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5 Things Teaching is Teaching Me About Myself

If you had told me a year ago that I’d be nearing the end of my first year teaching a high school class, I’d think you’d gone off your rocker. I wasn’t looking for a job, let alone a hard job that requires quite a bit of preparation. I love being self-employed.

But here I am, a few weeks away from completing my first foray into teaching high school English. And I’ve surprised myself how much I enjoyed it.

Now, let me be clear right out of the gate: this is a very part-time job for me, so I’m not remotely comparing what I do with the otherworldly work done by full-time teachers the world over. I only know what I know from my own experience, and it’s been this: teaching a class of 16 high schoolers once a week at a unique, Socratic method, learner-driven school.

I’ll share more this week on the podcast about what I’ve learned about teaching. Here, I’m thinking through what I’ve learned about myself by saying yes to something unexpected.

I was leading my first-ever Literary London when I replied “yes” via email to the woman who’d offered me the role of teaching English to high schoolers a few weeks prior. Looking back, I see the correlation between leaping into the unknown void of leading an international group trip and agreeing to commit weekly to a task I’d never before done. At the time, though, I thought I was just plain nuts.

There was a short season in college when I thought of turning my English major into an education degree I could use in a career. By junior year, though, I realized I was more cut out for writing and research than helping others do the same. So, I added cultural anthropology for a double-major liberal arts degree, and was off to the races.

So when friends, rather out of the blue, asked if I’d be interested in taking on the monumental task of helping teenagers prepare for their future via books and writing, I was overwhelmed at the thought. What’s that maxim about those who can’t do, teach? It felt the opposite to me: those who can’t teach, do.

I said yes anyway. The endorphins from a successful Literary London were pumping through my body, and I chose to replace the feeling of overwhelm with the feeling of privilege. What a privilege it would be to lead these kids through the world of books I love so much. What an honor to do so.

With only a few weeks until the first day of school, I scrambled like mad to create a reading list and basic syllabus for the entire school year (looking back, knowing now what I know, and I can’t believe it all came together as fast as it did). Being a Socratic school, I only needed to think through about 15-30 minutes of actual teaching per week, since the model of asking good questions and helping guide students through their self-driven growth would carry most of the weight.

Still… I had no idea what I was doing. The first day of school felt like cosmically diving into the deep end.

But I learned. And I stumbled through my mistakes, my hiccups, my lack of experience. And I got a little better every week. Here’s what I’m still learning about my own inward growth from the art of teaching.

Practice is a real thing.

We tell this to kids all the time: if something’s hard, just keep practicing. You’ll get there. But it’s just as true for us adults.

I’ve learned this from writing and traveling — I get better at these things the more often I do them. Waiting to get better before I do something is like learning how to lift weights, paint, or speak a foreign language by watching YouTube videos. You can research all you want, but the only way to improve is to get out there and do it, first as a beginner. You stumble and bumble, you feel like a toddler, but eventually, you find your balance and bearing.

The more teaching hours I logged, the better I got. The best way to get better at something in life is to do it regularly.  

Admitting what you don’t yet know makes you human.

It felt weird at first, when a student would ask me something I didn’t know, and I’d have to answer, “You know, I’m not sure. I’ll find out.” But they never batted an eye at this response. They didn’t expect me to know everything, because they’re smart, and they know people don’t know everything.

One of my favorite definitions of a reliable mentor is “someone who’s about three steps ahead of you.” They’re not so far down the road that they’ve forgotten what it’s like to be where you are, but they are indeed ahead of you, clearing the way and pointing out the bends in the road. They’re still walking the path, too. They’re still learning how to put one step in front of the other. They’re not perfect in their field. Heck, they very well may have a mentor of their own, three steps ahead of them.

Once you feel like you know everything, you’ve stopped growing. Admitting you’re still learning and you don’t know everything makes you a valuable mentor, not unreliable.

Good questions don’t always require neat, tidy answers.

I was reminded of this last week, as we wrapped up Night by Elie Wiesel. His memoir just… ends. No final thoughts about the meaning of life, tidy reflections on the meaning the Holocaust, on why he endured what he did. It just ends, with him looking in the mirror, unrecognizable to himself having not looked at his reflection since before his internment at Auschwitz. The end.

Sure, it’s sometimes good to look back and extract meaning to some events or circumstances. It’s good to ask if there’s a greater good behind a challenge. It’s good to ask God for whether there’s a reason to things. But those things aren’t always necessary for the steady work of daily life. Perhaps the best way to become a better human is learn to sit with good questions, to ask, to listen, to sit with the waiting.

The older I get, the less black and white I see in the world, and way more gray. It makes the few black and white all the more precious.

Being around people is really good for me…

I’m an introvert. I’m also an enneagram 4w5, which means I can spend all day in my head and enjoy the company. It doesn’t take much people time for me to need to drive back to my station and refuel. Because of these things, writing is a great vocation for me.

The problem is, I need people, and I need to be around them. If I’m not careful, I can go days barely talking to anyone beyond the barista, the librarian, and my family. Teaching once a week has been just the thing I need to get me out of my head and around three-dimensional people. 

Not only has it been good for me to remember the intrinsic value of working on something collective with others — a school, functioning well because other adults and students make it so — but it’s made may “main” job even better. Doing something completely different and entirely unrelated to the dubious efforts of “growing an audience,” “building a brand,” or “promoting a platform” (after all, I spend pretty much my entire Wednesday focused on only 16 teenagers) has made my craft as a writer even better.

I write better. I feel like I podcast better. I have a better perspective on the role of social media in my life and work. I have one less weekday to do all my work, so I essential-ize it and get more done that actually matters: more writing, better podcast chats, less Instagramming and more making time for my patrons.

I don’t think I’m exaggerating to say being around 16 teenagers and a few other smart adults has been a game-changer in my work the other days of the week.

…So is saying yes to something hard.

Unless it spins me straight out into my no-good panic zone, I’ve never not found value from saying yes to something hard. Be it leading a group of women in another country, writing a book, starting a thing that may not work, or whatever — saying yes usually means growth.

That doesn’t mean there’s not risk involved. That thing may not work. I’ve said yes to ideas that’ve turned out to not be classically successful. But I grew from them. I learned. I became a better human because of them.

The same has been true with my saying yes to teaching this past year. It’s been hard, but it’s been good.

And so, I’ve said yes to another school year. Am I ready for a summer break? You better believe it. But these kids, they’ve grown on me. I’m glad I said yes.

p.s. At the end of the week on the pod, I’ll share what teaching is teaching me about teaching.

Reading Time:

6 minutes





  1. Aimee

    I was just thinking last night, “Gee, I wish Tsh would tell us more about what this teaching high school gig has been like for her. I’m really curious!” and then I woke up to this post 🙂 Thank you so much for sharing! It sounds like a wonderful school and a wonderful experience.

    • Tsh Oxenreider

      Glad to assuage your curiosity! 🙂

  2. Lucy

    So happy to read your reflections on being in the classroom. It can be the hardest job at times, forcing you to dig deep and keep showing up, hopefully with a smile on your face! But also gratifying and humbling, with a sense of helping to pass on the baton of learning that past teachers passed to us somewhere down the line. Just this week a student told me that I had unlocked her love of our subject. With tears in my eyes I told her that I felt just that way about my former modern language teachers, as they had opened up a whole new world (quite literally) for me aged 14. Nothing beats that feeling. And you get to buy a new academic planner now for 2019-20! 🙂

    • Tsh Oxenreider

      I love that, Lucy — must have been music to your ears!

      And ha! about the 2019-20 planner… I suppose you’re right. Right now, though, I just want a margarita to kick off the summer. 🍹

  3. Jolyn

    Hi Tsh,
    I enjoyed your podcast and blog post this week. I am a nurse and will be teaching a health class next school year to highschoolers, which feels so intimidating right now. I’ve never taught anything to middle or high school. I loved all the things you have learned throughout teaching. Thanks for the insight! I always look forward to the weekly podcast. I feel like it’s my time to grow and learn!

    • Tsh Oxenreider

      Jolyn, I completely felt the same way, but I think there’s something special about teaching a subject that you interact with daily as part of your main career… An angle that’s really appreciated in the classroom! In my (very limited) experience, anyway. I bet you’ll be great!

  4. Ashley R

    I’ve been thinking about contacting you for about a month, since I said yes to my own once a week, high school English teaching gig for next year (homeschooled 9th and 10th graders, so I have to develop a two-year teaching cycle of books). I would LOVE to know what you put on your reading list and how you structured your classes. I would especially love any resources you have for better implementing the Socratic method. That’s something I’m going to have to ease my students into because it isn’t what they are doing in their Middle School class. I’m so excited to have three hours a week to do something I really love and the chance to be in a community of smart teachers who are passionate about alternate forms of education. I’m hoping I’ll find, as you did, that this work will fuel my passion in other areas of my life, which are feeling pretty stagnant these days.

    • Tsh Oxenreider

      I’ll have to jot this down as a future post idea! I’m very much still a student here, but Socratic method is definitely one of those things that’s harder before it gets better… I haven’t really gotten into it yet, but one of my colleagues just shared this post about the value of “planting” good questions in our students’ minds to get them going. Maybe that’s a good start for you, Ashley?

  5. Caroline Starr Rose

    I’ve been holding onto this to read and savor. I’m so glad you said yes to something hard and unexpected. Teaching was one of my greatest joys. I know your students have learned so much from your guidance just as you’ve learned from the experience, too. Enjoy your well-earned summer, and here’s to the year ahead.

    • Tsh Oxenreider

      Thanks, Caroline!

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