Money is a weird thing for me. I left the classroom in the fall of 2016 to work at a tech start-up. It’s been a long journey and I often feel scummy when dollars come up. I want to share this experience with others because I always felt limited by what I knew was possible. This isn’t a 1969 moon landing with all of America watching, but knowing what is possible will help everyone be the best version of themselves. So in this, I hope to provide a bit of my experience for any teacher who is struggling to figure out what to do next.
The first time I got a bi-monthly paycheck that was equivalent to my entire yearly teacher salary, I just stared at the computer screen and felt an overwhelming sense of pride. It was extremely difficult to pivot careers and to make this type of thing possible. My wife and I would often take walks with our dogs and talk about what we’d do when our careers “took off”. Mine had officially taken off. I had been out of the classroom two years and six months. The second time it happened, I was already planning about how to make it happen for a third. The scale changes very quickly.
The desire to get out of teaching almost always includes some financial motivation. Even a 10% increase from a teacher salary can be life changing, much less doubling or tripling that salary. Knowing your worth and leaning into this aspect of the transition out of teaching is mandatory and being naive can only cause damage.
When I first started to get curious about moving outside of the classroom I reached out to everyone I knew that could possibly know something I didn’t. This was a high number of people. I reached out to my college friend, Dane, who had become quite well connected in the tech start-up world. He was the first person I had ever heard of going to an “incubator” in California. At age 24 he moved from Texas to San Francisco and got a rent controlled apartment in The Mission and now flies back and forth between NYC and California as a VP at a SaaS (Software as a Service) tech company. His world was mind boggling and intimidating to me. I had imposter syndrome just asking him for help. At the time, I was making $45,000 as a teacher in one of the most expensive cities in America. The previous year, I became a homeowner. I got my property tax statement around the same time as I got my raise for the next school year. My home would cost me $960 more per year in taxes but my raise was $500 to get me to $45,500. I was effectively net negative $460. I drove Lyft and Uber for 6 months to make up for my extra expenses and I felt like I was wasting my time. All of a sudden, in that moment, I became a grouchy old man complaining about taxes. Ironically those property taxes fund the schools and thus pay the teachers so this scenario was quite painful.
During one of our conversations he asked me how much I wanted to make. I had thought very hard about the number I needed to feel really great about a transition. I thought to myself what extra work I’d be doing without summers off and what that would equate to. I thought about my property taxes. I thought about how I wanted to get married and possibly start a family. All of these numbers swirled around my head and like a mathematical savant, I leaned back in my chair, crossed my arms, and confidently stated $60,000 as if I were negotiating a massive merger between two railroad companies. Dane paused. He then said, “You should aim higher.” I found myself sinking in my chair a little bit. I couldn’t tell if my goal salary was just based on lack of data points or if it was a reflection of what I viewed as my worth. Either way I realized that I had to come to terms with money in a way that was previously never an option.
“You should aim higher.”
According to the Bureau of Labor Statistics, for 2018, the median annual wage for high school teachers was $60,320. The range for teachers is vast. Not only does it depend on years in seat, type of advanced degree, or subject area that causes these changes but the geographic location greatly inflates the median numbers. The lowest 10 percent earned less than $39,740, and the highest 10 percent earned more than $97,500. The median for Texas is $57,800. The median for New York is at the top of America’s list at $81,290 whereas Oklahoma, who popped up on the national news cycle with their teacher strike, came in at $41,280. What is even more critical to understand is where do these wages fall in line with the wages of the country. The National Association of Colleges and Employers (NACE) calculates that the preliminary average starting salary for graduates from the class of 2018 is about $50,004. There is an inherent disconnect when the median salary of a group of dedicated, hard working, well educated professionals with upwards of 20 years experience is not far off from the salaries of the students they taught just a few years prior.
I recently had this same conversation with my friend, Jeremy. He was in the middle of an interview process and we met up over a drink to walk through his situation. I asked him the same question that Dane asked me. He said he did the math. As a teacher in a very demanding charter school, his salary was higher than average at near $53,000. He figured that he worked 10 months out of the year and if he took that rate and came up with a yearly salary to make it worth it, his ideal minimum number was $64,000. What he really hoped for was a salary of $70,000. The sales job he was applying for had a base salary of $42,000 and if he performed at quota, his yearly salary would be $65,000. And the job came with uncapped commissions which meant that if he worked smarter and harder, he could make even more money. Teachers are always trying to work smarter and harder.
The day after my conversation with Jeremy I had another meeting with a current teacher. When I asked him this question he simple exhaled a breath of frustration and just said “more”. I encourage anyone looking to pivot careers to really examine how much they need, how much they want, and cross reference that number to the career options. No one wants to hire a desperate burnt out teacher. Know your number and make it happen.
The idea that the only way to give back to the world is to also be poorly paid is false. Most teachers I meet with have a martyrdom complex that still personally comes knocking for me. These types of deep, emotional feelings often keep us locked in place. We often convince ourselves that our low pay makes sense. We get summers off. We get nice holiday breaks. Sometimes our work hours are shortened. But we know, the summers are shorter than the parents realize. Our holiday breaks are wonderful but if you can’t afford to travel then a staycation it is. The time perks are not a perk. It’s borderline mandatory to get that time away from the classroom to refresh yourself. Bottomline is, and this is obvious, but teachers are severely underpaid, under-appreciated, and misunderstood. However, this is about how you can transition into your future. Part of that is accepting how things will be different and shifting expectations to match a future reality.
So when Dane told me to aim higher, I thought, “$70,000!” He kind of laughed at me again and said, “Shoot for $80K”. $80K. I thought, “Wow! That’s more money than I’ll ever need.” My first job offer was a pre-sales job that required me to book meetings for the sales team. My base salary was negotiated to be equal to my teacher salary and if I hit quota my total yearly salary would be $80,000. I didn’t know if it would be easy to hit quota but once I realized that the harder I worked the more I could get paid, I made sure that every month I was making more than I was as a teacher. At that time, my wife decided to pivot herself and go back to school full time. With the help of small loans and big grants to cover tuition, I was able to float the household needs because of my new job. Two years of this and my wife worked hard to became a college graduate and now has an amazing career of her own. This would not have been possible without our decision to pivot my career change. This is what makes a life trajectory different. People talk about the pay and as a consumerist society we think the pay increase will lead to the newest electronics or an upgrade in vehicle, but what we don’t talk about, and we should, is the amount of pride and accomplishment I felt that I could take 100% ownership of the household finances while my wife took two years to better her own life. Our life trajectory is different because I left the classroom.
I would always try to figure out the best path for my students and give them life advice that provided them with the optimum trajectory. It just so happened that for me to take my own advice, I’d have to metaphorically find a new classroom.