Best Results Organizing

Every few years, I share a series of tax-related organizing tips for readers. Recently I’ve received inquiries from first-time filers asking for how to even begin the process. So, today’s post mixes tax-related news with a larger baseline of how to accomplish preparing and submitting your 2023 tax return.

Note: I’m neither an accountant nor a tax preparer. I don’t even play one on television. But I do help my clients find, organize, and make sense of the documents they need in order to prepare their tax returns.

ESSENTIAL TAX INFO TO KEEP ORGANIZED

Tax Deadlines

The federal Tax Day is April 15, 2024 (unless you live in Maine or Massachusetts, where it’s April 17, 2024).

If you file a (valid) extension request, you must file your tax return by October 15, 2024. Note, you still have to PAY what you (estimate that you) owe by April 15th to avoid a fine. However, if you strongly believe you’re not going to owe anything, you may file late (without filing for an extension) and there’s no penalty fee. But then you’ll also be delaying getting a refund if you’re owed one, so Paper Doll advises against procrastinating.

How To Prepare and File Your Taxes

You have a variety of options for how you prepare and file your federal taxes:

• Prepare your taxes yourself on paper forms. Like a caveman. And you’ll have to do your own math.

• Hire an accountant or CPA firm. You still have to gather all of your forms and your receipts and tell your tax preparer all the wiggly little oddities in your life last year, but you won’t have to do math. The complexity of your return (and how well you organized your supporting document) will determine the cost of the service.

• Visit a tax preparation service like H&R Block or Jackson Hewitt. Find them in independent storefronts or at desks inside big box stores, like Walmart. However, you may want to reconsider this option. 

Color Of Change, in collaboration with Better IRS, just released a report called Preying Preparers: How Storefront Tax Preparation Companies Target Low-Income Black and Brown Communities. In it, they cite that many of these companies are unqualified, hiring non-accountant “unenrolled tax preparers,” who are neither credentialed nor certified in tax policy and regulations, and who do not adhere to continuing education requirements — and in 43 states aren’t even obliged to meet basic standards!

As such, many of these unenrolled preparers have been found to have made excessive errors; indeed, one study by the U.S. Government Accountability Office (GAO) found that only 10% of preparers at large tax prep chains calculated tax refunds correctly! Additionally, many of these companies are preying on low-income and minority taxpayers by charging for advances on refund checks, and promoting unnecessary tax products and high-interest refund anticipation loans.

• Use online tax preparation software, like TurboTax, H&R Block Online, TaxAct, Cash App Taxes, and Free Tax USA. They’ll hold your hand through prompting questions and you won’t have to do the math, but you’re ultimately responsible if you misunderstand a question or make an error. And it can be pricey!

The IRS already receives copies of our income information directly from employers, banks, investment companies, etc., so why do we have to do all of this? And why is it so expensive, especially for those who don’t even owe? Because these companies lobby and bribe — ahem, sorry, contribute — to congressional representatives’ election campaigns to prevent the federal government from creating a free option for all!

More Affordable Filing Options

The IRS estimates that Americans spend an average of $250 to prepare and file their taxes, but there are options for lessening that burden.

• If you are age 60 or older, make $64,000/year or less, are disabled, or need language support, you can get free help from IRS-certified volunteers in the Volunteer Income Tax Assistance (VITA) or Tax Counseling for the Elderly (TCE) programs. 

• • • Find VITA and TCE program locations at the IRS locator page.
    • Seek related help from the AARP Tax-Aide Service.
    • The United Way can connect you to preparation and filing assistance via MyFreeTaxes.

• If you’re a member of the military (or a military family), you can prepare and file a federal return and up to three state returns, for free, through MilTax. Eligibility requires that you are:
  • • An active-duty service member, and/or their spouse and dependent child(ren).
    • A member of the National Guard and National Guard Reserve (no matter your activation status).
    • Survivors of deceased active-duty service members, National Guard, or National Guard Reserve members (without regard to activation status or conflict).
    • Honorably discharged, retired service members from all branches, including the Coast Guard, if you’ve been discharged within the past 365 days.
    • Designated family members of service personnel who’ve been authorized to manage the eligible member’s financial affairs during deployment. Similarly, any designated family member of a service member deemed “severely injured” and not capable of handing their own financial affairs.

• If your 2023 adjusted gross income (AGI) was $79,000 or less in 2023, you can use the government’s Free File program. Here, the IRS partners with online tax preparers each year and eligible users (for 2023 filing, that means those with an adjusted gross income (AGI) of $79,000 or less) can file federal taxes with no fee. (State tax costs vary.)

However, the contracted companies change year-to-year, so if you prefer to maintain your data in your account, making it easier to do year-to-year comparisons and be prompted to recall charitable recipients and sources of W2s, 1099s, etc., next year you may have to decide between switching to a new program partner or paying for what was once free.

Some past participating partners in the Free File program have been problematic. The Federal Trade Commission (FTC) found that TurboTax engaged in deceptive advertising (forcing up-selling), and investigated H&R Block for improperly handling and deleting customer data (as well as for deceptive advertising).

Unsurprisingly, both companies have supported legislation to ban the IRS from offering free tax filing services. 

• If you qualify, try the US government’s new Direct File trial program. Only 12 states (Arizona, California, Florida, New Hampshire, New York, Nevada, Massachusetts, South Dakota, Tennessee, Texas, Washington, and Wyoming) are participating in this trial effort.

Direct File eligibility is limited to those with income from employment (reported via W2), unemployment compensation, or from Social Security, so self-employed individuals, gig workers, and those with pensions can’t use it. To try Direct File, you have to take the Standard Deduction and can’t itemize. (You can have up to $1500 in interest or savings bond income, but not earnings through payment apps, rent, or prizes. Wages are limited to $200,000, or $125,000 if you are filing Married Filing Separately.) 

Unfortunately, Direct File’s future is uncertain. The Biden administration allocated $15 million from the Inflation Reduction Act for IRS to evaluate the viability of a a free online tax preparation and filing service, with $80 billion apportioned for over the next decade. However, Congress’ debt ceiling agreement “clawed back” some of those funds.

Special K: It’s Not Just for Breakfast Anymore

Do you have an online platform on Etsy or eBay, or use a payment platform to sell through your website? Then you may have heard rumblings about the 1099-K form finally getting the $600 rule up and running. Well, it’s been delayed again. 

The rule is designed so that anyone who receives money from a third-party network like Venmo, Cash App, PayPal, Square, or Stripe for having made $600 or more in sales for either goods or services would receive a Form 1099-K by late January or early February (when we’re supposed to get all of our 1099s). But the IRS has repeatedly delayed implementing the rule, so some people have received 1099-Ks and others haven’t, causing confusion.

So, if you got a 1099-K, check to make sure the numbers match the income you believe you received. (If there’s a mismatch between your records and the form, contact your financial network and correct it before you file your return.)

If you didn’t get a 1099-K, that doesn’t mean that you can fib to the IRS! You must report all taxable income, even if someone who was supposed to send you a form didn’t do their job.

Photo courtesy of Chris Potter/CCPix at www.ccPixs.com under CC 2.0

START THE TREASURE HUNT

Know What You Spent

Start by gathering expense information, like:

• receipts for tax-deductible purchases — check paper receipts as well as email confirmations of purchases
• statements or summaries from ongoing accounts. (On Amazon, select the year from the drop-down under Your Orders in your account. Don’t forget to check the tab for digital orders, too!)
• online financial dashboards — Mint closed in March, so plan to find a new dashboard like Quicken Simplifi, Empower, or YNAB.

Gather tangible information in a folder labeled Tax Prep 2023, or use something like the Smead All-In-One Income Tax Organizer. Just having it all together will be the first step toward tabulating the correct amounts.

Gather Ye Forms

Most of the essential data you’ll enter into your tax return will come as supporting documents called information returns. These are sent to you by others — employers, banks, brokerage houses, schools, casinos, etc. — and they’re required to mail them by January 31st! That scary-but-official mail you threw on top of the microwave the week before Valentine’s Day? Move the oven mitts and get looking! 

The rest of this post is an update of past year’s posts, laying out the different kinds of forms you might need.

Broads via GIPHY 

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MONEY YOU RECEIVED

W-2 (Wage and Tax Statement)

If you were an employee at any point in 2023, your employer should have sent one W2 copy to you and one to the IRS, reporting how much you were paid (in wages, salaries, and/or tips). If applicable, it should also indicate how much money was withheld from you and paid to federal and/or state governments for taxes and FICA (Social Security and Medicare).

Federal, state, and local taxes, FICA, unemployment insurance, and a few other withholdings are considered statutory payroll tax deductions. Statutes (that is, laws) require them, so your employer can’t just blow off withholding this money and sending it to the right agencies. 

Sometimes, a court might rule that an an employee’s wages may be garnished, but this has nothing to do with sprigs of parsley. People behind on child support payments or who owe money in lawsuits may have money removed from their earnings, before it ever gets to their paychecks, to ensure it goes directly to whomever is owed.

Your W-2 may also report voluntary payroll deductions. These are amounts withheld from your paycheck because you’ve granted permission. These may include your portion of health and life insurance premiums, contributions to your 401(k) or other retirement fund, employee stock purchasing plans, one-time or ongoing donations to the United Way, union dues, etc.

Photo by The New York Public Library on Unsplash

Did you get multiple copies of the same W-2? Employers submit copy A directly to the Social Security Administration for FICA and keep copy D for their own records. Copies B and C are for you (the employee) – you send one to the IRS with your federal tax return and keep one for your own records. Then, they provide copies 1 and 2 to file with applicable state or local tax authorities. (I’ve never figured out why W-2 copies 1 and 2 aren’t called E and F. Did the same person who came up with this decide that bras should be sized as A, B, C, D, DD, DDD, F, FF, and G, skipping E entirely?)

I've never figured out why W-2 copies 1 and 2 aren't called E and F. Did the same person who came up with this decide that bras should be sized as A, B, C, D, DD, DDD, F, and G, skipping E entirely? Share on X

In theory, a W-2 should be mailed to the address listed on your W-4. (Don’t be confused. The W-4, is the form that tells your boss how much to withhold based on your number of dependents you have.)

Smaller companies may just hand you your W-2 instead of mailing it, but if your W2 is missing, consider: 

• Did you change employers last year? You should have received W-2s from each employer. (If you changed jobs at the same company, you’ll receive one W-2 from each employer, not one per position. If you changed companies within a larger corporation, though, you may get one for each.)

• Did you change addresses since you filled out your W-4? There’s only so much a former employer will do to track you down to give you your W-2. Keep the Madge in HR updated!

Don’t assume that if you don’t have your W-2, then nobody knows what you made. Remember, the IRS got Copy A. The IRS knows what you made, so be sure you do, too! (If your former company went out of business or is otherwise not returning your calls, the IRS has a procedure to allow you to file your taxes in the absence of a W-2.)

Examine your W-2 it carefully. Do the numbers seem right? Compare them to the final pay stub you got for last year. Calendar years may end mid-week (or even mid-pay period), so the numbers won’t correspond perfectly, but they’ll be close enough for you to spot if something is seriously wrong. The sooner you call your employer’s attention to an error, the sooner you can prepare your return.

W-2G (Certain Gambling Winnings)

Gambling Photo by Aidan Howe on Unsplash

The W2G is the freewheeling cousin of the W-2. While a W-2 is for money you make while working, the W-2G is what you get while playing. If you win more than $600 in any gambling session at a casino – whoohoo! – the “house” should request your Tax ID (generally your Social Security number) and either prepare a W-2G on the spot or send it to you in January.

Casinos aren’t interested in keeping up with your losses, just your winnings, so they only tell the IRS about what they paid you. If you gamble and want to deduct losses, the IRS requires you have provide receipts, tickets, statements, or other records to support both your winnings and losses.

1099s (Income)

A 1099 is a form that basically says, “Hey, we paid you some money for something, but you weren’t an employee.” You get a copy; the IRS gets a copy. Easy-peasy.

There’s not just one type of 1099; actually, there are 22 different kinds of 1099s.  Some of the more common are:

1099-INT

This form reflects the interest income you receive from interest-bearing savings and checking accounts, money market bank accounts, certificates of deposit, and other accounts that pay interest. It also notes whether foreign or U.S. taxes were withheld and if there were any penalties assigned for early withdrawal from an interest-bearing account.

Internet-only banks may require you to log into your account to get your 1099-INT, so don’t count on it coming by mail. If you received less than $10 in interest, your bank may not send a 1099-INT.

1099-DIV

Do you own stock or other taxable investments? This form indicates the dividends or capital gains you received as an investor. Your broker, plan services company, mutual fund company or other type of investment company will send this form. Not all dividends are created equal; ask your tax professional if you have any that seem unusual or complicated. Whether you receive dividend checks or your dividends are held in a DRIP (a direct re-investment plan), if you didn’t earn at least $10 in dividends, you are unlikely to receive a 1099-DIV.

1099-G

This random form is subtitled “Certain Government Payments” and can cover everything from state unemployment compensation to tax refunds, credits, and offsets at the state and local level. It can also be used to report payment of taxable grants, agricultural payments, and other nifty things where a state or local government gives you money. 

1099-NEC 

This new(ish) form replaces some uses of the 1099-MISC. If you’re self-employed (a freelancer, an independent contractor, etc.), you should get a 1099-NEC. However, 1099-NEC just started in 2021, so people unfamiliar with it may send you a 1099-MISC by mistake. 

Another problem is that even if someone paid you for doing work as an independent contractor, they may not know they should be sending you a 1099-NEC. So, if you are self-employed or irregularly employed, it’s essential to keep track of your own incoming revenue. Otherwise, if the person who paid you ever gets audited, it could trigger some messy situations for you, too.

1099-MISC 

Now that this form no longer covers income for freelances and independent contractors, it’s truly  more “miscellaneous.” Seriously, it’s the junk drawer of tax forms!

It’s used to report payment of royalties, broker payments, certain rents, prizes and awards, fishing boat proceeds (yes, really!), crop insurance proceeds, and some payments to attorneys that wouldn’t be reported on a 1099-NEC, like if you received a settlement and had to pay an attorney a portion of it. In general, once people get used to the 1099-NEC, you’ll only get this miscellaneous form to report truly miscellaneous payments.

SSA-1099 (Nobody knows why the numbers and letters are reversed on this one form! It must be done by the same people who label the copies of W-2s and bra sizes!)

If you receive Social Security benefits, you should receive an SSA-1099. (Non-citizens living outside the US, like widows/widowers receiving spousal Social Security benefits, may get a SSA-1042.) The 1099-SSA tends to come on a long form, folded and sealed such that it makes its own envelope. It may look like junk mail, so watch out and replace it, if necessary!

A 1099 doesn’t always indicate that you were literally paid money. For example, a 1099-C indicates that someone forgave a debt, like a mortgage or a credit card balance. You may owe tax on forgiven debts, and the 1099-C alerts the IRS that since you didn’t pay money owed, and got to keep it in your pocket, it’s as if you received money.

1099s sometimes hide in plain sight. Sometimes, instead of sending a 1099 in a separate envelope, a bank or brokerage house may include a 1099 form in the same envelope — sometimes perforated at the bottom of a quarterly or end-of-year financial statement. Be sure to check all that boring-looking official mail. Brokerage houses often sent multiple forms as a “combined 1099,” scrolling across multiple pages. Check the reverse sides of forms, in case you’re missing one.

MONEY YOU PAID

1098 (Mortgage Interest)

A 1098 is not a 1099 with low-self-esteem. The vanilla, no-frills 1098 reflects the interest you paid on your mortgage, which is generally deductible on your federal taxes. Renters don’t get 1098s; neither do homeowners who’ve paid off their mortgages. 

There are also sub-types of 1098s for things other than interest on property loans:

• 1098-T indicates tuition you paid; you’ll get this from a college or training school.
• 1098-E shows you’ve paid interest on a student loan and will come from your lender.
• 1098-C indicates the donation value of a car, boat or airplane by fancy-pants, monocle-wearing Mr. and Mrs. Thurston Howell.

Photo by Diego F. Parra from Pexels

1095-A (Health Insurance Statement)

The 1095-A is also called the Health Insurance Marketplace Statement. If you purchased coverage through a state or federal exchange, this helps you determine whether you are able to receive an additional premium tax credit or have to pay some back.

Related forms include the 1095-B (supplied by companies with fewer than 50 employees), detailing the the type of coverage you had, the period of coverage, and your number of dependents, so you can prove you had the Minimum Essential Coverage (MEC) required by law. A 1095-C is similar, but for employers with more than 50 employees.

SPECIAL 1040 FORM FOR SENIORS

Are you a senior? If you are over 65, instead of filing the standard 1040 form, you can file the 1040-SR. The main benefit is that this form, when printed, uses a larger font and provides easier readability. 

FINAL THOUGHTS

If you receive a mysterious form, or have questions about how to use a form, the IRS has a surprisingly easy Forms, Instructions and Publications Search. Again, I am a Certified Professional Organizer, not an accountant, so please address any concerns to a tax specialist.

Making sure you have all of the necessary forms in hand will make it much easier to prepare your tax return. Once you file your taxes, make a list of all the forms you received this year, and tuck that list into your tickler file for next January. Check off each form as it arrives, and you’ll have a better sense of when you’ll be ready to start working on your 2024 taxes in 2025.