Boo! The scariest month of the year is here and ramped up in 2020 because of the coronavirus pandemic.
Read about the history of jack o'lanterns
Oct. 1: In addition to medically masked adults and costumed child-size Halloween goblins and ghouls 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 that their deadline to file extended 2019 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, like your W-2 and any 1099s and receipts associated with your self-employment income, be it full-time or side hustle earnings. This tax preparation checklist can help.
Oct. 5: 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, the IRS/tax software industry partnership that offers eligible taxpayers access to online tax preparation programs and federal return e-filing at no cost. 
This year 10 software companies are participating at IRS.gov's Free File webpage. It's available for taxpayers with adjusted gross income of $69,000 or less regardless of filing status. If you make too much to use the online software, look into using Free File's fillable forms.
Oct. 12: So another week slipped by without you filing your taxes. No judging. I've been there. The good news 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 or check in on some work from home Zoom calls, this is a great day to deal with your extended taxes. The IRS has some final filing tips.
Oct. 13: Some restaurants that closed earlier this year as part of pandemic precautions across the country have reopened. Other eateries stuck with take-out meals and deliveries. Whether you're able to dine in or still getting food brought to your house, remember to tip your server or delivery person.
If a tip isn't included in your food delivery charge, click the image above to calculate how much to tip the person who brought it to you.
As for servers who now are back on the job, remember that your
tips are taxable income. If you worked at least some of September at a job where you got gratuities, you need to account for them today if they came to at least $20 last month. Use
Form 4070 to report your tips today to your employer.
Oct. 15: It's here! The absolutely, positively final filing deadline for your 2019 return. Get your
Form 1040 and any of the now just three schedules you need 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 by either the IRS or your software provider could turn into a costly late-filing issue.
If you're sending in an old-fashioned
paper return, check with your Post Office to make sure you get your tax envelope there in time to be postmarked today. That's your paper filing proof of timely tax filing.
Today's also the deadline to touch base with the IRS if you didn't get a COVID-19 economic impact payment and want the money this year. This is the case if you didn't have to file a return for 2018 or 2019. The only way the IRS will know where to send your coronavirus stimulus money is for you to provide your info using the online
Non-Filers Tool. If you don't do so by today, you'll have to wait until 2021 for your money.
Oct. 21: Now that your 2019 return is finally done, it's time to work on reducing your 2020 tax bill. One easy step to take now is to
review your payroll withholding. If you find, whether you filed this month or back in July, that you owed a lot or got a big refund, you should use the IRS'
online withholding tool to make sure a more appropriate amount of income tax comes out of each of 2020 remaining paychecks. If your withholding tweak gets you more money each payday, consider putting some of it into your
retirement savings.
Oct. 25: Many folks' retirement money is in a workplace account, typically a 401(k). That's just one of the employer-provided benefits that companies offer their workers. And October is open enrollment season at many companies. Take time to carefully
review what's offered before enrollment ends.
Oct. 31: Sure, it's Halloween. But even scarier than the ghosts and monsters wandering your neighborhood tonight is the knowledge that we still have another month of
hurricane season ahead of us. If your area hasn't been hit by any tropical system so far, good for you. But your luck might not hold, as the Atlantic and Gulf of Mexico hurricane season runs through the end of November. So that you're ready for another
Hurricane Laura or, hopefully, a less severe storm,
prepare now.
Uncle Sam's official
forecasters at the National Oceanic and Atmospheric Administration (NOAA) expect 2020 to bring as many as 19 named storms, with six to eight possibly becoming hurricanes. Three to six could reach major status, which is category 3, 4 or 5 with winds of 111 mph or higher. Regardless of the count, it only takes one to wreak havoc. The countdown clock below can help you keep track of how many more days you have to worry about tracking any size or type of tropical storms.
You also might want to check out the ol' blog's special
Storm Warnings.
These multi-page collections of posts offer tax advice on preparing for, recovering from and helping those who sustain damages from the many ways that that weather goes wild.
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.
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