irs: Learn how to beat 2025 estimated tax penalties - 10/16/25 11:52 AM
Here’s an important tax planning strategy that can save you thousands in penalties if you’ve missed estimated tax payments for 2025.
The Penalty Problem
When you don’t make your 2025 estimated tax payments on time, the IRS charges a non-deductible 7 percent penalty that compounds daily.
Because penalties are not deductible, they are considerably more costly than deductible interest.
Simply writing a check today won’t erase the penalties. It only prevents them from growing further. But there is a powerful way to make them disappear entirely.
The One Perfect Solution
By using a retirement account with 60-day rollover provisions, you can eliminate estimated tax penalties instantly. Here’s … (3 comments)

irs: OBBBA: How itemizers can win - 10/16/25 11:46 AM
The recently enacted One Big Beautiful Bill Act (OBBBA) includes several permanent changes that directly affect taxpayers who itemize deductions. Some provisions take away opportunities, while others preserve valuable tax breaks. Here’s what you need to know—and how you can plan to win.
Permanent Repeal of Miscellaneous Itemized Deductions
The Tax Cuts and Jobs Act (TCJA) suspended miscellaneous itemized deductions for 2018-2025. The OBBBA makes that suspension permanent.
This means you can no longer deduct unreimbursed employee business expenses, investment expenses, or other items previously subject to the 2 percent adjusted gross income (AGI) floor. If you incur employee business expenses, the solution is … (2 comments)

irs: OBBBA gives Section 529 plans a makeover that you will like - 10/16/25 11:43 AM
Section 529 plan accounts—also called “qualified tuition plans” (QTPs)—have long provided a powerful tax-advantaged way to save for education expenses for children, grandchildren, and even yourself.
While contributions to these accounts are not federally tax-deductible, the money in them grows tax-free, and withdrawals remain tax-free when used for qualifying education expenses.
The recently enacted One Big Beautiful Bill Act (OBBBA) makes Section 529 plans more valuable than ever by expanding the types of expenses you can pay with these funds.
Expanded Education Uses
Historically, families used Section 529 funds primarily for college costs, with up to $10,000 per year available for K-2 tuition.
Beginning … (1 comments)

irs: New Trump accounts - 10/16/25 11:39 AM
The One Big Beautiful Bill Act (OBBBA) introduced a brand-new savings vehicle: Trump Accounts. At first glance, they appear to be traditional IRAs, but they come with special rules for beneficiaries under the age of 18. Used wisely, they can provide a powerful head start on your child’s financial future.
Free Starter Money for Newborns
As part of a pilot program, parents of U.S. citizen newborns in 2025-2028 can elect to enroll their child in a Trump Account. Once the parent makes the election, the federal government will deposit $1,000 of free seed money into the account.
Starting July 4, 2026, parents, grandparents, or … (10 comments)

irs: No tax on overtime? - 10/16/25 11:35 AM
Do you regularly earn overtime pay? If so, the One Big Beautiful Bill Act (OBBBA) may help lower your federal income tax bill.
New Overtime Deduction
Before 2025, the IRS taxed every dollar of your overtime pay as ordinary income. Beginning this year (2025) and continuing through 2028, the OBBBA allows a new temporary deduction for qualified overtime income:
Up to $12,500 each year for single filers Up to $25,000 each year for married joint-filers This deduction applies whether or not you itemize deductions.
What Counts as Qualified Overtime Income
Qualified overtime income includes only the extra pay you earn for overtime hours—generally, the portion … (3 comments)

irs: OBBBA charitable giving shake-up - 08/15/25 12:41 PM
Do you contribute to charitable organizations? If so, recent legislation—the One Big Beautiful Bill Act (OBBBA)—includes significant changes to the tax treatment of charitable donations, starting in 2026. Some are helpful, others less so, depending on your income and filing status.
Good News for Non-Itemizers
Currently, taxpayers who take the standard deduction (i.e., don’t itemize) generally cannot deduct charitable contributions. That will change in 2026.
Beginning in 2026, non-itemizers will be allowed to deduct cash donations to charity up to
$1,000 per year for single filers, or $2,000 per year for married couples filing jointly. Note. Contributions to donor-advised funds are excluded.
New Limits for … (5 comments)

irs: OBBBA's new 1099 filing rules - 08/15/25 12:36 PM
Filing tax forms is never fun—but it’s important to stay ahead of changes that can reduce your reporting burden.
If your business pays independent contractors (non-employees) for services, you are required to file IRS Form 1099-NEC if total payments exceed a specific threshold. For decades, this threshold has been $600 or more in a calendar year. Failing to file can result in substantial penalties.
That threshold is about to change.
Thanks to the One Big Beautiful Bill Act (OBBBA), beginning with payments made in 2026, you file Form 1099-NEC if you pay an independent contractor $2,000 or more during the year. Starting in 2027, … (3 comments)

irs: OBBBA enhances your SALT deductions - 08/15/25 12:28 PM
If the $10,000 cap on state and local tax (SALT) deductions limits your write-offs, here’s good news: the One Big Beautiful Bill Act (OBBBA) temporarily increases the cap starting in 2025.
From 2025 through 2029, you may deduct up to
$40,000 if married filing jointly, or $20,000 if married filing separately. The limits adjust annually for inflation beginning in 2026. But unless extended by Congress, the cap returns to $10,000/$5,000 in 2030.
There’s a catch. The increased deduction phases out if your modified adjusted gross income (MAGI) exceeds
$500,000 (joint filers), or $250,000 (married filing separately). The phaseout reduces your SALT deduction by … (1 comments)

irs: OBBBA adds a possible senior tax deduction (ages 65 and older) - 08/15/25 12:24 PM
If you are aged 65 or older on December 31, 2025, you have a new opportunity for tax savings.
The One Big Beautiful Bill Act (OBBBA) created a new bonus tax deduction—available for seniors beginning this year (2025). You can claim this deduction whether or not you itemize.
How Much Can You Deduct?
If you qualify, you may be eligible for a bonus deduction of up to $6,000 per person. For married couples filing jointly—where both spouses are age 65 or older—the total potential deduction is $12,000.
Important. If married, you must file a joint return to benefit even when only one spouse qualifies; filing … (5 comments)

irs: Turn your corporate vehicle into a tax smart asset - 07/18/25 12:00 PM
If your S or C corporation owns a vehicle that you also use personally, there are important tax rules you need to follow—and smart planning can help you save significantly.
Let’s say you use a corporate vehicle 80 percent for business and 20 percent for personal use. The IRS doesn’t allow “free” personal use. You either
include the value as W-2 income, which increases your tax burden; or reimburse the corporation, which often results in lower taxes and no payroll tax implications. Here’s why this matters: if structured correctly, your corporation can deduct 100 percent of the vehicle’s costs, including depreciation, fuel, … (3 comments)

irs: Life insurance - you don't need to die to collect - 07/18/25 11:59 AM
Could you use a quick infusion of tax-free cash? Your life insurance policy may provide one. And you don’t have to die to collect.
To access money from your life insurance policy without dying, you must have the right type of policy—a permanent life insurance policy that lasts your entire life, such as whole life, universal life, variable life, or indexed universal life. A cheap term life policy doesn’t provide any lifetime cash benefits.
Permanent life insurance includes a savings component. The insurance company puts a portion of your premiums into a cash value account, and this sum grows over time on a … (4 comments)

irs: Your retirement plan exposes you to a $150K penalty - 07/18/25 11:57 AM
How would you like to owe the IRS a $150,000 penalty because you failed to file a simple two-page form? It can happen all too easily if you have a solo 401(k) or another self-employed retirement plan.
If you’re self-employed and you have a qualified retirement plan, such as a solo 401(k) for yourself (and your spouse, if applicable), Form 5500-EZ must be filed with the IRS once the assets in the plan exceed $250,000. The form is usually due July 31 each year.
You—the business owner—are the plan administrator or plan sponsor and the one responsible for filing Form 5500-EZ. You can … (11 comments)

irs: Personal vehicle used for business can produce a big surprise deduction - 07/18/25 11:55 AM
If you’ve used your personal vehicle for business—whether you’re a sole proprietor or you received mileage reimbursement from your S or C corporation—there may be a valuable tax deduction waiting for you.
When you use the IRS standard mileage rate (or when your corporation uses it to reimburse you), the mileage rate is not just a substitute for gas and maintenance. You’re also claiming “embedded depreciation”—a hidden deduction built into the mileage rate.
Here’s where the surprise comes in: when you sell or trade in that vehicle, you could be eligible for a significant additional deduction tied to that depreciation.
Let’s say you bought … (8 comments)

irs: Why landlords should file Form 1099-NEC - 07/18/25 11:54 AM
If you own rental property, you may have heard that you’re not required to file Form 1099-NEC for contractors, such as plumbers or handymen. While that’s often true, choosing not to file could cost you valuable tax savings.
Filing 1099s helps position your rental activity as a trade or business—a critical step if you want to claim the 20 percent Section 199A deduction or deduct repairs under the de minimis safe harbor.
Here’s how it works:
Section 199A allows a 20 percent deduction on net rental income—but only if your rental qualifies as a business. Filing 1099s supports that claim, and it can … (2 comments)

irs: Beat the Estimated Tax Penalty with Strategic Planning - 05/14/25 11:34 AM
If you’re making quarterly estimated tax payments, missing a deadline can be costly. The IRS currently charges a 7 percent penalty for underpayments—and since penalties aren’t deductible, the real cost can feel closer to 11 percent.
But here’s good news: strategic withholding can often help you avoid or erase those penalties—even late in the year.
Here’s why: while estimated tax payments are due on set dates (April 15, June 16, September 15, and January 15), withholding is treated differently. The IRS considers tax withheld from W-2 wages or IRA distributions as if paid evenly across all four quarters—or on the actual date withheld, … (4 comments)

irs: IRS Makes It Harder to Use the Section 530 Safe Harbor - 05/14/25 11:29 AM
It can cost you a bundle if you misclassify a worker as an independent contractor instead of an employee for federal employment tax purposes.
The IRS can make you pay back payroll taxes plus penalties—in some cases, these can equal 40 percent of gross payroll or more. That’s the bad news.
The good news: hiring firms have a “get out of jail free” card—the Section 530 safe harbor.
If your company qualifies for Section 530 relief, the IRS can’t impose assessments or penalties for worker misclassification, and you may continue to treat the class of workers involved as independent contractors for employment tax … (3 comments)

irs: Your Motive Makes a Scam Loss Deductible - 05/14/25 11:25 AM
Scams are incredibly common.
According to recent Federal Trade Commission data, consumers reported losing more than $12.5 billion to fraud in 2024. They reported losing more money to investment scams—$5.7 billion—than any other category. Older people are particularly prone to being scammed.
If you’re the victim of a scam, can you deduct your losses as a theft loss? In the past, you often could because losses due to fraud and larceny were deductible theft losses subject to certain limits.
All this changed in 2017 when Congress enacted the Tax Cuts and Jobs Act (TCJA). The TCJA added a new provision to the … (3 comments)

irs: Protect Yourself: Digitize Tax Receipts - 05/14/25 11:22 AM
When it comes to IRS audits, one of the most common reasons taxpayers lose deductions is the lack of proper documentation.
While your credit card or bank statements prove you spent money, they don’t show what you purchased. Without supporting receipts or invoices, these records are considered “naked”—and during an audit, that’s a problem.
To fully protect your deductions, especially for business-related expenses such as meals, travel, vehicle use, and gifts, you need to keep receipts that document five key facts: the date, the amount, the place, the business purpose, and the business relationship. The best way to do this is by … (0 comments)

irs: TCJA Winners and Losers—Business on the Chopping Block - 12/16/24 10:38 AM
Prepare for tax changes.
The Tax Cuts and Jobs Act (TCJA) has been part of our tax landscape for nearly seven years, shaping how businesses and individuals plan their finances. With an eye toward the end of 2025, when many key provisions expire, here are some critical changes that could affect you and your business.
Expiring Provisions: Mixed News for Businesses
Some of the most impactful changes, including lower individual tax rates and the qualified business income (QBI) deduction, are slated to sunset after 2025. Here are some highlights:
Lower individual tax rates. Rates under the TCJA are generally lower, but thresholds for higher … (1 comments)

irs: U.S. Supreme Court Makes It Easier to Challenge IRS Regulations - 12/16/24 10:35 AM
Over the years, the IRS has enacted voluminous regulations that interpret ambiguous tax code provisions or fill in administrative gaps.
Indeed, IRS regulations dwarf the tax code: the tax code is about 2,600 pages long, while all the rules written by the IRS amount to over 16,000 pages.
Think an IRS regulation is unfair or overreaches? Until now, there wasn’t much you could do about it. A 40-year-old legal rule called Chevron deference (or the Chevron doctrine) required courts to defer to government regulations so long as they were reasonable. After all, the IRS and other federal agencies were the experts.
Because of … (2 comments)