Before You Ask AI About Your Money, Ask This One Question First
You’ve been chewing on something for a week. Maybe it’s whether to convert part of your IRA to a Roth this year. Maybe someone at a cookout mentioned a stock and you can’t stop thinking about it. So you open ChatGPT, or Gemini, or whatever’s already on your phone, and you type the question out. […]
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. […]
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 […]
What You Can Safely Ask AI About Social Security and Medicare — and What You Should Never Trust It On
Part 1 of a plain-English series on using AI safely for the money decisions that actually matter. Here’s a scene playing out in a lot of homes right now. Someone’s a year or two from claiming Social Security, or trying to pick a Medicare plan, and the paperwork makes their head spin. So they do […]
How to Remove Your Personal Information From the Internet: A Plain-English Guide for Seniors
Heads up: this post contains affiliate links. If you buy through them I may earn a small commission at no extra cost to you. I only recommend what I’ve used or genuinely evaluated. Full disclosure here. Here’s something most people over 60 never find out until a scam call gets a little too personal: your […]
Best Password Manager for Seniors: Easy Tools to Protect Logins Without Remembering Them All
Heads up: this post contains affiliate links. If you buy through them I may earn a small commission at no extra cost to you. I only recommend what I’ve used or genuinely evaluated. Full disclosure here. More than 1 in 3 adults over 65 reuse the same password across multiple accounts — making them one […]
ChatGPT vs Gemini vs Copilot: Which AI Assistant Is Actually Worth Your Time After 60?
I’ll be honest with you. When I first heard about ChatGPT, I thought it was just another tech fad — something for college kids and Silicon Valley types, not for someone my age trying to build a real business and manage real life. I was wrong. But I was also right to be skeptical of […]
What Is a VPN and Why Every Senior Should Have One
Heads up: this post contains affiliate links. If you buy through them I may earn a small commission at no extra cost to you. I only recommend what I’ve used or genuinely evaluated. Full disclosure here. I want to start with a story that happened to a friend of mine at a Panera Bread. He […]
Making Money Online After 60: What Actually Works, What Doesn’t, and How Long It Takes
I want to start by telling you what this article is not. It’s not a pitch. It’s not a “follow these three easy steps to financial freedom” story. It’s not an ad dressed up as advice. What it is: an honest account of what’s actually working for people our age who are building income online […]
Is AI Safe to Use? The Real Risks, What AI Can’t Do, and the Rules to Follow
Heads up: this post contains affiliate links. If you buy through them I may earn a small commission at no extra cost to you. I only recommend what I’ve used or genuinely evaluated. Full disclosure here. If your first question about AI is “But is it safe?”—that’s actually the right question to ask. It tells […]