Jermaine Gassaway is an educator and author known for his work on educational equity and teacher diversity. He wrote Unopened Books: Multiplying the 2% and When You Arrive: A Children’s Book About Racism. In this Q&A, he talks about what success means to him, on his own terms and in his own words.
How do you personally define success?
I define success as growth you can measure against where someone started, not where someone else finished. A student who moves from struggling to grade level has succeeded, even if a classmate down the hall is further ahead. I learned to think this way early, because my own path did not look like anyone else’s around me. Success has to be measured against your own starting point, or the word stops meaning anything.
Was there a moment you remember first feeling successful?
Getting accepted to boarding school on a scholarship was the first time I felt it. I had written to the Board of Education at 14 asking to transfer schools and been told no because of my zip code. The scholarship letter felt like proof that a door could open even after one had already closed. That feeling, of a closed door followed by an open one, is still how I recognize success when it happens.
How has your definition of success changed over time?
When I was younger, success looked like a single achievement: get into the school, get the degree, get the job. Now I think of it as something closer to a pattern. One good year does not make a successful career, and one good test score does not make a successful student. I look for whether the pattern is trending the right direction, not whether any single moment is perfect.
What role has failure or rejection played in how you think about success?
The rejection letter from the Board of Education mattered more than most of my acceptances. It forced a decision I would not have made otherwise, which was to leave home at 14 and go to Mississippi for school. I do not think you can talk honestly about success without talking about the rejections that came first, because most of the time, the rejection is what points you toward the door that actually opens.
Do you think success looks different depending on where you start?
Yes, and I think that gets lost a lot. Two students can work equally hard and end up in very different places because they started from different places. That is not an excuse to lower expectations. It is a reason to measure growth honestly instead of comparing everyone against the same fixed line. I built a lot of my thinking around teacher diversity out of this same idea: the starting conditions in a classroom shape what success can look like inside it.
What does success look like for the students and teachers you write about?
For a student, it might be finishing a book they said they could not read. For a teacher, it might be reaching a kid nobody else could reach that year. Neither of those shows up on a resume, but both are real. I wrote Unopened Books partly because I wanted to put language around forms of success that do not get counted anywhere official.
Has writing books changed how you think about success?
Writing forced me to sit with ideas longer than I normally would. With When You Arrive, I had to think carefully about how to talk to children about something as hard as racism, and there was no shortcut through that. Finishing the book felt like a form of success that had nothing to do with sales or reviews. It was the satisfaction of having said something true, in a way a child could actually hear it.
What advice would you give someone who feels like they are behind?
Look at your own line, not everyone else’s. I did not have the same starting point as most of my classmates growing up, and if I had measured myself only against them, I would have quit early. Instead I paid attention to whether I was moving forward compared to where I had been. That is a more honest measure, and it is one anyone can use, regardless of where they started.
What is one thing people misunderstand about success?
People treat it like a finish line instead of a direction. I do not think I have ever felt “done.” Every time I have reached something I once considered success, whether it was a scholarship, a degree, or finishing a book, it turned into the starting point for the next thing. I have stopped waiting for the feeling of being finished, because I do not think it is coming, and I have made peace with that.