Nobody at Social Security Is Counting Your Hours. That Is Not the Same as Being Safe.
I wrote recently about the 45-hour rule and what the side-hustle guides leave out: How Self-Employment Can Cost You Social Security Before Full Retirement Age. That piece worked from Social Security’s public pages. This one works from the regulations underneath them. Three things turned up that are true in the primary sources and wrong or […]
Hobby or Business? The Rule That Decides Whether You Can Deduct Anything
Quick Answer The IRS draws a hard line between a hobby and a business, and in 2026, that line costs real money. If your side activity is a business, you can deduct your expenses against your income. If it’s a hobby, you report every dollar you earn and deduct nothing. There is no middle ground. […]
The 1099-K Threshold for 2026 Is $20,000, Not $600 (Here’s Why Your AI Assistant Says Otherwise)
Quick Answer: For the 2026 tax year, a payment platform or online marketplace is only required to send you a Form 1099-K, a tax form reporting the gross payments you received through that platform, if BOTH of these are true: your gross payments exceed $20,000 AND your transactions exceed 200. Both conditions must be met. […]
How Self-Employment Can Cost You Social Security Before Full Retirement Age
Social Security has a worked example sitting on its own website. It is worth reading before you start anything. A man the agency calls John Smith retires from his job at 62 on June 30, 2026. He has earned $37,000 that year. On October 5 he starts his own business. He works at least 15 […]
AI and Your Taxes When You’re Self-Employed: What’s Safe, and What Gets You an IRS Notice
Part 2 of a plain-English series on using AI safely for the money decisions that actually matter. If you work for yourself — freelance, contract, a little side income, a small business — tax time hits different. There’s no employer quietly handling withholding for you. You’re tracking your own expenses, guessing at quarterly payments, and […]