It's Better To Jump Before You're Pushed

Heath Madom on his move from high school English teacher to "the dark side," AKA the district

Not everyone who leaves teaching leaves education, and not everyone who leaves teaching leaves for good. This week’s interview is proof. I connected with Heath through one of my oldest friends. I really appreciated his candor, his nonlinear career path, and his broad, nonfinite perspective on the job. Also, anyone who has an ice cream blog is fine by me! Thanks for taking the time to chat, Heath. I’ll be expecting a pint the next time I’m in Oakland!

Introduce yourself! Give us your name, location, number of years you spent teaching, what subject and grade level you taught, and number of years since you’ve left teaching.

So I'm Heath Madom. I’m originally from Long Island, New York. But I’ve lived in Oakland, California on and off since 2003. I taught for a total of eleven years.

When I graduated from college in 2001, I taught seventh-grade English in Brooklyn for two years. And then I went away from teaching for a long period. I attended law school, and after graduating, I spent almost a decade working in the labor movement, mainly for SEIU and AFSCME. I also did a year with CTA, trying to organize charter school teachers. 

Then I went back into the classroom for about nine years, mainly teaching tenth-grade English, up until this last school year. 

To me, I've only been out of the classroom for seven weeks, since school started, because that's when it really hit. I was like, “Oh, yeah, this feels weird.”

What brought you to teaching, both originally and when you returned after organizing?

At the time when I was making the decision in college, I didn't have a lot of vocabulary for it. But I always felt like I wanted to do some kind of service work and have a career that was service-focused. The jobs I gravitated toward always tended to be jobs working with kids. In college, I worked in a Head Start, in an after-school program, and as a teacher's assistant one summer.

I think the reason I gravitated towards those jobs is because I like being around people. I like interacting with others. I like the social element that comes along with teaching—or at least sometimes I like it! So being a teacher just seemed like a natural fit.

I left [that first time] after two years, because I was just too emotionally immature, at 22, 23 to deal with what you have to deal with as a teacher, especially amongst a bunch of seventh graders. 

As much as I believe in what unions do and why they're necessary, the work is very steeped in conflict. It's very adversarial in nature, and I'm not that kind of person when it comes down to it.

So I went to law school and did a lot of work in in unions. The thing I came to realize working in unions is: as much as I believe in what unions do and why they're necessary, the work is very steeped in conflict. It's very adversarial in nature, and I'm not that kind of person when it comes down to it. Interpersonally, I like to collaborate with people. I like to be in harmony. When you’re working in the labor movement, you're fighting—if you're working for a union that's worth anything. (And there are some unions that aren't.) You're fighting the boss; you're in a battle. And that just started to take its toll. 

I started to reflect, and was like, “You know, I think teaching is actually a good fit for me.” And when I was going back into teaching, I already had one kid and another kid was on the way, and I was married. Maybe it was the dad vibes, but I felt like, “Oh, yeah, being an educator is a better fit for me.”

What did you like about teaching? 

I like being in relationship and in community with people. In my career, I've always gotten along well with other teachers in general. There's some teachers who are like, “Oh, you're an ass, you don't belong anywhere near children.” But those people are few and far between. Everyone else, I just vibe with on a professional level. I'm like, “Oh, these people are cool; they’re good people.” Even though we don't get as much time to work together as we want, I enjoy working with other teachers.

Maybe it was the dad vibes, but I felt like, “Oh, yeah, being an educator is a better fit for me.”

And at the end of the day, I like working with students. There's so many kids who you develop these great relationships with. And you get to know aspects of their lives, and really help them, and be a positive influence. So I think the relational aspects of the job I really enjoy. Or enjoyed.

What was was challenging or unfulfilling?

I think the emotional labor is the hardest part. 

Emotional labor is necessary to do the job well, especially within a urban public school setting like OUSD. Some days I would come home just emotionally spent. When you've given all of yourself, and had to make so many decisions and have so many conversations, you get home and you’re just done. I didn’t want to engage at the level that maybe I really needed to with my children. I would get short-tempered, because I was expending all of my emotional labor during the day, and I didn’t have enough to give it home.

I never enjoyed grading. As an English teacher I would dread reading student essays. There was this teacher I worked with at Oakland Tech who’s now retired. He's a funny guy and had all this like wisdom, and he always referred to student writing as “egregious prose.” It's not fun. It's just brutal. Nobody chooses to read academic work for fun.

I figured out how to be pretty decent at classroom management. I would lean into my dad energy. I was never one of those teachers that kids were scared of. I think kids sense pretty quickly, like, “Oh, you're a soft person. You're not going to be the mean guy you pretend to be like. I can see through that.”

Some days I would come home just emotionally spent... I would get short-tempered, because I was expending all of my emotional labor during the day, and I didn’t have enough to give it home.

So I would have to lean into my nagging dad energy and also building relationships with kids… I always felt like I was not being true to myself in a certain way. I didn't want to be like the authoritarian and the disciplinarian. Some of the leftist political ideals I had when I was younger butted up against the disciplinarian role that you have to take as a teacher.

That was part of it: I just didn’t want to be a classroom manager anymore. I'm tired of dealing with it. I don't want to do that, or I want to break from that at least. If I have to do that at home with my kids, I'm not gonna do it at my job.

Also the of structural stuff: the class sizes, the expectations, the lack of resources. It just like burns you out. 

What brought you to the decision to leave?

I just felt like I needed a break. We had just had another strike in Oakland. And I was like, “This district is so dysfunctional; I just can't do this.”

This friend of mine who was a teacher for ten years and got his PhD, I was talking to him about it. And he told me, “It's better to jump before you're pushed.” Meaning, make the decision at the right time. 

I always felt like I was not being true to myself in a certain way... Some of the leftist political ideals I had when I was younger butted up against the disciplinarian role that you have to take as a teacher.

I talked to my two co-principals and said, “After this year, I'm leaving. I'm going to take a break. I don't know what I'm going to do, but I can't come back to the classroom. I just need a break.”

They were super supportive, and they appreciated me giving them a heads-up. It allowed the school to find someone to replace me in advance, and I got to transition that person. 

There are some people who teacher their whole career, like 40 years, and I have so much respect for the people who do that and do it well. But most teachers you talk to have one foot out the door. It’s like everybody's on a countdown. “I got another year or two, and then I'm doing something else.” 

I recently saw one former colleague, and she was like, “Why did I come back this year? I just can't do it.” And she’s a good teacher. My other colleague who came back, she's like, “I gotta find something else.” It's just like everybody's on the countdown.

Most teachers you talk to have one foot out the door. It’s like everybody's on a countdown. “I got another year or two, and then I'm doing something else.” 

In our staff bathroom last year, they had this little bulletin board where you could put note cards. One appeared that said, “There’s twelve weeks to spring break.” Then it was started getting crossed off: “11 weeks of spring break, 9 weeks.” Part of it is the nature of the work: it's very time based. You have a year with students to do the work, before they move on to someone else. But part of it is this psychology, like, “I can't wait till this is over, because it's just so hard.” Like, “I just feel so beaten down. When do I get a break?’”

Among teachers, that's always in the back of mind: “What is my expiration date? When do I have to say I'm done?”

For me, I could see it coming, and I wanted to get out ahead of it. Because I've seen some teachers leave in bad ways where they just don't tell principals until, like, two days before school starts, almost as a fuck-you. That's just unprofessional. I don't want to do that. I want to give people a heads-up and do it the right way.

Part of it is this psychology, like, “I can't wait till this is over, because it's just so hard.” Like, “I just feel so beaten down. When do I get a break?’”

A lot of people who've mentored me have been like, “You know, it's good to take breaks.” There are many teachers who take multiple breaks throughout their career. They might teach 25 years, but they take four breaks in the all those 25 years, and then they come back recharged.

But I think most teachers are also thinking about it in that one-foot-out-the-door way.

So you had this year to start looking—what did you do? What kind of plans did you put in place?

In terms of the teaching, I hate to say it but I feel like I phoned it in a bit, and that felt not great. 

In terms of the the job stuff, I started reaching out to folks early. Over the course of my time in the district, I’d met a lot of people and developed a lot of good relationships with folks. So I started letting them know. I did a lot of outreach in like September, sending out emails saying, “Hey, I'm gonna be looking for jobs come January, when the positions start opening up. So I just wanted to give you a heads up.” And then I followed up with those folks. 

Because I was looking for jobs in education out of the classroom, I was only reaching out to former teachers or admin folks, like principals and people in the Central Office who are like coordinators. 

And then a woman in the Budget Office was like, “We have an opening if you're interested.” I applied and interviewed, and then they offered me a position. It was the first position I got offered, and I took it.

So what is your current role with the district?

I guess the best way to describe me is like a cross between a budget compliance officer and a budget customer service rep for principals and admin staff at school sites.

There are many teachers who take multiple breaks throughout their career. They might teach 25 years, but they take four breaks in the all those 25 years, and then they come back recharged.

I have to make sure that schools have an actual budget plan, and that they actually spend in accordance with the allowability for [grants and measures]. There's a lot of bureaucratic stuff, because principals will submit receipts or requisitions for authorizations to pay people. I have to double check the spreadsheets, make sure everything matches up. It's like a lot of compliance work.

At the same time, it's a lot of customer service. Principals will ask, “Can I use these funds?” and then I have to get on the phone with them and talk them through what they can and can't do, if they have to move some stuff around to make it comply with the budget. The rules I'm learning are crazy. There's so many. 

What do you like about your current role?

Frankly, it's a lot easier than teaching. I have a very defined set of work tasks: reconcile this spreadsheet, create this analysis of the budget, contact these schools, and collect this data. It's very measurable in a way that teaching's not. It's just like, “Here's a discrete task. Please get it done.” I find that to be a lot easier and a lot less stressful than teaching.

I have a lot of flexibility. Like I'm having this call right now during the workday with you. I can set aside some time to do this, because I have no other meetings right now. I just get the work done when I get it done. I have flexibility to go pick up my kids and bring them to whatever practice or lesson they have. If I need to, I can go run an errand. I work from home, which I don't totally love, but I'm also really appreciating that aspect.

What kind of feelings have come up for you in the transition out of the classroom?

I appreciate the piece you wrote about grief on your on your Substack. There's been some feelings of grief, and of guilt, and of like, “What am I really doing right now? What use am I? Is my job really that essential?” 

“What am I really doing right now? What use am I? Is my job really that essential?” 

I feel like I'm cheating a little bit. People keep telling me, “Listen, you deserve a break. You should just enjoy this job. It's a good fit for your work-life balance, and for your family. It doesn't have to be forever, so just enjoy it right now.” All that's true, and yet I still have those feelings.

In a district like Oakland, where there's such a contentious relationship between teachers and the district, you kind of internalize this idea that the central office is the dark side. “They’re over-staffed and bloated, and the real work is here in the classrooms with students.” 

And there's some truth to that. So I’m just grappling with all those things.

How are you moving through that? How are you managing those feelings?

It's hard to describe how I manage it. Politically, it feels a little weird. I do get in my mind, like, “Oh man, I'm not in the union anymore. I'm part of the dark side—management.”

But then part of me is like, “That stuff's all bullshit.” So much of what passes for radical left politics isn’t really that. I guess that's one way I've been justifying it to myself. 

And just in terms of usefulness, every day I try to do something useful like for other people. I've been volunteering more at like the Alameda County Food Bank. I'm just trying to find little ways to feel [give back]. 

Politically, it feels a little weird. I do get in my mind, like, “Oh man, I'm not in the union anymore. I'm part of the dark side—management.”

Even if my work doesn't have the immediacy the same way it does with teaching, the work I'm doing is important. Like, I'm putting together a report. If we don't send it, we'll get fined. [OUSD] used to get all sorts of fines, and our department has been really instrumental in turning that around. 

But I still have to convince myself. Because it's so abstract and so not in community with others. 

What if anything could lure you back into the classroom, or what could have kept you?

I'm not sure anything could have kept me. I think a lot of this has to do with where I'm at in my life right now. This is a time where my kids have a lot of needs, and we have a lot of needs as a family. Someone's got to be home to take care of house shit. Someone's got to be around to get the kids to this appointment. I took my daughter to an orthodontist appointment on Friday. So in that sense, I don't know that anything could have kept me right. 

I think I'm gonna be back in a classroom at some point, because it's just kind of who I am. 

Unlike some of the other people you’ve interviewed, I'm not convinced that I'm not going to be inside a classroom at some point in the future. I've taken a break once before and come back. I think I'm gonna be back in a classroom at some point, because it's just kind of who I am. 

I think if I go back, when I go back, I’m gonna be really picky about the school and the setting. Maybe I’d teach AP classes, or something in that kind of context, where I might feel less of the drain of classroom management and emotional labor.

What kind of like advice or wisdom would you want to share with somebody who's either considering leaving or considering a break?

The piece of advice I would give is be proactive. Just go out and start emailing people, getting in touch with people in different departments within a district, or spaces outside the district, like nonprofits. Just start asking. I mean, you kind of have to.

I realized last year that there’s no position waiting for me. I have to go and figure it out. 

Let them know, “Hey, this is what I want to do.” And be very clear: “I want to take a break from teaching. And here are some things I'm considering.” Even if yolu don't get any response back, so what? Just go to the next person be like, “Hey? If you have any positions, keep me in mind.”

And I get it, because I don't like doing the networking thing. But you gotta put yourself out there. I didn't have a Linkedin profile until like last year. I was like, “I guess I gotta get one of these if I really wanna move into the next position.” I realized last year that there’s no position waiting for me. I have to go and figure it out. 

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This interview has been edited for length and clarity.