I was a pretty good teacher

I taught for seven years and every spring the burn out would creep back into my life. Each year was different but as I headed in June I couldn’t help but think to myself “If not this, then what?” I went into this profession with an enthusiasm and vigor to change the world. Teaching can feel a little bit like one of those expensive, fancy haunted houses that pop up around Halloween. You want to go into it because it seems exciting and different and your friends say it will be awesome and then a small child runs at you with a knife and you scream and look for the exit.

In the summer of 2016 I decided it was time and I took a huge leap of faith and entered the tech world. It was the scariest thing I’ve ever done. I don’t mean that flippantly. I truthfully mean that it was as difficult as a breakup. In fact it felt just like that. When people ask me how my teaching is going a year after I left, it’s like they’re just finding out a friend is newly single and they give you that look like “Should I high five you or hug you?” Nearly three years after leaving I still have folks ask if I’m still teaching. When pondering leaving the classroom I felt like my entire identity was about to change (or so I thought) and I had no idea where to start. I felt the need to do something different creep in over time until it was simply time. The hard part was that my internal metric of when it was time did not align with the rest of the business world and I had to be nimble in my navigations. I didn’t know where to start. I went to friends for help. And now friends are coming to me for help. So that’s where the advice for this comes from. I’ve had about a two-dozen educator friends talk to me about my process and about twenty strangers reach out via the Internet. This is that initial advice.

First things first- stop telling yourself “I’ve only ever been a classroom teacher. My resume is nothing compared to people that have been doing other things.”

STOP IT. STOP IT RIGHT NOW. You need to start looking at the bigger picture here. Most jobs that are entry level have a ramp up process for new hires. No one expects you to hit the ground running and know everything on day 1. I’ve also heard the following stupid sentences “But my degree is just in History. They wouldn’t care about that.” “I only taught basic subjects like Algebra I. You taught Statistics!” We should all stop comparing ourselves to the fictitious competitor to our perfect job. It matters less than we think it does and our stupid brains should never be the reason we don’t reach our goals. You will get hired because you have soft skills beyond compare.

STOP IT. STOP IT RIGHT NOW. You need to start looking at the bigger picture here. Most jobs that are entry level have a ramp up process for new hires. No one expects you to hit the ground running and know everything on day 1. I’ve also heard the following stupid sentences “But my degree is just in History. They wouldn’t care about that.” “I only taught basic subjects like Algebra I. You taught Statistics!” We should all stop comparing ourselves to the fictitious competitor to our perfect job. It matters less than we think it does and our stupid brains should never be the reason we don’t reach our goals. You will get hired because you have soft skills beyond compare. How do you get your soft skills noticed? Well, the first thing I did when I started to look was show my resume to my sister. She lovingly tore it apart and told me nothing in it made sense to her. I had to translate my teaching resume into world resume. My teaching resume had something to the effect of:

Geometry and IB Math Studies Created Problem Based Curriculum Committee Member — Head of School Search Committee Member — Strategic Planning

Which translated to:

Develop problem-based learning curriculum for Geometry and IB Math Studies Member of Head of School Search Committee — Interview Head of School Applicants Member of the Strategic Planning Team — Dream and plan future of the school, develop 5 year plan

So look at your resume and see where you can further explain your soft skills. Teachers lead and organize anywhere from 3–6 meetings a day with groups of people that need to be inspired. They plan and deliver presentations. They think big picture while somehow still having the ability to pick up on the details. They can read rooms and understand human connection. They can cater content and think on their toes when the situation changes. They can handle pressure and intense situations. WHO WOULDN’T WANT TO HIRE THAT PERSON?

I had to explain to the rest of the world what I did using verbs that connect to the jobs I wanted.

How do you know what jobs you can do?! Well that’s a really good question. I didn’t start with that so much as “What companies fit with the reason why I want to get out of teaching?” If you haven’t read Simon Sinek’s “Start with Why?” I highly recommend it. You’re more likely to get hired when your application makes sense. When you say “I taught for X years until I realized _____ and that’s what led me here” then people think of you differently. The mistake a lot of people make I think is the _____ part. They think it has to be deep and grand and poetic. You know it could be as simple as “I realized I never worked much with adults and as I developed things with my team I realized how much joy I get from leading and developing with my peers. I think it’s time I give myself the opportunity to grow in that realm.” Find a company that interests you and monitor their jobs until something fits with you.

Explain yourself in a cover letter even if there isn’t one required. According to government statistics there are 3.2 million teachers in America. That includes the bad ones. Assuming you aren’t a bad one you’re going to want your future employer to know the difference. A cover letter makes all the difference. The cover letter should address why you are looking for such a big change.

It’s whom you know not what you know. I had coffee dates with around a dozen strangers in the process of getting my first job out of the classroom. One of them claimed to have plenty of “recovering teachers” on his team. That phrase struck me. All teachers need someone to stand up for them and say “This person deserves a shot at something new.” I would HIGHLY recommend finding people on LinkedIn that used to be teachers who now work in your prospective industry. I hit up tons of strangers and each of them helped me out in some way. Reaching out and saying “I saw you were a teacher but now you do X, I’d love to hear your story. Can we meet up for coffee?”

You won’t have to completely start over. I was worried that I’d have to get a job for the same teacher pay but now work 12 months out of the year. I will say that’s not what happened at all. I’m extremely lucky but people need to know that it’s possible to double your salary in your first job out of the classroom. It may not be possible at your geographic location but simply knowing that it’s possible to have a rewarding job that improves your quality of life can be encouraging. You can do it too.

Be patient but get over the idea that the timeline will be favorable. I know a lot of teachers who say “Yah I look for jobs every April-May but nothing really ever works out.” The part that made my job transition so difficult is that I had to quit 3 weeks into the school year. I went to the Meet the Teacher Night with my replacement and then started my new job the next day. That was incredibly stressful and I felt like I was abandoning my students. But I tried looking for a job in April through June and got no bites. The job I ultimately got and love didn’t get posted until mid July and by the time my final interview came around I had to start class the next Monday. If you’re open to the idea of moving on but don’t open yourself up to the idea of quitting mid year, you may be missing the best opportunity. Businesses aren’t going to operate on a May-August hiring calendar. If you really want a new job you may have to accept that the timeline will be less than favorable for both you and your school.

So that’s it. My story is just an anecdote and I have no idea how replicable it is. I’d love to hear from others. It took me 4 months to get a new job and I applied to well over 30 positions. I had 6 phone screen interviews and only two in person interviews so be patient. I think the most important take-aways are that you (the teacher) deserve a job that fulfills you and you can make it happen. When we (teachers) spend all of our energy wishing the best for our students and wanting them to reach their maximum potential we can sometimes forget that we deserve the same. Sometimes that means teaching for 50 years. Sometimes it means leaving.

But no teacher can be great with one foot out the door. Good luck.