Faith & Finance with Rob West
Did you hear about the guy who tried to pay his taxes with a smile? Unfortunately for him, the IRS still prefers cash. All jokes aside, failing to file your taxes for several years is no small matter—but it’s not the end of the road, either. Kevin Cross joins us today with practical steps to help you get back on track. Kevin Cross is a Certified Public Accountant (CPA) who has headed CPA firms in Florida and now Georgia. He has studied the tax code extensively and specializes in representing taxpayers before the Internal Revenue Service (IRS).

Did you hear about the guy who tried to pay his taxes with a smile? Unfortunately for him, the IRS still prefers cash.
All jokes aside, failing to file your taxes for several years is no small matter—but it’s not the end of the road, either. Kevin Cross joins us today with practical steps to help you get back on track.
Kevin Cross is a Certified Public Accountant (CPA) who has headed CPA firms in Florida and now Georgia. He has studied the tax code extensively and specializes in representing taxpayers before the Internal Revenue Service (IRS).The further you fall behind, the more difficult it is to catch up. But rather than beginning with the year you first missed, he recommends filing your most recent return first—say, 2024—and working backward as needed. This shows the IRS that you’re attempting to come into compliance, not ignoring your obligations.
Falling behind on taxes is more common than most people think. Life events like divorce, disability, job loss, or even the rise of gig work can trigger tax complications. For example, many gig workers receive a 1099 for the first time, try to file using online software, and are shocked to discover they owe thousands. Rather than seek help, they freeze—and the following year’s return also goes unfiled.
Of course, COVID didn’t help as many people have been struggling since then to get back on track.
A common misunderstanding is that you must always file. If you’re not going to owe anything, you don’t have to file. That includes many senior citizens who live solely on Social Security.
However, if you're due a refund, you have up to three years to file and claim it. Miss that window, and the refund is forfeited.
Importantly, there’s a difference between not filing and Sometimes you don’t know what you owe—or if you owe—until you file.
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Even if you don't owe taxes on the sale of a primary residence, for example, the IRS won't know that unless you file. If you don’t, you might receive a letter saying you owe thousands in capital gains tax—money you could’ve avoided paying.
Don’t let fear keep you stuck. The IRS can work with you. Options include payment plans or even an offer in compromise, which may reduce your total tax liability.
Filing late taxes doesn’t have to be terrifying. With the right help and a step-by-step plan, you can get back on track—and even experience peace of mind. The IRS just wants to see you trying. Start with today, and take it one step at a time.
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