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January 2019 Tax Season Filing Tips

Buckle up! We're dealing with tax reform changes

Tax tip pencilHappy New Tax Year! But how happy will we be as we finally discover the real life, bottom line, practical effects of tax reform?

That's one of the many questions to be answered this year.

The 2019 filing season is the first in which we deal with the many changes that took effect Jan. 1, 2018, under provisions of the Tax Cuts and Jobs Act (TCJA). It's one thing to read about hem as we did all of last year. It's another to put pencil to tax form — or keyboard to software — and see what the new laws really mean to our tax bills or refunds.

Are you ready? Me neither.

But we can work through this together, with the tax information and advice contained in this spanking new version of tax tips for the 2019 filing season.

Not necessarily daily: Long-time readers have no doubt noticed a missing word. Yep, this year's tax tips are no longer daily. Personal commitments and changes mean I need to pace myself a bit more.

But fear not dear readers! I promise you'll still get lots of valuable filing information on the ol' blog. It's just that not all of it will be designated as a tip.

But I promise you won't be shortchanged. I'll be posting links to relevant blog tax topics several times a week at, as in prior years, the top of the ol' blog's right column. They'll be there through the April filing deadline, just under the old-school yellow No. 2 pencil tip image.

Also like in previous filing seasons, once a tax tip is posted, it will be will be archived on a monthly tax tip page. Since you're reading this, you know the January 2019 is live. The February, March and April tip collections will go up when those months arrive. You'll find those links at the bottom of this page.

Focus on filing: The final 2019 tax tip reassurance is that these pieces of advice from now through the April deadline will focus of ways to fill out your Form 1040 (and yes, this season we all will be using that one form. There, a hint about an upcoming 2019 filing season tax tip!

That said, I won't overlook the fact that this year's season of filing 2018 returns overlaps with necessary tax planning for our 2019 taxes.

This overlap means that some of the tax tips will, as they have for years, also offer information on what we need to do now to reduce our upcoming current year tax bills.

And with that and all the tax tip housekeeping taken care of, I give you the list of January 2019 Filing Season Tax Tips.

  1. Dual Tax Day 2019 deadlines — Do you know when your 2018 federal tax return is due? Your answer depends on where you live. For most U.S. taxpayers, it's the traditional April 15 filing deadline. Taxpayers in Maine and Massachusetts, however, have until April 17 to get their 1040 forms (and any taxes due) to the Internal Revenue Service. (Jan. 5, 2019)
  2. 6 top tax issues of 2018 and what to expect in 2019 — It's that fun time, when tax years overlap. Before we wade too deep into return filing specifics, check out this broader look at what happened in the tax world in 2018 and predictions on what we might see in 2019. (Jan. 6, 2019)
  3. Estimated tax payment #4 is due Jan. 15 — If you have income that isn't subject to payroll withholding, then you pay (or should be paying) quarterly estimated taxes. The prior tax year's last payment is due Jan. 15. And even though we're in a partial government shutdown, the law demands you meet all tax deadlines. An easy way to pay is electronically, like using EFTPS, which hasn’t been hampered by the shutdown. (Jan. 10, 2019)
  4. Free File 2019 is open with taxpayer protection upgrades — The Internal Revenue Service and tax software manufacturers' alliance is back for its 17th year. In 2019, taxpayers whose adjusted gross income last year was $66,000 or less can use Free File. (Jan. 13, 2019)
  5. 5 Free File tips — The Internal Revenue Service has opened Free File in advance of the full start of the 2019 filing season on Jan. 28. Here's how to determine whether you qualify to use this no-cost tax return preparation and e-filing program and, if so, how you can get the most from it. (Jan. 14, 2019)
  6. Government shutdown could revive tax refund advance products — If the possibility that the government shutdown could delay your refund and you honestly just can't wait, take care if you opt for a refund advance product like a loan or line of credit. They might help in the short term, but if you don't pay close attention to the details, you could end up in even deeper financial distress. (Jan. 15, 2019)
  7. Unemployment benefits are taxable — If you got unemployment benefits, don't forget to report the amount when you file your tax return. Yes, unemployment benefits are considered taxable income. (Jan. 18, 2019)
  8. IRS explains the new 20% small business pass-through tax deduction — Small business owners this filing season can claim a new tax deduction. But it has one downside. It's quite complicated. The Internal Revenue Service has finally issued guidance on how the new deduction works. (Jan. 19, 2019)
  9. IRS offers tax penalty relief to some who didn't have enough withheld — Confusion about the many changes under the new tax law could mean some taxpayers didn't withhold enough from their paychecks or underpaid their estimated taxes. No worries, says Uncle Sam. The Internal Revenue Service is cutting those miscalculating filers some slack this year. (Jan. 20, 2019)
  10. New tax law prompts new philanthropic strategies — Many folks spend MLK Day volunteering at their favorite service-oriented charity. Those with less free time opt to donate to nonprofits that support the goals of the Rev. Dr. Martin Luther King, Jr. on his federal holiday. But tax law changes have shifted how some donors now make potentially tax-deductible charitable gifts. Here's a look at two strategies — donor advised funds and bunching contributions — that could help maximize their tax-break potential. (Jan. 21, 2019)
  11. Gig economy tax tips — Some furloughed federal workers have been doing gig work to help cover their lost income during the partial government shutdown. Whether you are part of the contracting world in the short-term or as your full-time way of making a living, you'll have to deal with some tax matters. (Jan. 22, 2019)
  12. Key 2019 tax filing (and paying) deadlines — Taxes are all about the numbers. There are, of course, the amounts we enter on our tax returns. And then there are the dates on the calendar that we must meet. Check out theses key 2019 tax season due dates. (Jan. 24, 2019)
  13. 2018 tax return checklist and Schedule A review — The 2019 filing season, during which we'll file our 2018 tax year returns, is the first under the extensive new Tax Cuts and Jobs Act's many changes. Here's what you'll need to fill out the new Form 1040, as well as a look at documents necessary if you opt to itemize using the also-new Schedule A. (Jan. 25, 2019)
  14. New 1040 form and schedules — Taxpayers will deal with various new tax laws this filing season. There's also a major change to what we will file. There's now only one Form 1040 — the 1040A and 1040EZ are gone — and it's been totally redesigned. (Jan. 28, 2019)
  15. BOLO for these tax statements needed to file returns — The opening of every filing season there is a rush by millions of taxpayers to submit their returns. Many of us, however, can't yet file our 1040 forms. We're still waiting for one or more of these tax statements. (Jan. 29, 2019)

But wait, there's more! As I mentioned, as soon as January wraps, you can check out February's (and March's and April's) Filing Season Tax Tips. When those months and tips arrive, the links below will become live.

February 2019 Filing Season Tax Tips

March 2019 Filing Season Tax Tips

April 2019 Filing Season Tax Tips

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Today's Tax Tip

  • Tips for first-time filers — Welcome to the tax paying club! The only initiation rite for this large society is filling out your first Form 1040. These tips for first-time taxpayers can make the process a little less intimidating. Even if you're a tax veteran, check them out; some of the advice applies to all us filers. (Jan. 24, 2023)

  • Tax Tip; click pencil for all tax tip links

  • The 2023 Tax Tips offer ways to file your annual return, along with post-filing advice, important tax news and, of course, ways to cut your current tax year bill. You'll find the monthly assemblages on their own respective pages: January, February, March, April, May, June, July, August, September, October, November and December. Remember, tax tasks and tips don't stop after you file your annual return!

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    Kay Bell — Native Texan
    (the blog title totally makes sense now, right?). Professional journalist. Tax geek.

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  • Tax Year 2023 Countdown!

    Happy New Tax Year! Are you ready to file your 2022 tax return? Me neither. But at least this year we're getting some extra time to file and pay any tax we owe. Even better, it's not COVID-19 pandemic related. Tax Day 2023 is Tuesday, April 18. This later date is because April 15, 2023, is on Saturday, and the next business day, Monday, April 17, is Emancipation Day.
    When this Washington, D.C., holiday falls on the day our federal taxes are due, it bumps Tax Day nationwide to the next business day. So this year, we have until Tuesday, April 18, to finish our federal forms and, if we find we owe, come up with the money for Uncle Sam. The states that follow the federal tax calendar, which is most of them, also tend to abide by this date change.

    The countdown clock below should help us from missing out on making important tax-saving moves the rest of this year. Plus, the Tax Moves below the counter will list some timely tasks to take care this first month of 2023, and each of the remaining 11 when they arrive. They'll speed by quickly when you're having tax fun!
    Note: I'm in the Central Time Zone, so adjust accordingly for where you live.


Time for Tax Tasks


  • monthly tax moves


  • 🎆 Happy 🎉 New 🥂 Year! 🎆

    via GIPHY

    Hello 2023! I cannot tell you how happy I am to see you! I know, I said that about 2021 and 2022, but I really, really mean it. And I'm hoping you reciprocate, you brand spanking new year, on the personal front by letting go of COVID-19, and, on the tax side, by making this the year that taxes also get back to normal. Don't laugh. A gal can hope!

    Jan. 1: Once more for the official date — Happy New Year! One way to make things more enjoyable on the tax front is to get organized this month. Early this month. It will help you keep track of the myriad tax documents — W-2 earnings statements, 1099 forms, charitable donation receipts, year-end account statements — that will soon be on their way to your email or snail mail box. You'll need those (and more) to file your 2022 tax return as soon as the Internal Revenue Service starts accepting them.

    Jan. 3: It's the first official work day of 2023. It's also a deadline for employers, including those who are self-employed, who took advantage of the COVID relief option in 2021 to defer the employer's portion of the Social Security payroll tax; that's 6.2 percent of each worker's wages. If you didn't remit thr taxes before the end of December, today is the absolute final due date for paying the balance of those postponed tax collections.

    Jan. 6: It's Friday, the end of the first holiday-shortened work week of 2023. Even though most of us are thinking about filing our 2022 returns when the IRS opens filing season later this month, we also need to start our 2023 tax planning. Start with the inflation adjustments that apply to a variety of tax situations. You can find this year's figures in the ol' blog's 10-part tax inflation series.

    Jan. 9: Tonight, TCU's Horned Frogs and Georgia's Bulldogs face off at SoFi Stadium in Los Angeles to decide the men's college football championship. Thousands of fans are rooting for their teams. Even more people with no personal connections are betting on the game, thanks to the Supreme Court's 2018 ruling to allow states to accept sports wagers. If you're one of those bettors and your pick pays off, remember that you'll owe taxes on your winnings. The good news is that you won't have to share your luck with Uncle Sam until you file your 2023 return next year. The better news is that there are ways to reduce your taxable winnings.

    Jan. 10: Do you work as a server at a restaurant or at any other establishment where gratuities from customers are part of your compensation? I hope you got lots of financial thanks for doing your job well, but remember that those tips are taxable income.

    restaurant check tip iStock
    Whether you're dining in or, still COVID leery and getting food delivered to your home, if a tip isn't included on your restaurant or delivery bill, click the image above to calculate how much to tip the person who brought it to you.

    If you got at least $20 in gratuities in November, you must account for the tips today by using Form 4070 to report last month's tips total to your employer.

    Jan. 13: It's the first Friday the 13th of 2023. That might not worry you, but even non-superstitious folks are frightened a bit by taxes. However, on this or any other day, don't fear, or fall for, these 13 scary, but wrong, tax myths.

    Jan. 16: Every Martin Luther King Jr. Day, millions of people commit to a day of service.

     MLK Day logo
    Click image to find out ways
    you can volunteer on MLK Day.

    Taking time on the Rev. Dr. King's holiday to volunteer at a charity isn't tax deductible, but some costs associated with volunteering could help reduce your tax bill if you itemize.

    Jan. 17: Today is the due date for the final estimated tax tax payment for the 2022 tax year. It's usually on the 15th, but that fell on Sunday. Then Monday was the federal MLK Day holiday. So the final estimated tax payment deadline was shifted to the next business day, Tuesday, Jan. 17.

    Jan. 17: This date isn't firm yet, but the IRS and its Free File Alliance partners usually offer their no-cost online tax preparation and electronic filing program Free File around the middle of January. When the special Free File website at IRS.gov is available, take advantage of it if you qualify.

    IRS Free File; click image for details

    Free File last year was open to taxpayers whose adjusted gross income was $73,000 or less, but that earnings limit should be bumped up a bit for the 2023 filing season. Whatever the amount, the income level applies to all filing statuses.

    Jan. 23: If you make too much to use Free File, and don't want to use its Free Forms option, you always can purchase your own tax prep software or high a tax pro to handle your taxes. If you looking to hire someone, get to it now. At this point, if you can find a tax preparer taking new clients, you'll be at the end of the filings list. But at least you'll be on the list.

    Jan. 27: It was this week last year that the IRS started accepting and, more importantly, processing tax year returns. If you plan to be among the earliest of filers, you need to make sure you have all the necessary information and documentation. Check out this list of the statements, documents, and forms you'll need before you start work on your return.

    Jan. 31: Wow! The first month of 2023 is over? Time really does fly when you're having tax fun. We'll keep it going here in this new year with new Tax Moves to Make each month, which you also can find on their monthly tax tips pages. January already is filling up!

    Small Business Tax Calendar: Important filing, deposit and record keeping dates throughout the year that your company needs to know. You can get more tax calendar information at the IRS' online calendar page and view the full year's important business and individual tax dates in IRS Pub. 509.

State Tax Help

  • Don't forget your state taxes!
    Forty-three states and D.C. collect personal income taxes. But even if you live in of the seven states without an income levy, you still face other state (and local) taxes.

    State Tax Departments provides links to your state's Web page. The companion page, Tax Tidbits, is the compilation of blurbs about each state's tax laws. And for more state tax news, check out all our state tax bloggings.

Tax Forms

  • Tax Forms
    Thanks to our increased use of tax preparers and computer software, many of us don't see our tax forms until we sign and file them. But knowing what's on these documents, either in paper or digital form, and why the IRS wants it is key to understanding our tax system. And knowledge definitely is power, especially when it comes to tax savings. Find this valuable information in the ol' blog's special Tax Forms 2023 page.

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    I am not a professional tax preparer.
    The content on Don't Mess With Taxes is my personal opinion based on my study and understanding of tax laws, policies and regulations. It is provided for your private, noncommercial, educational and informational purposes only. It is not a recommendation of any specific tax action(s) you should or should not take. Similarly, mentions of products or services are not endorsements. In other words, my ramblings on the ol' blog are free advice and you know what they say about getting what you pay for. That's why when it comes to filing your taxes, I urge you to get additional, professional, paid-for guidance from an accountant, Enrolled Agent or other qualified tax preparer who is familiar with your individual tax circumstances.

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COVID-19 & Taxes

  • COVID-19
    Coronavirus has wreaked havoc
    on the 2020 and 2021 tax seasons.
    These three Coronavirus (COVID-19) and Taxes pages have details:
    March-July 2020,
    August-December 2020,
    January-December 2021, and
    January-December 2022
    You can find medical coronavirus resource links in the next section.

COVID-19 Resources

  • COVID-19
    Need help finding a coronavirus vaccine in the United States?
    Call 1-800-232-0233
    or TTY 1-888-720-7489.
    More information and resources at:
    CDC Vaccines
    CDC Booster Shots
    HHS Combat COVID
    USA.Gov COVID Info

January 2023

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Tell it to the Hill

  • DMWT Politics Posts
  • While it's easy to rail at the IRS, for the most part we can thank — or blame — our tax laws on Congress and the White House. So if you have an issue with tax legislation or want a tax bill passed, you need to let your federal legislators and the White House occupant know of your concerns. You can find out who in Washington, D.C., to contact (and how), as well as get information on your local lawmakers for matters, tax or otherwise, closer to home, at USA Gov.

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