Individual Strategies Archives - Page 5 of 20 - Think Outside the Tax Box

Individual Strategies

By Peter J Reilly CPA

Tax Tales I Let Slip in 2025: From Whistleblowers to Easement Woes and Beyond

One of my greatest frustrations as a tax writer is that I just don’t have the time to cover everything that I notice. Early in my blogging career, when I was younger and had more energy, I set myself on a Monday, Wednesday, Friday schedule like the college professors I envied. Even that did not keep up with everything I noticed, so periodically I would do a post that had short blurbs about interesting things I didn’t dig further on. Here is an example from 2010 of a post that covers an entity not considered a church by the IRS, S corp shareholder basis issues, definition of alimony and two Chief Counsel Advices on TEFRA issues. So here are some things for 2025, that I opened a file on but never managed to make an article with.

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Side Hustles and Tax Tussles: Tax in the Gig and Share Economy Part Three

The past month we've explored how side hustles can affect your client's taxes. You're now equipped to help them avoid most side hustle tax tussles, but there is one other major area of the gig economy that we must cover. That is when your clients decide to share their personal property for a fee. Don't confuse this concept of the share economy with your client renting out real estate, like we discussed in part 2. The IRS has a different definition for personal property, one that does not include real estate. Which, you guessed it, means there are different tax implications. To help you avoid tax tussles for your clients, we're going cover the following: ● What's the difference between personal property and real estate? ● Where do we report personal property rental income? ● What can we deduct from personal property rental income?

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Side Hustles and Tax Tussles: Tax in the Gig and Share Economy Part One

I can recall looking for a part time job in local newspapers when I was in high school. Sometimes a friend and I would ride around with our $2.29 per gallon gas looking for places that were hiring. Facebook was gaining popularity but not for job posting. So, searching for jobs on my phone via an app was unimaginable. Advances in technology have changed the way that we do things in the world. Everything an individual needs to find a job is right at their fingertips. There are more opportunities to find gigs and be your own boss if that’s what one desires. There’s no question that the way people find ways to earn income has changed. What has not changed is the fact that the IRS wants their share of the income earned. But how do we apply the tax code to these new ways that taxpayers are earning money? We are going to break that down in this three-part series. Whether your client is doing odd jobs on an app like TaskRabbit, driving for Lyft, renting out their home or car, you will know how to guide them. This is what we are going to cover today with a focus on rideshare, delivery, and other service gigs.

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What Clients Should Know About Innocent Spouse Relief

Some clients marry into tax trouble – and then have no clue how to get out. Others are on the cusp of a separation or divorce and want the uncoupling (at least in the eyes of tax authorities) to start ASAP. Few clients who need the IRS tool called “innocent spouse relief” to unshackle themselves from a spouse’s tax mess (either one that spouse brought to the marriage or one they racked up later) seem to know about it. Here’s what to tell such a client about what this relief does and does not cover and what your client will have to prove before they can qualify – as well as how difficult this relief can be to get.

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Death and Taxes: What Clients Should Know About the Death of a Spouse

Even your most financially savvy client isn’t going to think clearly after the death of their spouse. Taxes will be last on their minds. That’s where you’ll come in, nudging them toward tax and money moves both immediate and long-term, from filing returns to budgeting income to taking a step-up in basis. Above all, don’t assume grieving clients know these details or that they’ll remember them in one of life’s toughest moments.

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Navigating the Plagiarism Minefield: Strategies and Solutions for Certified Tax Planners

In the AI era, especially with tools like GPT, plagiarism isn't just copying another's work, but also presenting AI-generated content as one's unique thought without understanding or modifying its output. It's about intent and attribution. If someone blindly takes an AI's output and presents it as their own, especially in professional or academic settings, it can be considered a form of plagiarism. For certified tax planners, understanding and addressing this nuanced form of plagiarism is crucial for maintaining professional integrity and credibility.

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When Does Married Filing Separately Make Sense?

If your clients are married, at this time of year they’re probably choosing to file their taxes under the status of Married Filing Jointly. But is MFJ the best move? Married folks have other options; one of them is Married Filing Separately (MFS). Despite this status sounding like someone’s dressing for divorce court, it can be useful in certain circumstances – or harmful.

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How to Deal with Huge Tax Debt

The only thing scarier than owing Uncle Sam a lot in taxes is being unable to pay the bill. Luckily, the Internal Revenue Service has ways for you to whittle what you owe. Just make sure which method works for you, depending on such factors as the size of your tax debt and what you can afford to pay and when. Don’t panic. Here’s how individual taxpayers can proceed – and what to watch out for.

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Client Alert

Health Savings Accounts vs Flexible Spending Accounts

With the rising cost of healthcare, our clients are looking to save money where they can, especially if they can save money on their healthcare costs and taxes at the same time. As their trusted advisor, you can offer them a basic understanding of what savings tools are available to your clients. Some of the tools available will come in handy if there is a minor unexpected tax bill this spring. That is why today we’re going to look at the triple tax advantaged health savings account (HSA) and the health flexible spending account (FSA). We’ll look at what they are, who is eligible to open one, and how they can save your clients money each year.

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