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January 2026

Crossroads: Beyond the Lesson

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How do we recognize when our vision for helping others is misaligned with what they say they need? When do we push forward, and when do we let go?

Beyond the Lesson

You signed up to tutor high schoolers at risk because you believe education is the key to opportunity. One student, Jordan, has been behind for years, and without intervention, they won’t catch up. Without a high school diploma, Jordan is more likely to face limited job opportunities, lower pay, and fewer options for further education or training.

Then, after a session, Jordan says, “I don’t care about school, but I like talking to you. The program coordinator follows up, suggesting you shift to a mentorship role, focusing on conversations about Jordan’s life. This is a role that you are interested in taking on, but you know in order to do this type of mentorship well, you would need to include exercises and activities, leaving no time for schoolwork.

If you shift to mentoring, the academic progress you’ve fought for will likely stall. Still, if they don’t care about school, does the tutoring even matter?

What do you say to the program coordinator? Do you keep pushing for what Jordan needs, or pivot to what he seems to want?

Jewish Compass

The Talmud (Ta’anit 24a) recounts a teacher who engages with students who don’t want to learn and briefly takes them to see his fishpond. Looking at the fish soothes them and gently brings them back to reading. He doesn’t ignore what the students want, but he ultimately uses it as a strategy to get them ready to learn.

Rather than imposing a single path, Jewish wisdom teaches the importance of meeting people where they are. “Educate a child according to their way, and even when they grow old, they will not turn from it” (Proverbs 22:6). True guidance means adapting to the learner’s needs, rather than forcing them into a predetermined path.

How do we recognize when our vision for helping others is misaligned with what they say they need? When do we push forward, and when do we let go?

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