January 2019 Tax Season Filing Tips

January 5, 2019

Buckle up! We’re dealing with tax reform changes

Happy 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.

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)
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)
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)
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 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)
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)
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)
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)
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)
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)
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)
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)
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)
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)
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