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Kick the Can

Tom Sedoric  |  April 6, 2021

MANY EYEBROWS were raised during a recent city budget meeting in Portsmouth, New Hampshire. According to the Portsmouth Herald, the city manager told city councilors that Portsmouth’s mandated contribution to the state retirement system would balloon from $290,000 to a whopping $1.9 million per year. Councilors called the development, which would cause a sizable increase in the city’s 2022 budget, “ugly” and “a kick in the shins.” Had anyone been paying attention,

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Outside the Box

Michael Flack  |  March 31, 2021

MY FIRST JOB AFTER college was as an officer in the U.S. Navy. I was an engineer on a nuclear-powered submarine, the USS Albuquerque. While I didn’t make the Navy a career, it left one indelible imprint on me: the need to understand how things work.
Before ever setting foot on the Albuquerque, I spent more than a year learning exactly how nuclear power propelled a submarine, everything from how to operate a valve—it isn’t as simple as you think—to how the reactor worked on a sub-atomic level.

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Lost Abroad

Michael Flack  |  January 15, 2021

ONE OF THE GREATEST business books I’ve ever read is Antifragile by Nassim Nicholas Taleb. In it, he postulates the idea that, while things that become damaged by stress are considered fragile and things that resist stress are considered resilient, “there is no word for the exact opposite of fragile,” things that become stronger due to stress. So, he coined the word “antifragile” and then wrote an entire book about the subject.

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Retirement Gambit

James McGlynn  |  January 13, 2021

INSPIRED BY THE TV series The Queen’s Gambit, many people suddenly want to master the game of chess. But I’m more interested in mastering the practical world of retirement gambits—and that means matching wits with Congress and the IRS.
During my working career, I saved money in taxable brokerage accounts, IRAs and 401(k)s, but never focused on Roth accounts. At age 55, having left my last employer, I had two things that compelled me to begin—time and reduced income.

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Taxing Endeavor

Andrew Forsythe  |  January 5, 2021

I’M A DINOSAUR. Not only do I prepare my own tax return with no help from an accountant or tax preparer, but also I do it by hand. Yep, that’s right—no TurboTax or other computer program.
I really can’t use the computer programs because I often attach an oddball form or two that they don’t offer. On top of that, I always add “annotations” to parts of my return. These additional explanatory notes may be helpful to the IRS.

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The Taxman Cometh

James McGlynn  |  October 23, 2020

LATE LAST YEAR, Congress voted to kill off the so-called stretch IRA, which had allowed those who inherited retirement accounts to draw them down slowly over their lifetime. Many folks were surprised by the stretch IRA’s demise, but they shouldn’t have been.
When a tax break or some other government provision benefits only a few folks, Congress often changes the law. Think back to 2015. That year, Congress eliminated the ability to “file and suspend” Social Security—another strategy that tended to be exploited only by a privileged few.

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State of Taxation

Richard Connor  |  October 21, 2020

ONE OF MY FAVORITE things to do is sit on our local beach with a cold beverage on a beautiful day, and talk finance with interested friends and family members. This past Labor Day weekend, I did just that with a soon-to-be retiree.
One of the big issues facing him and his wife: where to live. He had been relocated to New York by his employer. But he and his wife are natives of the Philadelphia region,

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Much Appreciated

Richard Connor  |  August 31, 2020

WHAT’S YOUR CAPITAL gains tax rate? It’s a crucial number to know—and it could open the door to some big tax savings.
Most investors are aware that there’s a significant difference between the tax rate on short-term capital gains—investments held for a year or less—and that on long-term gains, those held more than a year. Realized short-term gains are dunned as ordinary income, just like your salary or any interest income you earn, while long-term appreciation gets taxed at a lower rate.

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Working the Numbers

Richard Connor  |  August 4, 2020

THIS YEAR’S TAX DAY was the strangest I can remember. Amid the pandemic, the filing deadline had been pushed back to July 15, three months later than usual. And for me, it was our most complicated tax year ever. I had both retirement income and income from various in-state and out-of-state consulting gigs.
But the biggest complication stemmed from last year’s sale of our second home. This was a vacation home that we rented part-time and also used ourselves.

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Give Me Five

Rick Moberg  |  May 21, 2020

ARE YOU PLANNING to withdraw funds from your Roth IRA? If you aren’t careful, you could owe both taxes and penalties, even though you’ve already paid taxes on the money that went into the Roth. At issue: the IRS’s five-year rule. How do you sidestep its unpleasant consequences? Bear with me while I explain.
First, a word of caution: You don’t have to take distributions from your Roth IRA during your lifetime. Withdrawals are strictly up to you.

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To Roth or Not?

Rick Moberg  |  May 13, 2020

SHOULD YOU CONVERT your traditional IRA to a Roth IRA? Below, you’ll find five questions to help you decide. If you answer “yes” to the first three questions, you’re a good candidate for a Roth conversion. If you answer “yes” to all five questions, you’re an outstanding candidate.
Question No. 1: Are you taxed at lower rates today than you will be in future?
Roth conversions make sense if your federal and state tax rates today are below what they’ll likely be when you have to take required minimum distributions (RMDs) from your traditional IRA.

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Taking the Hit

Richard Connor  |  April 29, 2020

ONE OF MY GOALS for 2020: develop a plan for doing Roth IRA conversions over the next 10 years. Once the money is out of traditional IRAs and in a Roth, it’ll grow tax-free. Problem is, the conversion means taking a tax hit today.
So why am I interested? There are several reasons: lowering lifetime taxes for my wife and me, creating the flexibility to manage future tax bills and leaving a tax-free inheritance to our children.

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Numbers Game

Richard Connor  |  April 10, 2020

IT’S TAX SEASON—not something many of us look forward to. Although HumbleDollar’s readers may be ready and willing to tackle their own taxes, many others approach Form 1040 with dread. I’ve seen that firsthand.
This has been my second year as a certified volunteer tax counselor for the AARP Foundation’s Tax-Aide program, which offers free tax preparation for low-to-moderate income taxpayers, especially those age 50 and older. Earlier this year, Tax-Aide was providing this service at nearly 5,000 locations nationwide,

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Not Too Late

Richard Connor  |  March 23, 2020

WE OFTEN PREPARE our taxes, only to learn we owe a substantial sum to Uncle Sam. Most of us believe we can’t do much about this—and yet there’s one simple fix available to many taxpayers: Make a tax-deductible retirement account contribution this year for 2019.
Indeed, thanks to the stock market’s decline, this is a great time to shovel more money into your retirement accounts—and you may discover you can add to more than one account.

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Where’s My Refund?

Mike Zaccardi  |  March 19, 2020

WE LOVE TO procrastinate. Have you done your taxes yet? IRS data show that nearly a quarter of Americans wait until the last two weeks of tax season to file. It often feels like that nagging task that grows more arduous each year, though the result for many is a juicy refund.
The average federal tax refund is more than $2,800, so it can pay to get your taxes done sooner rather than later.

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