A Six-Week Job That Lasted 23 Years: A Profile on Gary Rubinstein

A slender, stern, but ambitious 31-year-old man prepared for his 8:00 a.m. job interview inside the Twin Towers on September 10, 2001. The towers stood tall and gray just like any other day, and the young man was ready to knock the interview out of the park. Even though he was relatively young, he already had a lifetime of experiences, from tutoring D1 athletes in math to publishing humor columns in magazines to getting job offers at Lockheed Martin and Goldman Sachs. Nevertheless, he moved to New York City in search of something new and different—something more adventurous. This interview was for a software engineering position—a well-paying job unlike some of his previous ones. Of course, the following day’s tragic events quickly rendered his interview null and void. However, this moment also provided a job opportunity for him at a nearby high school in Battery Park City. Little did he know, that opening would become his job for the next 23 years. This marks the beginning of a Stuyvesant legend: Geometry and Calculus Applications teacher Gary Rubinstein.

Born on Long Island in 1969, Rubinstein focused his childhood energy on two main interests. “I was good at math and at trumpet—those were my main things,” Rubinstein revealed. Nevertheless, he certainly also had a nerdy side, remarking, “[I liked] old classic arcade video games, such as Atari and Pac-Man. The Rubik’s Cube [also] came out when I was about 11. I couldn’t finish it, but I was in an era where there was no cheating, and it was impossible.” Although Rubinstein had many clear interests, he wasn’t confident in what he wanted to study in college. He entered Tufts University in 1987 as a math and philosophy major, but quickly changed his major once he arrived. “I didn’t continue in philosophy. I thought I wanted to go to law school [because law is a profitable career], and I thought philosophy was like logic.” It didn’t turn out to be that way, as Rubinstein elaborated.

Though Rubinstein’s attempt at philosophy wasn’t successful, his other talents shone instead. He discovered his love for writing as a humor columnist for the Tufts Observer. “I knew I always had a knack for writing, but I just never [saw] it [until then],” Rubinstein shared. His lifelong interest in math would also come into use when he saw an opportunity to become a math teacher. “In my senior year, when everyone was starting to register for the LSAT, someone gave me a flyer [for] an organization called Teach for America,” Rubinstein recalled. “The idea [of Teach for America] was that you could [teach for] two years in an inner city or rural school and get another job later. I thought that I could do this for two years, then I could [go to law school] after that,” Rubinstein clarified. Through Teach for America, Rubinstein ended up teaching math in Houston, Texas, for two years right after college. 

Unfortunately, teaching without experience came with its challenges. “I really struggled [with] my first year of teaching [middle school]. I wasn’t trained very well,” Rubinstein remarked. Feeling demotivated, Rubinstein almost wanted to quit after his first year. However, Rubinstein fared much better after transferring to another high school in Houston. “I did very well because I really learned so much from the mistakes I made the first year. I actually won the teacher of the year award at my school,” Rubinstein recalled. Even though he hadn’t originally planned to teach for more than two years, he enjoyed it enough to continue, transferring to Boulder, Colorado.

Instead of teaching high school, Rubinstein found a job as a math tutor at the University of Colorado Boulder. “It was a Division One college, meaning that [the students] were [talented] athletes,” Rubinstein described. He noted that he tutored students who would go on to be successful professional athletes. “I [tutored] a guy named Chauncey Billups, who was an NBA star [for the Detroit Pistons and] won MVP for the Finals. I also taught some football players, one guy being Koy Detmer [who] became an NFL player,” he recalled. 

Along with tutoring, Rubinstein continued to write, this time with more ambition than in college. “When I left Houston, I started to send my [humor] articles out to magazines, and they were starting to get accepted. [They] were in national magazines, [which] gave me a lot of confidence in my writing,” Rubinstein reminisced. Being committed and wanting to combine his main interests, Rubinstein had greater plans. “[Around] 1995 to 1996, I was going to write a book [about teaching]. Back then, there were a lot of movies [where] a young teacher goes in and wins everyone over [which inspired me],” Rubinstein reminisced. He published his first book about teaching, Reluctant Disciplinarian, in 1999, but would not write more books until years later.

Even though Rubinstein enjoyed education, he soon realized that tutoring and teaching weren’t working out financially. “I moved from Boulder to Denver [to go back to teaching], and I taught one year in Denver. But I realized that I really needed more money,” Rubinstein explained. Again taking a detour in his career path, Rubinstein realized he wanted to pursue something that wasn’t writing or math. “In college, I took one computer class, and I did really well in it. It never occurred to me to be a computer programmer,” Rubinstein said. He decided to go back to school, getting a master’s degree in computer science. 

After graduate school, Rubinstein continued juggling different jobs. “I worked at a [company] called Cirrus Logic [for a year], which made chips for disk drives and other things. I didn’t really love that job because I didn’t really understand the engineering aspect [and] I felt I wasn’t the smartest guy there,” Rubinstein recalled. “I wanted to be someone who was an expert in their field.” After his brief foray at Cirrus Logic, Rubinstein fortunately had options. “I had two job offers, one at Lockheed Martin [and] one at Quark. [Lockheed Martin] is a defense company, but I had some weird feelings about making bombs, so I didn’t accept that job. Quark made desktop publishing software, similar to what Adobe does now. I ended up choosing Quark,” Rubinstein explained. Although Rubinstein made a comfortable salary in Denver as a software engineer, he didn’t enjoy the job, similar to his experience at Cirrus Logic. “My job was to fix other people’s work, [and] it was tedious. I didn’t feel like I was using my creativity,” Rubinstein elaborated. Though he didn’t know it at the time, that would be his last job before his return to education.

In 2001, Rubinstein left Denver for New York City. Although he expected an easier time getting a job in New York, he had less success than he did in Denver. “I had a job interview [at Goldman Sachs] in the World Trade Center.” Rubinstein described. But despite his initial confidence, he had a blunder in the job interview. “I told them I didn’t mind having less money, but with [more vacation days.] They did not like that, and I did not get that job offer,” Rubinstein explained. After his interviews went poorly, Rubinstein was left temporarily jobless. “I stopped looking for jobs after that. Nobody was hiring after 9/11,” Rubinstein said. 

Returning to his teaching roots, Rubinstein eventually decided to work training teachers at a company named Teaching Fellows, where he trained one of the future teachers at a nearby high school in Battery Park City. “One of the people I trained [was] supposed to go to [a] low-performing school, but he got offered a job at Stuyvesant since a teacher quit after 9/11. But [the person that I trained] got fired in March 2002, then suddenly there was no one to replace him,” Rubinstein explained. That vacancy became Rubinstein’s opportunity. “[Stuyvesant] called me saying that I trained him, [and that I didn’t] seem to be teaching right now. They asked me if I could be a long-term substitute, so I did,” Rubinstein elaborated. At the time, he thought the job would be purely temporary: “I thought I was going to do this for just six weeks.”

Although Rubinstein didn’t originally want to teach at Stuyvesant after his six-week stint, chance would bring him back when his tutoring business failed. “[After Stuyvesant], I bought an SAT test prep company from relatives of mine in Long Island, but it didn’t do very well,” Rubinstein said. “I [ended up going] back to teaching in 2003, and [Stuyvesant] held the job for me,” he added. That would be the start of Rubinstein’s formal teaching career at Stuyvesant.

No longer on the search for a new job, Rubinstein was finally able to revisit many of his previous interests while teaching at Stuyvesant. Rubinstein wrote his second book about teaching in 2008, but admitted, “It didn’t do well.” Despite that, Rubinstein’s major success would come in 2011 when he co-wrote a children’s book, The Girl Who Never Made Mistakes. “I had a friend who was a cartoonist, and he asked me if I [could] help him with his book, and we became partners after that. That book has sold almost a million copies,” Rubinstein described. Even though not all of his books have been successful, Rubinstein still continues to write and enjoys it. “In 2007, I [started writing] a blog, [giving] advice to teachers,” Rubinstein recalled. The blog is not often used by Rubinstein today, but it still has occasional posts. Apart from writing, Rubinstein also pursued a stand-up comedy stint, showing his light-hearted side. “I did amateur standup comedy from 2005 to just two years ago. I posted clips [on YouTube] from different shows [I performed at],” Rubinstein recalled.

Even though Rubinstein appeared stoic upon arriving at Stuyvesant, his personality would eventually shine through. “When I came to Stuy, I [had] only taught at low-performing schools before. I was excited, [but] people were more fun than I expected them to be. The kids had more personality than I was expecting,” Rubinstein explained. Even though Rubinstein always enjoyed teaching at Stuyvesant, he learned to lighten up a bit. “For the first five or six years [at Stuyvesant], I didn’t smile, I was trained not to. I used to not let kids go to the bathroom [for] 10 years. Now I allow it, but I still don’t like it much,” Rubinstein remarked. But he has learned to be more joyful and show more personality, joking, “But now look at me, [wearing silly] Halloween costumes [and] singing songs [at the talent show].” 

Although Rubinstein has had a successful 23 years of teaching at Stuyvesant, much of it was merely due to chance. “I was an accidental teacher; I did not mean to become a teacher,” Rubinstein said. “Teach for America was supposed to be a two-year thing; Stuyvesant was supposed to be a six-week thing,” Rubinstein elaborated. Despite the game of life taking Rubinstein to unexpected places—both literally and metaphorically—maybe that is what makes Rubinstein such a passionate and loved teacher, renowned for his loving and bubbly personality behind an initially unassuming and serious face. When thinking back on his life so far, Rubinstein doesn’t have many regrets: “I kept just doing what seemed like the right decision at the time, and it all worked out.”