What I Learned Looking for my First Post-Teaching Job.

Thomas Rademacher
5 min readNov 17, 2022


The Office I Didn’t Get.

In my first few years of teaching I kept a word document of other jobs I could do. In those years of profound stress and struggle, I needed the reminder that teaching was a choice, and that though I felt woefully incapable of doing this thing I had dreamt of doing for years, I did have actual talents that could be applied elsewhere.

Yes, the list included things like “juggler” and “Toby from the West Wing,” but also things that felt even more fantastical as a career, like “writer,” and, since mostly what I seemed to do at work is stand in front of people and try to be a funny dude, “stand up comedian.”

After a few years, the list was lost to a technology upgrade, and the number of things that I could imagine doing that weren’t teaching had dwindled to zero anyway.

I stayed for a decade, then more and a few more years, and then it was time.

Last spring, I started looking for jobs outside of classroom teaching. There were months and months of applications that went unanswered. There were interviews, sometimes multiple, and twice even doing an assignment for a job opening. The closest I got to a job for like six straight months was having a dream that I started doing stand-up. I even woke up remembering the joke* that launched my career.

In the end, I had a few offers, all doing work that seemed fulfilling and interesting. I’m quite happy where I ended up (as an Acquisitions Editor for an education press), and talk about it enough that I’ve been getting a few DM’s or emails a week from people currently in the classroom asking for advice on how to transition out.

I’m not an expert. I’ve done this exactly once, and ended up applying to (I just went and counted my spreadsheet) 34 different jobs. That’s a lot, but from talking to a few different friends, I was lucky.

So, here’s some things I learned over half a year of job search. Hopefully you find some of it helpful, even if you’re not planning on going anywhere for a while.

  • Start doing stuff.

Ok, so I didn’t land a job as a curmudgeonly (but secretly big-hearted) communications director at the White House. But, many years ago, I reached out to a few different candidates at a few different levels to offer any help writing. I started answering some emails for a mayoral and then a governor campaign until both started getting real money. More recently, I’ve written a few white papers, done a few research projects, and even wrote a campaign launch speech. I got paid zero dollars for these things, but enjoyed doing them.

Importantly, while in a few different interviews, I ended up talking about these experiences a lot. They were things that not just augmented my teaching experience, but separated me from a lot of other applicants. The same is true of different organizations I volunteered for, projects I had contributed to, and writing I had done.

If you’ve got a decent idea of what you’d like to do after teaching, and there is any way to do even bits of it here or there, the experience is going to count a lot later on.

  • Join LinkedIn

Lots of jobs get posted there, and building up any kind of network in your new chosen field will be helpful.

  • Get ready to be disappointed.

You know how it sometimes feels like a lot of people don’t respect or understand all the work teachers do and the skills they build in order to do that well? Many times, these will be the people that you are interviewing with. Sometimes, even education-related organizations will not see any connections between the job you’re applying for and the problem-solving, flexibility, communication skills, people (and time) management, and organization it takes to teach. There are exceptions, places who have figured out just how good teachers are at adapting their skills. I found one in the end, but it was a bummer how rarely anyone seemed to think teaching had taught me anything.

Also, no matter how unimpressed I was in some interviews, or how much I felt like I had bombed them, it was never fun to get the email rejection (especially the form email after multiple rounds of interviews).

It’s just… it’s a lot. A lot of little (and big) gut-punches sprinkled throughout a week. It helped a lot to connect with a few people going through it at the same time, and also ice cream.

  • Know what you want and why.

Because first, like 90% of all job interviews asked me what the three most important things about a new job were for me. Mine were 1) Doing something that helps the world. 2) Working on/with a team. 3) Flexibility in hours/location. But also, the thinking I did to come up with that list was really helpful in any number of ways during the search, application, and interview process.

And second, no one’s going to get excited about you as a candidate if it feels like you don’t care what job you get so long as it’s not teaching. When you are asked why you want a role or why you are applying, focus on the reasons you want to move forward. This is a very bad time to get a little free therapy about all the parts of teaching that hurt.

That’s… that’s really all I’ve got. Except I will also say this: If it’s your time to leave,

then leave, and I wish you all the luck in the world in doing so. But if you’re not sure, especially if you’re in your first few years, maybe what you really need is a change of location, a new leader, a different role. Teaching is hard, it’s hard everywhere and always, but teaching in a school that is the wrong fit for you can make you feel like you were never meant to do it.

Either way, I’m rooting for you.

* “If you buy your kid an ice cream, and they drop their cone, it doesn’t mean you lost an ice cream cone, it means you paid double for one.” That’s it. That’s the joke. I am not a stand up comedian.



Thomas Rademacher

Author of It Won’t Be Easy, Raising Ollie, and 50 Strategies for Learning without Screens. 2014 MN Teacher of the Year @mrtomrad on everything www.mrtomrad.com