Executive Summary
The first time I was handed a confidential separation agreement, I didn't have long to decide. It was full of things I never knew I could ask for. I was ready for that day only because I'd spent years preparing for it.
The habit started at the beginning of my career, during the dot-com bust. I watched colleagues learn they'd been let go when their laptops stopped working. They lost a paycheck, but they also lost the proof of their own work and the contacts they needed to find the next job. My personal and professional life sat on one work laptop, too. So I started keeping a go-bag.
This fall's wave of voluntary buyouts is why I published this piece now. Flock Safety gave roughly 1,500 employees until Oct. 2 to decide, and Microsoft made the first buyout offer in its history this spring. A buyout feels like a choice, and partly it is. But the window is short and the terms are unfamiliar.
The bag holds five things: a quarterly record of results with real numbers ("grew revenue 22% year over year with flat headcount," not "grew revenue"), praise in other people's words, your own calendar, a short list of people to call first, and a recruiter file. Mine goes back more than a decade. One rule covers all of it: only what's truly yours. Never company property, client data, or anything confidential.
I'm not an employment lawyer, but I've sat on both sides of these conversations. If an offer is on your desk today, turn "months" of pay into actual dates, price out what exercising your options will cost, and ask what's negotiable beyond the cash. And if you were let go this morning, don't sign anything yet. Keeping the bag current takes about fifteen minutes a quarter.
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