Maybe you should quit teaching. Maybe you shouldn't.
Let's figure that out before you blow up your life.
If you leave
You should understand the pension you are giving up, what health coverage actually costs, which of your skills another employer will pay for, and how to talk about fifteen years of teaching to someone who has never set foot in a school.
If you stay
You should stay because you looked at the alternatives and chose this one. Staying deliberately is a completely different life from staying because you believe you have no options.
This is not a book about how teaching sucks
It is not a promise that you can leave on Friday and make six figures by Monday. It is not an inspirational quote collection disguised as career advice. And it is definitely not a guarantee that leaving education will make your life better.
The purpose is simpler: make staying or leaving a choice instead of a financial or psychological trap.
What the book actually covers
Twelve chapters, in the order the decision actually happens — not the order that makes for a tidy pep talk.
- MoneyThe three numbers you need before you can evaluate any offer: what survival costs, how many months you can cover, and what a job would have to pay to be worth taking.
- PensionWhat you have actually earned, what happens if you leave, what changes if you stay, and how to price the trade instead of guessing at it.
- InsuranceFour possible doors after your district plan ends, what each one costs, and the gap between your last day of coverage and your first day of new coverage.
- SkillsWhich parts of teaching translate, which parts don't, and how to build evidence for the gap before you need it.
- DocumentsUsing AI without turning your resume into fiction, and rewriting a teaching resume for people outside education.
- PeopleBuilding a network before you need one, and asking questions that get you real answers about a job.
- The searchHow a job search actually goes, why rejection at the top of the funnel is normal, and how to interview after fifteen years of not interviewing.
- The exitReading a whole offer, negotiating when you have never negotiated, resigning well, and what the first year on the other side is really like.
Money is stored choice.
Chapter 2, Know Your Number
Who wrote this
I taught for fifteen years at the same high school — engineering, robotics, computer science, CAD, and 3D printing — and then left for technical work in a different industry. I resigned before I had another job lined up, which I do not particularly recommend and would probably do again.
I am not a career coach. I am someone who made this exact decision, prepared for it seriously, got some of it right, and can tell you where the expensive surprises are.
Get the worksheets
All fourteen tools from the back of the book are here as free printable PDFs — the three numbers, the pension decision sheet, the health coverage comparison, the skill-gap matrix, the rest. No email address required.