gary M. Schwarz. With a $1,851,878 tax deficiency, it is the largest hobby loss opinion since 2019. (The really big dollar cases tend to settle.)

Consult, Don’t Convince: Turning Discovery Calls into Advisory Opportunities
The most successful accountants aren’t the ones who pitch the hardest, they’re the ones who listen the most. When you ask better questions, you can diagnose problems that clients didn’t even know they had, which then helps us clarify outcomes instead of listing services. When we shift from “convincing” to “consulting,” discovery calls stop being “sales” conversations and start becoming advisory conversations. And advisory conversations naturally lead to advisory engagements.
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.

