Guest Article Archives - Page 2 of 54 - Think Outside the Tax Box

Guest Article

By Joshua Youngblood, EA, CTRS, CRETS, NTPI Fellow

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.

READ MORE

The Return of Taxable Student Loan Forgiveness: Planning Considerations for 2026 and Beyond

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.

Read More

One of the Most Important Things a Tax Advisor Can Do: Help Their Client Stay in Business

CPAs routinely help clients improve tax efficiency, yet one of the most consequential advisory questions is whether the business itself could remain operational after a significant uninsured loss. Tax planning improves after-tax cash flow and strengthens annual performance, but continuity planning determines whether the enterprise can withstand disruption long enough to recover. When an adverse event threatens operations, liquidity and stability often matter more than marginal tax savings. For that reason, the discussion of risk funding deserves to sit alongside traditional tax strategy in any comprehensive advisory relationship.

Read More
Client Alert

Are You Committing Filing Status Malpractice?

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.

Read More
Client Alert

Syndicated Easements: Fresh IRS Offer and the Perils of Post-BBA Gamesmanship

The IRS has issued a statement about a new settlement offer that is going out for conservation and historic preservation easement disputes. It is similar to previous offers, but there is one big difference. The partnership will not have to make a payment at the time that it accepts the offer. Other than that, it is similar to the deal offered in 2020. Taxpayers get to deduct what they are out-of-pocket as an ordinary deduction and are subject to a 10% penalty. In general, the out-of-pocket donation might be around 20% to 25% of the claimed charitable deduction. The Tax Court, on average, has been allowing 6%, although results vary. There is usually a 40% penalty in the decided cases.

Read More

TAX COURT ROUNDUP – August 2026

One would think that now, with summer doldrums and vacation days planned, Tax Court operations would slow and we could all go away. Not this month; six full-dress T. C. opinions and some Memos and miscellany fall like a summer cloudburst. Busy times.

Read More

What’s New With Hobby Loss: Recent Developments in Section 183

Recent developments in the Section 183 (Hobby loss) area have not led me to change my basic conclusions. Taxpayers who have a sincere objective of ultimately making a profit should not hesitate to claim losses from the underlying activities. That is so even if you believe that profits are improbable. It is critical that they meet the standard of behaving in a businesslike manner. The other regulatory factors should not be ignored, but often there is not that much you can do about them. Reilly’s 18th Law of Tax Planning – Honest objective trumps realistic expectation.

Read More

The Art of Income Shifting: Powerful Planning Strategies That Stand Up to Scrutiny

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.

Read More
Client Alert

The Capacity Problem: Why Your Firm Can’t Grow Until You Fix Delivery

We’ve all said it: “Once busy season ends, we’ll fix this.” But the pressure never leaves, it just shifts. Extensions, quarter-end, planning season, and year-end come one after another. When a firm wants to grow, the real challenge is not, “Can we get more clients?” but, “Can we deliver quality service at scale without overburdening our team or diminishing client experience?” This is the true capacity problem behind growth.

Read More
1 2 3 4 … 47
  • NOT A Subscriber YET?

    SUBSCRIBE TO GET ALL OF OUR
    GREAT ARTICLES AND RESOURCES!

  • Scroll to Top

    turn new laws into new opportunities download our FREE ebook

     

    Download Our FREE Magazine!

    Download Our FREE Magazine!

    Thank you for subscribing to Tax Law Pro

    You are granted a non-exclusive, non-transferable, revocable license to access and use Tax Law Pro by Think Outside the Tax Box, Inc., strictly according to these terms of use.