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EP 06 Jessica Wolvington: From Teacher to Software Engineer

Welcome to another episode of the Teacher Career Coach podcast. I’m your host, Daphne Williams. In this episode, I’m showcasing the career path of former teacher, Jessica Wolvington, a teacher who successfully transitioned to the role of a software engineer.

Listen in as we have some honest conversations about our experiences with imposter syndrome, burnout, and work-life balance in this new career.

Don’t forget to stay tuned until the end of the interview to learn her suggestions of other careers in her industry that are also good bets for teachers.

Listen to the episode using the podcast player or subscribe on Apple Podcasts or Spotify! The episode transcript is available below.

DAPHNE WILLIAMS
Jessica, thank you so much for joining me today. I’m really excited to hear your story and be able to share it with all of my audience. I want to ask you first to tell me a little bit about your journey in education and your role as a teacher.

JESSICA WOLVINGTON
Yeah, for sure. I did the whole shebang. I did my undergrad in education. I double-majored in special education and childhood education. Got certified off the bat and then actually moved to London to get my master’s in education. It was like all I thought I was going to do for the rest of eternity.

After I finished my master’s, I moved back to New York and found a job as a third-grade teacher in Brooklyn and worked there for a year. This is after having worked in schools in London and also in New York as I was doing my student teaching.

I’ve had an experience in the classroom ranging from the West Village where the kids were wearing coats that cost more than two months of my rent to inner-city schools in London where it was really rough.

So, once I got back, I spent a year in a third-grade classroom and that was the end of it for me.

DAPHNE WILLIAMS
That last classroom and your experience that last year was really what ultimately made you decide that you wanted to leave teaching altogether?

JESSICA WOLVINGTON
Exactly. It was a combination of my experiences across the years in a variety of schools, in a variety of districts. Honestly, literally, in various countries the challenges were always the same. And it was very rarely the children.

Actually, it was never the children that were the problem. It was everything around it. The administration, the lack of support, the zero work-life balance ever. I’d be up on Sunday morning thinking about my kids who weren’t going to eat until tomorrow. I’d have to spend all weekend grading or talking to parents. When I wasn’t at work, I was thinking about work or working. That was a huge challenge for me. The lack of support and administration was ongoing. That was really a deal-breaker for me.

DAPHNE WILLIAMS
That’s something that I always tell my audience is one of the first steps I asked you to think, “Would changing grade levels, schools, or districts help me fall back in love with career again?” For me, personally, I switched districts, and it reinforced that it wasn’t a good fit for me. It sounds like you went all over the board, and you realize just something about this position wasn’t really working for you.

I want to transition into what job do you do now.

JESSICA WOLVINGTON
Yeah, I did a true 180.

I’m a software engineer now.

I write code all day which is a huge change, to say the least.

DAPHNE WILLIAMS
I feel like when it comes to technology-savvy careers, especially software engineers are probably at the top. A lot of teachers talk themselves out of feeling like they’re even smart enough for the roles. Which is insane but we have just such low career self-esteem that switching is really scary.

I was curious how did you decide on that specific career direction?

JESSICA WOLVINGTON
That’s a great question. For context, I never identified as a math or science or numbers person in general. I just always a language person. English, foreign languages, what have you. I don’t think I passed my high school geometry class. That was how non-math or sciencey I was. When it came down to leaving teaching, which I just spent six years of my education and thousands of dollars in education to do, I was so desperate to get out. I was considering anything.

All options were open. Nothing was off the table. My one requirement was I didn’t want to have to go back to school for another year or two or whatever it was. I started looking into options for new careers that; (A) I could change into rapidly, or at least within a shorter timeframe than going back to traditional school; (B) that would pay more; and (C) that would allow me to have the flexibility within various industries. I didn’t want to be pigeonholed only into education. That research led me to speaking to anyone and everyone under the sun who I knew in any capacity. Reaching out to acquaintances from high school, from 15 years ago, that level of outreach. One person I knew had done a software engineering boot camp, which are intensive, three month long coding boot camps. Literally six days a week, 12 hours a day that take you from basic knowledge of JavaScript to being able to get a job.

My mom, actually, was a software engineer in the 80s and had been telling me since I was 15 that I would really enjoy this, and I should give it a go. Every day I was like, “No, Mom. You don’t know me. You can’t tell me what to do.” Of course my mother, ultimately, was right and I ended up loving it. To make that jump, I quit teaching in the summer, spent a month over the summer still getting paid—thank god for the DOE—learning to code. I was learning how to write JavaScript from online programs, applied to one of these boot camps that started in the fall, did the program for those three months. The hardest three months of my entire life, but three months nonetheless. After those three months, they actually hired me on to help teach the program as a TA, so teaching experience coming in handy. By the time I finished those couple of months as a TA, I was employed full time as a software engineer. It worked out better than I could ever imagine it could.

Moral of the story is you don’t need to have those skills that you think you need to have.

You just do it. You learn it. You figure it out. I’m so glad I made that jump.

DAPHNE WILLIAMS
Oh yeah. After I left, I’ve pushed myself to do things I never thought.

I kind of wanted to go back to what you said about how that three months was the toughest? Was it just the amount of work that they were asking you to do?

JESSICA WOLVINGTON
It was everything. I had an enormous amount of imposter syndrome. I was a third grade teacher in this room full of brilliant people, some of whom had Computer Science degrees already, some of whom had been the quintessential “I’ve been coding in my mom’s basement since I was seven [and] JavaScript was my first language” kind of people. I just felt so out of my element, out of depth, just trying to understand what the heck was going on. That was a huge portion of why it was so difficult.

Not to say there weren’t other people like me in that program. There were musicians and artists and other people who came from really non-technical backgrounds. I wasn’t alone in that, but definitely was a challenge. The actual content itself is hard. You’re learning how to code from a very limited background.

DAPHNE WILLIAMS
Kudos to you for sure.

JESSICA WOLVINGTON
Thank you. Yeah, just the content it can be really overwhelming. The pace of the course I did is lightning speed so you’re constantly absorbing information. They use the analogy of drinking from a firehose. You’re just overwhelmed with new information every single day. If you can’t keep up then you kind of fall behind. That’s the idea of this boot camp model is you have to stay at the pace of everyone around you and understand it all.

You’re getting help along the way, but it’s a not super forgiving. The pressure and the desire to leave teaching really pushed me through all that, but it sure wasn’t easy. And really long hours. Six days a week likely from 8 a.m. until 10 p.m. most days. It is your full life to make that transition, but that’s the price you pay for doing it three months.

DAPHNE WILLIAMS
I appreciate your honesty and transparency about that process as well. I know a lot of people who are thinking of changing into something like this might hear about these boot camps, and they should know that they might be putting themselves through something that’s really grueling and challenging, especially if it’s condensed into such a short timeframe.

Do you feel like the work-life balance of teaching kind of set you up to succeed in that?

JESSICA WOLVINGTON
Oh, absolutely. The flip side of things is these people who were coming in from more nine-to-five, office life jobs were so overwhelmed. For me, I was like, “This is hard, but I’d take a day of this over parent-teacher conferences or even a day in the classroom any day.” I had the autonomy. I could go to the bathroom when I wanted to. I could step out when I needed to.

It was so challenging, but the challenge in compared to say the classroom for me was a swap I’d make any day, and I think definitely equipped me to handle that stress and the pressure better than I would have otherwise.

DAPHNE WILLIAMS

Teachers are definitely resilient.

You said that even during that boot camp it was really strenuous, but you were already seeing the benefits of how it was a better fit for you personally. How do you feel like this job compares to being a teacher in your opinion? Work-life balance or how the salary compares if you’re comfortable getting into that? Just let me know how your life has changed.

JESSICA WOLVINGTON
Yeah, absolutely. Literally about as different as you can possibly imagine. Where do I even begin? In this transition, [I] left a relationship that wasn’t the right fit for me, in addition to the career that wasn’t the right fit for me. In this new career transition, I met my now fiancé. So, personally, huge shifts. In terms of quality of life, currently my salary is tripled from what it was when I was teaching. So that’s great.

My first job after the boot camp and after teaching (so my first job as a software engineer) I remember five o’clock hit, and everyone left. I start packing up my computer to bring it home with me. Someone’s like, “What are you doing?” I was like “Well, I’ve got to bring it home to work.” They were like “No, you don’t. You leave it here.” “You mean I leave my work at work?” They’re like, “Yeah, that’s the whole idea.” I’m like, “Well, what do I do with my night?”

I was just so taken aback by the fact that I could have a life now I could have the time to pick up a hobby. To go see my friends. I didn’t have to get home by eight o’clock so I go to bed at 9 p.m. I could stay up until 11 p.m. because I didn’t have to be at work until 9 p.m. or 9:30 p.m. or even sometimes 10 p.m. I got the option of working from home a couple days a week, so I could literally just roll out of bed for my first meeting.

All of that was just so utterly foreign to me coming from a teaching background. I genuinely spent the first couple months of that job trying to find something to occupy my nights with because I was so un-used to having free time. It was a huge change.

DAPHNE WILLIAMS
That’s exactly what I went through as well. That’s how I started my first side business. I left the classroom, and I got my first career as an educational consultant, and I realized I had all this extra time and all this extra energy, even on the weekends and nights that I’m spending with my loved ones. I also can continue to grow extra income or start pursuing other things even on top of this job, which I never would have imagined doing six months prior to that.

I wanted to ask a question that is something that everybody asks me, especially when they’re thinking of leaving teaching. Do you miss having the summers off?

JESSICA WOLVINGTON
[Laughter] No, not at all. I remember when I was a teacher I would say I would much prefer to just have a less stressful day today and remove my summers than have a stress packed eight or nine months and then like a kind of stress free couple of months, but with the anxiety of knowing that it’s all coming for you in the fall.

That being said the difference is I can now take a vacation when I want to take a vacation. I don’t have to be dependent on the education holidays or the prescribed days off that you have when you’re teaching. Which is great. I love that. Teachers deserve to have that time off, if not more, but the downside is you don’t have the autonomy to decide when you want a vacation. You are adhering to the most expensive vacation times because everyone has those times off to take with their kids. Not that anyone can take a vacation in real time right now. So, no. Short answer: no. I do not miss having a summer. It would be great, but I also have the option to take my summer as I will with my vacation days.

DAPHNE WILLIAMS
One thing that I tell people to always think when they’re considering that question is it’s gonna be different for everybody. It sounds like you and I were coming from the same place where we were so burned out. We were absolutely miserable. Our weekdays, our weekends, during the school year were so terrible that it didn’t really make up for it for having this month or that month of vacation space that we were willing to sacrifice that to be happy year round.

If you’re coming into this and you’re listening—and you’re actually pretty satisfied in your career and you’re liking teaching—but maybe you want to make a little bit more money… Maybe you’re just kind of looking at what else is out there, but the summers are huge for you and your family, then maybe it’s not the right move for you. There’s gonna always be pros and cons for every single person with every huge decision like this, so this isn’t gonna be a one-size-fits-all answer. It sounds like you and I are kind of coming from the exact same situation.

JESSICA WOLVINGTON
Yeah, exactly. I’m 100% on the same page.

DAPHNE WILLIAMS
100%, where I’ve had positions where I have flexible paid time off that as long as there wasn’t anything huge coming up, you could take two weeks paid time off whenever you wanted. With teaching, I remember feeling guilty that I wasn’t allowed to even take a sick day, even if I was sick. That’s not just sub plans, but it’s administration talking to me like I didn’t have the right to take a sick day, and I shouldn’t have been such a burden to them. The shift of culture from where I was at to where I am now has been huge, but that’s not going to be everybody’s situation or a universal answer.

I wanted to ask, too, what would be the first thing that you would advise a teacher to do if they were also interested in becoming a software engineer?

JESSICA WOLVINGTON
Talk to anyone in the field who is a software engineer currently. It doesn’t have to be someone who made a transition to another career just talking to people and seeing if it’s a career that you’re interested in because it does have its own challenges. It’s not like this perfect world for everything is hunky dory all the time.

For me, personally, it was the right fit, and

I don’t think I would have made the jump if I hadn’t spoken to people who were in the industry to confirm that was a good fit for me.

That’s definitely the first thing I would do.

DAPHNE WILLIAMS
Networking is huge, and I feel like people put so much pressure on themselves where networking sounds like it’s such a scary process. I know you reached out to a couple of people, just acquaintances that you have happened to be in this industry to feel them out, but other than that people can go to Facebook groups. That still counts as networking. Going into Facebook groups created just for this specific industry.

JESSICA WOLVINGTON
Yes, exactly. I even went so far as to reach out to people on LinkedIn, like cold reach out. Like, “Hey, I see you’re a software engineer at this company. I’m curious about what you do. Do you have time for a 10 minute chat?” and weirdly enough that sometimes actually was successful.

DAPHNE WILLIAMS
I’ve met some of the most helpful people on LinkedIn. This specific path that you went into it’s a technical role and in some of the technical roles you will need to learn those technical skills.

I was curious if you’ve encountered other people who are former teachers or other roles within the industries that you work that would be a good fit for former teachers as well?

JESSICA WOLVINGTON

Weirdly enough, a lot of the skills that I learned as a teacher are helping me advance in my career now.

Like in promotions or leadership opportunities. Things that I think I passed over for if I hadn’t had those skills I learned as a teacher have become really, really clear to me even in the past year or so.

Teaching skills are so important and so helpful.

Teachers do so much more than the rest of the world sees that can translate into careers that one would never necessarily think of as the first stop for a teacher after teaching.

Software engineering, for example, there are so many things I do on a day-to-day basis that are teaching skills like organizing. Even the code writing itself. You’re problem solving, and that is what teachers do 12,000 times a second in the classroom is problem solve.

That being said, I work with people who are former teachers who are software engineers. Many of them actually. It’s a staggering number, considering. A lot of math teachers end up being software engineers, I’ve seen. Product. A lot of people go into products because I think being a product manager or project manager that is a lot of teaching skills in that organizing, communication, planning, timelines, having to communicate complicated ideas to people who might not understand what the heck you’re talking about. All of that is literally what you do as a teacher. Those careers, like product and project management, you find those roles at literally every single company. That’s a huge one.

DAPHNE WILLIAMS
Have you found yourself still excited about education in the way that you’re overly helpful in your role and maybe you want to help other people learn software engineering or walk through new hires on the onboarding process?

JESSICA WOLVINGTON
Yeah, I find myself involved in mentorship very frequently. I love mentoring. I love speaking to people thinking about a career change. I find myself facilitating meetings, explaining things to new hires, and I even used to run JavaScript 101 workshops. Things like that. The love of teaching is still there. That never went away for me. Just kind of manifested itself in a different way.

DAPHNE WILLIAMS
That same thing happened for me where I still want to keep creating things to help other people and taking hard-to-understand information into smaller bite sized pieces. So, I’m happy to hear that you’re in the same boat as me.

JESSICA WOLVINGTON
For sure.

DAPHNE WILLIAMS
Oh, really quick, how long have you been a software engineer? Somehow I missed that.

JESSICA WOLVINGTON
Yeah. Three years? Three and a half years.

DAPHNE WILLIAMS
You can tell that this is your lifelong career?

JESSICA WOLVINGTON
Yeah, you know, I don’t see myself writing code forever. I see myself going more into managerial track for technical things like engineering manager or maybe CTO one day, we’ll see. I think I’ll say in tech in some respect forever.

DAPHNE WILLIAMS
That’s also a great point. At the beginning, you were talking about how you didn’t know where to go. A lot of teachers find themselves kind of holed into this corner because teaching is supposed to be there forever career but there’s not a lot of upward trajectory in a career path that makes a lot of sense besides being a teacher, maybe working for your district and curriculum in some way, or becoming an administrator.

Once you get into a role where you find a good fit, you can continue to grow, you can continue to shift and I think that’s the exciting thing that some people were missing in their careers. They found themselves stagnant where they weren’t able to constantly be growing and shifting and adapting into new positions.

JESSICA WOLVINGTON
I completely agree. Honestly, that was one of the most fun things about this new career for me was (A) I get to negotiate my salary, are you serious? Not just preordained every year incrementing by whatever it is. I get to actually ask for what I want and what I know I’m worth? That was a game changer. That was very exciting. And the growth. Even in three and a half years, I have gone from junior software engineer to now I lead a team, which is really cool. Again, to your point, there’s a lot more room for opportunity to go in different directions or to pivot or to be like, “You know what? I want to go this way this year,” or what have you.

DAPHNE WILLIAMS
Going back to that salary negotiation. That was a huge game changer for me. I was able to negotiate my salary for the first time, and that’s something that I actually teach the members of the Teacher Career Coach Course to do it. It’s not 100% of the time that it’s negotiable. Sometimes you go in and they have an offer and that’s the offer, but a lot of times it’s worth asking. I’ve personally been able to talk up $10,000 more on a salary and I’ve had course members who have been negotiating their salaries successfully who said they never would have even known how to do it or to do it. Teaching salaries are just on this pay scale and we’re not comfortable or used to being able to negotiate with salary. There’s a strategy behind it. You can’t be too greedy.

JESSICA WOLVINGTON
Absolutely! Yes. There’s a certain anxiety that comes with it. It’s like “Oh god, they’re going to take it away from me,” but 99.9% of the time, they don’t take it away and the worst thing you can do is ask for more. Usually, you get something and there’s a lot you can negotiate to that’s not just salary. You can negotiate an education stipend or extra money for traveling to conferences. There’s so much wiggle room when it comes to things you could ask for, which is, again, not something you can do in teaching because it’s all so prescriptive. Which is so unfair because teachers do more work than everyone else in the world.

DAPHNE WILLIAMS
All of this varies on what companies you work for, what industry you’re working in. It’s not going to be every single company is able to do that, but there are definitely options out there.

JESSICA WOLVINGTON
Absolutely, yeah.

DAPHNE WILLIAMS
Jessica, I wanted to thank you so much for taking the time to speak to us today. It was so great that you shared your story, and I know a lot of teachers are going to be really excited to come learn from this podcast episode. I just wanted to thank you.

JESSICA WOLVINGTON
Of course! And thank you so much for having me.

DAPHNE WILLIAMS
Jessica is a prime example of how equipped teachers are to conquer almost any position that they put their mind to.

Imposter syndrome is something that many of us face but identifying when we’re suffering from it actually helps us to push past our insecurities.

Thank you so much for joining us and as always, please make sure you subscribe to stay tuned and leave a review to help other teachers find this support and community. I’ll see you on the next episode of the Teacher Career Coach Podcast.

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