Oct. 1: Boo! Welcome to the scariest month of the year.
Screenshot from GIPHY In addition to Halloween goblins, ghouls and hundreds of kids descending on your neighborhood at the end of this month, one of the scariest October items is that countdown clock a little higher up in this column. It's a stark reminder for millions of ultimate
procrastinators — No, I'm not one this year. Amazing, I know! — that their deadline to file extended 2018 tax returns is nearly over. Don't worry. I'll remind you again as Oct. 15 nears.
But why push the deadline?
Gather all the
documents you need to file your Form 1040, including 1099s and receipts associated with your
self-employment income, be it full-time or side hustle earnings. This
tax preparation checklist can help.
Oct. 4: OK. You're ready to finally file that Form 1040 before the 15th. Great! Now make sure you don't overspend to do so. Check out
Free File.
This IRS-tax software industry partnership program that provides no-cost return prep and
e-filing option is open for business through the October extension deadline for taxpayers whose income is $66,000 or less.
Oct. 10: If your job compensation includes
tips and you received $20 or more in gratuities in September, use
Form 4070 to report them today to your employer.
Oct. 14: So another week slipped by without you filing your taxes. No judging here. I've been there. The good news this year is that today is the federal Columbus Day holiday or, in many states and cities, now designated
Indigenous People's Day. If you don't have to head into the office, it's a great chance to work on your taxes. The IRS has some
final filing tips.
Oct. 15: It's here! The absolutely, positively final filing deadline for your 2018 return. Get your Form 1040 — remember, there's now
just one tax return under the Tax Cuts and Jobs Act (TCJA) changes — en route to the IRS today or you'll face
penalty and interest charges.
E-filers, whether using the previously mentioned Free File or a paid-for tax software package, technically have until midnight their time to hit "enter" on their computer keyboard. But I suggest you don't push that deadline. A late technical problem could turn into a costly late-filing issue.
If instead you're sending in an old-fashioned
paper return, check with your post office to make sure the envelope is postmarked today, the paper filing proof of timely tax filing.
Oct. 21: Now that your 2018 return is finally done, it's time to work on reducing your 2019 tax bill. By now, you're probably familiar with how the TCJA changed your tax filing and planning. But it never hurts to review your prior year's tax return, whether you just filed it last week or earlier in the year. It's a good foundation to look at what tax breaks you qualified for might be able to use again on this year's taxes.
Note, too, that inflation has upped many tax-related actions. The income tax earnings
brackets have been expanded a bit. So have the
standard deduction amounts.
And definitely look at how much you can put this year into tax-favored
retirement savings and
medical accounts. Not only can they help lower current tax bills, they could pay off in the future.
Finally, peruse the Taxpayer Advocate Service's
Taxpayer Roadmap.
This publication, designed along the lines of a subway map, shows the
stages of a taxpayer's journey through our elaborate tax system.
Oct. 25: Those retirement and medical accounts also are part of many workplace benefit plans. Since October is the start of the annual benefits enrollment open season at lots of companies across the country, it's a good time to carefully review those employer-provided perks, such as 401(k) plans and flexible spending accounts (FSAs) for both
health and child care purposes, to make sure you make the most of your options.
Oct. 28: With more than two months left in 2019, now's is the perfect time to set up your tax deduction
bunching strategy. Here you gather potential write-offs together into one tax year to ensure you have enough qualified expenses to meet some of the popular deduction thresholds. This typically covers the itemized deductions for medical, home-related and charitable deductions.
Oct. 31: What's scarier than the ghouls and goblins wandering your neighborhood tonight? Another month of the
hurricane season.
We've been lucky so far, with only Hurricane Dorian along the eastern seaboard and
Tropical Storm Imelda in Texas causing major damages. But with a month officially left, we
can't let down our storm guards.
The countdown clock below can help you track the days until the formal Nov. 30 end of the annual hurricane season.
You also can find tips on getting ready, physically and financially, for hurricanes, as well as tax help for recovery efforts and tax deductions for donations to those who are hit by natural disasters at the ol' blog's
Storm Warnings pages.
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.
Everyone should know that if you receive rental income from renting a dwelling unit, such as a house or an apartment, you may deduct certain expenses. Basically, the amount of time you personally spend at your second home determines how much tax you might owe on rent, as well as deductions you can claim against the property. Lots of second-home buyers rent their property part of the year to get others to help pay the bills. Very different tax rules apply depending on the breakdown between personal and rental use. The best tax deal is for short-term rentals. If you rent the place out for 14 or fewer days during the year, you can pocket the cash tax-free.
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