One of the strangest things about leaving teaching is that the decision can feel almost impossible to reconcile with the person who became a teacher in the first place.
Most of us didn't stumble into the classroom. We were pulled there by something. A teacher who changed us. A subject that made the world feel bigger. The first time a kid understood something because of the way we explained it. Somewhere along the line, teaching became more than a job. It became part of the story we told ourselves about who we were.
Which is why wanting something different can be so disorienting.
You can love what teaching gave you and still become exhausted by what it asks of you. You can believe deeply in the work and still want more financial freedom, more room to grow, or simply the chance to find out what else you might be good at.
You can leave without pretending the person who once felt called to teach was wrong.
Your Second Syllabus is about that next chapter.
Each week, I'll share practical guidance for teachers figuring out what comes next — how to explore different career paths, translate your experience, position yourself for roles outside education, and make smarter decisions about things like graduate school, resumes, interviews, and career pivots.
Over time, I'll also build out more tools, guides, and resources designed to make that transition a little less mysterious — and a lot more manageable.
And I know that chapter can be built because I built one myself.
I left the classroom, went back to school, explored different corners of the business world, and eventually made the leap into corporate life. Today, I'm a product manager at JPMorgan Chase.
I don't think my path is the path every teacher should follow. That's the point. I want to help you figure out what your path might look like — and make the transition with more clarity, confidence, and understanding of what your experience is actually worth.
It's about understanding what you built in the classroom, figuring out where those abilities can take you next, and giving yourself permission to explore parts of your career — and yourself — that you may not have had room to explore before.
But to explain why I believe that so strongly, I have to start with why I became a teacher at all.
Ask a teacher why they became one and, more often than not, the answer doesn't start with a job.
It starts with a person.
A teacher who pulled something out of you that you didn't know was there. Who took the thing you were embarrassed to care about and treated it like it mattered. Who gave you somewhere to belong — or saw a version of you that you weren't quite capable of seeing yet.
Those moments have a funny way of becoming careers.
Mine started freshman year of high school.
Middle school is a cloud of angsty confusion for almost everyone, and I was no different. Mine took the form of shyness, awkwardness, and a persistent hope that I would somehow figure out where I belonged.
High school felt like an opportunity to flip the script.
The shy, awkward middle-school kid I had been decided to do something completely out of character:
I auditioned for the school play.
It was Pride and Prejudice.
I had spent weeks working on a monologue, which did absolutely nothing to calm me down once I walked into the audition room.
My heart was racing. My body had gone rigid. Around thirty other students were there, many of them upperclassmen who seemed perfectly comfortable being loud, theatrical, outlandish — all the things I very much was not.
They looked secure in their own skin.
I was trying to figure out what to do with mine.
Showing up had been my act of courage.
Once I got there, I sat in the corner and tried my best to disappear.
Then the director walked in.
He was in his late thirties, happy-go-lucky, a little mischievous, with what I can only describe now as a vaguely Shakespearean presence. He had just arrived at our small rural high school and decided, somewhat audaciously, that he was going to stage its first theatrical production in nearly thirty years.
He explained how the audition would work, looked around the room, spotted me tucked away in the corner —
and voluntold me to go first.
I was horrified.
I went anyway.
He eventually cast me as Wickham: arrogant, charming, womanizing Wickham — perhaps not the most intuitive casting choice for a painfully shy fourteen-year-old.
That was sort of the point.
He made me watch Top Gun because, in his estimation, I needed to study arrogance. He wanted a strut. Swagger. Someone who entered a room expecting people to notice.
Then he'd pick my brain. What did I think of the character? Why would Wickham behave that way? What was I trying to communicate when I walked across the stage?
He wasn't just telling me what to do.
He was treating my ideas like they were worth hearing.
Little by little, the shell cracked.
My confidence grew. My social skills grew. So did my fascination with storytelling and the strange power it has to make people see themselves — or someone completely different from themselves — more clearly.
But the most important thing he gave me wasn't theater.
It was the experience of having a teacher look at a kid who was trying very hard not to be noticed and decide, No. You're going first.
He saw something in me before I knew how to see it myself.
And somewhere along the way, I realized I wanted to do that for other kids.
That's why I became an English teacher.
At 22, I took my first job: a maternity-leave position teaching sixth-grade English in a Title I district in Revere, Massachusetts.
I had plenty of moments where I had absolutely no idea what I was doing.
I also got attached to those kids almost immediately.
One boy in particular could derail a room in seconds. He was smart and good-hearted underneath it, but constantly chasing the kind of attention that came from being the loudest person in the room.
We had rough days.
We also figured each other out.
My students wrote in journals regularly, and on my final day covering the leave, I asked them to reflect on what had gone well while I was their teacher — and what I could have done better.
His entry was honest. He acknowledged that he knew he had made my life difficult at times.
And then, at the very end, he wrote:
"Because of you, I am smarter."
I still remember it.
And if you're a teacher, I'm guessing you understand why.
When I returned to Revere full-time, I eventually built the school's first theater program while teaching English and working toward my master's degree.
There wasn't much of a budget. So we fundraised, borrowed, improvised, and figured things out as we went.
We put on four plays.
But the part I'm proudest of happened after those students left.
When they reached high school, they kept asking for theater. Eventually, they convinced a teacher there to start a program too. Years later, that program staged In the Heights. Lin-Manuel Miranda sent the cast a video. The story made the local news.
I had nothing to do with that production.
That's exactly why it meant so much.
Something we'd started had outgrown me.
For a long time, moments like that made the exhaustion feel worth it.
Then the balance changed.
COVID accelerated it, but there wasn't one cinematic moment when I suddenly knew I was done. Administrations turned over. Working conditions stayed frustrating. Kids seemed less able to focus and harder on one another — and sometimes on us.
And I was tired in a way that a week off wasn't fixing anymore.
I was 30. I had spent eight years building a career I had once desperately wanted. I had earned a master's degree, taken on more responsibility, and still had three roommates because the math of the life I wanted didn't work.
Meanwhile, I watched friends in corporate jobs travel, change companies, get promoted, earn more money, and sometimes close their laptops and have the rest of the evening belong to them.
I felt guilty for noticing.
Eventually, though, I let myself say it:
I wanted out.
Leaving wasn't glamorous.
I boarded dogs through Rover to bring in extra money while applying to entry-level corporate jobs. I tried to rewrite a résumé built almost entirely around schools into something people outside education could understand.
I knew I had done difficult things.
I just didn't know how to explain why they counted.
Eventually, I went to Notre Dame for an MBA.
Business school didn't hand me one neat answer about what I was supposed to become. It did something more useful:
It gave me room to experiment.
I worked across marketing, brand, operations, strategy, consulting, and sustainability projects. Later, I joined JPMorgan Chase in a rotational program and kept exploring.
Today, I work in product, with a strong connection to marketing.
And even that wasn't some career I had circled on a whiteboard when I left teaching.
I found it by trying things.
That's something I wish I had understood earlier.
Your second career doesn't have to reveal itself to you in one cinematic moment.
You're allowed to explore.
And somewhere along the way, I realized something else:
I hadn't started from zero.
Product managers spend enormous amounts of time translating — between engineers, marketers, strategists, executives, and customers. A huge part of the job is figuring out what each person needs and adjusting the message without losing sight of the larger objective.
One day it occurred to me:
Wait.
I know how to do this.
Teachers do it constantly.
Who understands already? Who needs more context? Who needs a different explanation? How do I adjust for one person without losing everyone else?
In my old career, we called that differentiation.
Turns out corporate America has quite a few uses for it too.
And that's where Your Second Syllabus: Classroom to Corporate begins.
This isn't a newsletter about how to become a product manager.
And it's not an argument that every teacher needs an MBA.
It's for the teacher staring at a job posting and thinking: I couldn't possibly do that.
It's for someone who has spent years investing in students and has finally decided it might be time to make a serious investment in themselves.
Because the problem usually isn't that teachers have no transferable skills.
It's that education has its own language, and nobody teaches you how to translate it.
That's what Your Second Syllabus is here to help with.
Not just how to leave teaching.
How to understand what you're actually good at, explore what's out there, position your experience so other people understand its value, and build a second career that fits the person you've become.
A syllabus doesn't do the work for you.
It gives you a path through something you haven't learned yet.
Consider this your second one.
To start, I've put together a free Transferable Skills Translator: eleven things you already do as a teacher, translated into language employers actually use.
You can grab it here:
If you're somewhere between the career you built and the one you haven't figured out yet, I'm glad you're here.
Christian