MANY OF MY CLIENTS are freelancers who are legally required to make estimated tax payments. I remind them that the IRS takes a dim view of freelancers, self-employed individuals and others who miss deadlines for making those quarterly payments. Miss just one, says the IRS, and it might exact a sizable, nondeductible penalty.
Who are in the IRS’s crosshairs? Individuals who receive income from sources not subject to withholding and whose tax liability exceeds $1,000,
JUST BEFORE SANTA arrived in 2017, President Trump signed legislation officially titled the Tax Cuts and Jobs Act, which was described by both supporters and opponents as the most comprehensive overhaul of the Internal Revenue Code since the Tax Reform Act of 1986.
The many new rules that are now on the books are mostly prospective, meaning they apply to returns to be filed for calendar years 2018 through 2025. They aren’t retroactive to calendar year 2017.
WITH LOWER TAX rates in the offing, many of my clients tell me they’ve heard it pays for them to accelerate deductions for 2018 into 2017. How, they ask, does that tactic benefit them?
They beam when I alert them to two breaks. First, they qualify for deductions one year sooner. Second, they lose less to the IRS when they apply their deductions against higher-taxed 2017 income, instead of lower-taxed 2018 income.
I decide to prolong our chat and caution them not to take their eyes off the calendar when they write checks at year’s end.
I RECEIVE MANY queries about taxes. Most of the questions people send are pretty much the same: They want my advice on how to lose less to the IRS.
Most of the answers I send back are pretty much the same: I advise them to plan ahead and stay on top of tax-law changes, especially whether they will be hurt or helped by the Republicans’ proposals for the most sweeping revisions in more than 30 years.
MY CLIENT ROSTER includes investors who have suffered enormous losses on their stock market investments. To ease their discomfort, I steer the conversation to what they’re entitled to deduct for capital losses. While the IRS imposes strict limits on simply writing off such losses, I assure my clients that there are perfectly legal, IRS-blessed opportunities to sidestep these restrictions.
The big hurdle is a deduction cap of $3,000 for both married couples and single filers.
SOME OF MY CLIENTS are political junkies; others don’t follow politics. Either way, they’re mostly aware that the Affordable Care Act, a.k.a. Obamacare, overhauled the rules for medical insurance. But lots of them are unaware that ACA’s overhaul also significantly changed some tax laws—and those changes adversely affected their pocketbooks.
I remind my clients that ACA included a provision that increased Medicare taxes for employees with high incomes. Similarly, it increased self-employment taxes for freelancers with high incomes.
WHEN TALKING with home sellers, I’ve long ceased being surprised by how many routinely overlook or fail to take maximum advantage of a valuable tax break: the exclusion when unloading their principal residence.
The exclusion—meaning you pay no taxes—is capped at $500,000 for married couples filing jointly and $250,000 for singles and married couples filing separate returns. I frequently need to remind sellers that these exclusions apply to profits, not sales prices.
WANT TO BOOST YOUR after-tax wealth? Grab copies of your latest tax return and investment statements—and ask yourself these 10 questions:
What’s your marginal tax rate? That’s the tax rate on the last dollar of income you earn each year. It’s a crucial piece of information as you decide which retirement accounts to fund and how to invest your taxable account. You can get a quick estimate using Dinkytown’s calculator.
Do you expect your marginal tax rate to be higher or lower once you’re retired?
MANY SENIORS needlessly incur hefty penalties or overpay their taxes. The reason: They don’t understand the strict rules that govern removing money from their tax-deferred retirement accounts.
The IRS sets the year you turn age 70½ as the deadline to begin taking RMDs, short for required minimum distributions. (For 2020 and later years, the starting age is 72.) The feds allow some leeway for the first of your RMDs. But this is a tricky exception.
DON’T GIVE INVESTING advice to clients. That’s something I’ve repeatedly learned as a tax lawyer. Still, when financial markets gyrate, many clients want advice about taxes, especially the seemingly simple rules for capital gains—and I have a longstanding fondness for eating three times a day.
Let’s start with the basics. Take an individual who sells an investment that she has owned for more than 12 months. Any increase in its value from its cost basis is taxed at her long-term capital gains rate—15% for most individuals,
IN 1934, WHEN I WAS age one, a federal income tax return was one page, and came with two pages of instructions. It was hand carried to the house by a live postman. The IRS regulations were 200 pages—though some say it was 400—all of which were memorized by the tax author J. K. Lasser.
When I was a young man in the workforce, we still got the several-page income tax form by mail,
LIKE MOST PEOPLE, I’ve made my fair share of financial blunders. I’ve also had some successes. But I definitely spend more time beating myself up over my errors than celebrating my successes.
Undoubtedly, my biggest mistake fits into the relatively obscure category of asset location. If you aren’t familiar with the term, I can explain it by way of an example. Suppose you have two investment accounts: a retirement account and a standard, taxable account.
THE FEDERAL TAX CODE now contains over 10 million words, so it’s no surprise that most Americans score an “F” when it comes to understanding taxes. A few years ago, I would also have flunked.
But following my divorce, I knew I needed to educate myself on financial topics. While I could tell you how much I took home each month, I didn’t have a clue how much I paid in taxes, much less what my marginal tax rate was.
AROUND THIS TIME of year financial advisors and the media start talking about taking tax losses. The notion: You sell underwater investments in your taxable account, and then use those realized capital losses to offset realized capital gains and up to $3,000 in ordinary income.
There’s nothing wrong with taking tax losses, though I think the notion is oversold. Unless you’re an active trader or a really bad investor, you probably won’t have any losses to take.
IF YOUR GOAL IS lower investment costs, the financial world has never been friendlier. Let’s say you want to buy the broad U.S. stock market. You can choose between a Schwab exchange-traded index fund that charges 0.03% of assets per year, an iShares ETF that levies 0.03% or a Vanguard mutual fund that costs 0.05%.
Those expense ratios are truly astonishing: If you had $100,000 to invest in the broad U.S. market, your annual fund expenses would be just $30 or $50.