If You Stick With It, It'll Happen

This week’s interview features James Potteiger. I first noticed James through his incredibly insightful and helpful LinkedIn posts. What struck me most in this interview was how intentional James was in his transition. He didn’t just throw resumes at random job openings, hoping companies would take a chance on him. He researched, networked, upskilled, and networked some more.

James’ story really reflects how much hard work a successful transition can take. This interview is chock full of tips and insights into the job application process. It’s a long one but a goooood one, so dig in. Thank you James!

Introduce yourself! Share your name, location, what you taught, and for how long.

My name's James Potteiger. I taught high school social studies, primarily 11th grade world history, for 17 years.

I was at the same school, same position, same classroom for all 17 years. It was a small department, and I was the last teacher hired before a couple of my colleagues retired.

It's been about five and a half months since I left at the end of the 2024 school year.

What brought you into teaching, originally?

I decided early on that teaching was my path. In 4th grade, I had an influential teacher who was in his first year, and I loved being in his class. I remember going home and telling my parents that I wanted to go into education. That desire stuck with me all the way through college. I walked into my first classroom at the age of 24, teaching students who were sometimes only months younger than my college classmates.

What went well in your teaching career?

Building relationships with students was key to my success.

I also loved being [students’] advocate... I wasn't afraid to speak up.  I think schools need people who are willing to challenge the current thinking and why certain decisions are being made. 

One of my proudest achievements was helping students start a gay-straight alliance. I had always been vocal about advocating for different beliefs and policies, so when the students approached me for support, I was on board.

What made you start thinking about transitioning?

As we came back from the COVID lockdown in the fall of 2020, I was looking out into a corporate world that was making all sorts of changes [like] hybrid working environments. And then education was, “We're going to go back to normal.”

I distinctly remember several conversations with an administrator, telling her, “But normal stunk. Normal had a lot of problems, and we shouldn't want to go back to normal. We should want to fix some of those issues.” 

[COVID] was an opportunity. A lot of companies were taking that opportunity to create better environments, to do things that might make them more appealing so that employees didn't keep leaving. People were applying lessons of COVID and asking, “How can we make that better?”

And education was all about, “We're going to go back to normal.” I did not see an interest in, “How can we improve things? How can we fix some of the challenges and really rise to the moment in a new way?”

For me, that was the last break of, “I don't want to be in this world anymore.”

There’s the old saying that “to improve is to change, and to perfect is to change often.” And I just didn't see a desire or a willingness for education to change.

When did you make the decision to leave?

I began seriously searching for new opportunities in the fall of 2022. That was when I fully committed to the idea of moving on from education. I focused on networking, reworking my resume, and exploring different roles outside teaching, particularly in learning and development.

I made the first step that a lot of people make: “Well, learning & development and instructional design is the place where so many people go, so that's where I should go.” And so that was the beginning of my search.

One of the big things that helped narrow it down was going out and meeting people who knew what was out there. [I discovered] there are just so many possibilities. It seems overwhelming at first. Then once you start looking, it gets even harder because there are so many jobs that you didn't even know existed when you started looking.

You have to just keep evaluating and finding out what it is you want. There was a lot of inner questioning, like, “What is it about this role that I'm after? What does that job look like? What is appealing from a skill set? What in the day-to-day appeals to me?”

So networking… was a big thing for me because it was a way to learn about roles from people who knew them far better than me because they had done them.

I relied heavily on LinkedIn for my searches and to network. The process wasn’t easy; it took a lot of trial and error to find the right strategy. I see a lot of people looking for the perfect strategy. Like, “What's the path that you need to be on to get somewhere?”

Being on the other side, having been through that process, I don't think there's a perfect path. I think there's a lot of great paths that you could take. Mine was the route of networking.

Once I had reached that point of [targeting] client or customer success, then it was about finding the industries and companies that hire someone for that. Certain industries that are not as open to someone transferring in because they want very specific industry experience. They want certain credentials that obviously I didn’t have. So [it’s important to understand] that you're not going to be a great fit for everyone.

Rather than focusing on who that eliminated and worrying more about losing out on these opportunities, I really honed in on the industries that would be interested in me. For me, it was finding the companies that I wanted to work for, finding companies that were good employers.

As I networked and met people in different fields, I discovered customer success could be a good fit for me.

Then I identified former teachers within those companies. This was important for two reasons. First, these individuals understood both the education field and the role I was pursuing. They could translate my teaching experience into relevant skills, helping me see how my background applied to the new position.

Second, their presence indicated that the company was at least willing to entertain the idea of hiring somebody from education... I wasn't trying to blaze a new trail and educate a company on what teachers could do. They already hired this person. Clearly, they know what that person's capable of, so there is a path there. It might not be well-trodden, but it at least exists.

Beyond networking, what additional steps did you take during this time to pursue your new career?

I pursued a certification in customer success management through SuccessHACKER. It was relatively low-cost, and I got it on discount, so it wasn’t a huge investment of time or money. I wanted something manageable. I wasn’t interested in programs that took two years to complete.

Find a way to upskill that isn't a massive barrier of time or money. A lot of people aren't taking that step, so you stand out from the crowd, even though it might seem like a really simple thing. It did come up in my interview; they mentioned that they had seen my certification on LinkedIn. They asked, "What's something valuable that you got out of this?"

Once you get a certification, you can put on your LinkedIn and post about what you got out of it. That's another way to engage with other people in that community and meet them.

Networking for me was a big motivator. I joined a group called CX Exchange, which hosts calls with industry professionals discussing various topics.

The first meeting was kind of like, “How do you belong here?” There was that imposter feeling that a lot of people coming from education deal with. A big part of getting over that was just going to those meetings and contributing different ideas. Because there really are so many crossover things. No matter what you decide to transfer into, there are so many skills that you can bring to the table in a role outside of education. Being around people doing that helps you understand it in a solidified way.

Being around people speaking that language, learning their vocabulary, starting to think like people in that field—once you get to interview, that's a huge leg up. A lot of people are going to struggle with that. Starting that early, learning their language, and being able to connect the dots from your transferable skills to what that job does was a big deal.

How did you manage to balance your job search with teaching full-time?

The job search was a constant give and take, with natural ebbs and flows, something I was familiar with after years of teaching. Some parts of the year were busier than others, so I had to find ways to balance my time. I used any available moments, like lunch breaks, to search online, gradually shifting time away from teaching responsibilities to focus on my exit strategy.

Many people struggle with this transition, but it's crucial to prioritize what will ultimately support you. Continuing to devote all my time to teaching was part of why I wanted to move on. I was looking for a role where that level of commitment wouldn’t be the expectation.

In hindsight, I didn’t always manage my search time effectively. Like many, I assumed that spending more hours on it would speed up the process, but that wasn’t the case. I often found myself scrolling through LinkedIn, afraid of missing an opportunity. Looking back, I should have stepped away from the search more often and trusted the process.

Can you talk about the actual resignation and the logistics of getting your current position? How did that all go down?

The school year had just ended, but my job search started months earlier. Around Christmas of 2023, I had a networking call with the company I now work for. I loved everything I heard about them, but at the time, there were no job openings.

That experience reinforced an important lesson: many people apply the moment a job is posted, making it difficult to stand out. So instead of just applying blindly, I focused on networking with companies that weren’t hiring yet, knowing that when an opportunity did arise, having a referral could put me ahead in the process.

That strategy paid off. By March, I heard that openings were likely coming soon. I was advised to have my resume ready, monitor the company’s website, and stay engaged. When a position was posted in April, I applied right away. The hiring process moved quickly. In about three weeks, I went through a phone screen and two interviews, received an offer, and resigned shortly after the school year ended.

What is your new job, and how long have you been in it?

I am now an Implementation Specialist at Reward Gateway, an HR tech company. My primary responsibility is managing a project that involves migrating clients from an acquired platform to our system, which includes creating and configuring their sites.

I've been in this role for about five and a half months now, and the change has been incredibly positive. Recently, we even hired another former teacher, and some leaders asked if I could connect with her to help her adjust, which I appreciated.

The flexibility I have now was a big thing that I was looking for. I think that's important for people to keep in mind: “What's the thing that you really want on the other side of this?” Knowing that helped me to eliminate a lot of roles that I was looking at. But if it didn't offer the thing that I wanted the most, it was best to continue looking.

What advice would you give to someone transitioning from education to a new field?

Having a target role or a specific skill set in mind is crucial because job titles vary across companies, but the required skills may be the same.

Narrowing this down is a key first step. You can refine it later. I adjusted my own target midway through. So you’re not locked in, but having that clarity helps you make a strong case for yourself.

One analogy I always go back to is the Pontiac Aztek—a vehicle that tried to be everything but excelled at nothing, making it undesirable. In education, versatility is essential. Teachers have to be content experts, curriculum developers, tech troubleshooters, and relationship managers for students, parents, and administrators. But in a job search, you get to define what you want to focus on. Instead of being a jack-of-all-trades, highlight where you can bring real value in a specific role.

Having a target industry was also a game-changer for me. I focused on HR tech and wellness companies because I wanted to work somewhere that valued employee well-being, something I felt was lacking in education. This helped me answer a common interview question: “Why this company?” My response not only explained why I was leaving education but also why I was drawn to them. It made my transition story clear and compelling.

When networking, be intentional. Send connection requests with a message explaining why you want to connect. A simple message can make networking much more effective.

Prioritizing connections with former teachers who transitioned into new roles was incredibly helpful. I found that when I connected with customer success professionals, I immediately felt at home. If you attend networking events and genuinely enjoy the people in that space, it's a good sign that the role might be right for you. Conversely, if you find yourself in a meeting and realize you wouldn’t enjoy working in that field, it's valuable to know early so you can pivot.

Finding a target role, choosing an industry, and networking to refine your direction are huge parts of the process. Just as important is coming to terms with moving on from education. That transition starts with updating how you present yourself. Many teachers worry that they’ll only be seen as educators. But if your LinkedIn headline still says “teacher,” you’re reinforcing that perception.

Make your LinkedIn reflects that, make your resume reflect that, and do that groundwork. It’s crucial to presenting yourself as capable of doing things beyond education. Which we know teachers can. Obviously, many of us are out here doing different roles. We can do it.

But presenting that argument for yourself is great prep work for an interview down the road. You have to be able to connect the dots. Yes, you've run a classroom. You've done all these different things, but how does that connect to this role?

Is there anything else you'd like to add?

If you feel like you need to take a break, take a break. You can always come back to it. The job search will be there, and there are many opportunities at different companies. If you stick with it, you'll get there.

The Bureau of Labor Statistics talks about the typical job search being 5 months. If you're making a transition, chances are it's probably going to be longer than that. So have a reasonable timeframe. It's a tough market, there are still opportunities to be had out there. If you stick with it and do the work now, you put yourself in a great position for when the market turns, and there are more opportunities.

So if you feel like you need a break, maybe you need a break, and that's fine. Don't look at any job postings. Don't worry about applications. Just take a week and don't bother. Whenever you pick it back up, you'll come back to it with more energy. And you'll get somewhere.

But if you stick with it, it'll happen. As frustrating as it might be, it's just going to take a little bit more work.

This interview has been edited for length and clarity.