Routes to Pivot – Hindered by what I knew was Possible

When I first started my pivot, I was so clueless as to my options for both types of jobs and ways to make it happen, that I found it difficult to make progress. I was hindered by my lack of exposure and, to the extent at which I can help, I want to make this a bit easier for anyone looking for their own pivot. I’ve met with enough teachers to see a pattern emerge of what works and what doesn’t work in pivoting their career. I tossed around each of these ideas for my own pivot three years ago, including the one that doesn’t work. And there is only one that doesn’t work. Let’s start there. 

Do you have any hopelessly single friends? Does every conversation with them turn into an emotional deep dive about the state of their love life? Is it emotionally draining to even keep up with the latest news? Do you wish there was a dating app for a smaller segment of people that arranged marriages so you can move on with the conversation? When I first realized I wanted to leave the classroom, I became that person. I cringe at the thought now of how many times my conversations with friends turned inward about myself and I grasped and clung to any possibility of regaining solid ground. It was emotionally draining. I felt like I had people analyzing my resume on my behalf the way people frantically deliberate their dating app profile picture. Which adjectives should I use to describe how awesome I am but still look really humble? And honestly, the job hunt feels a lot like dating. It’s filled with immediate hopes, rejections, navigations of conversations where you read into what people say. It’s exhausting. Getting into this desperate state where you just want to have something work is the only way to make it not work. The good news is that if you enter this state, it’s possible to escape it. The bad news, even if you do the other things right you can find yourself proverbially swiping right on any job with a salary and health insurance. 

The most important thing is for the pivot to move you forward. The routes I’ve seen work well are as follows: 

  1. The Grad School Pivot AKA if I don’t want to teach then I’ll go back to being a student for a new beginning
  2. The Bootcamp AKA I want to develop a concrete new skill to open doors
  3. The Network AKA I’m going to talk to enough people until someone helps me open a door
  4. The Movin’ on up to Central Office AKA I want to stay in education but I want to flex muscles outside of the classroom

I interviewed my friends who have done the aforementioned pivots in the hopes of helping others figure out what is the best route for them.

1. My friend Lucy did the grad school pivot. Lucy taught middle school social studies as part of Teach for America. 

What did you teach? Middle school social studies in Memphis, Tennessee. My undergraduate was in history.

How many years did you teach? 2 years for Teach for America. One of the problems was I didn’t feel like I was improving as a teacher as fast as I wanted to improve. I didn’t feel equipped. I was looking for something I felt like I could be better at. I got burnt out on charter schools and, looking back, I wish I had tried other types of schools but I was really excited about going into public policy.

What masters did you get? LBJ School -Master of Public Affairs

How long did it take? 2 years

What did it cost you? Americorp funded and instate tuition- I had a graduate research assistant appointment and teaching Assistant appointment so it was free. I’d recommend everyone find ways to make it affordable because typically there are.

What immediate doors did it open for you? The networking opportunities are amplified when you go to a professional school. The benefit isn’t the curriculum or what you learn, it’s about the network you develop.

Was it worth it? Would you do it again in order to pivot out of teaching? Grad school was definitely worth it for my route. There are other routes to where I want to be professionally. While in grad school I worked for the legislature and I got exposure to really interesting state agencies that I think I’d like to work for in the future. There are pockets of innovation within state organizations that are doing awesome work.

What was your job title for your first job post grad school? I was dead set on doing K12 policy. I wanted to work in state or district level. The first job I got was working in policy in higher ed and I completely fell in love with it. I had a misconception that equity issues were concentrated in K12 and learned that isn’t true. I found there were a ton of connections to my work as a teacher in the higher ed policy realm. I worked on metamajors and math pathways for community colleges to the four year.

Any advice for teachers who are considering the same?
You need to think about the investment you want to make. I didn’t gain skills in that degree and I wouldn’t recommend anyone go to grad school and take on debt. If you’re considering a program that costs a lot you should consider why. I wasn’t personally going to take on a lot of debt so that changed a lot of my outlook.

Female teacher perspective here- you often don’t know your value and worth. You’re doing  a really hard job for not much money so it’s also a mental pivot to know your actual worth and advocating for yourself and demanding it in your first job. You need to recalibrate your worth. It’s not obvious to others what you’ve done as a teacher but many don’t know how to articulate that. Be able to describe that to an employer or a grad school interviewer.

2. My friend Sean decided that becoming a project manager was closely related to his high school administrator duties and did a boot camp.

What did you teach? Middle School Social Studies then later was Dean

How many years did you teach? Seven!

What masters did you get? Master of Education, Secondary

What bootcamp did you do? Project Management (PM), UT Extended Campus

How long did it take? 2.5 months

How much did it cost you? $4,000

What immediate doors did it open for you? I firmly believe that the PM certification helped me get my current job. I don’t really know if it was for the content, though. The classes I manage are in the same building that I attended classes in. Familiarity was important to them. In addition, I had just finished an evening class while holding down a full time job, which most of the students in our bootcamp are doing. Familiarity with their situation was also important to them. Was PM important to them? I’m not really sure. I did find out after I got the job that there were about 13 other people vying for my position. In addition, LinkedIn sends me PM job opportunities about once a week. There are a lot out there.

Was it worth it? Would you do it again in order to pivot out of teaching? Absolutely.

What was the title of your first job post program? Student Success Manager

Any advice for teachers who are considering the same? You have skills that are valuable in the non-teaching workforce. Don’t feel trapped or discouraged by your current situation. Also, don’t feel guilty for wanting to leave teaching. YOU are not responsible for every student in your community, or the state of public education in America today. You have a life, perhaps a family, and your needs are important, too. Politicians and voters at large are responsible for turning a noble profession like teaching into an over-worked, micro managed, under funded, under compensated, insanely stressful and litigated mess that it is today. You’ve done the best you can with the shit sandwich they handed you. Go live your life.

3. The network is the approach that I took. Man is it exhausting. I’ll answer the same questions as my friends.

What did you teach? High school math

How many years did you teach? Seven

What was the network approach? I hit up anyone and everyone who could possibly help me find a job. I had countless email threads, phone calls, and coffee meet ups. I spread myself pretty thin over the summer months to find a company that would hire me but ultimately the job I got was connected through a friend of a friend. The tough aspect of this approach is that it feels like it’s dependent on who you know. If you don’t know anyone then you have to start the process of getting to know folks. 

How long did it take? 4 months

How much did it cost you? Free but I probably spent $50 on other people’s beverages.

What immediate doors did it open for you? I got a great sense of what my options were and the cultures I was looking for. It taught me how to job hunt which is a great life skill in general. 

Was it worth it? Would you do it again in order to pivot out of teaching? It worked for me but I can see why others would avoid it. Depending on your personality, this might be a nightmare. 

What was the title of your first job post program? Business Development Representative (entry level sales)

Any advice for teachers who are considering the same? Use LinkedIn and don’t be afraid to meet strangers. It’s human nature to help people and if someone doesn’t want to help you, they won’t both responding. Try to find former teachers that have already blazed the trail and can connect you to the right places. If the job you’re applying for uses the soft skills you have a teacher, you can network your way into the job. 

4. My friend Jenna comes from a family of educators and knew that’s where her heart belonged. After a few years in the classroom she saw the gross injustices that are passed onto our public education system by our legal and legislative bodies. Her pivot, law school. Three semesters in she realized that while the end goal of improving the system remained, she realized that for her, law school was them most unnatural way to do it. So she pivoted to main office to help create change at a broader scale. 

What did you teach? I taught mathematics: Algebra I and AP Statistics, then Dual Enrollment Statistics through UT.

How many years did you teach? I taught for about 8 years.

What degrees do you have? BA in Math

What central admin job did you get? Secondary Math Specialist

What immediate doors did it open for you? Depends on what you mean by doors. Although a Master’s degree was preferred, it was not required for my position. So although I was hired because of my experience, the jobs “above” me that I could potentially move into later (supervisor, director, etc.) were unavailable unless I decided to go back to school for my Master’s degree.

Was it worth it? Would you do it again in order to pivot out of teaching?
Yes. I had always wanted to be a teacher. In my classroom, I felt I had improved over the first several years of teaching, then I felt like I stopped growing. I worked as an instructional coach for a short while before becoming a math specialist for the district and as a specialist, I finally felt like I was growing again as a professional. Supporting teachers was a totally different ballgame.  Most teachers take a lot of ownership and pride over their teaching. So working to help them improve required a delicate balance of letting go, positive encouragement, and constructive criticism. One thing I felt I always struggled with as a teacher was planning/asking questions that allowed my students to engage in deeper learning. I was constantly working to ask questions that didn’t just tell them what the next step was. And while I did improve over my time as a teacher, I felt my ability to ask questions drastically improve incredibly rapidly as a specialist. Adults (and students) need broader and deeper questions that really make them think in order to grow. I had to up my questioning skills in this position.

In this role, I was also allowed/encouraged to attend professional development outside of my district. Hearing from other specialists or teachers always challenged my way of thinking and pushed me outside of my comfort zone. This was not encouraged as a classroom teacher in my district. It would take small miracles and/or outside funding to allow me to attend quality professional development outside my district. 

Then, when I would come back, I always challenged myself to deliver similar PD that I had received in a way that was effective for my teachers and authentic to my own style. I felt I grew professionally with every training/PD I delivered. 

Any advice for teachers who are considering the same?
Don’t be afraid to reach. I know many people who wouldn’t have considered applying for the specialist position without a Master’s degree. I was confident in my teaching abilities, math knowledge, and ability to learn and that is what got me the job. 


So where does that leave you? Some pivot routes may not be options but thanks to the internet, online masters degrees and bootcamps are always options. The routes for each individual will be different based on geography, opportunity, time limitations, and interests. Knowing what else you can do is half the battle. Knowing how to fit into this outside world is a big obstacle. I often sit with teachers who don’t know where to begin. The next step I’ll focus on is the down and dirty tasks of pivoting and the steps to ensure that every individual can answer the question “If not this, then what?” 

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