“How do I get out of teaching?”

Over the past several months, I have had numerous conversations about this with former colleagues and teachers that are friends of friends. While I wish I could tell you it’s as easy as getting a certification in another field or that I know the exact path out, the truth is that my journey from teaching to the corporate world was time consuming and indirect. I can say with certainty that anything worth having is worth working hard for – and – transitioning out of teaching is no different.

That said, I learned some things along my winding journey that I think will serve you well if you’re looking to transition out of education. Before I dive into education exit strategies, I will address the elephant in the room: What about being an agile educator? Why am I sharing how to leave education? 

For one, I plan to share plenty of helpful approaches for teachers who wish to stay in the classroom in future posts. Stay tuned!

Secondly, whether you’re an educator or not, there’s no denying that public school teachers aren’t paid what they’re worth. In Virginia, it’s almost criminal what teachers are paid for the job they do, in addition to the litany of “other duties as assigned.”

Teachers, I can’t fault you for leaving or staying in the field. We all tolerate a different pay threshold in relation to our family economic situation. If you are sick of barely making ends meet while simultaneously being stretched mentally from the second-hand trauma of the job and/or culture of thankless overwork, I hear you.

Paul Simon sang about “50 Ways to Leave Your Lover.” Well, here are 6 ways to leave your teaching gig. While these methods work in most adjacent career fields, I specifically tested them with success in charting my course from being a high school humanities teacher to Agile Delivery Lead/scrum master in a financial firm that operates like a tech organization. 

I will share these transition steps in the vein of a “stop, start, continue” retrospective.

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🛑 Stop applying to jobs on LinkedIn or employer websites and instantly getting rejected. I spent hours writing detailed cover letters that never mattered. :( (cringe) It's like the adage, students don't care what you know until they know that you care. Well, employers don't care what you know until they know someone that can attest to what you claim to know. Okay, so not as catchy but you catch my drift, right? :D

🟢 Start networking like your life depends on it – because it does if you really want to get out of teaching. For getting up the courage and being appropriately prepared when reaching out to professionals in your desired field, I recommend checking out the suggestions of my agile mentor, Mike Vizdos, in his blog post on “3 Steps to Landing Your Dream Job.” Find connectors like Mike. I first met him through ScrumRVA and we kept running into each other at agile events and conferences. I cannot thank him enough for his guidance in all steps of the job hunt. To pull from his writing style; thank you, Mike. (smile.)

Ultimately, a person – not a job application or cover letter – will help you get your foot in the door in a new workplace. You won’t know who that person will be until it happens so treat everyone like they’re going to be THAT person. I am enormously grateful and indebted to Jenn Moore, for being my person and quite literally changing my life. Thank you, Jenn. 

🛑 Stop writing education buzzwords on your resume. Words like differentiation and phrases like vertical curriculum alignment have no meaning to business folks. While those skills may come in handy for your job, especially if it involves interacting with people, they take up precious space on your resume and will not have the same impact they do in education. 

🟢 Start putting skills and certifications that are relevant to your next role at the top of your resume. The business manager doesn’t care if you have ten years experience teaching; they want to know if you can do the job they want you to do in business. Lead with their language! Don’t just hope they’ll be able to figure out the parallels between education and their role in the private sector. Make it clear and easy for them to see within the first ten seconds examining your resume. 

Even if I had to do it over again, I would adjust further. While the National History Day (NHD) project is near and dear to my heart and I truly believe it revolutionized the way I taught high school humanities (in an agile way that I clearly conveyed in my interviews), I wouldn't lead with it on my resume. I would lead with coaching agile on the first point! Bump bullet points 5-7 up to the top of that list of accomplishments and duties. There are several additional ways I evolved my resume over time to be more marketable in the private sector, but prioritizing job relevant skills at the top of the resume is chief among them! 

🛑 Stop waiting for an interview to begin learning and studying the field of agile, learning and development, SaaS Sales, or wherever you’re trying to go next.

🟢 Start immersing yourself in the deep dives today/now! Read all the things! Interact with the professional LinkedIn and Twitter communities of practice (CoPs). Search for your job-relevant space on Meetup. Attend those Meetups/CoPs. Brush up on your quantitative skills and business mindset so you’re not stressed the night before a business case interview. Treat this like physical fitness; small, incremental gains add up over time. It’s more about consistency than an all out single sprint. Think like James Clear, author of Atomic Habits:

“People often think it's weird to get hyped about reading one page or meditating for one minute or making one sales call. But the point is not to do one thing. The point is to master the habit of showing up. The truth is, a habit must be established before it can be improved. If you can't learn the basic skill of showing up, then you have little hope of mastering the finer details. Instead of trying to engineer a perfect habit from the start, do the easy thing on a more consistent basis. You have to standardize before you can optimize."

This is especially true if you aim to be a leader in the field. Big name companies want thought leaders – the best, the brightest, and the well practiced. With a competitive market, you'll already be a day late and a dollar short, compared to folks who have been doing whatever you're trying to break into, for years. It won't be enough to meet the minimum requirements– learn and know as much as you possibly can as soon as you possibly can. Practice the next step⬇, which will help vastly expand your knowledge and experience. 

🛑 Stop lurking. 

🟢 Start contributing. It doesn’t matter that you’re a novice. We’re all on a learning journey with many of us at the beginning. If you’re not willing to put yourself out there, why should a hiring manager stick their neck out for you? With less experience, taking you on in the private sector is a risk. How can you make that risk more appealing and promising? Preview and showcase your abilities by volunteering to organize and facilitate Meetups or other events in your content area CoPs. 

Did you just take a scrum master course and find a ton of similarities between it and your current role? Share it. Post on LinkedIn, Twitter, and/or blog about it. Make yourself and your unique perspective known! Share it with your colleagues and students. Apply it in your own life, professionally and personally. Don't ever let your recent learning go to waste! 

As an educator, you know transfer and application of learning is critical to higher level thinking and commitment of lessons to long term memory. Remember to take those final, ultimate steps in your own learning journey. Learn by doing! Practice what you preach!

🛑 Stop waiting for a new opportunity or permission. Just like the adage – dress for the job you want, not the job you have – 

🟢 Start doing the job you want at the job you have now. Make your classroom agile. Lead and influence your colleagues through conversations, 1:1 meetings, department meetings, faculty meetings, and conferences. Do it regardless of title – like a politician answering the question they want to answer and not the one that was asked. These experiences will also help you provide specific, real-world answers to field-specific questions once you finally land an interview. I was told well after being hired that what set me apart from numerous other candidates for my contracting role was that my responses in the interview were experiential– not theoretical; I demonstrated that I had already applied and essentially served as an agile lead in my teaching career. 

🛑 Stop letting guilt and shame prevent you from achieving your dreams or, even simply attaining a sense of healthy, financial stability. Only you know what's right for you and your family. For many of the teachers I coach that are transitioning out of education, they grapple with an onslaught of powerful, sometimes overwhelming emotions. After all, most of us get into teaching because of the sense of meaning it holds; to be able to pay it forward and/or because we were inspired by the teacher(s) we had growing up. I'll never forget several moments in my transition that I totally bawled like a baby– most unnervingly so the day I decided to throw in the towel for real and one of the days I was packing up boxes of teaching supplies I had collected for almost a decade. In those moments, it hurt to feel some sense of defeat, despite also knowing that I had accomplished so much over the years, perhaps in some ways I might not even realize yet. We always wish we could do more for our students. Teaching is high touch, human work. It’s only natural to feel moved in this way. Make space for yourself in recognizing and understanding these feelings. Then… 

➡ Continue leaning into your own growth and learning! I keep two quotes in mind to help focus on the importance of my own growth. I have also shared these quotes with my teams, as a way to hone what’s working and what’s not working for us and our processes in retrospectives. 

Garry Tan, co-founder of Initialized Capital, early employee at Palantir Technologies, and a partner at Y Combinator from 2011 to 2015, shared his best career advice on Twitter:

“At every job you should either learn or earn. Either is fine. Both is best. But if it’s neither, quit.”

Similarly, Deb Liu, president and CEO of Ancestry.com, senior executive at Facebook known for supporting development of Facebook payments platforms, and now regularly blogging on a substack called Perspectives, shared a good reminder from the mayor of Redwood City, California, Giselle Hale, who shared her best career advice from her first manager, Dan Bain:

“You’re either ripening or rotting.” 

I found both quotes, by the way, through following my own advice of “immersing myself in the deep dives/learning communities” and continuing “leaning into my own growth and learning.” 😉

So, how are you doing in your current role: learning, earning, ripening, or rotting? If you’re not feeling somewhere in the range of the first three descriptors, it might be time to more seriously consider applying my six strategies for charting a course out of your current role. 

Stay tuned for my future blog posts to help with your continuous learning journey! 

As always, thank you for your time. 

Feedback and suggestions for future posts are welcome via the contact button on this page, connecting on socials, and/or through the form below. To receive agile and education insights directly to your inbox, sign up for a free Jamboard template for a stop, start, continue retrospective like this one, as well as The Agile Educator Monthly Newsletter.