I Didn't Know Who I Was Outside Of Teaching

This week’s interview is with Anna Treesara, a researcher-tutor-coach-consultant virtuoso. I connected with Anna over the topic of grief and loss of identity when leaving teaching, and found her insights so helpful and inspiring. I’m incredibly grateful Anna took the time to sit down with me, just weeks before her first baby is due to arrive! Best wishes and thank you, Anna!

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.

I'm Anna Treesara. I live in Chicago, where I was born and raised. I taught right out of college for about four years. I did one year abroad in Thailand and then three years in Chicago, at a charter school. From there, my professional journey has gone all over the place, but has ultimately stayed within the realm of education. 

I left teaching officially in February 2018 and transitioned to a nonprofit company that focused on workforce development, providing internships for students and helping them develop soft skills. I did that for about a year and a half before I felt like  there was something else that was still calling out to me. I wanted to explore what else was in education.

I took a step back, as well as a leap of faith, and started my own tutoring company in November 2019. Since then it's evolved to also include career coaching services for teachers transitioning out of the classroom. And so all of that's gone very well. I can’t believe it’ll be five years this November!

And then full-time, I've done a couple of things. I started working at an education technology company, first doing customer support and then customer success. I did that for about three years before transitioning to my current full-time job, which is in education research. 

Why did you become a teacher?

It was my lifelong dream since I was three or four years old. I'm a child of immigrants; my parents are both from Thailand, and I was born in Chicago. As a child of immigrants, the options presented to me were: teacher, doctor, lawyer. I didn't know how much else was out there, honestly, and how you can still make an impact outside of being a teacher, doctor, or lawyer. But out of the options that were presented to me, I felt the most drawn to teaching. 

My parents loved to tell this story from when I was in first grade. Because my parents were learning English, I would come home from school and teach them about pronunciation, how to read, how the long vowels worked, how the short vowels worked—things like that. My parents told me how I was such a good teacher to them, and it stuck: I wanted to be able to teach others as well. 

I taught English because that was what I was most drawn to: English language in Thailand, and then high school English in the States. I wanted to make an impact in kids' lives and help make sure that they could achieve their academic goals.

Briefly describe your experience teaching. What did you like about it? What did you find challenging or unfulfilling?

It was hard, and part of why I left was I experienced a lot of burnout.

As a job right out of college, teaching at a charter school was a really good experience for me. In terms of systems and structures, the school was very organized, but the demands were also pretty heavy. Charter school systems can be pretty demanding on teachers, and they also tend to pay less than public schools. I think that's a common misconception that folks have. 

I was a founding staff member at that charter school, which meant that every year we didn't have enough teachers. I had to loop up with my students, so I was creating a brand new curriculum every single year. So it wasn't this process of, “Oh, second-year teaching is better, because you can tweak your curriculum or improve it.” I was creating a brand new one every year. That was one piece. 

I really respect charter schools for their emphasis on data-driven decisions, but I felt like a lot of those decisions  and the work leading up to them essentially came down to the teacher. At one point, we were asked to create daily quizzes and have them graded within 24 hours. It wasn't manageable, because again, I was looping up with students every year. I had over 200 students, so to create daily assessments and have them graded within 24 hours and have that feedback back to the students—it just wasn't sustainable. So that was my breaking point. The asks kept coming, to a point where I was like, I don't see an end in sight here.

What brought you to the decision to leave teaching? What was the breaking point?

The demands kept piling up, year after year, to where I felt it just wasn't sustainable to stay long-term. [My departure] was not super planned. It just got to such a breaking point that I needed to step away in the middle of the year, which was one of the hardest things.

But options really opened up for me after that. I had already been applying to roles, so it worked out really well. I was able to start my next role pretty immediately in March 2018. So I had a little two-to-three-week break.

What emotions came up for you in leaving teaching (fear, grief, guilt, relief, etc)? How did you handle these feelings?

Absolutely lots of anxiety, lots of fear of the unknown. Because when you're a teacher, you don't know what you don't know. The teaching world is such a bubble that it’s hard to understand what goes on outside of it. So I was definitely in for a culture shock in terms of what the world outside of teaching was like.

I experienced almost an identity crisis because my entire life, I had thought I would be a teacher forever. This is who I am. I’m Ms. Treesara, you know? I didn't know who I was outside of that. You take away the classroom, you take away everything that you've tried to achieve to become a teacher, and then you're left questioning, What's left? Who am I, really? 

You pour your heart and soul into a teaching career, so when you pivot and change careers, you're like, I don't know what's left of me anymore. Even though you might still have an impactful role, or you might have better hours, or a little bit more of a work-life balance, it's still jarring and destabilizing. You have to think through, What am I doing? What's my purpose now, if I'm not in the classroom with students every day? 

For me, the identity crisis was really hard to come to terms with. I had to accept that I was no longer a teacher. I had to revamp the definition in my head of what an “educator” is, and what it means to be a lifelong educator and lifelong learner, rather than this very binary and limited definition of what a teacher is.

What specific factors did you have to consider in your transition? Did you have financial responsibilities, such as dependants, student loan debt, etc? Is there any type of privilege that aided your transition, such as a spouse or family member who supported you, contacts in other industries, an “in” on a job, etc? 

I was very fortunate. At the time I was dating my now-husband, and we were living together. I was able to land a role within a few weeks, right after I had left... I took a pay cut, but for me, the balance and the mental shift were just so necessary that it was worth it. 

Then we got married, and I was able to jump onto my husband’s health insurance. That's when I was able to take a step back, quit my full-time job, start a tutoring business, and figure out where I was going to go next.

I consider myself very, very grateful. I know that that's not everyone's situation. We didn't have kids at that point; it was just the two of us. I was just so fortunate to have had that opportunity to explore. I know not everybody does, but if people do have an opportunity to jump on their partners' health insurance [and explore non-full-time options], it does make a difference. It’s a big game-changer, for sure.

Tell us about your first year out of the classroom. What lessons did you learn? What successes did you have? What challenges did you face? What, if anything, would you have done differently?

First of all, the fact that I could go to the bathroom any time I wanted—that was a big difference. I would find myself sitting at my desk and still subconsciously holding it. And then I’d be like, Why am I doing this? The bathroom is right there. I'm not waiting on a passing period right now, or for students to enter my classroom. So that was a big shock. 

Email communication was a big learning curve for me… making sure my email communication was professional, making sure I was responding to emails right away. In jobs outside of teaching, professional communication is a huge thing. And scheduling meetings, knowing how to use your calendar—all of these things that aren’t a big priority in teaching.

What are you currently doing for work? What do you like about your current career or job?

My current full-time role is in education research, on the client-success side. I work closely with Ed tech companies and Ed tech founders to match companies with school systems… to implement their tools and provide feedback. I also do some internal operations, because I found I really enjoy building team culture and making sure people feel great about their jobs as well as supporting them to do their best work.

Then on the side, I have my tutoring company, which also doubles as my career coaching company. I don't do as much of the tutoring myself anymore. I have a small team of independent contractors who do most of the tutoring… I just run the operations and the logistics of the company. 

For the career coaching, I help teachers revamp their resumes, help them prepare for interviews, help them optimize their LinkedIn profiles—truly anything that helps them figure out their next steps to transition out of the classroom.

I'm taking a little bit of a step back from career coaching for the next few months because I’m expecting my first kiddo toward the end of this month! But I’ve put out resources for teachers: they can independently go through my workbook, which provides a more financially accessible point of entry for folks who are trying to transition out of the classroom.

What skills and knowledge from teaching were you able to utilize in your new career? What gaps in skills or knowledge did you have, and how did you address those?

I always lead teachers toward anything in customer support or customer success, because teachers are so relational. Customer success is all relationship management, when you think about it. All the different stakeholders you're interacting with at the school level—administrators, parents, other teachers, and so forth—it's all managing relationships. I was able to transfer a lot of those people skills and relationship management skills directly into my roles.

I also carried over organization systems, efficiencies, classroom management, and systems procedures. Those skills make a really good fit for any operations role, where you're working with people to make sure they feel supported.

In terms of skill gaps, I would say again that email communication and professional corporate jargon were a learning curve. That's still something I struggle with—figuring out, Okay, what are the words I need to use? What's the corporate lingo? Because every industry is different, right? You need to learn that corporate lingo, so you feel really confident in both email and verbal communication.

What, if anything, could have kept you in the classroom? What, if anything, could ever lure you back?

That's a really good question. I do often get lured back, when I'm at school visits, and I'm like, Oh, this is so nice! There's all these really cool AI tools now. I wonder if they would have kept me in the classroom.

Hmmm… what would have kept me? More support? I know that's very vague and broad, but I think that's really why teachers end up leaving—they don't get enough support. 

I don't know exactly how that would have translated, though—whether it was a person helping me grade, or a person helping me create [quizzes], or a system, or an AI tool. I think someone just asking, “What are those things that can be taken off your plate so that you can truly have more energy to facilitate, give intentional feedback to students, and make sure you’re actually customizing and tailoring their learning accordingly?” I think that could have kept me.

Also, more appreciation. More value recognition. I don't know that that’s always top-of-mind for administrators, because there are so many demands on them, too… The change really needs to start with the whole system, figuring out, What are all the pressures and demands from the top down? What is the root problem here? 

Other things that would make teaching more ideal are smaller classroom sizes and more manageable student-teacher ratios. Because if you do have to do all of this work, it would feel more manageable with a smaller class size.

Finally, what advice, tips or wisdom do you have to share with current teachers considering a career transition? Is there anything in specific you wish you’d known or prepared for?

Start earlier than you think. The job market is really rough, even for those who have left teaching already, so start earlier than you think.

And really, really lean into networking, because you truly don't know what connections will be valuable for you. It might seem silly to have a 15-minute coffee chat, but you never know if down the line that person is working at XYZ Company, and you need some sort of in. You just really never know, so take up every single coffee chat you can get. 

And then, number three, if you are in a position where you're able to swing it financially, be open to part-time and contract work, because that truly does open doors... I worked part-time in a contractor role at an Ed tech company. No one knew that a pandemic was coming. In 2020, when there was a need for me to increase my hours, I was able to go full-time... So if you're in a position like that, take it because you just never know what doors might open up for you.

It's also a great way to test-run a company and see if you really like it. Whereas, if you end up joining a company full-time, it's a little bit stickier, right? You feel like, I gotta stay here. I have a full-time salary. Now I'm a little bit more tied. 

But when you have part-time or contract work, you get a really good feel for the company, their core values, and if it’s actually a place you would want to go full-time, or if it’s just a good resume-builder. Because even those part-time gigs can give you that additional experience that you really need outside of the classroom.

Anna’s tutoring company Tutoring Tree can be found here.

Anna’s career coaching and consulting services can be found here.

Anna’s workbook for transitioning teachers can be found here.

This interview has been edited for clarity.