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The Ultimate Year End Tip Guide and the Search for the Great Shelter
Coming up on the end of the year, year end planning is kind of a ritual for me. I take my first pass in early November and will do it again no later than December. It is pretty boring. I thought it would be worthwhile to do a survey of a variety of year end tips articles. What is going on here is something like Ahab’s hunt for the great white whale. I am looking for something to help out HENRY. HENRY stands for High Earnings Not Rich Yet. I wrote about the quest in 2019. I found nothing much for HENRY then, and this year’s batch of advice articles really does not offer much. The articles do not all say exactly the same thing, but there is a lot of commonality. Due to the sophisticated nature of the readership of TOTTB, I will just allude to the tips, not explain them in detail, because I am going someplace else with this. There is nothing dramatic for HENRY coming from conventional advisers, which accounts for HENRY’s vulnerability to sketchy tax shelters. I will share a bit about what I have seen in that department and reflect a bit.
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CURRENT EDITION
State Tax Planning with the “80/20 Company” Exclusion
Many multinational groups find that foreign-source dividends and other income earned by domestic affiliates are fully or partially subject to state income taxation, even where the federal system provides an exemption. This state-level “leakage” can be material – particularly in high-tax jurisdictions – and is often overlooked because the income appears sheltered at the federal level. For groups with predominantly foreign operations, a starting structure or a restructuring that causes one or more domestic affiliates to qualify as an “80/20 company” can substantially reduce or eliminate state taxation on that income.
Real World Ethics: What Happens When a Judge Doesn’t Understand Tax Law
We all know how messy tax returns can get when couples who used to file jointly divorce and there are children (and tax credits) involved. It’s often difficult to explain the rules surrounding Head of Household filing status and the various tax credits available to parent-clients who have separated or divorced. But what happens when the clients misunderstand and decide to fight about it in family or divorce court? The following case study says “nothing good” can be a horrifying and frustrating answer to this question.
Explore Our Free Articles
Get a taste of our comprehensive tax planning insights with four featured articles, free for everyone.
2026 Summer Education Series Event Calendar
Think Outside the Tax Box is thrilled to bring you the 2026 Summer Education Series, sponsored by Sandy Bay! The fifth installment of this beloved annual series, we will be bringing our loyal subscribers monthly webinars featuring some of the brightest minds in tax all summer long. Each webinar will
Contracts, Signing Bonuses, and the Substantial Presence Test
In tighter job markets, recruits are often offered signing bonuses (and sometimes moving expenses) to join a firm. Sometimes construction workers temporarily relocate to jobs in other states while they are employed by the company that hired them in their home state. This article reviews some of the foundational tax
Start the Year Right: Your WISP Doesn’t Have to Be a Tax Season Nightmare
The mere mention of a WISP makes most tax professionals want to suddenly lose their internet connection. It sounds bureaucratic, technical, and deeply unfun. But here’s the good news: creating and maintaining a WISP does not have to feel like a compliance root canal. And ignoring it can turn into
The Corporate Vault: How to Use a C Corporation to Stockpile Cash for the Future
When most people think about saving for the future, their minds jump to retirement accounts—401(k)s, IRAs, maybe even defined benefit plans. But business owners have another option that often goes overlooked: using a C corporation as a strategic savings vehicle. By leveraging the flat 21% corporate tax rate, smart income
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Inventory Expensing and The Cash Method: Changes from the TCJA
Join Lucien P. Gauthier as we discuss these two changes made by the TCJA in depth.
Taking the Mystery Out of Revised Energy Credits for Individuals
Learn valuable tips to help your clients claim the new residential energy and electric vehicle credits.
Tax Season 911
Your preparedness plan to create tax savings and survive the busiest of times without falling into old habits!
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Featured Authors
Amber Gray-Fenner is an Enrolled Agent and tax practitioner specializing in tax returns, planning, and representation for individuals and small businesses. She owns Tax Therapy, LLC in Albuquerque, New Mexico.
Matt Metras, EA, owns MDM Financial Services in NY, specializing in bookkeeping and taxation for cryptocurrency clients. He’s an educator on cryptocurrency taxation and actively engages in community advocacy.
Jeff Stimpson, has been a tax and finance writer for 25 years. Hee contributes to publications like Accounting Today and Financial Advisor. His other credits include sales tax, technology, and practice management, residing in New York.
Annette Nellen is a professor and tax program director at San José State University, with extensive involvement in tax organizations and a focus on tax policy, cryptocurrency, and education.
Peter J Reilly graduated from the College of the Holy Cross, worked in CPA firms like Joseph B Cohan and Associates and CCR LLP, and now runs a tax practice while writing for Forbes.com.
Thomas Gorczynski, EA USTCP CTP, is a tax expert known for speaking and educating on federal tax law. He’s editor-in-chief of EA Journal, co-author of the PassKey Learning Systems EA Review Series, and runs a tax practice in Phoenix, Arizona.
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