Although I’m well into my adult years, nothing makes me feel like I’m “adulting” quite like trying to make sense of employee benefits. Not my mortgage, not the bills — it’s this. Each year when open enrollment rolls around, I get a sinking feeling that I’m about to make an expensive mistake. After all, my entire family’s health coverage rests on understanding what I’m reading in the PDFs and slide deck given to me by the HR department.
To be fair, HR is always willing to help, but sometimes I’m not even sure which questions to ask. So, like a lot of people, I just guess my way through open enrollment.
But this year, I tried something different. Having used ChatGPT to plan everything from meals to travel, I asked the chatbot to walk me through my employee benefits step by step — from heal

Tom's Guide

5 On Your Side Sports
The Federick News-Post
America News
New York Post
New York Magazine Intelligencer