📅 October 15 waits for no one

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Plus how your tax anxiety is lying to you, and why it’s time to catch up on your back taxes.  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌

​ Happy Tuesday! October 15 is getting uncomfortably close, but panicking is still the least effective tax strategy.  This week, we’re tackling what happens when you can’t pay your tax bill, why you should quit having nightmares about the IRS, and why October 15 is a good deadline to take charge of the tax returns you’ve been putting off. Plus, we’ll take a look at how a 1990s rapper learned that even if the hits stop, the bills keep coming. This week’s lineup: 🛑 If your tax bill is bigger than your bank account, you’ve got options. 😱 Back taxes are real. Your worst-case scenario probably isn’t. 📆 Missed a few filing deadlines? Borrow this one. 🎵 MC Hammer’s biggest financial hit never made it to the radio.   Tax Strategies 🛑 Can’t pay your taxes by October 15? Here’s what actually happens. Photo by Towfiqu barbhuiya on Unsplash The Quick & Bristly: October 15 is your deadline to file, not a second chance to pay. If your tax bill is bigger than your bank balance, file anyway. Then look at payment plans, an Offer in Compromise, or other IRS options. Your tax return is finally done. But before you can even pop the cork, you realize that you owe the IRS more than you can pay by October 15. You have options, but first we need to talk about a deadline you already missed. Bad news: your tax payment was due in April An extension gives you six more months to finish and file your return. It doesn’t buy you six interest-free months to figure out how you’re paying the bill.  If you still owe taxes from April, interest has been accruing on the unpaid balance. And as if that wasn’t enough, the IRS can also charge a failure-to-pay penalty. With the IRS, procrastination comes with a price. Can’t pay? File anyway. Seriously. If you filed an extension, October 15 is still your filing deadline, and you do not want to be late.  That’s because missing the filing deadline adds another unsavory character to the story: the failure-to-file penalty. And the moral of this story? Waiting to file your taxes – even if you don’t have the funds to pay your tax bill – isn’t going to solve the problem. So file the return, even if you can’t pay everything you owe. Which brings us to the obvious question… I still don’t have the money. Now what? You know you owe. You know you’re already late. And several thousand dollars aren’t just going to materialize in your checking account. So, what exactly are you supposed to do next?  If you’re expecting the answer to be “just pay up,” you’re in for a surprise. The IRS is surprisingly flexible. ➡️ Find out what “flexible” really means   PRESENTED BY TAXQUOTES Can’t pay what you owe? You have options. The IRS is more flexible than it feels like right now, but figuring out which path actually applies to you isn’t always obvious. TaxQuotes helps you sort through what’s possible based on your income and situation, and can help stop wage garnishments, liens, and levies along the way. The process is handled from start to finish, so nothing gets overlooked. ➡️ Schedule your free consultation   Tax Strategies 😱 Back taxes are real. Your worst-case scenario probably isn’t. Photo by Rinck Content Studio on Unsplash The Quick & Bristly: If you owe back taxes, you don’t need to panic – but you shouldn’t ignore the problem, either. Open the notices, know the process, and take action before collections escalate. You owe the IRS money, and suddenly, every envelope in the mailbox looks ominous. Before you start saying your goodbyes to your paycheck, bank account, and maybe even the couch, don’t let your anxiety fool you. The IRS collection process doesn’t happen overnight. First, check your mailbox Once the IRS assesses what you owe, it sends a notice explaining your balance and requesting payment. That balance includes your unpaid taxes plus penalties and interest, which keep growing until you pay. If you get that notice, open it. Check the amount and the deadline, and plan to pay what you can. If something looks wrong, take action: call the number on the notice, visit an IRS office, or file an appeal.   What you shouldn’t do is stash the notice in a drawer. You may forget about it, but rest assured, the IRS will not. Your stuff isn’t going anywhere yet This is usually where the anxious mind jumps ahead a few chapters. You get the notice, you don’t pay it, and suddenly the IRS is taking your paycheck or the device you’re reading this on. But the IRS collection process has several steps before it gets anywhere near that point. A tax lien is a legal claim against your property. If the IRS files a Notice of Federal Tax Lien, it becomes public record and can make it harder to get credit.  A levy goes further. That’s when the IRS actually takes money or property to satisfy your debt. But even that doesn’t happen without warning. The IRS generally must send a Final Notice of Intent to Levy and give you at least 30 days to request a hearing before moving forward.  Here’s what your anxiety left out The IRS has some pretty heavy tools in its arsenal. But there’s a long road between “I owe back taxes” and “the IRS is coming to collect.”  And you have more control over what happens along that road than you think. ➡️ Here’s how to take the wheel   ALSO PRESENTED BY PERSONALLOANS.COM Owe more than you can pay right now? If the number on your tax bill doesn’t match what’s in your account, a personal loan can help close the gap. PersonalLoans.com connects you with lenders offering $1,000 to $35,000, so you can cover what you owe now and pay it down over time. ➡️ See your options here   Tax Strategies 📆 Haven’t filed taxes in years? Here’s why October 15 is still your moment. Photo by Christopher Luther on Unsplash The Quick & Bristly: Your late tax returns aren’t going away, but neither is your chance to get caught up. Use October 15 to figure out what you need to file, track down your records, and start clearing out your backlog. October 15 is the deadline to file if you requested an extension back in April. And it may have you thinking about that return you need to file. And the one before that. And maybe even the one before that. While it isn’t technically a deadline for back taxes, consider October 15 your cue to finally get back on track. You forgot about your tax returns. The IRS didn’t. Whether you genuinely forgot or just “forgot,” those late tax returns aren’t going anywhere. Neither is the IRS.  The longer you wait, the messier it gets. If you owe, penalties and interest keep stacking up. The IRS can also prepare a Substitute for Return using information it already has. Translation: the IRS creates a return on your behalf, but it may not include all of your deductions and credits. So, those tax benefits you planned to claim? The IRS isn’t doing that work for you.  And don’t let an empty bank account stop you from filing. Filing and paying are two separate issues, so you don’t have to sell a kidney or dig into the couch cushions to come up with every cent. File now. Figure out the payment plan later. Your refund has an expiration date But what if the IRS actually owes you? Not only are you leaving money on the table now, but you may miss out on cashing in entirely.  If you’re owed a refund from an unfiled return, you generally have three years from the original due date to file and claim it. If you miss the window, you can wave goodbye to that refund check. Missing years? Start with missing paperwork. Here’s your October 15 homework. Figure out which returns you actually need to file. Then start gathering W-2s, 1099s, and other records. If you’re missing something, IRS transcripts can help you track down income reported under your name.  And you don’t have to go at it alone. If you’re several years behind, can’t find records, owe a big balance, or have a complicated situation, it may be time to call in a tax pro. October 15 isn’t your official deadline, but it’s a pretty good day to finally cross “file my taxes” off your to-do list.   Photo by Dylan Gillis on Unsplash Thursday, we go to work. The TaxStache Business Edition is built for owners and operators. Quick hits on entity structure, quarterly deadlines, deduction strategy and the IRS rule changes that actually affect your bottom line. Would you like to receive our Thursday Business Edition? Yes! Count me in. No thanks.   Celeb Tax Cases 🎵 MC Hammer’s tax troubles prove the IRS can touch this Image by Andres M. The Quick & Bristly: MC Hammer learned the hard way that you have to keep making money to live like a millionaire. After pumping out hits, he faced bankruptcy and tax problems that followed him for nearly 20 years – keeping him in the headlines long after the music stopped. MC Hammer built an entire career around telling people they couldn’t touch this. Apparently, the IRS didn’t get the memo. From Hammer Time to hard times Stanley Kirk Burrell – better known as MC Hammer – became one of the biggest stars of the early 90s. He made millions – and became almost as famous for how quickly he blew it on everything from a massive entourage to a mansion worthy of its own episode of “Cribs.” It’s unknown how much was spent on parachute pants. By 1996, Hammer filed for Chapter 11 bankruptcy with millions of dollars in debt. The case was later converted to Chapter 7. But in 2002, Hammer and his wife were denied a bankruptcy discharge after failing to satisfy the conditions of a settlement agreement. While that case was playing out, another financial problem was brewing: unpaid federal income taxes. Tax troubles were too legit to quit Years later, Hammer’s old tax bills took center stage for an encore. The federal government sued Hammer and his wife for unpaid taxes from 1996 and 1997. The government won, and he appealed. He lost that, too.  Nearly two decades after MC Hammer’s bankruptcy began, his tax debt was still his most loyal follower. And what happened next is still unclear, as there are no reliable reports confirming whether he ultimately paid the judgment.  MC Hammer’s tax debt is an extreme example, but the lesson is pretty simple. Don’t assume that bankruptcy wipes out what you owe the IRS. If bankruptcy and tax debt are on the table, don’t try to freestyle it; talk to a tax or bankruptcy professional. An old tax bill is a comeback that nobody’s ready for.     The quick (and slightly prickly) stories we didn’t have time to get to: 💰 The IRS put nearly 39,000 high-income nonfiler cases worth a potential $15.7 billion on hold because it didn’t have the resources to deal with them. The IRS has since moved the cases forward, much to the disappointment of everyone else involved. 🤖 Side hustlers using free AI tools reported twice the median monthly income than those who aren’t using AI – plus they saved nine hours each week. Yet another win for working smarter, not harder. 🤥 Approximately 870,000 borrowers tied to an estimated $39 billion in suspected pandemic loan fraud are barred from future Small Business Administration loans and programs. Turns out, forgivable loans aren’t so forgiving when fraud enters the picture. 📅 October 15 isn’t just the filing deadline — if you owe the IRS, it’s also your best shot at getting ahead of the balance before penalties keep adding up. TaxQuotes offers a free consultation to help you see what your options are. Get started here. (sponsored).   Follow us for even more great tips, tricks, and deadline reminders. Facebook | Instagram | LinkedIn