A New Text Pairing for The Great Gatsby

Leslie Odom, Jr., self-improvement, and the American Dream

Need an informational text to pair with F. Scott Fitzgerald’s The Great Gatsby? A text that offers real-life tips your students can apply to their lives? Earlier this month, I discovered a non-fiction book that adds contemporary relevance to Jay Gatsby’s Jazz Age motivations while also serving as a way to further engage students on a personal level with the novel. Here it is:

Failing Up: How to Take Risks, Aim Higher, and Never Stop Learning by Leslie Odom, Jr.

If you’re unfamiliar with the author, Leslie Odom, Jr., maybe you just missed the memo (lol), so here’s a quick CV:

  • Tony Award-winner for Best Leading Actor in a Musical;
  • Grammy Award-winner for principal singer on the Hamilton cast recording;
  • recording artist with a Billboard No. 1 ranking debut album;
  • television performer on Law & Order: SVU, Grey’s Anatomy, CSI: Miami, plus others.

Yes, Odom’s career is that impressive. With that being the case, Odom’s positive life advice and personal experiences can inspire students to better their lives and accomplish their dreams, not to mention introduce them to the genre of self-improvement reading.

The Great Gatsby by F. Scott Fitzgerald

Self-improvement was a central tenet of the fictional Jay Gatsby. In chapter 9, readers learn about his youthful aspirations when Gatsby’s father, Henry Gatz, upon traveling from Minnesota to his son’s funeral, shows Nick Carraway his son’s tattered copy of Hopalong Cassidy. Inside the back cover, young James Gatz (Jay Gatsby’s birth name) had years earlier written his daily schedule and “general resolves.”

The schedule lists “Rise from bed 6 a.m.; Dumbbell exercise and wall-scaling 6:15-6:30; Study electricity, etc. 7:15-8:15; Work 8:30-4:30; Baseball and sports 4:30-5:00; Practice elocution, poise and how to attain it 5:00-6:00; Study needed inventions 7:00-9:00.” The general resolves, listed next, include “No more smokeing (sic) or chewing; bath every other day; read one improving book or magazine per week; save $5.00 [crossed out] $3.00 per week; be better to parents.”

This to-do list spells out just how aspirational and destined for greatness the young James Gatz felt himself to be.

Failing Up inside page spread
Even though the book runs 194 pages, it’s a quick read. The tone is conversational and the pages feature ample spacing between lines.

This endearing glimpse into the future Jay Gatsby’s psyche provides readers an intimate look into his underlying, integral impulse: the drive to be better.

I think young James Gatz’s desire to — and I’m being general here — be a better person is one we all share. It’s also central to the notion of The American Dream, where hard work, preparation, perseverance, and a desire to provide for the next generation serve as touchstones.

Odom’s Failing Up, in essence an autobiographical account, resonates with similar messages, even ruminating on the American Dream itself, as in this excerpt:

“For me, Hamilton was my first real brush with the American Dream. I’d gone to Hollywood a decade earlier in search of it. All these years later, I could see that every triumph and every failure, every lesson learned along the way, was available for me to access and use to ensure that I made the most out of this moment. A Broadway musical about the Founding Fathers — a piece of art in part about slave owners and their American Revolution — bought me freedom. The American Dream had a new spirit and a new context for me now.”

Leslie odom, jr. | failing up chapter 8, page 167

Reading about how Odom accomplished his goals and his ultimate starring role in Hamilton may provide a current-day connection to Jay Gatsby that students can relate to.

Here are two additional benefits of adding this book to your Gatsby unit:

  • Its brevity makes it an easy add-on to your unit.
    • Even though it’s 194 pages in length, those pages flash by. The reading is very conversational. You won’t find overly complex vocabulary and, for our self-improvement purposes, that’s fine. In addition, the book can be read cover-to-cover or you can pull individual chapters or excerpts for mini-lessons.
  • It’s written by an accomplished, relevant celebrity of color.
    • Many students will be familiar with Odom. Reading about his childhood in Philadelphia — including elementary school troubles and pre-teen aimlessness — will be relatable. His many failures, hard work, initial aversion to risk, and ultimate successes should have appeal and value.

Bonus lesson idea: Inferencing skills

Failing Up by Leslie Odom, Jr.

As an extra bonus, each of the book’s nine chapters can potentially provide practice in inferencing. Since some chapters’ central messages are not explicitly stated in the titles, divide students into groups and have them read to identify the central message Odom offers. For example, chapter two is titled “The Big Break,” but its central message is prepare for success. Another: chapter three is titled “What You Own,” but one of its central messages is to make the most of whatever gifts you’ve been given. Your students should have fun parsing out Odom’s tips.

I’m glad I spent some time with this book. After all, I came to this book in a round-about way. My daughter ordered it a few years ago. I remember at the time thinking it looked interesting, but didn’t take the time to read it then. However, this summer, spurred on by an end-of-the-year mini-unit on Gatsby, my mind returned to it. I’m so glad it did. I hope Leslie Odom Jr’s. Failing Up makes an intentional, informational text pairing for you — one that helps your students connect in a new, personal way to The Great Gatsby.


Marilyn Yung

By the way, I’ve been on a Gatsby kick lately. I’ve been collecting resources, thinking about the book like literally ALL THE TIME (because it’s that kind of novel!), making a Jazz Age documentary viewing guide, and breaking down the 2013 film chapter by chapter.

If you teach Gatsby, you need to become a subscriber (sign up below) because more posts are on the way!

Thanks for reading! Feel free to leave a comment below or via my contact page. I’d love to hear from you!

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One more Leslie Odom, Jr.-related post… a poetry article in the Wall Street Journal that delves into song lyrics, rap, and Hamilton. Pretty awesome!


ELA BRAVE AND TRUE by Marilyn Yung | Love teaching. Make it memorable.

Published by Marilyn Yung

Writes | Teaches | Not sure where one ends and the other begins.

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