What If I Haven’t Filed Taxes in Years? with Kevin Cross

Falling behind on taxes can feel overwhelming. Maybe you missed one year, then another. Maybe a job change, a divorce, an illness, a death in the family, or a season of financial hardship made it hard to keep up. Or perhaps you started gig work, received a 1099 for the first time, and were surprised to discover that you owed more than expected. Whatever the reason, failing to file your taxes for several years is serious—but it is not the end of the road. The IRS would rather see you come back into compliance than continue avoiding the issue. The most important step is to begin. Kevin Cross has helped many people walk through this very situation, and his counsel is simple: don’t panic, don’t ignore it, and don’t assume it’s too late to get help. Start With the Current Year If you have not filed taxes in several years, your first instinct may be to go back to the earliest missed return and start there. But Kevin often recommends a different first step: filing the most recent tax year. The goal is to show the IRS that you are trying to come back into compliance. Filing the current year helps convey that this was not willful neglect but a season when something went wrong, and that you are now taking responsibility. The further behind you are, the harder it can feel to catch up. But beginning with the most recent return can give you a clear starting point and stop the pattern from continuing. Why People Fall Behind There are many reasons someone may stop filing taxes. Some are self-employed or gig workers who receive a 1099 and discover they owe thousands of dollars because taxes were not withheld throughout the year. Others fall behind after a divorce, death, disability, job loss, or another major life disruption. Since the COVID years, many people have also struggled to keep up with their tax responsibilities. Once one year is missed, it can be easy to feel overwhelmed and avoid the next one, too. But avoidance only makes the problem heavier. The path forward begins with gathering information and getting the right help. Not Filing Is Different From Not Paying It is important to understand the difference between not filing and not paying. If you owe taxes, the April deadline matters. You can file an extension to extend the time to file your return, but that extension does not extend the time to pay any tax you owe. However, if you are due a refund, there is generally no penalty for filing late. But there is a time limit. If you wait too long—typically more than three years—you may lose the ability to claim that refund. Some people may not be required to file at all. For example, if Social Security is your only source of income, you generally do not need to file a federal tax return. But the challenge is that many people do not know whether they owe or not until their information is reviewed. Other income can change the picture, such as interest, dividends, retirement distributions, self-employment income, or the sale of a home. Even a home sale that qualifies for the primary residence capital gains exclusion may still need to be reported properly so the IRS understands why no tax is owed. Gather Your Wage and Income Transcripts One practical step is to request a wage and income transcript from the IRS. This transcript shows what the IRS has on file for you, including W-2s, 1099s, mortgage interest forms, retirement distributions, and other tax-related documents. You can request this through the IRS website. Searching for “IRS wage and income transcript” should take you to the right place. This can be especially helpful if you do not have all your old tax documents. It gives you a starting point for reconstructing the missing years. Work With a Qualified Tax Professional While you can download your transcripts yourself, you may not know what to do with them once you have them. IRS transcripts do not look like regular tax forms, and catching up after multiple missed years can involve more than simply filling out returns. That is why Kevin recommends working with a tax professional who understands tax representation and IRS procedures. A qualified CPA, enrolled agent, or tax professional can help determine which years need to be filed and how to communicate with the IRS. According to Kevin, the IRS typically focuses on the past six years when bringing a taxpayer back into compliance. That does not mean every situation is identical, but it does mean you should not simply assume you need to start with a very old return from decades ago. A knowledgeable professional can help you determine the proper path. The IRS Will Work With You Many people avoid filing because they are afraid of what they might owe. But the IRS has options for taxpayers who cannot pay everything at once. Depending on your situation, those options may include a payment plan or, in some cases, an offer in compromise. The key is to take the first step rather than remain silent. Ignoring the problem will not make it disappear. But taking action can begin to restore order, clarity, and peace of mind. A Faithful Step Forward Taxes may not be pleasant, but handling them honestly is part of faithful stewardship. Romans 13:7 says, “Pay to all what is owed to them: taxes to whom taxes are owed, revenue to whom revenue is owed.” If you have fallen behind, do not let shame keep you stuck. Begin with the next faithful step. Gather your documents. Request your transcripts. File the current year. Then find a qualified tax professional who can help you walk through the rest. And if you would like to find a trusted financial professional who shares your values, visit FindaCKA.com to connect with a Certified Kingdom Advisor® (CKA®) near you. On Today’s Program, Rob Answers Listener Questions: I have about $18,000 in credit card debt. I may have the opportunity to work in Alaska’s fishing industry for three months and earn enough to pay it off quickly. Should I contact Christian Credit Counselors before I go, or wait to see how much progress I can make during those three months? I have a Thrift Savings Plan and plan to retire within the next five years. I was told I could roll over part of my TSP into something that would protect the principal, keep it from going down, and still leave my TSP open for contributions. Is that wise, and is it really guaranteed not to lose value? I’m 59 and have contributed to my company’s traditional 401(k) for years, with a 50% employer match. I’m near the end of my career and likely at my highest income level. Should I keep contributing to the traditional 401(k), or would a Roth option make more sense? I’ve been studying the Bible for just over a year and recently began tithing. I want to honor the Lord faithfully, but I’m not sure where the tithe should go. Biblically, who should receive it? Resources Mentioned: Faithful Steward: FaithFi’s Quarterly Magazine (Become a FaithFi Partner) Christian Credit Counselors Our Ultimate Treasure: A 21-Day Journey to Faithful Stewardship by Rob West Wisdom Over Wealth: 12 Lessons from Ecclesiastes on Money Look At The Sparrows: A 21-Day Devotional on Financial Fear and Anxiety Rich Toward God: A Study on the Parable of the Rich Fool Find a Certified Kingdom Advisor® (CKA) FaithFi App Remember, you can call in to ask your questions every weekday at (800) 525-7000. Faith & Finance is also available on Moody Radio Network and American Family Radio. You can also visit FaithFi.com to connect with our online community and partner with us as we help more people live as faithful stewards of God’s resources. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.