I recently chatted with five colleagues who all came to teaching after rich and diverse careers in the military, tech, the law, medicine, and higher education fields. They shared their reasons for becoming educators, what they bring to the teaching profession from their earlier careers, and how their career trajectory supports their personal and professional goals to lead a life of learning. Below are condensed versions of our conversations.

Mawee Aguon, Upper School English Teacher

What was your previous career, and how has it influenced your teaching style?

I was a US Army Officer. I think being an officer in the military influenced my teaching style because within the military you must have time management, attention to detail, and have to be able to create relationships with people. I think that all shows up in my teaching when creating lesson plans, helping students with their writing, and creating classroom community. 

What made you decide to switch to teaching?

I always wanted to be a teacher, even when I was young. I actually got my undergrad degree in English and education while doing the ROTC program. I always knew that when I got out of the military, I wanted to use my degree and be a teacher. And that’s exactly what I ended up doing.  

How did your experiences prepare you for the challenges of teaching?

My experience as an Army officer prepared me for the challenges of teaching because I had to have the ability to set boundaries and expectations with my soldiers similar to how I do in the classroom with students. As an officer, I also had to manage large groups of soldiers, which translates into classroom management. I think being an officer also helped prepare me to work under pressure. Teaching can be a demanding and pressure-filled role. 

What aspects of teaching were most surprising to you?

I think something that surprised me most about teaching is how personal it is. I did not have to be quite as personal or vulnerable in the Army. But with my students, especially when it comes to teaching English and pushing students to be vulnerable in their writing, I have to mirror that for them.  

How do students react when they find out you had a different first career?

They don’t believe me at first. When you look at me, no one would guess I was in the Army, let alone a field artillery officer that dealt with large cannons and large groups of soldiers. Most times, I think my previous experience helps me get my foot in the door with my students. 

How do you incorporate your past career experience into your lessons? 

I prioritize writing about your own experiences. I have written and shared pieces of my experiences in the Army to mirror the writing I ask the students to do. When getting vulnerable in journaling, I'll ask students to write and then orally share experiences they’ve had, and I’ll share some personal experiences I’ve had while serving that relate to the journal prompt. 

How have your life experiences helped you connect with students in a unique way?

I think we all experience what it means to deal with outside pressures, tragedy, joy, ambition, etc. I think by sharing my past experiences, they see me as human. And they see that experiences and feelings can be somewhat universal. 

Kate Kerkering, Upper School Science Teacher

What was your previous career, and how has it influenced your teaching style?

Prior to becoming a teacher, I had a few different careers. My undergraduate degree is in English literature, and my first career was working in international relations. After working for a few years, I decided to return to school and pursue a career in medicine. I went back to the University of Washington to complete my science requirements and to attend medical school. I worked in medical research before eventually deciding to stay home and raise my kids. 

How did your experiences prepare you for the challenges of teaching?

Each of these career paths has influenced my teaching. My first career taught me a lot about working with a small, dynamic team to get a lot of work done, and I draw upon those skills with my collaboration partners in teaching. Medicine gave me a great background in science, and being a parent greatly influences how I approach my students. I try to see my students as complete human beings, and I have a much better understanding of the complexities facing high school students since my own kids are in college and high school. 

How do students react when they find out you had different careers?

Students generally appreciate that I have had different careers. I get a lot of questions about health and medicine, particularly as they relate to what we are discussing in Biology class. Students seem to value a real-world application to the content they are learning in the classroom. 

How do you incorporate your past career experience into your lessons? 

I always have a random biology fact to start each class. Usually, these facts are not so random and are related to our lesson in some way. Perhaps because of my background, I often choose facts that are related to health and medicine.

How have your life experiences helped you connect with students in a unique way?

I think my time in medicine explaining complex health processes to patients has helped me think through how to explain science in lots of different ways. In addition, I really believe that teaching is about building relationships with students, just as the key to good healthcare is the relationship between the physician and patient.

Mike Kim, Upper School English Teacher

What made you decide to switch to teaching?

I had just finished up my 10th year of practicing law, and it was a good time to check in with myself about whether I was doing what I wanted to do at the outset of my career, and how I was feeling about where I was going in my career. I came to realize that maybe practicing law was never really a great fit for me, so I revisited one of my first dreams in high school—to be an English teacher.

How did your experiences prepare you for the challenges of teaching?

Right after law school, I practiced immigration and family law, which gave me the opportunity to better understand professionalism and honed my ability to write in a really crisp and clear manner. I'm really grateful for the ways in which it made me think about writing, and I carry that into my teaching practice. 

I also had to take initiative and stand behind my work. I put my bar number on every brief that I submitted. Being nimble, curious, and taking ownership are all things that I practice now as a teacher.

How have your life experiences helped you connect with students in a unique way?

Throughout my previous career, I often felt like I knew nothing. And that’s such a valuable experience to embrace. I think many people, as we all get older, experience this even though we have a ton of knowledge and experience. I think that translates to my experience with students, where they are often demonstrating that they know things that I don’t know anything about. I want to be curious. I don’t want to be in a position where I know everything. 

How do you incorporate your past career experience into your lessons? 

As a tax attorney at Amazon, I was an Excel nerd. When I thought about becoming a teacher, I imagined that I wouldn’t get to use Excel anymore. But instead, I use Excel every day! I have students take quick surveys at the beginning of class and show the results in Google Sheets, or I use it to track grades or moments in the classroom.

What aspects of teaching were most surprising to you?

Something that is really delightful is how ready students are to unpack really complicated topics and texts. When I was in high school, I didn’t have the language to talk about identity in the same way that I think 9th and 10th graders who I’ve been in classrooms with are very ready to talk about. And they’re open to continuing to develop that skill.

Aaron Sokoll, Upper School History Teacher

What was your previous career, and how has it influenced your teaching style?

I was in a PhD program studying the history of American religion and was planning to become a university professor. That did not work out, so I started working for a state department–funded program bringing researchers from around the world to UC Santa Barbara to study American religion. I got a great background in international exchange through that program that led me to the International Programs Office at George Washington University. From there, I became an executive assistant to the CEO and CTO at an autonomous vehicle technology company, where I wore many hats including program manager, product manager, and government affairs manager.

How did your experiences prepare you for the challenges of teaching?

When I got the job at UPrep, my previous experiences played a role in supporting my classroom transition. I was hired to teach United States History, and so my background in American religion was really great for bringing in more about the history of religion into our curriculum. My experience on the policy side of a business has been helpful for teaching Civics and class discussions about how decisions get made in government and how citizens push for changes. The start-up culture, where you may wear many different hats, prepared me to be a teacher and being able to realize that sometimes you have to switch what you are doing in class because what you planned just isn’t working.

What made you decide to switch to teaching?

I really like being in a classroom. I like teaching and I like learning, too. When I arrived at the technology company, I was learning about software and was in a number of different roles and it was super fun. I was in front of policy makers and lawmakers talking about tech issues and educating them and it seemed really useful. Now as a teacher, I have my own vision for the world. But I want my students to know that I am curious about their visions, and that there are different ways to think about the world. That’s why I became a teacher.

What advice would you give to others considering a career switch to teaching?

For me, coming from a university into a high school classroom, it’s so different. At the university, I never taught a student twice, even though I taught in different departments and at different times. At UPrep, I have the opportunity to build relationships with students and see them grow.

There’s a level of realization that you’re going to have to be okay with not knowing what you’re doing. The transition into teaching can be really great. But it may also be really hard, especially for people who have had a career for a while and know what they’re doing in their job. You need to be okay with feeling like a fish out of water and understand that at first you won’t know everything that you need to know.

Arthur Watson, Computer Science Teacher

What was your previous career, and how has it influenced your teaching style?

I worked in the software industry for 30 years in a variety of technical and management roles and retired after 20 years at Microsoft. That experience gave me a solid foundation in several important aspects of teaching. I provide clear learning objectives, present information in multiple formats, and coach effective use of class time for both individual and collaborative work. I encourage students to explore and understand problems before trying to solve them, to view learning new programming language features as a step towards building interesting projects, and to reason across multiple layers of abstraction.

What made you decide to switch to teaching?

Education is a core value in my family, and I’ve always had teaching in the back of my mind as a potential second career. I’ve enjoyed plenty of teaching-adjacent activities over the years, from teaching assistantships in grad school to leading industry engineering teams. About 10 years ago, I got some classroom experience teaching computer science as a Microsoft TEALS (Technology Education and Learning Support) volunteer. After that, it was only a matter of time. 

How did your past experiences prepare you for the challenges of teaching?

Working around the clock on software projects was good preparation for giving students prompt feedback on projects and tests.  

How do you see your non-traditional background as an advantage in the classroom?

My industry experience helps me relate the topics my students are learning to the work done by software professionals, and to prepare students for both academic and career success. My experience working on large software projects with many contributors helps me support students approaching problems in their own ways.

What advice would you give to others considering a career switch to teaching?

Volunteer in a classroom, talk to experienced teachers about their day-to-day experiences to confirm you understand the role, and work through family and financial considerations in advance. Consider what aspects of your current job you find most satisfying, compared with what you expect to find most satisfying as a teacher. If you decide to pursue a teaching career, complete a teacher certification program even if it isn’t required for your target position.

What’s one thing you wish you knew before becoming a teacher?

I wish I’d known how much I’d enjoy interacting with students in class every day.

READ MORE ABOUT HOW MEMBERS OF OUR COMMUNITY LEAD A LIFE OF LEARNING HERE.

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