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What Being a Teacher Taught Me About Money

Though I have spent the last 11+ years working as a personal finance writer, I’m actually an English teacher by training. Teaching seemed like natural a progression for me: as in,


English majorbookstore employeechronically underemployed literary typegrad student in English educationEnglish teacher.


(Scientists may not have studied this life cycle with as much scrutiny as they have given the caterpillarchrysalisbutterfly transformation or Computer Science majorSilicon Valley tech brocryptocurrency proselytizer process, but it is well understood that English majors do often end up in a classroom at some point in their pupae-to-adulthood cycle.)



So becoming a freelance writer who specializes in personal finance is a bit of a left turn for a former English major like myself. It might even seem like teaching high school English has little to do with my current career.


But while there are a lot fewer requests for hall passes to the restroom, not to mention very little call for me to use my teacher voice (which can stop a charging rhino in its tracks), I’ve found that my career in education actually prepared me very well for writing about money—not to mention how it has shaped my own philosophy of finance.

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The Known/New Phenomenon


I was recently a guest on the podcast Standard Deviations, hosted by Dr. Daniel Crosby. On the show, Dr. Crosby told me a story about a friend of his who wanted to get into stock market investing. This friend, who had extensive experience in real estate investing, was horrified to learn that historical returns in the stock market included some years when investors lost 35% of principal, even though the historical average return was quite good. Dr. Crosby asked me how we can better talk to folks like his friend who get spooked by the potential risks in investing and shut down, even though they would be better off jumping in.


Back when I was getting my degree in education, I learned about something called the “known/new” phenomenon for teaching. This phenomenon describes how it is easier to learn something new if we start with something we know. For instance, if a child is well-versed in baseball but struggling with math, using her favorite baseball players to teach how their statistics are calculated will give her a known place to start learning something new. Statistics can seem unrelated to anything the baseball-lover cares about, until we pair it with something she already knows well.


Something I used to do quite often when I was a kid was another form of this educational practice. Though a good English major is “supposed” to read a book before seeing the movie based on it, I’d often flip that on its head and watch the movie before reading the book. Watching the film before reading the book meant I felt supported in understanding the story’s broad strokes while leaving me open to learning new things that were changed/omitted/elided over/different in the original book. This meant I was able to engage with stories I would have otherwise skipped because I didn’t feel up to reading something that seemed challenging.


Similarly, counseling Dr. Crosby’s friend on stock market investing can start with what he already knows well: real estate. Rather than jumping into the wide world of stocks, or even the smaller and less overwhelming world of the S&P 500, it would make sense to introduce this friend to real estate-based stocks. Real estate investment trusts (REITs) are companies that own or finance income-producing real estate and trade on major stock exchanges. Since Dr. Crosby’s friend knows real estate well, he can start his stock market investing from a place of knowledge and confidence, because he’ll feel comfortable evaluating REITs’ risk and reward potential. Once that becomes known, he can continue to expand from that known to a related new investment.

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The known/new phenomenon is a great place to start with teaching yourself new things, as well.

  • If you feel intimidated by investing, start by investing in a company or industry that you know well.

  • If you have no idea how to get out of debt, start with what you know how to do—such as leaving your credit cards at home and removing your payment information from online retailers. Let that be your initial strategy as you slowly learn new tactics for paying down your debt.

  • If you’re not sure how to make a budget, start with something you feel confident about, like getting the best deal at the grocery store, and pair that with a monthly grocery spending plan.

No matter what you want to learn, there is a place to start, with something you already know well. Starting there will help you feel a lot more confident about adding new skills and knowledge.


Shock and Humor Are Memorable and Motivating


I taught American literature to high school juniors for two of my four years as a teacher. Rather than teach chronologically, which was the traditional method, I created units about the American experience, such as the immigrant experience in America, women’s experience in America, Black experience in America, etc. One of my units was the experience of religion in America, for which I assigned the book A Prayer for Owen Meany by John Irving.


Though I was teaching 16- and 17-year-olds, I believed strongly that they benefitted from being read aloud to, so I would have a read aloud day for assigned books about once every two weeks. I made sure to time my first day of reading aloud to coincide with the first instance of the F-word in the book—and I read it aloud.

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Side note: this did get me in trouble with the parents of three students the second time I taught the book. They requested I switch their children to a different book that didn’t have “such filthy language.”


I said no problem and assigned The Poisonwood Bible by Barbara Kingsolver for those kids. My sister, upon hearing of this, called me a subversive bitch…which you’ll understand if you’re familiar with both books and can guess as to how the parents of these three kids knew each other. It’s still the best compliment she ever gave me.


It probably wouldn’t surprise you to learn that Owen Meany was the most popular book I assigned my students, though it was no more or less challenging or meaningful than any of the other literature we read that year. The fact that their strait-laced and mild-mannered English teacher offered them a book that included bad words and she was willing to read them aloud herself (as well as read Owen’s voice with the high-pitched nasal scream that Irving describes) meant the kids were invested in this book in a way that just didn’t happen with Huck Finn or The Yellow Wallpaper or Narrative of the Life of Frederick Douglass.


Being a little shocking and humorous is what Joe Saul-Sehy and I were going for with our book Stacked, because we know it’s going to get more investment from non-money nerds than the usual dry tone used for money conversations.


Coming at financial issues from an unexpected or funny place is going to get you better outcomes than treating it as only slightly less fun than a colonoscopy. That’s true whether you’re trying to improve your own money game or bring a partner on board with household money management. Finding a way to surprise yourself and your financial partner with humor will make things much more memorable and motivating.


Find Inspiration from Unlikely Sources


Though I never taught the book Maus by Art Spiegelman, the recent news about it being banned by a school system in Tennessee has reminded me of how reading it created unlikely connections in my mind.


Maus is a graphic novel about the Holocaust, which tells the story of Spiegelman’s father, Vladek, and how he survived Auschwitz.


Prior to World War II, Vladek and his wife Anja were well-to-do Jews in Poland, but the Nazis took away all that they had built. Reading about how the rug was pulled out from under Vladek and Anja helped to craft many of my philosophies of life.


To start, though many people might seek financial security, Maus makes it clear that no amount of money can ever make you secure. It is always possible for that wealth to be taken away, either by despicable people, as in Vladek and Anja’s case, or by unfortunate circumstances. If you are counting on your money to protect you, you’re counting on the wrong thing.


But what Vladek did next helped me to come to another important realization: you may not be able to count on your money, but you can count on yourself.


Vladek was an incredibly intelligent and resourceful man. When he and Anja were moved to the ghetto, he figured out a way to continue to support his family, despite rules against Jews conducting business in the ghetto. He consistently found ways to barter skills for better treatment for himself and Anja. Even after Vladek was taken to Auschwitz, his ability to make connections with other people and keep an eye out for opportunities helped him maintain contact with Anja, who was placed in another camp, and survive the horrors.


When I sat down to read Maus originally, it never occurred to me how profoundly it might influence me. Though the subject matter of this graphic novel is incredibly grim, and my realization that there is no such thing as financial security is hardly a positive one, I still came away with a sense of hope that we can count on ourselves and our skills, even in the face of horror.


I encouraged my students to find similar inspiration in unlikely sources, and I think we can all learn things from unexpected places. Whether you’re reading something a teacher assigned, watching the latest streaming show on Netflix, or just chatting with new people, letting your mind find connections between new information and your own experiences can lead to improbable and important new insights.


Life is a Classroom


My teaching career may have been relatively short-lived, but it taught me to be a lifelong learner. Learning the fundamentals of teaching, both in grad school and on the job, made it clear how I could both communicate better with others and keep my own sense of curiosity alive. It may be a cliché, but my students really were my teachers—and they taught me well.

Think back to your own favorite teachers. What did you learn from them? What skills did they teach you that you use to this day? And have you thanked them?