“You Need Someone to Ask You the Hard Questions”: Sammy Oge Finds His Bearings

Before Sammy Oge showed up at a City Tutors event in Midtown, he already knew the name. Back when City Tutors lived inside City College, he watched it take root. Years later, as the program grew into a wider support system, he circled back at a moment when he needed it.

Oge had been working as a data analyst engineer at the Department of Transportation. The pandemic scrambled the work and, eventually, the role. He was applying again, trying to decide what came next, and looking for a steadier way to plan. “I wanted to hear from people who were already where I hoped to go,” he said. “Not just about getting a job, but about whether it was the right job.”

Through City Tutors, he matched with a mentor and began meeting every other week. The sessions did not produce an instant offer. They did something else he now counts as more important. “We answered the basic questions that shape everything that follows,” he said. “What am I good at. What do I care about. How do I talk about that without sounding scattered.”

The mentor was Liz Goldenberg. He chose her because she was farther along in her career and could speak from the long view. “Her questions were not soft,” Oge said, smiling. “She asked, ‘Is this really the work you want to do. If the opening is there, why you. And why now.’”

They practiced interviews and debriefed the ones he was taking. They sorted loose ideas into a few clear stories he could carry into a room. “I am a creative and an engineer,” he said. “It is not always easy to draw one line through that. Liz helped me get organized.”

He also began to build habits. Goldenberg talked about time blocking and preparation. She told a story about stepping into an elevator and finding herself next to Michael Bloomberg. There was no time to warm up. “You have to know what you will say in the moment,” Oge said. “That is training. Daily practice.” He started carving out time to rehearse the short version of who he is and what he wants to build.

At the same time, Oge leaned into the in-person side of City Tutors. “I am not a Zoom person,” he said. “Meeting face to face changes the conversation.” Company visits and panel nights offered something he could not get from a job post. He heard how the work actually feels, saw the places where it happens, and tried on different paths for a night.

Paramount stands out. He met Gianni, a technical recruiter who would later appear at another City Tutors event, and listened to how hiring looks from the other side. “For a second I thought, maybe I could do technical recruiting,” Oge said. “I am still a builder. I like to get my hands dirty. But hearing what they look for helped me think about my own applications differently.” He also visited Citi and a handful of other offices that, until then, had existed mostly as logos. “Sometimes it is the first time you walk into a building like that,” he said. “It makes the next step feel closer.”

Oge is now in graduate school, studying Interactive Telecommunications. The program fits the way his mind wants to explore, which creates a different challenge. There is more to learn, more to try, and more need to focus. He credits mentorship with giving him a way to hold both curiosity and clarity. “You can have many interests and still present a clear center,” he said. “City Tutors helped me practice that.”

He is quick to point out what mentorship did not do. It did not hand him a script. It did not reduce risk or eliminate doubt. It did, however, make the next step visible. “You need someone who knows the terrain and will ask you the hard questions,” he said. “That is what I got.”

Oge’s view of community shifted, too. In undergrad, mentors helped him win fellowships and internships. He already believed in the model. The difference now is the scale and consistency. “City Tutors creates the space and the rhythm,” he said. “It is on us to use it. But having that ecosystem changes the odds.”

He still shows up at events when he can. And he still counts the small, unrecorded moments as the ones that matter most: the honest answer from a professional who does not need to impress anyone in the room, the recruiter who explains how they read a résumé, the founder who admits it took years to find a voice.

“It is not overnight,” Oge said. “It is practice, refining, and being ready when the door opens.”

If there is a simple way to describe what City Tutors gave him, it might be this: permission to blend what he is good at with what he cares about, and language to offer that blend to the world. The job he wants is still a moving target. The path toward it is steadier.

“I love education,” he said. “I love helping people get to their next step. City Tutors matches that energy. It reminds you that you are not doing this alone.”