A Teacher’s Story

Chapter 17: The Guilt She Carried

When Ms. N was assigned to be my mentor teacher during my student teaching at the ULW teaching program, I did some research on her. From what I could find online, she cared a lot about students and was always available to them. Students commented, “Ms. N has a math camp open before school, during lunch break, and after class.”

In our first conversation, we introduced ourselves and established how we would work together. I heard from classmates that some mentors treated teacher candidates like free labor and subordinates, but Ms. N treated me as an equal. She readily admitted that during COVID, she was learning everything from scratch and hoped we could learn from each other.

We had similar backgrounds. She had been working in the financial industry before becoming a teacher, as a tax lawyer inside a big Wall Street bank. She started her teaching career in her 40s, about the same age as I did. She was working from her garage, while I was working from my basement. Both had unstable Internet connections at times.

Ms. N spearheaded the accelerated math pathway program, a very popular math program in this Title-1 school, which receives federal funding for having a large proportion of low-income students. As the only qualified teacher to teach the advanced classes, she had to teach six classes with over two hundred students.

The program had its own unique challenges, as the students joined with very different levels of prior knowledge. She knew well how to teach the courses and engage students before COVID, but for remote learning, she had to find a new approach. She was working eighteen-hour days to get everything ready and spending a lot of time adapting her teaching to the new learning environment.

During the first few sessions, I observed and took notes as she struggled with engaging the students. After the class, I gave her a few suggestions and provided supporting material. She used them and got a much better reception from students. For the next class, she suggested that I teach the class on my own while she would stand by to help with anything I needed. From then on, I started teaching some of her classes independently. She was always supportive and let me drive my own teaching but gave me detailed feedback when the classes ended.

Ms. N had been working long hours since her school started remote learning, and many times, she had to ditch her old approaches. She had to replace her school-assigned laptop five times to get it working and wasted an enormous amount of time. Students were having all kinds of problems, from online learning logistics to troubles at home to lack of motivation, while she had to wait six weeks for her assistant teacher (me) to be on board because of bureaucratic delays. She always retained a calm and caring attitude, no matter how discouraging things were. However, when she needed to share her account password with me, I learned it was “I-hate-LWPS***” (LWPS stands for her employer, Lake Wobegon Public Schools).

Whenever I asked for help, she immediately got on it. She didn’t talk much about how she helped, but she was actively helping me behind the scenes. In mid-semester, an African American boy was transferred to my class and found it challenging. He sent me a message full of desperation. I encouraged him and sent a message to Ms. N, who was in a better position to offer more assistance. We were both busy, and I didn’t hear from her about the issue.

After a week or so, the student suddenly showed more enthusiasm and initiative in class. Out of curiosity, I asked Ms. N: “Did you do anything?” She replied, “Yeah. I talked to another teacher who could help him.” First, she invited the student to talk, encouraging him and offering him time to work together, but she got no reply. She then thought of a colleague, a young African American male teacher with a body full of tattoos. Maybe a teacher like him could connect with the student better than an old white lady like her. She asked that colleague for help, and it worked out well. That was why my student got motivated and started to reengage in learning.

During one session, a student struggled with a practice problem and turned on the speaker. The entire class could hear the parents in the background explaining the problem to the student. The explanation was incorrect, and the whole class could hear it. Ms. N did not ignore it but told the student: “I think the comment got the right answers, even though it was not for the problem we were asking. It is so great to have some family help on this.” It was so positive and authentic that it quickly got the student out of embarrassment.

In the advanced class, four students had Individual Education Plans (IEPs) to accommodate their learning disabilities. One of them, David, regularly stayed after class to get every problem correct, no matter how long it took. He was in special education all through elementary school and was told that he couldn’t even be at the general level. But through the program and his relentless effort, he was on the advanced track and doing well. One day after the class, he wrote, “I am always at my happiest when I get to think about math problems.” That made the day for Ms. N and me.

Ms. N and I often tried to invite, cajole, and lure students to participate, but to little effect. I asked my son Matt for advice and came up with a program called Participation Appreciation. Every week, I gave out two $10 gift cards for those participating the most in a class (more than $10 was deemed inappropriate). It resulted in better participation and more interactions with the students, who opened up to me about some of their life situations in follow-up conversations.

A few students saw through my trickery and refused to be bribed by the prize, but most took it with gratitude. Some students wanted the money for video game credits, but several students wanted gift cards for groceries or Target to help their families rather than things for themselves. I was surprised, but Ms. N knew better. Her own children attended private middle school and came to help with her summer classes every year. They said these students were more mature than the privileged kids in their schools. Later, they both changed to public school.

In the fall, Ms. N told me a journalist was talking to her, and I started to pay attention. One day in December, she appeared on the front page of our local newspaper with a feature story. Some of the details added to what I already knew about her:

“She started as a lawyer at General Electric in New York City, in a department that she said was dominated by men. She remembered coming home after a long day, taking a shower at 2 a.m., and thinking: What am I doing with my life? Her father, a teacher, died, and she saw how former students honored him; it made her think about what her tombstone would say: ‘She was a really average lawyer,’ perhaps. Her office closed, and she moved back.”

“She noticed that only 5% of advanced math students were Black, even though they made up nearly half the school’s enrollment. In her quest to change that, she found an ally in W, who was then the principal. These kids, she thought, were all capable of the same academic achievement — they just hadn’t been given the opportunity. So she and W tried to accelerate all kids in math.”

Ms. N was a little concerned about how the school would react to it. The administrators’ responses to the news story were generally positive, but some teachers were jealous. One asked her in a confrontational way: “Why were you the one who was interviewed and written about? We all worked hard.”

Reader responses were enthusiastic: a donation was made to support a scholarship in her name; several lawyers messaged her saying that they wished they had the courage to do the same; online commentaries were full of admiration, and one person offered to pay the full cost of upgrading her garage where she conducted her online teaching. Ms. N’s mother was so proud that she hung the clip of the story prominently at home. As her protegee, I sent the story to all my friends in excitement.

As we became friends, Ms. N told me more about her decision to make the dramatic career change and move from Manhattan to here, the hometown of her then-husband (she was divorced when we met). The one thing that influenced her decision most was her father’s funeral. On that day, the whole town emptied and lined up around the block to show their respect. After teaching at the same school for forty years, he touched on the lives of so many people in the tightly knit community that practically everyone knew someone he had taught.

It reminded her of an earlier situation when she worked at GE Capital in the 1990s. General Electric was widely regarded as the world’s greatest company at the time, and GE Capital was its crown jewel (although later, it would become the problem child that brought GE down from its glory). Under the leadership of then-CEO Jack Welch, it went on a spree of acquisitions. On one occasion, Ms. N was tasked with restructuring a business after a merger, a process that often involves layoffs or closures to boost earnings and satisfy Wall Street.

The business’s main factory was in a small town in the Rust Belt, similar to her hometown in Ohio. When it was shut down, many locals lost their jobs, and the town was devastated, much like what was described in the book Hillbilly Elegy, the best-selling memoir that launched the political career of Vice President J.D. Vance. The decision was not hers to make and would have been executed regardless, perhaps more ruthlessly than she had. But seeing the misery of so many families while her colleagues celebrated with $1,000-a-bottle champaigns, she carried the guilt all these years and worked hard to redeem herself.

Her journey as a teacher was not all smooth. She always knew she wanted to teach at a low-income school. Other people warned her that a school like this would doom her career, but she was determined to prove them wrong. In the first few years, she worked at a school that didn’t value her and provided little support. She didn’t even have a dedicated classroom like all the other teachers. She kept learning and improving the craft of teaching during those years.

After she moved to her current school, she found a supportive environment where her resourcefulness, determination, and result orientation, combined with deep empathy for underprivileged students, enabled her to spearhead the math empowerment program.

The past several years had been stressful for her, and she was no longer the Wall Street lawyer who could routinely work until 2 a.m. At the end of my six-month student teaching under Ms. N, she wanted to hire me as her replacement, and I was very interested. However, even with her help, I couldn’t overcome the bureaucracy to get the position. The position required years of teaching experience and an additional certificate, which I didn’t have. Nevertheless, she gave me the highest rating for my student teaching and ability to connect with students, and she continued to be my mentor after our formal relationship had ended.

During my six months of teaching with Ms. N, I never stepped inside her classroom. I walked around the school once during that period. It was located south of downtown, in a neighborhood largely populated by recent immigrants. The school facility was new, modern, and well-equipped. It seemed that the government was throwing a lot of money at trying to improve education. Yet, fewer than 35% of students were on track for college-level learning, and regular attendance declined from 85% before the pandemic to less than 70% afterward and never recovered.

Perhaps it was the pandemic, but I didn’t feel unsafe and wondered why several police cars were parked nearby. Soon, I found out the reason. During the curriculum night, right before the school was scheduled to reopen for in-person learning, there was a shooting outside the main building. A fourteen-year-old student from the school was arrested with a gun, and the school reopening ended up being postponed for a week. I was concerned for Ms. N and texted her.

She was inside a classroom when she heard the shooting. She was only a little shaken because, over the years, she had dealt with similar situations, sometimes going to court to make depositions for her students facing criminal charges. She took a look outside, quickly figured out the situation, and then calmly returned to preparing lessons for the upcoming semester.

(I am publishing chapters of a new book. It has just won the . This is chapter 17, about my mentor teacher who quit Wall Street in her 40s and started teaching the poorest kids in our region.)

To read the book from the start, see . )