EXPERTS OFTEN ARGUE that tax-avoidance strategies shouldn’t drive our financial plans, especially as Congress is forever fiddling with the tax rules. And yet many of us end up making decisions based on federal tax policy, which is loaded with incentives designed to change behavior and advance social goals.
That’s certainly true for my wife and me. Despite the tax code’s many provisions—and its 75,000 pages of complexity—four big-picture tax considerations have largely shaped how our financial lives have turned out,

On Fidelity.com, under “viewpoints.retirement,” one currently finds a post titled “Create Income That Can Last a Lifetime” (https://www.fidelity.com/viewpoints/retirement/income-that-can-last-lifetime). At the end of that post, there is a note on “RMDs and annuities,” which states, in part, the following:
The SECURE Act 2.0 that went into effect in January 2023 allows IRA income annuity owners the choice to aggregate their income annuity with their other IRAs for the purposes of determining their required minimum distributions. If you are 73 and older,

My husband and I are new retirees, age 63 and 61.  Fortunately, we have enough savings to wait until 70 to collect SS, but this means we need to spend from our savings to cover living expenses.  Which should be spent first? Taxable accounts or 401Ks (we have about 65% of our assets in tax deferred 401Ks, most of the rest is in regular taxable accounts, and some in Roth accounts.  Obviously we are saving the Roths and doing some conversions,

My SO had a fixed indexed annuity out of the penalty phase and wanted to earn a better interest rate than the 2.5% rate it had earned over the last 10 years.  She did a 1035 exchange into a Multi Year Guaranteed Annuity ladder for 3-5 years at roughly 5.85%. This is a taxable (non deferred) account that will shelter the money from taxes for the length of the annuity.  She will not need lifetime income as her current guaranteed income floor is more than sufficient to cover expenses. 

I WAS INSPIRED BY Rick Connor and other HumbleDollar contributors to sign up for the AARP’s volunteer-run Tax-Aide program. After completing 48 hours of training at a local college and passing the required tests, I volunteered two days a week at two different senior centers. I completed my first tax season in April.

Two clients, with whom I spent extra time, stood out. The first was a widow in her late 60s whose husband had always handled their finances.

MY TAX RETURN IS too complicated by far, and yours probably is, too. I lose hours looking up figures online, then toggling over to TurboTax to enter them in different boxes. It doesn’t help that I tend to pile, rather than file, important financial papers.
I take the job in stages because it’s so boring. I’ve also learned not to file early because late-arriving mail can upset my math. It happened again this year,

I SOLD A MUTUAL FUND in my taxable account that was up an average 6% a year over the past 10 years—and ended up with a tax loss. That’s right, I took a loss on this international fund, even though it had returned 6% a year. How does that happen?
Suppose you bought one share of a mutual fund for $12 on Jan. 3. Over the course of the year, the fund’s investments fare well.

YOU’VE HEARD OF asset allocation. But how good are you at asset location?

On that one, I’d have to give myself a failing grade, but I hope to pass the test someday. I’ve realized I could save myself hundreds of dollars a year in taxes by relocating much of my safe money to tax-advantaged accounts, while being more aggressive with stocks in my taxable account. Those moves would leave me with the same overall stock allocation,

IN RECENT YEARS, I’ve confronted a choice: I could fund my solo Roth 401(k)—or I could use the dollars to cover the tax bill on a large Roth conversion. I wish I could do both. But after using my earned income to pay living expenses and make financial gifts, I don’t have the necessary cash.
My choice: Go for the big Roth conversion.
Why? In part, it’s because I’m focused on shrinking my traditional IRA before I turn age 75 and have to start taking required minimum distributions (RMDs),

JANE IS A SINGLE woman in her 80s, sharp and friendly. She’s a former state employee with a solid retirement income. Unfortunately, she’s suffered some health issues in the past few years that have forced her to make serious changes.
I became aware of her issues when she came into the local AARP TaxAide site where I volunteer. She was the last client of the day, and the other scheduled client had rescheduled, so she got our full attention.

OUR INCOME TAX SYSTEM is based on voluntary compliance. Taxpayers are responsible for reporting all their income and paying the required taxes.
In assessing tax returns, the IRS differentiates between tax avoidance and tax evasion. Tax avoidance is “an action taken to lessen tax liability and maximize after-tax income,” while tax evasion is “the failure to pay or a deliberate underpayment of taxes.”
What are the major sources of tax evasion? Under-reporting income seems to be No.

I RECENTLY WROTE an article about our purchase of a new primary residence, and our plans for our existing beach house. On the same day, HumbleDollar published a companion article that I also wrote. That second piece discussed the tax implications—and complications—of converting a former primary home to a rental property.
We had purchased the new home using a mortgage, and our plan was to refinance the beach house and use those funds to pay off the mortgage on our new primary residence.

ALBERT EINSTEIN reportedly once said, “The hardest thing in the world to understand is income taxes.” Which makes me wonder: How did I end up wandering into this mind-boggling field? 

I like knowing how my money gets taxed because it helps me better control our finances. By managing taxes, we can significantly boost how much money we have for retirement.

Why is the tax system so complicated? The system is trying to do more than just collect taxes.

SAVINGS YIELDS SOARED in 2023—and all that interest income is now showing up on people’s tax returns.
Forbes published historical average money-market rates based on FDIC data. The average rate in 2020 and 2021 was 0.1%. That jumped to 0.15% in 2022 and 0.59% in 2023. But remember, those are averages, and it isn’t difficult to find higher yields. For instance, interest rates on high-yield savings accounts are up sharply since spring 2022.

RETIREMENT CAN—ironically—take work. It requires us to restructure how we think about both our time and our finances. That rethinking extends to tax planning, which tends to move to center stage once we quit the workforce. Already retired or approaching retirement? There are several tax strategies worth considering.
But before we review specific strategies, it’s worth pondering a more fundamental change wrought by retirement. During our working years, the usual goal is to minimize our tax bill each year.