The 10 Most Important Things to Get Right on Your Taxes

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It's not really a season people get psyched for.

There’s no Tax Season Santa, or a Tax Bunny that leaves little audit slips throughout your garden. No one buys a new bathing suit for Tax Season, and it doesn't even smell of gingerbread or anything. If anything, it probably reeks of pencil shavings and Turbo-Tax sweat. So would it help if we renamed it Start Doing Money Right Season? Or Hit Reset and Improve Your Finances Season? Because we kind of like this season (we're the Doing Money Right business, after all). And we think it's a pretty good excuse to set yourself up for next tax season — not to mention your retirement.

To help celebrate what we reluctantly admit is the world’s least sexy season, we've devised these ten tips to not just survive the season, but become a tax-season financial genius.

#1 File on time.

The tax deadline is April 15. Get ready! It's easy to procrastinate –– the eaves definitely do need to be cleaned, and yeah you probably should buy a new dishwasher before the in-laws visit. But, please, do yourself a favor and put taxes at the top of the to-do list this month.

Here's why. If don't file your taxes you'll have to pay a penalty of 5% of the amount you owe the government, every month you don't file, up to a maximum penalty of 25%. That's called a failure to file penalty. You'll also have to pay interest on your unpaid tab. And a lesser fine of 0.5% — called a failure to pay penalty — per month (up to a maximum of 25%) until you make good on what you owe.

If you're not going to be able to pay, the first thing you should do is file an extension before tax day. That eliminates the 5% failure to file penalty (though you'll still incur the 0.5% failure to pay penalty). The IRS advises that you pay what you can, file an extension, and give them a ring to explain what’s up. They’re humans, after all, and have been known to extend deadlines and waive penalties for a range of good excuses.

But the better plan is simpler. File on time; save money.

#2 Wait, you know what is better? File electronically — and do it early!

File a paper return, and the IRS promises to issue your tax refund check in six to eight weeks. But file electronically and it's fewer than three weeks — and even less if you choose to have your refund issued direct-deposit to your bank. And our advice is always: the sooner you get your money, the sooner you can put it to work for you. Compounding is your friend, it makes your money grow, and it only works with time.

That check can also make you feel better about yourself in other ways. Like you can get a jump on maxing out your retirement accounts for 2020, which is liable to make you feel disciplined, virtuous, and generally superior to everyone in the world.

Unless, of course, you’re carrying any credit card debt. In which case your advice is: obliterate that credit card debt first, since no market gains will ever outpace the rates you pay on your plastic.

#3 If your refund was too big, don’t congratulate yourself. Make some changes.

If you got a fat refund check, it does not, in fact, mean that you’re a financial genius. It means you paid the government too much over the year. Money you could have been putting to work for you. So consider making an adjustment.

For instance: ask your employer to withhold less in taxes. Or you increase pre-tax auto-deposits to your 401(k) through your employer. Not only will you be putting money away, you’ll be slashing your reported income — and your taxes for next year.

#4 You've Got Until April 15 to Max that IRA — Get as Close as Possible

For a lot of us, the best thing we can do for our tax bill (and our future) is to contribute as much as possible to our retirement accounts. Because in most cases, every dollar you put in means a smaller tax bill. That means that even if you maxed out your 401(k) at work, you should probably still contribute to an individual IRA (note that Traditional IRA deductions are limited or non-existent if you have access to a 401(k) or are above a certain income threshold). And if you became a freelancer, then you should become acquainted with a vitally important thing called a SEP IRA.

If you think you're too late, you're wrong. Just because it's 2020 now, as far as contributions go it can still be 2019 until the tax deadline.

How does it work? Here are four very good reasons to max out your contributions (and one warning about keeping track of how much you've contributed)

First: contributing now means decreasing the risk that you retire and discover you’re broke and need to sell your plasma.

Second: Every dollar you contribute to an traditional IRA gets subtracted from your taxable income. If, say, you make $75,000and contribute the under-50 maximum of $5,500 to a traditional IRA, your taxable income becomes only $69,500; that means you'll be in line to save more than a thousand dollars in taxes, depending on your bracket.

SEP IRAs can be even better for reducing your tax bill (if they make sense for you). That's because SEP contribution limits are higher than regular IRA limits — the IRS lets you contribute 25% of your net income, whatever it may be, up to a maximum of $54,000. The tax savings are quite substantial.

Third: in certain cases the government will allow you to take money from an IRA without paying the 10% early withdrawal penalty. You can withdraw $10,000 to buy a first house (and your spouse can kick in 10,000 from his or her’s too!), for instance; or use your IRA to pay expenses associated with higher education for you or your kid. Just remember that even though you avoid the 10% early withdrawal penalty, ordinary income taxes still apply to the distribution.

And now for the warning: Don't go over the contribution limit. All money over the limit will incur a 6% annual penalty as long as it stays in your IRA.

#5 If you got married, get tax married!

If you tied the knot, congratulations are in order not only because you found someone who thinks you’re as great as you always suspected you were, but you’re also in line to save big tax bucks. And a lot of those savings comes from filing jointly.

Here's why. Filing jointly usually puts you in a lower tax bracket than you'd be in if you filed individually.

And don't forget: if you got married anytime on or before December 31, 2019, that means you were married for the entire year in the eyes of the IRS.

There are exceptions — if one spouse, for instance, experienced a catastrophically expensive medical event, they might want to file separately, since medical bills can be deducted if they represent more than 10% of reported adjusted gross income, a more likely scenario for an individual filer. And the same goes for student debt payments.

#6 If you got divorced, you might not be enjoying much, but take the deduction and run.

OK, they took half the savings and the whole dog. There’s a financial silver lining. Alimony — not to be confused with child support payments — is tax deductible.

#7 Collect some green for going green.

The US government — at least for now — still incentivizes making environmental decisions that help everyone. So if, in 2019, you bought a plug-in electric car, you qualify for a $7,500 tax credit. (And states like California, New York, and New Jersey add some state tax breaks too.)

Taxpayers who renovated their homes to run on solar, wind, or geothermal energy can deduct 30% of the improvement costs. Even if you took smaller steps towards energy efficiency — installing windows, doors, and insulation that meet Department of Energy standards — you can deduct up to $500.

#8 When it comes to deductions, leave no stone unturned.

A statistical majority of us who work at 9-to-5s, or 10-to-7s, or my-God-I’ve-worked-200-days-in-a-row-until-midnight-why-did-you-make-me-think-about-that won't itemize their deductions. For 2019, that's $12,200 of individuals and $$24,200 for married couples filing joint.

For some freelancers it can be smarter to itemize deductions. There are the well-known deductions, like health insurance premiums for instance. But you shouldn't neglect the more obscure deductions — like those for expenses associated with hobbies, baggage fees for business travel, work uniforms, safe deposit box rental, tax preparation, legal fees, moving costs, job search outlays, and expenses related to volunteer work. (The IRS has a handy section of its website dedicated to the self-employed here.)

#9 That said, don't push it.

There are certain deductions that are catnip for IRS auditors, chief among them, the home office deduction. The IRS allows you to deduct rent or mortgage payments based on the percentage of your home that is used as a place of business. The higher percentage you deduct, the more you run the risk of audit. And should you be audited, you will have to not only provide photos and perhaps welcome a visit from an auditor, you will also need to demonstrate that the part of your home is “regularly” and “exclusively” used as an office, and that the office is the principal place of your business.

So just because you work at an investment bank and think watching Billions will give you the skills you need to vanquish the guy in the next cubicle, your couch is not a home office. The IRS offers

an entire publication on the subject.

#10 Harness your real estate.

If you bought a house in 2019, super news! Not only do you get to experience the feeling of owning a really cool collection of walls, floors, pipes, wires and places to sleep, you’ve also acquired a significant tax deduction generator. All interest paid on up to $750,000 of mortgage loans are deductible, as are all state and local taxes (aka SALT). You can also deduct any interest on a home equity loan used to fix up your house, as well as mortgage insurance, prepayment penalties and even mortgage late charges you paid.

One more note: though home improvements are not tax deductible, we suggest you invest seventy nine cents in a file folder into which you can stick all home-improvement related receipts. Because every dollar sunk into improving a house can be added onto what you paid for the house. And that will reduce the capital gains you'll pay when you sell. (This is helpful for people who make a profit of more that $250,000 when they sell, since the first $250,000 is tax-free as long as it's your primary residence and you've owned it for at least two years.)

OK. Maybe it's not the stuff of national holidays. But it's still pretty important. So: happy taxing!

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Money Diaries


Margaret Atwood


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