Taxes

ROTH IRA IS A powerful account. It grows tax-free and withdrawals are tax-free during retirement. Roth IRA also has income limits.
For 2025, if you are filing your taxes as single and make less than $150,000 ($236,000 if married filing jointly) of modified adjusted gross income, you can contribute a maximum amount of $7,000.
But if you make $165,000 (single) or $246,000 (married jointly), you are ineligible to contribute to a Roth IRA directly.

With Roth conversions touted as a savvy move—pay taxes now, enjoy tax-free withdrawals later—it’s tempting to jump in. But what if the U.S. tax system shifts from income taxes to leaning heavily on tariffs? This idea, gaining traction in 2025 policy debates, challenges conventional wisdom and suggests a contrarian take: maybe we should limit Roth conversions.
Here’s why. Converting a traditional IRA to a Roth means paying income tax upfront at today’s rates. The payoff is tax-free growth and withdrawals,

Here is how we use Social Security benefits voluntary withholding to pay all of our estimated Federal tax obligation. This eliminates the need for quarterly filings and payments and is as painless as when taxes were withheld from our employee paychecks.  And since most of our income as well as expenses are on a monthly cycle (including a monthly RMD withdrawal moved to our brokerage account) the monthly automatic tax payment keeps everything in balance and on budget.

My wife passed away in June. Our 2024 MFJ tax return was in the first IRMAA premium tier.  Our 2024 MAGI was $256K which included a $106K Roth conversion. The 2024 tax return will be the basis for my SS Part B fee including the IRMAA premium. That would put me in the 4th IRMAA premium tier for single filing. I expect SSA will initially show me in the 4th premium level. At that point, I can file an IRMAA appeal using FORM SSA-44 to request that they use my 2026 income estimate instead which will save me a lot of money.

Last month, the IRS issued final regulations related to several provisions of the SECURE 2.0 Act relating to employer sponsored retirement plan catch-up contributions. Some plans allow additional, or catch-up, contributions for employees 50 and over. For 2025, the regular limit is $23,500. The catch-up limit for those aged 50 and over is $7,500.  Starting in 2025, there is a higher “super catch-up” limit of $11,250 or those turning age 60, 61, 62, or 63 during the year.

I am 65. I plan to execute ROTH conversions over the next 10 years before I hit  RMDs. Obviously, handling the taxes at the conversion is front and center, pay with cash on hand or take out from the conversion. I understand there is an option to ROTH convert into Fixed Indexed Annuities, where the bonus (15-18%) may cover the entire tax burden. The one I have looked at is a 5-year contract, then you can take the money and put it back into the market.

I WAS RANDOMLY scrolling on social media and saw this post:

“Can you just open an LLC and write things off?”
That’s a real question someone asked, and I’ve seen this question asked many times.
There are a lot of misconceptions around LLCs, their purpose, and how LLC changes your tax structure. With TikTok, there are “tax experts” sharing terrible advice, so let me clarify how it could be useful.
 
First, what is an LLC?

The IRS just published their 2026 inflation adjusted numbers.
Some notes:
1. Standard Deduction
In 2025, the standard deduction for a single taxpayer is $15,750 ($31,500 for married filing jointly). In 2026, the standard deduction is increasing by $350: $16,100 (single), $32,200 (mfj)
2. Brackets
2025 brackets:
10% for income $11,925 or less ($23,850 MFJ)
12% for income over $11,925 ($23,850)
22% for income over $48,475 ($96,950)
24% for income over $103,350 ($206,700)
32% for income over $197,300 ($394,600)
In 2026,

IMAGINE YOU ARE already doing all things possible to minimize your taxes:

You are maxing out your pre-tax 401k
You do tax loss harvesting
You did tax efficient placement
You are maximizing Roth IRA through Backdoor Roth

But what other strategies can you use to minimize taxes? You also might not want to start a business or buy real estate.
Another option that many people aren’t aware of is the cash balance plan (CBP).

Significant changes to tax law took effect in 2018. I heard some interesting comments from clients. Some didn’t believe taxes went down because their refunds didn’t increase. To be fair, taxes did go down for most people, but so did tax withholding from paychecks, keeping many refunds level with prior years. I guess people didn’t notice the extra take home pay. 
The other thing I sometimes heard was that they thought their tax return would fit on a single piece of paper.

THE IRS JUST released a new form called Schedule 1-A, which includes all the new tax bill deductions.
I wanted to quickly go through some of it, so that you are more aware of the new potential savings opportunities.
I’ve previously discussed some portions of the bill, but this is the first time we have a peek of the new lines.
All of these deductions are in addition to the standard deduction or itemized deduction.

The IRS released a draft Form 1040 and the new  Schedule 1-A for 2025. It shows calculations for the new some OBBBA deductions, including the No Tax on Tips, Overtime, Car Loan Interest, and the Enhanced Senior Deduction.

This morning the IRS in IR-2025-91 announced that the pending Secure 2.0 final regulations regarding catch-up contributions to qualified retirement plans will be published tomorrow, 9/16/2025, in the federal register.
My initial reading of a summary has two key takeaways for me.
A requirement that catch-up contributions that will require such catch-up contributions to be ROTH for certain taxpayers based their on earned income ($145K indexed) of the prior tax year.
The effective date of the new catch-up provision will now be for tax years after 12/31/2026,

Humble Dollar frequently posts articles about TIPS – Treasury Inflation-Protected Securities. This post is not about inflation protected bonds.
The OBBBA includes new code 224, a deduction for tax years 2025-2028, for up to $25,000 in qualified tips received during the year for cash tips received by an individual in an occupation that customarily and regularly received tips before 2024. That code section also includes subsection 224(d)(2)(B) which provides that tips do not qualify for the deduction if they are received in the course of certain specified trades or businesses —

I keep a spreadsheet that helps me estimate my current year taxes. As a result of tax changes from the Big Beautiful Bill and further tax changes resulting from the recent Ohio budget bill, I expect tax savings in 2025 in the neighborhood of $1800 on the Federal side and $300 on the State side. And, I expect further savings in 2026.
Political discussions are forbidden on the Humble Dollar site and this post is not political commentary.