Individual Strategies

Remember the dreaded student loan “tax bomb?” For the past few years, it's been easy to forget about it. Thanks to a temporary federal tax exclusion enacted during the pandemic, borrowers who received student loan forgiveness between 2021 and 2025 generally didn't have to include that forgiven debt in their taxable income — leaving many borrowers (and their advisors) to wonder if the tax bomb would eventually disappear for good. Unfortunately, Congress allowed the temporary exclusion to expire. Beginning in 2026, forgiven student loan balances may once again be treated as taxable income. While that sounds like a major change, the reality is that most borrowers didn’t benefit from these tax-free years in the first place. For most borrowers, forgiveness is still years away, and there’s no crystal ball for what future federal policymakers may do. In the meantime, advisors may need to revisit planning conversations that many assumed were behind them. And depending on where a borrower lives, their federal tax bill may be only part of the story.

A lot of client meetings still start with the same assumptions: W-2 in a U.S. state, mortgage nearby, a 401(k), maybe some RSUs, and a college-savings plan. Yet many of those “simple” clients now own an apartment in another country, freelance for a foreign company, or have parents wiring money from overseas. The tax code does not see those details as background color; it treats them as organizing facts. This is where citizenship, residency, and domicile quietly step onto center stage. For planners, the challenge is not memorizing every cross-border rule. It is knowing when a client is no longer “just domestic” and shifting your planning framework before you stumble into penalties, double taxation, or blown opportunities.

Consider this article your periodic reminder that, for married taxpayers, filing jointly is an election and not the default (and certainly not the only) filing status option. It is important in a busy practice to remember to offer this option to clients who may benefit from filing separately, even if they don't ask.

Income shifting strategies address taxation at its most fundamental level by directing income to taxpayers in lower brackets or with offsetting deductions. Unlike many tax strategies that merely time recognition or enhance deductions, effective income shifting can permanently reduce the tax burden on a given dollar of income—often creating tax savings that compound year after year. In this article, we'll explore systematic approaches to income shifting that create extraordinary value for clients while maintaining impeccable compliance.

The credit for dependent-care expenses (such as daycare costs) has long been stuck at 20% for "average" taxpayers. It finally gets a permanent boost in 2026 (for returns filed in 2027). Also, the amount of money a taxpayer can put into a dependent care assistance program is increasing by $2,500 for 2026. This change presents a chance for taxpayers and tax pros to reevaluate which is better – claiming the credit or using a flex plan.

In recognition of the 250th anniversary of the adoption of the Declaration of Independence on July 4, 1776, let’s review 250 years of tax history. Our nation’s tax systems have evolved over two and a half centuries as ways of doing business and living have changed. Also, expectations of services the public wants and needs from the government have grown, resulting in tax changes to generate increasing amounts of tax revenue. Along the way, lawmakers have considered principles of simplification, equity, fairness, economic growth and effective tax administration that have shaped our tax laws. This article offers questions and answers to cover a range of interesting aspects of our federal tax history.

Reilly’s Sixteenth Law of Tax Planning – Being right without substantiation can be as bad as being wrong – is particularly apt when it comes to charitable contributions. The case law makes it clear that there is not much wiggle room in rules relating to substantiation and reporting of charitable contributions. We’ll dig into the rules here.

The Jeffrey Winick tax story is about one of the simplest methods of not paying taxes. That simple method of not paying is simply not paying. Winick is a very successful real estate broker specializing in retail leases. The company he founded, Winick Realty (now rebranded RTL), has in the past been listed as one the top five of retail brokers in New York City. As far as my friend Grok can discern, Winick managed all this with no formal education beyond high school. That makes it extra impressive. I identify with him just a bit. He grew up in Kew Gardens Hill, Queens, New York, and is 75 years old. I also grew up not far from Manhattan and am 74. I sometimes fantasize about living in Manhattan. He's living there, and apparently he was really living. His lifestyle was a major topic in the litigation.