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Retirement Tax Planning — Retirement Plans for the Sole Proprietor

Many of the same tax advantages perceived as being only available with entity taxation are also available to Schedule C sole proprietors and that includes funding retirement plans. It’s perfectly OK to start and continue to run a business as a sole proprietorship filing a Schedule C for when it makes financial and administrative sense to do so. There are a number of advantages to having a retirement account. Of course, when you contribute to a retirement account, you can deduct your contributions from your taxable income. This can result in significant savings come tax time. Additionally, the money in your retirement account grows tax-free. This means that you can potentially earn a lot more on your investment than you would if it were subject to taxation. A retirement account gives you the peace of mind that comes with knowing you have a cushion to fall back on in retirement. No matter what happens in the markets, you will always have access to your retirement savings. This can provide a great deal of security during uncertain economic times. While retirement accounts can be a great way to save for the future, there are also some potential drawbacks to consider. For one thing, retirement accounts often come with strict penalties for early withdrawal. This means that if you need to access your savings before retirement age, you may be subject to significant fees. Additionally, retirement accounts can be complex and confusing, making it difficult to keep track of your progress. While retirement accounts can be a helpful tool for saving, it’s important to be aware of the potential drawbacks before you decide as a sole proprietor whether or not to open one. Click here to explore the different types of retirement plans available to sole proprietors and the pros and cons of each.

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CURRENT EDITION

Lessons Learned from the Tax Court: An Olive Branch in Tax Court

“Everything is deductible until the audit” is an adage frequently repeated in the tax preparation industry. Generally, it’s mentioned tongue-in-cheek, but today’s taxpayer (and her tax pro boyfriend) may have taken it a bit too literally. Additionally, cutting corners may seem like a time-saving strategy in the moment, but the potential to backfire can’t be ignored. In this case, the taxpayer is about to learn things the hard way.

Two Tax Systems: The Fundamental Divide That Shapes Every Client Strategy

As tax professionals, we must recognize a profound truth that most Americans never fully grasp: The United States doesn’t have a single tax system, it has two fundamentally different systems operating in parallel. Understanding this dichotomy is perhaps the most important insight you can share with your clients, as it forms the foundation for virtually every advanced tax strategy.

Explore Our Free Articles

Get a taste of our comprehensive tax planning insights with four featured articles, free for everyone.

2025 Winter Education Series Event Calendar

Think Outside the Tax Box proudly presents the 2025 Winter Education Series! This October through December, we are bringing our loyal subscribers five webinars featuring some of the brightest minds in tax. Each high quality webinar is filled with engaging content, actionable insights for your clients, and they all come

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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.

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As an annual subscriber, you gain complimentary access to our series of expert-led webinars. Each session is designed to provide you with insights, skills, and knowledge to excel in your field. Discover what’s coming up and secure your spot today.

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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