Meet Jonathan, Your Private Tutor

Until my senior year in high school, I had my eyes set on becoming a sports journalist or a lawyer. But when some of my classmates struggled with calculus, they came to me for help. Several of them noted my ability to break down the concepts, causing me to wonder if perhaps teaching was a field to consider. In the second semester of my freshman year of college, I declared Mathematics Education as my major.

Straight out of undergraduate school, I got a job at a high school not far from where I grew up. I enjoyed teaching math there, but I was immature. The teaching skills were all present, and many students complimented me on my abilities, and I still remember a few saying that, thanks to my influence, math had gone from their least favorite subject to their most favorite subject. But I didn’t have the necessary professionalism at that time, so I left the classroom for an extended period of my life.

After several years of drifting from job to job, getting whatever I could find, I reached a sort of early midlife crisis. I considered law school but found it too expensive. I eventually settled on graduate school to pursue a master’s degree in secondary education.

At the age of 40, I completed my degree and reentered the field of education as a teacher. The grad school experience showed me that I still had excellent teaching skills, but now I had the necessary maturity as well.

For the first four years back in the teaching saddle, I taught at an alternative school and did lots of substitute teaching. At one point, I served as the sole teacher for two boys who had been expelled from public high school. From 2014 through 2015, I tutored as what might now be called a side hustle. My plan then was to cobble together a living as a tutor and a substitute—at least until I landed another full-time teaching job.

My plans changed unexpectedly in the fall of 2015, launching my career in a new direction. I had been tutoring through three different organizations, so tutoring had become a viable part-time job. But in the summer of 2015, an online platform launched its digital learning studio, meaning I now had a tool by which I could connect with students remotely. As the school year started up, the requests for my services started pouring in, and by the end of October I was making more as a tutor than I would have as a teacher. Within a few months, I made the bold decision to leave teaching behind and go all-in as a professional tutor.

Initially, I tutored students only in math subjects, but I soon expanded my repertoire to gain more business. I have always been an excellent test-taker, so I educated myself on the SAT and ACT. My interests in test prep soon expanded to include the GRE, GED, and ASVAB tests as well. By 2016, the bulk of my tutoring sessions focused on test preparation.

Tutoring has been my full-time job for a decade now, and in that time I have helped more than 500 students prepare for tests. My approach is to present not only the test material, but also the strategies one needs to navigate it. Almost 40 years after those classmates first acknowledged my propensity for explanation, I continue to use that ability as I break down the complexities of test preparation and help students understand both the content and the approach to reach their goals.