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10 Tax Deductions You Forgot Were Legal

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Tax season can feel like a maze, and it’s easy to miss out on valuable deductions that could put more money back in your pocket. Many people focus on the obvious write-offs, like mortgage interest or charitable donations, but there are plenty of lesser-known tax deductions that are perfectly legal and surprisingly easy to claim. If you’re looking to maximize your refund and keep more of your hard-earned cash, it pays to know what’s available. The IRS tax code is full of opportunities for those who know where to look. Let’s explore ten tax deductions you might have forgotten were legal, and see how you can take advantage of them this year.

1. Out-of-Pocket Classroom Expenses

You can deduct up to $300 of unreimbursed classroom expenses each year if you’re a teacher, counselor, or classroom aide. This includes supplies, books, and even some professional development courses. Many educators spend their own money to create a better learning environment, and this tax deduction is a small way to recognize that effort. Make sure to keep your receipts and document your purchases, as the IRS may ask for proof.

2. State Sales Tax

Did you know you can choose to deduct either your state income tax or your state sales tax? This is especially helpful if you live in a state with no income tax or if you made big purchases, like a car or major appliances. The IRS even provides a handy calculator to help you estimate your deduction. This legal tax deduction can add up quickly, especially for those who made significant purchases throughout the year.

3. Medical Miles

Most people know they can deduct medical expenses that exceed 7.5% of their adjusted gross income, but did you know you can also deduct the miles driven for medical care? For 2024, you can deduct 21 cents per mile for trips to the doctor, pharmacy, or hospital. Keep a log of your trips and mileage, and don’t forget to include parking fees and tolls. This often-overlooked tax deduction can make a real difference if you or your family have frequent medical appointments.

4. Student Loan Interest Paid by Someone Else

If someone like a parent pays your student loan interest, you can still claim the deduction as long as you’re not claimed as a dependent. The IRS treats the payment as if it were given to you, and then you paid the lender. You can deduct up to $2,500 in student loan interest, which can help lower your taxable income. This is a great example of a legal tax deduction that many recent graduates overlook.

5. Jury Duty Pay Given to Your Employer

If your employer pays your full salary while you serve on jury duty, but requires you to turn over your jury duty pay, you still have to report the jury duty pay as income. However, you can deduct the same amount on your tax return, effectively canceling it out. This legal tax deduction ensures you’re not taxed twice for fulfilling your civic duty.

6. Home Office for Side Hustles

The home office deduction isn’t just for full-time freelancers or remote workers. If you have a side hustle or small business, you may qualify for this deduction—even if it’s just a part-time gig. The space must be used regularly and exclusively for business, but it doesn’t have to be a separate room. You can deduct a portion of your rent, utilities, and even internet costs. This legal tax deduction can be a game-changer for anyone earning extra income from home.

7. Tax Preparation Fees (Certain Situations)

While tax preparation fees are no longer deductible for most individuals, they are still deductible for self-employed taxpayers, freelancers, and small business owners. If you fall into one of these categories, you can deduct the cost of tax software, e-filing fees, and even the cost of hiring a professional. This deduction can help offset the cost of getting your taxes done right.

8. Charitable Mileage

If you volunteer for a qualified charity, you can deduct 14 cents per mile driven in service of that organization. This includes driving to and from volunteer events, delivering goods, or transporting people on behalf of the charity. Keep a detailed log of your trips, and remember that parking and tolls are also deductible. This legal tax deduction rewards those who give their time as well as their money.

9. Job Search Expenses (If You’re Self-Employed)

If you’re self-employed and looking for new clients or gigs, you can deduct job search expenses like travel, resume services, and even some networking event fees. While this deduction is no longer available for most employees, it remains a valuable legal tax deduction for freelancers and independent contractors. Keep detailed records of your expenses to make the most of this opportunity.

10. Retirement Savings Contributions Credit

The Saver’s Credit is a little-known tax break for low- and moderate-income taxpayers who contribute to a retirement account. You could get a credit of up to $1,000 ($2,000 for married couples) just for saving for your future. This legal tax deduction is in addition to the regular deduction for IRA contributions, making it a double win for retirement savers.

Make the Most of Every Legal Tax Deduction

Maximizing your tax refund isn’t about bending the rules—it’s about knowing them. These legal tax deductions are often overlooked, but they’re available to anyone who takes the time to understand the tax code. By keeping good records and staying informed, you can make sure you’re not leaving money on the table. Review this list the next time you file and see which legal tax deductions apply to you. Your wallet will thank you!

What’s the most surprising legal tax deduction you’ve ever claimed? Share your story in the comments below!

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7 Capital Gains Rules That Will Shock First-Time Investors

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If you’re dipping your toes into the world of investing, you’ve probably heard the term “capital gains” tossed around. But what does it really mean for your bottom line? For first-time investors, understanding capital gains rules isn’t just a matter of curiosity—it’s essential for keeping more of your hard-earned money. The IRS has some surprising guidelines that can catch even the savviest beginners off guard. Knowing these rules can help you avoid costly mistakes and maximize your returns, whether you’re selling stocks, real estate, or even collectibles. Let’s break down the seven capital gains rules that might just shock you—and set you up for smarter investing.

1. Not All Capital Gains Are Taxed the Same

One of the first capital gains rules that surprises new investors is that not all gains are created equal. The IRS splits capital gains into two categories: short-term and long-term. If you sell an asset you’ve held for a year or less, your gain is considered short-term and is taxed at your ordinary income tax rate, which can be much higher than you expect. Hold that same asset for more than a year, and you’ll likely qualify for the lower long-term capital gains tax rate, which can be as low as 0% or 15% for many investors. This difference can mean thousands of dollars saved or lost, so timing your sales is crucial.

2. Your Tax Bracket Can Make Your Capital Gains Tax Zero

Here’s a rule that feels almost too good to be true: some investors pay absolutely nothing in federal capital gains tax. If your taxable income falls below a certain threshold, your long-term capital gains tax rate could be 0%. For 2025, single filers with taxable income up to $47,025 and married couples filing jointly up to $94,050 may qualify for this rate. This is a game-changer for retirees, students, or anyone with a lower income in a given year. Planning your sales around your income can help you take advantage of this surprising benefit.

3. The “Wash Sale” Rule Can Wreck Your Tax Strategy

Many first-time investors try to offset gains by selling losing investments, but the IRS has a sneaky rule called the “wash sale” rule. If you sell a security at a loss and buy a “substantially identical” one within 30 days before or after the sale, you can’t claim that loss on your taxes. This rule is designed to prevent investors from gaming the system, but it can easily trip up beginners who are simply trying to rebalance their portfolios. Always check your calendar before making moves to harvest tax losses.

4. Capital Gains Apply to More Than Just Stocks

Think capital gains only matter if you’re trading stocks? Think again. The capital gains rules apply to a wide range of assets, including real estate, mutual funds, bonds, and even collectibles like art or rare coins. Each asset class can have its own quirks—collectibles, for example, are often taxed at a higher maximum rate of 28%. If you’re selling a family heirloom or cashing out on a classic car, don’t assume the tax rules are the same as for your brokerage account.

5. Your Home Sale Might Be Partially Tax-Free

Selling your primary residence? You might be in for a pleasant surprise. If you’ve lived in your home for at least two of the last five years before the sale, you can exclude up to $250,000 of capital gains from your income if you’re single, or $500,000 if you’re married filing jointly. This exclusion only applies to your main home, not vacation properties or rentals. It’s one of the most generous capital gains rules out there, but you need to meet all the requirements to qualify.

6. State Taxes Can Take a Big Bite

Federal capital gains taxes are only part of the story. Many states also tax capital gains, and the rates can vary widely. For example, California taxes capital gains as ordinary income, which can mean a much higher bill than you expected. Some states, like Florida and Texas, have no state income tax at all, making them more attractive for investors. Before you sell, check your state’s rules so you’re not caught off guard by a hefty tax bill.

7. You Can Offset Gains with Losses—But There’s a Limit

One of the most useful capital gains rules is the ability to offset your gains with your losses, a strategy known as tax-loss harvesting. If your losses exceed your gains, you can use up to $3,000 of the excess to reduce your ordinary income each year. Any remaining losses can be carried forward to future years. This rule can help smooth out the ups and downs of investing but remember the wash sale rule and the annual limit.

Capital Gains Rules: Your Secret Weapon for Smarter Investing

Understanding capital gains rules isn’t just about avoiding surprises at tax time—it’s about making smarter decisions all year long. Knowing how your investments are taxed allows you to plan your buys and sells to keep more of your profits, avoid common pitfalls, and even take advantage of special breaks. Whether you’re just starting out or looking to fine-tune your strategy, these rules can be your secret weapon for building wealth.

What’s the most surprising capital gains rule you’ve encountered? Share your story or questions in the comments below!

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The IRS Algorithm That’s Flagging People Just Like You

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Have you ever wondered why some people seem to get audited by the IRS while others never hear a peep? It’s not just bad luck or a random draw. The IRS uses a sophisticated algorithm to flag tax returns for further review, catching more people than ever. If you think you’re flying under the radar, think again—this algorithm is designed to spot patterns, anomalies, and even honest mistakes that could trigger an audit. Understanding how the IRS algorithm works isn’t just for accountants or tax pros; it’s essential knowledge for anyone who files a tax return. By knowing what the IRS is looking for, you can avoid common pitfalls and keep your finances safe from unwanted scrutiny. Let’s explain exactly how the IRS algorithm works and what you can do to stay off its radar.

1. The IRS Algorithm: What Is It and Why Should You Care?

The IRS algorithm, officially known as the Discriminant Information Function (DIF) system, is a powerful tool that analyzes millions of tax returns annually. Its main job is to identify returns that are most likely to contain errors, omissions, or signs of fraud. The algorithm compares your return to others in similar income brackets and professions, looking for outliers and red flags. If your return stands out, you could be selected for further review or even a full-blown audit. This matters because an audit can be time-consuming, stressful, and potentially costly, even if you’ve done nothing wrong. According to the IRS, the DIF system is constantly updated to adapt to new tax laws and emerging fraud schemes, making it more effective yearly.

2. High Income? You’re Already on the Radar

If you earn a high income, you’re automatically more likely to be flagged by the IRS algorithm. The IRS pays extra attention to taxpayers over $200,000; the scrutiny increases as your income rises. Why? Higher earners have more complex financial situations, which means more opportunities for mistakes or intentional misreporting. In fact, IRS data shows that audit rates for high-income individuals are significantly higher than for those earning less. If you’re in this category, double-check your return for accuracy and keep thorough records of all your income and deductions.

3. Unusual Deductions and Credits: A Red Flag Magnet

Claiming deductions or credits that are much higher than average for your income level or profession is a surefire way to attract the IRS algorithm’s attention. For example, if you’re a teacher claiming thousands in business expenses or a freelancer with unusually high home office deductions, the system will notice. The IRS knows what’s typical for each category of taxpayer, so anything that stands out could trigger a review. To avoid problems, make sure you have documentation for every deduction and credit you claim. If you’re unsure whether something is legitimate, consult a tax professional before filing.

4. Self-Employment and Gig Work: More Scrutiny Than Ever

The rise of the gig economy means more people are self-employed or earning side income, and the IRS algorithm is watching closely. Self-employed individuals are more likely to underreport income or overstate expenses, whether intentionally or by accident. The algorithm cross-references your reported income with 1099 forms and other third-party data to catch discrepancies. If you’re self-employed, keep meticulous records and report all your income, even if you don’t receive a form for it. Remember, the IRS is getting better at tracking digital payments and online income sources every year.

5. Math Errors and Incomplete Returns: Easy Targets

It might sound simple, but basic math errors and incomplete returns are among the most common reasons the IRS algorithm flags a return. Even a small mistake can make your return stand out, especially if it leads to underpaying taxes. Double-check your math, use tax software if possible, and ensure every return section is complete. The IRS has automated systems that catch these errors quickly, and fixing them after the fact can be a hassle.

6. Large Charitable Donations: Generosity Under the Microscope

Donating to charity is a wonderful thing, but if your charitable contributions are unusually large compared to your income, the IRS algorithm will take notice. The system compares your donations to national averages for your income level, and anything that seems excessive could trigger a review. To stay safe, always get written receipts for your donations and make sure the organizations are IRS-approved charities. If you’re making non-cash donations, keep detailed records and consider getting appraisals for valuable items.

7. Foreign Assets and Cryptocurrency: New Frontiers for the IRS

The IRS increasingly focuses on taxpayers with foreign bank accounts, overseas investments, or cryptocurrency holdings. The algorithm is designed to flag returns that show signs of unreported foreign income or digital assets. If you have money overseas or trade crypto, you must report it—even if you didn’t make a profit. The penalties for failing to disclose foreign assets can be severe, so don’t take any chances. Use the appropriate forms (like FBAR or Form 8938) and consult a tax expert if you’re unsure about your obligations.

Stay Smart: Outsmarting the IRS Algorithm

The IRS algorithm isn’t out to get you, but is designed to catch mistakes and potential fraud. The best way to avoid trouble is to be honest, thorough, and organized with your tax return. Keep detailed records, double-check your math, and don’t be afraid to ask for help if you’re unsure. Remember, the algorithm always evolves, so staying informed is your best defense. By understanding how the IRS algorithm works, you can confidently file your taxes and keep your financial life running smoothly.

Have you ever been flagged by the IRS algorithm or faced an audit? Share your story or tips in the comments below!

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Here’s What You Should Know About The Tax Inflation Adjustments For 2025

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As we navigate the complexities of our financial lives, understanding the latest tax adjustments is crucial. The IRS has announced several inflation-related changes for the 2025 tax year, which could impact your tax planning strategies. Let’s explore these updates to help you stay informed and make the most of the available benefits.

Increased Standard Deductions

For the 2025 tax year, the standard deduction has been adjusted to account for inflation. Single taxpayers and married individuals filing separately will see an increase to $15,000, up by $400 from 2024. Married couples filing jointly will have a standard deduction of $30,000, an $800 rise from the previous year. Heads of households will benefit from a deduction of $22,500, which is $600 more than in 2024. These adjustments aim to reduce taxable income, potentially lowering the overall tax burden for many individuals and families.

Adjusted Tax Brackets

The IRS has also revised the income thresholds for tax brackets to reflect inflation. The top tax rate of 37% now applies to single filers with incomes over $626,350 and married couples filing jointly with incomes exceeding $751,600. Other tax rates have been adjusted accordingly across various income levels. These changes are designed to prevent “bracket creep,” where inflation pushes taxpayers into higher tax brackets despite no real increase in purchasing power.

Enhanced Earned Income Tax Credit (EITC)

The Earned Income Tax Credit, which supports low to moderate-income workers, has been increased for 2025. The maximum EITC for taxpayers with three or more qualifying children is now $8,046, up from $7,830 in 2024. Eligibility and credit amounts vary based on income and family size, so it’s essential to review the specific criteria to determine qualification.

Alternative Minimum Tax (AMT) Exemption Adjustments

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To keep pace with inflation, the AMT exemption amounts have been increased. For unmarried individuals, the exemption rises to $88,100, while for married couples filing jointly, it increases to $137,000. These adjustments help ensure that the AMT continues to target higher-income taxpayers as originally intended, preventing unintended tax burdens due to inflation.

Updates to Other Tax Provisions

Several other tax provisions have been adjusted for inflation in 2025. The monthly limitation for qualified transportation fringe benefits and qualified parking has increased to $325. Health flexible spending arrangement contribution limits have risen to $3,300. Additionally, the foreign earned income exclusion has been elevated to $130,000. These changes reflect ongoing efforts to align tax benefits with the current economic environment.

Keep Abreast of Tax Changes

Keeping abreast of these tax adjustments is vital for effective financial planning. Consider consulting with a tax professional to understand how these changes may affect your individual situation and to develop strategies that optimize your tax outcomes.

Were you already aware of these changes? How much of a difference will they make when you file your taxes this year? We’d like to hear more about your experience in the comments below.

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7 Ways to Report Your Income to The IRS When Your Employer Refuses to Issue a W2

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Tax season is stressful enough without having to deal with the added complication of your employer refusing to provide you with a W2. This can leave you feeling stuck without a W2, wondering how to report your income and fulfill your tax obligations. Fortunately, there are several options available to ensure that you can still file your taxes properly, even if your W2 is nowhere to be found. Here’s a breakdown of the seven steps you should take to report your income to the IRS when your employer refuses to issue a W2.

1. Contact Your Employer and Attempt to Resolve the Issue

The first step in handling this situation is to contact your employer directly. It’s possible that the W2 has been delayed or that there was a simple oversight in issuing it. Reach out to your HR or payroll department to inquire about the missing form. Explain your situation and politely ask when you can expect to receive it. Keep a record of your communications in case you need to escalate the issue later. If the employer continues to refuse to provide the form, it may be time to take further action.

2. Review Your Pay Stubs and Gather Your Income Information

While you’re waiting for your W2, gather all the pay stubs you have from the tax year in question. Pay stubs provide essential details about your earnings, tax withholding, and other deductions. The total earnings and the amount of federal, state, and local taxes withheld can help you estimate your income for the year. If your employer is not forthcoming with a W2, you can use these pay stubs as a reference for reporting your income. Make sure to compile all your pay stubs from the year, as they will provide a clearer picture of your total income and taxes paid.

3. Use IRS Form 4852: Substitute for Form W2

If you still haven’t received your W2, you can fill out IRS Form 4852, which serves as a substitute for the missing W2. Form 4852 allows you to report your income and withholding without relying on your employer’s W2. When completing this form, use the information from your pay stubs or any other records of your earnings for the year. You’ll need to provide details such as your wages, the amount of federal income tax withheld, and any other relevant information. Be aware that using Form 4852 may delay the processing of your return, as the IRS may need additional time to verify the information provided.

4. Report Your Income on Schedule C if You’re Self-Employed

If you were treated as a contractor or self-employed worker, rather than a traditional employee, you will need to report your income differently. In this case, you would file Schedule C (Profit or Loss From Business) along with your Form 1040. On Schedule C, you’ll report your total income from self-employment and any business-related expenses. Although this isn’t the same as receiving a W2, it still allows you to report your earnings to the IRS accurately. If you’re unsure whether you qualify as self-employed or what income to report, it’s a good idea to consult a tax professional for guidance.

5. File Your Taxes Using Form 1040

Once you have gathered all the necessary information—whether through Form 4852 or by reporting income on Schedule C—it’s time to file your taxes using Form 1040. This form is used by most individual taxpayers to report their income, deductions, and credits. You will include your total income, deductions, and the taxes you’ve already paid (through withholding or estimated payments) on Form 1040. Keep in mind that if you’re using Form 4852, the IRS may take longer to process your return, so be patient if your refund is delayed. Double-check everything on your 1040 before submitting to ensure accuracy and completeness.

6. Contact the IRS if Your Employer Continues to Refuse

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If you’ve made multiple attempts to reach your employer and they are still refusing to issue your W2, it’s time to contact the IRS directly. The IRS can assist in situations where an employer refuses to provide a W2. You’ll need to provide the IRS with details such as your employer’s name, address, and your dates of employment, along with copies of your pay stubs or other supporting documentation. The IRS may contact your employer to request the missing form on your behalf. However, keep in mind that the IRS might not be able to resolve the issue immediately, so it’s best to allow some time for them to act.

7. Consider Filing for an Extension if You Need More Time

If you’re unable to resolve the W2 issue in time for the tax filing deadline, consider filing for an extension. Filing for an extension gives you an additional six months to file your return, though it doesn’t extend the time to pay any taxes owed. If you expect to owe taxes, it’s crucial to estimate and pay the amount due by the original deadline to avoid interest and penalties. Filing for an extension can give you the breathing room you need to ensure your taxes are reported correctly, even if your W2 has not been provided. Remember, the extension applies only to filing, not to payment.

Don’t Let a Missing W2 Derail Your Taxes

It can be frustrating and stressful when your employer refuses to provide you with the necessary tax forms, but there are steps you can take to ensure your taxes are filed accurately. From contacting your employer to using IRS Form 4852 or Schedule C, there are several ways to report your income and avoid penalties. If you are unable to resolve the issue with your employer, contacting the IRS or filing for an extension can help give you the extra time needed to gather your documentation. Don’t let a missing W2 keep you from fulfilling your tax obligations—stay proactive and seek out solutions.

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Five Money-Saving Tasks That’ll Help You Cha-Ching! in the 4th Quarter

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I love the sound of the cash register ringing, don’t you?

If you’re going to be successful in your financial life, treat it as if it’s a business and you’re trying to hear that awesome cash register sound. If you don’t, you’ll always prioritize yourself behind more “important” activities like your job (nevermind that the job is there to help your net worth…that’s probably the subject of another post).

Every business has a mandatory list of activities that can’t be ignored. So does your financial life.

Here are five items that MUST be on that list this quarter:

1) Mutual fund capital gains. Even if you don’t have mutual funds outside of an IRA now, you should learn how these rules work. When the manager (or system, for an index fund) trades stocks or bonds inside of the fund a capital gain is generated. Someone has to pay it, and there’s no real fair method, so the mutual fund company declares a date and divides the gain among shareholders of record. Even if you didn’t sell the fund, you’re responsible for your portion of the manager’s buying and selling.

With results so far in 2012 looking up, there’s a good chance you might get hit with a tax bill this year. Avoiding this tax is legal and easy. Find the dates the fund declares capital gains and transfer your money to a different fund in the same family. This avoids fees for switching and the manager’s capital gains tax.

Grab a calculator before you move any money. You’ll still be on the hook for capital gains taxes you generate by selling as well. The cost of switching might outweigh the savings you’ll realize from avoiding any taxes created by the fund manager.

2) The lemon drop. Hoping to skim off some of that skyrocketing Apple stock? Cover a portion of your capital gain by also selling your brother in law’s “can’t lose” loser. There’s no time like now to weed your portfolio of positions that aren’t going anywhere. Although you’re only allowed to show $3k in net capital losses each year, leftovers can be carried over to deduct in future years.

3) Charitable giving. Hopefully you’ve given to your favorite community non-profits throughout the year, but if not (and especially if you itemize), you’ll want to make cash and in-kind donations in before December 31. Keep receipts for your gifts. The IRS has tightened charitable giving laws in recent years.

4) Estimate your taxes and decide when to pay property taxes. If you own a home winter taxes are deductible either in December or January, your choice. Did you receive a big bonus this year? Take the extra deduction now to help lower your tax due. If you make too much, it might be a better idea to wait until next year. High income earners aren’t allowed to claim all of their itemized deductions (ask your accountant about whether you’re subject to phaseouts).

5) Goal evaluation and setting. The 4th quarter is the perfect time to begin thinking about your short and long term goals. Did you hit your benchmark in 2012? If not, what are you going to change in 2013?

While people generally talk a good game about benchmarking, most of my clients were surprised when I pulled the actual number out of their plan to see if they’d hit the mark during a year. By sticking with actual data and avoiding the “Yeah, it feels like I had a good year” you’ll be able to make the necessary course corrections to save the right amount of money in the upcoming year.

I’ll be addressing each of these areas in more detail during the course of the quarter, but do yourself a favor and schedule these tasks now. These are five activities that you don’t want to miss!

What other events are on your 4th quarter financial calendar?

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How to Pay an Ugly Overdue Tax Bill

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I just read that Christie Brinkley owes over $500,000 in back taxes. That’s an ugly place to be. Sadly, I’ve been there before (not $500,000, but still a sizeable chunk of money). I’d like to share that story here.

When I began advising people about money, my background was similar to the many professional athletes who become financial advisors: I had no training. I was exactly “that guy” the pros and financial books warn you about when they say “don’t hire the new advisor.” Sure, I’d passed a few tests and took classes sponsored by the company I was going to work for, but I’d been an English major in college with an emphasis in creative writing. Talk about “not in Kansas anymore.” I wasn’t even on the same planet.

Why I’m An Expert In This Area

So, there I was, learning quickly. My paranoia about my lack of knowledge and the ability to “dumb down” difficult financial concepts helped me with early success in my new field—probably because I was coming at those concepts from a similar non-finance point of view. I hauled in a nice income. I had a great relationship with my clients. If I didn’t know something (which was often), I said “I don’t know, but I’ll find out.” That happened a ton.

Here’s the bad part of the story. I was a 1099 independent contractor. (For those of you unfamiliar with “1099”, it means that I didn’t actually work for the company. Because I was technically independent, zero taxes were taken out of my compensation. Without an knowledge of the full impact of not paying taxes, this was a financial meltdown ready to burst.)

Near the end of my first awesome year a friend said, “Who is your accountant?”

Me (thinking): “Dude, I should get one of those!”

So, I did. I found a guy named Tom. He was a great number-cruncher, but a horrible financial coach.

Tax guy Tom: “You owe $26,000.”

Me: “WTF?”

Tax Guy Tom (clueless): “Do you want to attach a check to the return?”

Me: “WTFFF????” I’m pretty sure I yelled. Yeah, I screamed. I should have been screaming at myself. It didn’t matter. He couldn’t believe I was dumb enough to spend every penny of the money I’d made. The funny part now is that I had used all that money to pay down debt.

I’d committed every stupid mistake in the book.

So, what did I do? I made the brilliant decision not to file my taxes, thinking that I’d find a way to catch up.

Note to the world: It doesn’t work that way. You can’t catch up.

So, Christie, I understand an overdue tax bill. I know that today you say that it’ll all be paid quickly. That’s good. If you can’t, or if any other reader is in a similar situation, here’s what to do.  This is what I should have done:

Joe’s Awesome 7 Step “Get Your Overdue Tax Bill Paid” Plan (or “Here’s What I Did”)

1) Find good tax advisors. My advisor helped me file back taxes and face the music. By avoiding the overdue tax bill, it was becoming bigger and more difficult to pay. I thought I was finding a “good” advisor when I met Tom. ….but, had I known how to ask questions, it would have gone smoother. AND I should have known to interview more than one person. I found a guy with lots of pretty letters after his name and hired the first one. I needed someone who could walk a beginner through the process of receipts and “what’s deductible and what ain’t.”

2) Communicate with the IRS. You need to face the music sooner or later. What surprised me is how easy the IRS people were to talk with. I was ashamed of my overdue tax bill, but they deal with people that have late taxes all day, every day.

Here’s a tip: the IRS phone line gets busy, so if you’re going to call, do it right after they open. You should get right through (I now call whenever I have questions or am feeling lonely). In my case, they knew promptly what programs to point me toward. Why did I call the IRS? My tax advisor told me to call them. She said it would help me stay on top of the situation. She also talked to them from time to time. (I had to sign a paper giving her the limited power to discuss my personal tax situation with the IRS first.)

3) Decide which method works best. There are two general directions you can decide between if you can’t pay the entire overdue tax at once. First, you can opt for an offer-in-compromise. This is a settlement with the IRS to pay less than your bill. I couldn’t go this route because (as my tax advisor explained), I had a high income stream and there was a good probability—in the IRS’ eyes—that they’d be able to collect the whole amount sooner or later (it was going to take me 30 years, but they don’t care. They may be nice, but those IRS zombies live forever, apparently.—I HAD to have one IRS joke in this piece….). If you owe less than $25,000, you can apply for an installment agreement, and will usually be accepted as long as you haven’t been a repeat offender. For amounts more than $25,000, the IRS is a little more like a nervous loanshark. You’ll have to fill out some extra paperwork.

4) Fill out the appropriate paperwork. Here’s a link to the IRS page describing all the appropriate tools. Before anything, you need to file the appropriate tax forms, if you haven’t already. Once that’s done, if you owe more than $25,000 on your overdue tax bill (like I did), you’ll need to fill out Form 433F, the Collection Information Statement. If you’re pursuing an installment agreement, complete Form 9465, Request for Installment Agreement. For an Offer in compromise, read IRS Booklet 646. It explains thoroughly the process of applying to reduce the amount you owe the government.

5) Be prepared to pay a fee to set up the agreement. As of this writing, direct debit and online payment plans cost $52, while payroll deduction plans run $105.

6) Wait for an answer from the IRS. They’ll respond in writing. If you called the IRS as I recommend above, you may receive an answer while you’re on the phone with the agent.

7) Realize that speed is your friend. Confronting the pain today is better than waiting. If you’ve managed to accumulate $500k in debt, you’ll owe interest and may owe penalties if you didn’t communicate effectively with the IRS.

Forms Needed:

IRS Collection Information Statement, Form 433F

IRS Installment Agreement Request, Form 9465

IRS Offer in Compromise booklet 646

Have a tax issue you’d like to discuss? While AverageJoe and TheOtherGuy aren’t tax advisors, we can point you toward resources and strategies. Use the comment section below or email me at joe (at) thefreefinancialadvisor (dot) com.

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