Field notes
from the tax code.
Strategy, warnings, and the occasional rant, written by people who actually file returns for a living.
Tax Changes When You Become Your Own Boss
My Tax FellaTax Changes When You Become Your Own Boss
Going from W-2 to self-employed means you pay both halves of Social Security and Medicare, make quarterly estimates, and unlock new deductions. Here's the full roadmap.
Aug 18, 2026 · 12 min read
Lowering Next Year's Tax Bill Now
My Tax FellaLowering Next Year's Tax Bill Now
Use your 2025 return as a diagnostic tool: calibrate withholding, max out new 2026 retirement limits, and spring-clean your tax strategy before year-end.
Aug 18, 2026 · 14 min read
Should You Adjust Your Withholding After Tax Season?
My Tax FellaShould You Adjust Your Withholding After Tax Season?
A big refund is an interest-free loan to the IRS; a big bill can trigger penalties. Here's how to tune your Form W-4 in 2026 to keep your money in your pocket.
Aug 18, 2026 · 13 min read
Do You Have to Pay Taxes on Sports Betting?
My Tax FellaDo You Have to Pay Taxes on Sports Betting?
The IRS treats every sports betting payout as ordinary income, even if you never received a tax form. Here's how the new 2026 loss-deduction rule changes the math.
Aug 18, 2026 · 11 min read
When The Godfather Came to Town
My Tax Fella hosted a private fundraising event featuring special guest Gianni Russo, best known as Carlo Rizzi from The Godfather.
Jul 24, 2026 · 3 min read
Filed an Extension? Avoid These Mistakes
My Tax FellaFiled an Extension? Avoid These Mistakes
An extension is more time to file, not more time to pay. Here's the fine print most people miss.
Apr 18, 2026 · 4 min read
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