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The Moment You Realize You Need a Career Change

Early in my career, I made a massive pivot from selling commercial refrigeration to teaching high school and middle school math. I was inspired to make this career change after launching several projects and experiments that helped me confirm and develop my interest in this new field. Once I got into the classroom, I quickly distinguished myself as an outstanding educator thanks to a few strategies I implemented early in my journey to reinvention.

Back in 2007, I enjoyed a nice career.  I was a national account sales manager and my primary client was Anheuser-Busch. We sold them beer coolers that brought the temperature of their beer down below its freezing point.  In other words, really cold beer!

It was a dream job where I got to travel to all of A-B’s special events around the US including the Super Bowl. However, around mid-2007, I started to question whether this dream job was still so dreamy. I started to read up a lot about the tech startup movement going on in San Francisco and Silicon Valley.  I became intrigued by entrepreneurship, startups, and simply put, an alternative career path to success.

This curiosity led me to connect with other people who were also thinking about similar ideas and inspired me to pursue interesting projects and experiments outside of work. After about a year of experimenting, I made the full leap in pursuit of reinvention and a new definition of success!

The Challenge of Reinventing Your Career

One of the hardest parts about making big career pivots is that most of your skills and abilities are usually related to your current field.  Chances are, if you are looking to make a big pivot, you will require totally new skills that you don’t currently possess.

Another difficult challenge is trying to pivot into a new field with little or no results to show for your potential. It’s hard for anyone to take a chance on you if you don’t have any evidence of your ability to be successful. Add to that the fact that you have no network in this new field and no one to vouch for you. 

All this combined can easily make you feel like you will never be able to successfully reinvent yourself, let alone, get an interview in the new field! 

On my journey to multiple reinventions, I learned that we don’t have to sacrifice performance or success when making a career pivot.

Reinvention Never Starts from Scratch: How To Leverage Your Transferrable Skills

Who knew math students wanted to hear my sales stories?! 

When I began to work with students as a math teacher in the classroom, I often shared stories with students about my past work in sales. These real-world stories captured their interest in a way that allowed me to quickly build rapport with them. I leveraged that rapport to make an impact on their math performance quickly. Sharing interesting stories from my work proved helpful in making an impact early on in my teaching career and bought me time to develop some of the other skills (i.e. pacing, classroom management, curriculum planning, etc.) I still needed to learn.

You can always repurpose your experience and skills to differentiate yourself in a new field. The more different you are in the new field, the more intrigue and interest you will garner that you can leverage to set yourself apart from the rest.

This strategy didn’t just work for me.  When Leonardo Da Vinci pivoted from artist to military engineer he leveraged the skills he learned from his favorite hobby – building machinery for the special effects in pageants and plays. Between his mechanical engineering experience and creativity, he was able to assemble a strong case for why the Duke of Milan should hire him to be one of their military engineers. By repurposing his skills, he secured an exciting new job and hit the ground running in Milan.

How to Build Real World Skills and Results for Your New Career Path

Before I quit my first corporate career to pivot into teaching math, I launched projects and experiments in tutoring math so that I could figure out if I enjoyed this work while building real skills through practice.

The first experiment/project I launched was an online ad offering to tutor university students in math.  My first client replied to the ad and we got started right away. I worked with him for about 3 months and by the end of the engagement reflected on the skills and experience I had acquired in teaching math. It turned out that I really enjoyed it but I still had a lot to learn about making massive impact in short bursts of one hour sessions per week. When tutoring students, you have less time to make an impact that a classroom teacher. So I had to learn how to deliver explosive value in one hour per week increments.

My second experiment was to apply for a part-time job (approx. 10-12 hours per week) tutoring math at an after-school learning center. I did this while I still worked at my corporate job by day. 

Working at the learning center, I worked with a variety of students, sometimes more than one at a time, and developed the skills needed to be impactful in short bursts even while moving from one student to another, working on different math subjects and topics. 

Between these two experiments, I build a resume of results where I helped real students who struggled with math achieve their best results ever in the subject. Whether it was helping someone improve their standardized test scores or raising their grade up, I had stories and results to show for my efforts.

Setting Yourself Apart from the Rest

After I quit my corporate job, I continued to work at the learning center and launched my own tutoring business. However, I also realized that even though I was building real skills and experience, there might be some skills I would need to develop through more traditional education. I looked at graduate degree programs in education and didn’t find anything that resonated with me. 

I wanted to learn something that could supercharge my skills and give me an ‘unfair’ advantage needed to quickly catch-up to and differentiate myself from more experienced teachers. Eventually, I found the program I wanted and it wasn’t even under the education umbrella, it was in psychology!

At Walden University, I found a masters in psychology that specialized in executive coaching. I didn’t know anything about the coaching field at the time and when I read about the program it seemed to me that coaching skills would supercharge my ability to help students break through their limiting beliefs and confidence barriers to math. Since the masters program wasn’t targeted at aspiring math teachers, I knew that it would be a differentiator.

The ability and skill to coach students in math gave me a significant advantage in my pursuit to become a math teacher.

Putting It All Together And Finally Taking The Leap To Change Your Career

Now came another challenge – applying and interviewing for full-time teaching roles. Even with all of the experience I earned in teaching math and a shiny new masters degree in psychology, I still didn’t meet the traditional teaching role requirements. The main obstacle? I didn’t have a degree in teaching or a teaching certificate.

Nevertheless, I knew I had what it took to do the job and make a massive impact. I needed to find another way into the interview room with a school leader. This is where I put on my networking hat. During the summer when I was looking for a teaching role, a good friend invited me to attend a charity golf outing with proceeds going to a school district. The school district leaders were scheduled to be in attendance. I didn’t really play golf, but I took some lessons and learned enough not to embarrass myself. 

After a round of golf, everyone gathered for a luncheon and I introduced myself to someone reporting to the superintendent of the school and told her all about my work tutoring math both at a learning center and for my own business. She was impressed and introduced me to the superintendent. 

I had one shot at an elevator pitch to get his interest and fortunately I said enough for him to interrupt me and invite to a meeting at his office the following week. When we met a week later, I pitched him on my differentiated approach to teaching, shared my results, and presented the experience I had built over the last several years. Thanks to the strategies above, I had real results, powerful stories from the field, and differentiating skills that set me apart from other candidates.

Combining these three strategies positioned me to secure my first classroom teaching role!

When I got into the classroom, I hit the proverbial ground running. Even though I didn’t have classroom management experience, I had enough experience to get off to a strong start while I learned the other skills I was missing.

I went on to teach math at the high school for two years before transitioning to an all-girls middle school where I taught math for another two years. 

Do you feel like it’s time for a career change? Here are a few questions for you to ask yourself:

• What is a new field you’d absolutely love to get into?
• What skills, experiences, or results can you borrow from and bring to the new field that would set you apart?
• How can you begin to test your interest in this new field? 
• What small projects, experiments, or prototypes can you launch and test to start practicing in the new field and build the required skills?
• What ‘outside-the-box’ skills can you develop that will set you apart from people in the new field and give you that ‘unfair advantage’ right away? 
• Where can you go learn these skills? 

If you’re not sure where to start, I’d love to help guide you through this journey so you can build a life aligned with your values, passions, and purpose.