Individual Strategies Archives - Think Outside the Tax Box
By Thomas Gorczynski, EA USTCP CTP

Charitable Impacts of the One Big Beautiful Bill Act

For charitable-minded taxpayers, several provisions in the One Big Beautiful Bill Act (OB3 Act) will impact the tax reduction associated with their charitable giving starting next year in 2026. In one case, the change increases the deductible amount, but all other changes surprisingly reduce the value of charitable contribution deductions. This article will review how the OB3 Act changed the charitable contribution deduction landscape and strategies for tax year 2025 and beyond to maximize the tax reduction value from charitable contributions.

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Some Tips to Help Clients Make the Most of the New Tip Tax Deduction

The One Big Beautiful Bill Act relieves some of the tax burden that comes along with tip income for tax years 2025-2028. But not in some of the ways that it was initially explained. Yes, tip income is still taxable income. No, customers do not have to pay tips in cash for them to be deductible. But the tip does have to be voluntary, qualified, and reported to the IRS.

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Client Alert

The Think Outside the Tax Box OBBBA Quick Reference Guide

The One Big Beautiful Bill Act (OBBBA) marks the most sweeping overhaul of the tax code since 2017, reshaping rules across personal and business income, education, healthcare, and credits. To help you stay ahead of the curve, Think Outside the Tax Box is proud to share our Quick Reference Guide, designed to keep you and your clients informed, prepared, and proactive.

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Everything Old Is New Again: In Many Ways OB3A Is a Return To Obamacare 1.0

The good news is that none of the changes to the Affordable Care Act, Medicaid, or other health-insurance-related tax items in the One Big Beautiful Bill Act (OB3A) were retroactive to the beginning of 2025. The bad news is that the first set of changes is coming in 2026. The worse news is that some changes that were not included in the final version of OB3A are included in a new Federal Rule – but the provisions of the Federal Rule are only temporary. Basically, what we have is some federal rulemaking that was designed to give Congress time to codify the rule’s provisions into law, but only some of the provisions were codified – which simply means the provisions are merely temporary, not invalid. This article is going to discuss some of the important provisions concerning healthcare coverage that are included in OB3A, one that didn’t make it into the law, but that is in the new Federal Rule, and two that kind of blew up on social media but aren’t in OB3A or in the new rule.

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OBBBA Rundown: Provisions Affecting Individuals for 2025

Enacted into law on July 4, 2025, the One Big Beautiful Bill Act is the biggest set of tax law changes since the 2017 Tax Cuts and Jobs Act (TCJA). The provisions discussed in this article impact individual taxpayers for tax year 2025 and must be considered immediately for proactive tax planning purposes, future tax withholding, and estimated tax payment calculations. Clients have questions, and we can generally give them the answers they seek; however, some will require future IRS guidance for complete clarity.

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Helping Elderly Clients Avoid Tax Scams

Taxes are scary enough, even without the threat of scammers involved. While technology has in some ways made taxes easier than ever, like any tool ever invented by humans, these new technologies have also become the plaything of scammers looking to pull off cons. Elderly clients who often have large life savings can be easy targets for scams, whether because of social isolation or emotional and cognitive problems, or maybe just because they didn’t keep up with the latest IRS or FBI warnings about being careful on the internet. Some elderly victims learn too late that it takes serious effort to resolve thefts of money – and potentially years to fix identity theft. These clients need to be extra vigilant. Here’s what to tell them.

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Client Alert

1099 K(ickstarter): Crowdfunding and Taxes

Astronomical expenses crop up more than ever in our economy. From medical bills, business startups, a long-cherished artistic project, it feels like things are harder to afford now than ever. But the internet has also helped create a revolutionary way to raise large amounts of money for some of these causes: crowdfunding. But what does that mean for when the Tax Man comes calling?

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Client Alert

Dave Ramsey And His Critics

Somehow I got through the last thirty years without ever hearing of Dave Ramsey. Now when I go on YouTube, which I do way too often, there is usually a Dave Ramsey video or a video by one of his critics in my feed, sometimes several. I have also looked at a few of his books. I was once told that because I am an Aquarian I want everybody to get along. So I am going to try to reconcile Ramsey’s recommendations and the significant criticism of them.

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Don’t Forget About the Refund Statute Expiration Date

Have you ever found an amazing strategy for a new tax prospect that they missed in previous years? Even worse, have you realized that you overlooked a client’s eligibility for a credit when you prepared their tax return? Not only that, but you had them make an unnecessary estimated tax payment. Well, it may not be too late for your client and prospect to take advantage of those credits for the year in question. The fate of your client isn’t sealed after filing their tax return. The IRS gives taxpayers a set amount of time to make a claim for a credit on their return. The IRS calls the date that this time sunsets the Refund Statute Expiration Date.

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Client Alert
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