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
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
Should 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?
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
Do I Pay Taxes on My World Cup Airbnb?
Hosting fans for the 2026 World Cup can be profitable, but the IRS treats your Airbnb or VRBO income as taxable once you cross 14 rental days. Here's how to keep more of what you earn.
Aug 18, 2026 · 12 min read
Will Marriage Lower My Tax Bill?
For most couples, saying "I do" unlocks better tax breaks, wider brackets, and doubled deductions. But high earners and some low-income families can face a marriage penalty.
Aug 18, 2026 · 10 min read
Can I Claim Education Expenses for My College Student?
The American Opportunity Tax Credit can put up to $2,500 per year back in your pocket for each eligible student, and can even land you a refund check.
Aug 18, 2026 · 10 min read
How New IRA Tax Rules Could Cost Your Heirs
SECURE 2.0 forces most non-spouse heirs to empty an inherited IRA within 10 years, and many now face annual RMDs. Here's how to protect your legacy.
Aug 18, 2026 · 11 min read
What Digital Asset Moves are Taxable?
The IRS treats crypto as property. Selling, swapping, spending, and staking all have tax consequences, wallet transfers don't, but your records still have to prove it.
Aug 18, 2026 · 10 min read
New 2026 Tax Rules for Charitable Giving
The OBBBA gives non-itemizers a $1,000/$2,000 above-the-line write-off, and hands itemizers a new 0.5% AGI floor. Here's how to give without losing deductions.
Aug 18, 2026 · 9 min read
When The Godfather Came to Town
A private fundraising night with special guest Gianni Russo, music, stories, signed memorabilia, and a room that gave generously.
Jul 24, 2026 · 3 min read
Lowering Next Year's Tax Bill, Now
The moves you make in May matter more than the ones you make in April. Here's how to start the clock on next year's return today.
May 12, 2026 · 6 min read
Filed 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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