Taxes

Many American’s perception of the taxes they pay is seriously distorted. Many seem to believe that withholding from their pay is the taxes they actually pay or that taxes due at year end reflect higher taxes rather than likely under withholding.
A major misunderstanding is that the tax bracket they are in represents their real tax rate. I know taxes are complicated, but not that complicated. 
I conducted a simple exercise. Using several AI tools I calculate the 2026 federal income tax for a household with two young children earning the US median income.

Do a Roth conversion in November or December and you’ve made a smart move in a low-income year. You’ve also just bought yourself a tax problem.
The IRS wants its money as you go, not in one lump next April. And for estimated payments, it grades you quarter by quarter. Say you convert $100,000 in December and the conversion generates a tax bill in the low $20,000s. Pay it all with a single January estimated payment and you might think you’re square.

We have recently considered buying another property closer to family.    Since selling our current home may take some time we were thinking we could possible use a retirement Roth account to come up with purchase price rather then take a bridge or other loan.  We also do not have enough after tax money in regular accounts to cover the total purchase.  We have been here for many years so it meets tax deduction for primary residence sale. 

IF YOU’RE IN YOUR early 60s and retired, you probably have a lot of financial questions on your mind. The next few years may be among your lowest-income and lowest-tax-paying years. Your salary and bonus years are behind you. Social Security and required minimum distributions from your IRAs and 401(k)s have not started yet. You are hearing advice about doing Roth conversions during this low-tax window, and the arguments are compelling. You may also be thinking about consulting or part-time work to stay active and bring in some income.

In February, Guindy Sam wrote about taxes on foreign dividends and taxes, and I decided to quantify the issue using data from the index provider MSCI.
Quick reminder: some countries tax dividends at the source when they’re paid, similar to payroll withholding tax. US taxpayers can claim credit for these foreign taxes paid on their returns (the Foreign Tax Credit). But investors who do not itemize this benefit — those holding the stocks in IRAs, 401(k)s,

Here are the results of an exercise to make Social Security last at least 75 more years. I used the Committee for a Responsible Federal Budget (CRFB) estimator.
✔️Increase the payroll tax rate by 2% shared by employers (1% each) or raise the 2% only on employers
✔️Eliminate the taxable wage cap, and also accrue additional benefits based on those taxed earnings using a 15% accrual rate. The same percentage as the lowest accrual or “bend point” uses now.

The amount of misinformation out there about Social Security is astounding and to me very disturbing.  I put this fact sheet together. I hope you will share the next time you hear one of the outrageous claims being made.
The basic funding mechanism has remained essentially the same since Social Security began:

Workers and employers pay dedicated payroll taxes (FICA).
Benefits are paid primarily from those payroll taxes.
Any surplus is invested in interest-bearing U.S. Treasury securities.

RDQ kicked off what I’d call a ‘good ruckus’ with his Billionaires, taxes and you post. I thought I would dive deeper into the “and you” aspect of the conversation. 
What about the rest of us? Below are the results of two 2025 tax returns I processed, and one based on the AARP calculator for tax year 2026. Two are retired couples over age 65. 
I included a hypothetical worker-bee couple as well,

I WAS RECENTLY asked about strategies that high earners can use to reduce their tax bill.
Most people know the usual options. They contribute to a 401(k), fund a health savings account or make a Roth IRA contribution through the backdoor method. Business owners may have additional opportunities through retirement plans and business structures.
But there’s another strategy worth knowing about: the Mega Backdoor Roth (MBDR).
The MBDR allows some workers to put far more money into Roth accounts than the usual contribution limits permit.

“The window to make advantaged Roth IRA conversions closes in 2028” was the hook my friend Sherry got from the salesman at the free steak dinner. Scheduling an appointment with him was Sherry being reeled in.  Sherry asked if I would go with her to a meeting with the guy to discuss the proposal.
The  first thing I had to do was figure out what an “advantaged Roth conversion” even was. Feel free to correct me if I am wrong,

The U.S. tax system only taxes realized income—meaning money from a paycheck, a dividend payment, or the actual sale of an asset. If a billionaire owns $100 billion in stock and that stock grows by $10 billion in a year, they do not owe a single dime of income tax on that $10 billion increase until they sell the shares.
And neither does anyone else. I don’t pay on the growth in my IRA or any investment.

I mentioned this in a recent HD comment, but I think it deserves more discussion.
It’s time to scrap all tax-advantaged defined contribution retirement plans and replace them with one plan, one set of rules, uniform limits. No IRAs of any kind, no 403b,  no 401k, no nothing else.
Just a Universal Retirement Plan- Individual or employer sponsored. All contributions on an after-tax basis and tax and distribution rules following the Roth model. Everyone could contribute up to one (generous) limit. 

A friend shared an interesting idea from David Bach’s “IRA Flat Tax” proposal, and it got me to thinking.
Here is the white paper if you haven’t read it:
IRA Flat Tax White Paper – David Bach.pdf – Google Drive
The basic idea is simple: for a limited window, maybe 2026–2033, retirees could voluntarily withdraw money from traditional IRAs, 401(k)s, and similar retirement accounts at a flat federal tax rate — possibly around 12%.
The goal would be to make it easier for retirees to use the money they spent decades saving,

My opinion is that there is no such thing as a tax loophole. Plus it has a negative connotation I don’t think is accurate. In addition, there is a tendency to apply the word to others – mostly the wealthy, but not ourselves
Look up the word and you likely see something like “ A tax loophole is a provision, ambiguity, or gap in tax law that allows a person or business to legally reduce the amount of taxes they owe — often in ways lawmakers may not have originally intended.”
Long term gains are taxed at lower rates to make investing attractive.

I recently completed my 8th season performing volunteer tax returns. I’ve worked in 2 states (Pa and NJ), 3 counties, and 7 centers. All but one year was performed under the auspices of the AARP TaxAide program. In several years I also worked for a local program supporting the Division of Aging and Disability in Cape May County, NJ.
This year’s location was at a local library in Monmouth County, NJ. The center was open 3 days a week.