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How I Reinvented Myself From a Salesperson to a Math Teacher

Have you ever wondered if there was something you could be OUTSTANDING at and not just good or even very good? Are you maybe experiencing the inner yearning to embark on a fulfilling teaching journey, yet feeling unsure of where to begin? Perhaps you even find yourself pondering the question of how to become a teacher but you don’t have a degree so you don’t know where to start.

In 2008, I discovered that my day job in national account sales was something that I could, at best, be good at and on the occasional day, maybe very good.  Figuring this out wasn’t something that came to me based on my performance at work.  I figured this out while working a part-time job. 

The Moment I Heard the Call to Reinvent Myself

A year before my discovery, I was working as a valet parking attendant at night to make extra money to pay off my credit cards and student loans.  When I finished up my work at my corporate day job, I would go to the bathroom, get changed into my valet attendant clothes and sneak out of the office and into my car to drive to the restaurant where I worked the rest of the night.  Altogether my workday went from 8am until 1am three days a week.

Two years of working like this took its toll on me, so I decided to find another way to make some extra money.  I came up with an idea to tutor math since I used to make money doing that in high school.  I posted an ad on Craigslist offering my tutoring services and got my first client.  By the time I was done working with Patricio, I began to discover a passion for teaching math.  I followed that up by tutoring math part-time at an after-school learning center and then it happened.  Then I realized that I could become OUTSTANDING at teaching math if I chose to pursue it.  I continued to work part-time at the learning center while I considered how I might do something about this, exploring ways to turn my passion for teaching into a reality, even without the traditional degree qualifications.

My Reinvention Path: Quitting my Job to Become a Teacher

The decision to quit my job and reinvent myself into a math teacher was difficult and took me 6 months to make.  Since I still had $100K in student loans, I knew I had a responsibility to make monthly payments.  I also thought about health insurance, paying rent and utilities, burning bridges at my company, possibly ruining future corporate career prospects, and ultimately, ending up a massive failure. 

There was no shortage of naysayers and just a few supporters.  Mostly, I worried about this being an irreversible decision.  I wondered if there was a way to go into this with a backup plan.  In the pursuit of my dream to become a teacher, I wanted some assurances that if things went badly, I had a way out of my decision.  I thought about offering my company to work part-time as a consultant in order to keep some of my projects going.  I also thought about setting a deadline by which I had to successfully reinvent myself or go back to corporate.  Another idea I had was to cash in my entire 401k (pension) even with the 10% early withdrawal penalty and use it as a financial safety net.

In the end, it was all about my goal

No matter how many back up plans, the thing that motivated me the most was the possibility of becoming a math teacher. Even if I didn’t become one, tutoring students and helping students with math was fulfilling on its own.  After about 6 months of consideration, I decided to cash in my 401k and turned in my two weeks notice! 

Ultimately, this wasn’t about mitigating risks, although I did my best to mitigate the big ones; it was truly about pursuing something I wanted to become with all my heart.  I didn’t know when I would actually start teaching in a classroom or how I would approach it.  I just knew that what I was doing was not who I was anymore and it was time to move away from that and towards who I was becoming – a math teacher. 

My ‘What’ and ‘Why’ Came First, Then I Figured Out the ‘How’

The most important factor in my decision was not knowing HOW I would execute this reinvention.  Afterall, there are no books that teach us how salespeople can reinvent themselves into math teachers.  The most important factor was knowing what I wanted and why I wanted it. 

Tutoring Patricio and working at the learning center showed me that I was growing in a new direction and had other passions.  Those experiments and side-hustles helped me get clear about what I wanted and why I wanted to become a teacher so that I could decide once and for all that it was time to go after it. I could then map out unconventional routes to achieve my goal of reinventing myself as a math teacher, all without the constraints of a traditional degree.

I didn’t quit recklessly

Then I did all the planning I could realistically do knowing that there was no way I could mitigate every risk.  I simply made sure that I could make my minimum financial commitments, even if that meant cutting back on some expenses. 

And even then, the plan I put in place for making enough money to cover most of my living expenses fell apart just weeks after quitting.  Another week later, the 2008 recession started and any backup plans to go back to corporate evaporated as companies started mass layoffs.

However, none of that mattered because I decided I was going to pursue this no matter what happened.  I knew what and why I wanted it.  That meant no matter what happened, even in the face of the Great Recession, I was going to figure out a way forward.  Did it always look pretty?  No, however, every day I did what I loved and that was more fulfilling than anything I had experienced with a nice salary.

The Path to Becoming a Classroom Math Teacher

Before starting, it was easy to imagine this was going to be the scariest and most difficult part of the journey.  Afterall, this is where I had the most uncertainty.  There was no formal roadmap to follow to go from salesperson to classroom math teacher.  So I had to figure it out as I went along and I learned that the path can only become visible as you walk forward.  The more steps you take, the more of the path gets revealed.  This is the most beautiful part of the reinvention experience because it’s the part that no one can tell you about until you discover it for yourself.

After quitting my job, I spent several months feeling lost while I figured out my first official move.  I launched various projects and tested different ideas.  After several months, I figured out my next move – graduate school.  I decided I needed to learn about the science and art of creating personal learning transformations in students.  So almost 6 months to the day after I quit my job, I began my masters in psychology focused on executive coaching.

While studying, I launched my own tutoring business where I tutored as many students as I could manage while going to school.  After graduating, I continued to tutor, expanding into group tutoring or small group classes.  This ongoing work gave me a daily opportunity to develop my skills in transforming young people into high performing math students.  I trained as often as I could book clients.  The more clients I booked the more practice I got. After two years of transforming some of the most struggling math students into confident and interested performers in math, I got my big opportunity!

The Door to the Classroom Finally Opened

The biggest challenge I had getting into the classroom was that I was not a certified or licensed teacher.  Without this paperwork, you cannot legally teach in public schools.  Many people told me I made a big mistake pursuing a masters in psychology instead of a masters in education.  However, I felt strongly about my decision to learn about the brain and psychology in order to transform students more effectively after becoming a teacher.

So now I needed to figure out a way into the classroom and I never expected to find it at a golf course.  At best, I can hit a golf ball and find where it landed, but don’t ask me to direct it anywhere meaningful.  Nevertheless, a dear friend invited me to a school district’s fundraiser golf outing.  He bought several tickets and invited me and another friend. 

We attended and played quite badly, but we still had a great time.  Then at the luncheon I had the opportunity to meet the superintendent of the school district and tell him about my work transforming math students.  Before I could go on he turned and asked his assistant to book a meeting with me the following week. 

And then it happened…

At the meeting he heard and loved my ideas.  Then I told him that I didn’t have the necessary documentation to be a math teacher.  He said “don’t worry, I’m going to find a way to get you in there.  These kids need someone with your passion and energy to help them realize they’re better at math than their grades say they are.  I’ll find a way to get you in.”  [If you’re curious how he did it, reach out via Linkedin or Instagram and I’ll tell you.]

Four years and two months after quitting my job as a salesperson, I was in a math classroom realizing my dream of becoming a teacher. I defied the conventional need for a formal degree.  After teaching math for two years at an inner city public school I taught at a private all-girl school.  In total, I spent 4 years in the classroom after walking a 4 year journey to get there.

Reinvention takes as long as it’s going to take, however, what makes it great is that you can be fulfilled the entire way.  The day after my last day in the classroom, I received a dream job offer that launched my next reinvention – becoming an executive coach at a major tech company.

The journey to reinvention can never be fully mapped out, however, if you know what you want and why you want it, you’ll always find a way.