In this episode, Unpacking Education cohost Dr. Winston Benjamin shares his unique story of success. He retells his memories from growing up in Jamaica, his family’s journey to the Bronx in New York, and ultimately his move to Washington state where he earned his PhD.
As he tells his story, Winston explains the life lessons that he learned along the way and how those lessons have shaped him personally and professionally as an educator. By listening to his story, we can vicariously learn from his road to success. In turn, by implementing those lessons ourselves, we can help students be more successful in our classrooms. Through these insights, we can do as Winston says: “Let your kids be all they can be.”
Who can afford to run will run / But what about those who can’t, they will have to stay / Opportunity a scarce, scarce commodity
Buju Banton, from his song, “Untold Stories”
- Community Building (templates)
- Create Community and Nurture Connections (article collection)
- Deepen Connections to Accelerate Learning (article collection)
- Blended Learning as a Response to Trauma-Informed Instruction, with Elizabeth Buffington and Conrado Julian (podcast episode)
- Accelerate Learning by Making Connections: Build Trust Through Relationships, Community, and Connection (article)
Being Seen and Heard
As Winston reflects on his elementary school experience, he says, “I was made fun of a lot by other students in school. Because of the accent, I wasn’t hip enough. And it was just like the first few years, I was so silent. I didn’t participate. And that’s when I think people thought I needed speech support because I just didn’t talk. I just didn’t feel like anybody cared about me until I met Mr. Alejandro.”
Mr. Alejandro was Winston’s fifth grade teacher, who encouraged him to take part in the school talent show, playing the part of a Jamaican rapper. That was an impactful experience for Winston, and he reflects fondly about his relationship with Mr. Alejandro. He says, “Until I met him, I didn’t have any way of being seen because people just thought I was Black. They didn’t realize that I was a Jamaican kid that was just not talking because no one really heard me. That was a really hard thing.”
Mr. Alejandro and many other teachers helped Winston feel seen. Winston has taken the lessons he has learned and made it a mission of his educational career to help others also be seen. The following are a few highlights from our conversation:
- About Our Guest: Dr. Winston Benjamin was born in Jamaica. At a young age, his family moved to the Bronx, New York, where Winston grew up through high school. After high school, Winston worked at the Phoenix Charter Academy. Winston then moved to Washington state where he earned his doctoral degree and continues to work in educational leadership in the Renton School District. Every week, Winston also cohosts this very podcast, Unpacking Education.
- Growing Up Poor in Jamaica: Thinking back, Winston recalls, “I didn’t realize I was poor in Jamaica because everybody else looked the same way. We were all in the same muck, walking around barefoot with no shoes.” He shares, “The only thing that’s remaining from my house is the stone steps. We lived in a wooden shack with a zinc roofing on it. It was me, my mom, my dad, two brothers, and my sister in a small, one-room shack.”
- A Move to the U.S.: Winston’s parents tried for five or six years to get their family to the United States, but moving to the U.S. required sponsorship. In 1987, Winston’s grandmother visited from England. She had dual citizenship in the United States and in England. Winston describes the day she came to visit. “It was raining so hard that when she stepped in our yard, it was so muddy that she couldn’t believe that her grandkids were living there, so she signed the papers to get us to the states that year.”
- A New Context: Winston was young when he moved to the United States, so he had limited memory of life in Jamaica. However, going back later in life has given him new insight. He says, “I didn’t really understand the context of what we lived in at the time, right? It was always going back home that really made it make sense of how lucky we were to get out.”
- Difficult Experience at School: “I was made fun of a lot by other students in school,” says Winston. “Because of the accent, I wasn’t hip enough. And it was just like the first few years, I was so silent. I didn’t participate. And that’s when I think people thought I needed speech support because I just didn’t talk. I just didn’t feel like anybody cared about me until I met Mr. Alejandro. Mr. Alejandro was our fifth grade teacher.”
- Mr. Major: Mr. Alexander Brooks Major III was another teacher who made a significant impact on Winston growing up. “He would have us write HIM-Highly Intelligent Males. That was our superhero. We were HIMs. And ever since Mr. Major put that in our head, like we were HIMs, we were highly intelligent males, that stuck with me like no other level. I was valuable enough because I could make myself valuable. It’s not what others put in me, right? Like I already come with stuff.” Winston adds, “Also seeing such a big, big man being so warm and loving kind of gave me my personality, right? Like I’m a six-feet-tall baby, right? I’m just a lovable dude that most people think is mean. . . . He gave me a chance to really see different opportunities for what it is to be, like I could make up myself.”
- A Pivotal Experience: His experience on the debate team introduced Winston to racism. He recalls participating in the New York state championships. “Through that experience, I really learned the racism of the world.” People were “surprised that we were able to beat a group of White kids. We never got a trophy. We didn’t get anything. It was like a secondary ‘thanks for doing this.’ So for me, that gave me the initiative to always be vocal and push against, right? So that’s really where the initiative of being like, yo, fight for something that matters because I was so disrespected. I was so disrespected.” He feels like that experience gave him his voice.
- Miss Goldstein: Miss Goldstein introduced Winston to one of his favorite books of all time, Tuesdays with Morrie. He says, “If it wasn’t for that book, I wouldn’t have gotten my scholarship to college.” It turns out, Winston ended up having a conversation with a key scholarship representative about that book while riding on an elevator. Winston adds, “Miss Goldstein giving me opportunities to read books that were outside of my neighborhood really pushed on the ability to connect beyond.” He continues, “If it wasn’t for the communication of having knowledge outside of the Bronx, having knowledge outside of my little hood, you know what I mean, I don’t think I would have had those conversations to get me out.”
- Get Your Papers: Winston would tell his students at the Phoenix Charter Academy to “get your papers,” so you can shape your own future. After getting passed over for a school leadership position at that academy, Winston’s students told him to take his own advice and get an advanced degree. He took this advice and secured a scholarship to the master’s program at University of Washington.
- Dr. Geneva Gay: It was in Washington that Winston met Dr. Geneva Gay, who became a mentor to him in grad school and encouraged him to pursue his doctorate. Winston recalls her saying to him, “You’re actually smart. You should think about this PhD.” Before that, he says, “I never ever in my life dreamt about having a PhD.”
- Message to Young Winston: “It’s not you. Don’t feel ‘less than’ because your teachers didn’t see.” He would also tell himself, “Don’t be afraid. I was afraid of trying things and failing because if I failed…what would the opportunity be that I lost?”
- A Space for Stories: Winston urges teachers to give students space to tell their stories. He says, “I can’t tell you stories unless you give me a space to find an access point.” Along with a space for stories, Winston says, “Make sure you find ways to connect, and genuinely connect, to your students.”
If you are listening to the podcast with your instructional team or would like to explore this topic more deeply, here are guiding questions to prompt your reflection:
- What stands out to you as you listen to Winston’s story?
- What obstacles did Winston face?
- How did Winston overcome those obstacles?
- What obstacles do students face in your schools?
- What positive impact can teachers make on students who are struggling?
- What action steps does this episode prompt you to take?
Extend Your Learning
- “Untold Stories” (Buju Banton)
- Tuesdays with Morrie (by Mitch Albom)
- Personal Story Sharing as an Engagement Strategy to Promote Student Learning (by Dr. Richard Jeffrey Rhodes, Penn Graduate School of Education)