Upper Schoolers Learn about Teshuvah and Integrity from an Unlikely Visitor

As part of Ramaz’s commitment to helping students reflect on integrity during the Aseret Yemei Teshuvah, Upper Schoolers received a visit from Mr. Eli Tilson, a former businessman who shared his personal journey of choices, consequences, and repentance. Mr. Tilson spoke candidly about mistakes from his past, including a white-collar crime that led to prison time earlier this year for defrauding investors and concealing the truth. He also described his ongoing efforts to rebuild trust and live a life of greater honesty and responsibility. To get a sense of his story, please feel free to watch an interview of Mr. Tilson’s from last year on the Kosher Money podcast.

In the past, Mr. Tilson had not viewed lying as a big deal, often using it as an easy way to avoid discomfort or conflict. However, facing the consequences of fraud caused him to reevaluate, and now he prizes truth highly. Lying causes issues to fester, he explained, rather than getting resolved the way they need to be. Even if telling the truth can make a situation awkward or uncomfortable, it is important to say things directly. He added that truth telling “is a muscle,” and just like how, in sports, a person must work on “the fundamentals” in order to succeed when big opportunities come along, a person needs to practice truth telling even in small situations in order not to fall into the habit of lying in a more impactful moment. He stressed the value of empathy, which is a vital aspect of honesty, and highlighted his choice to take accountability and be honest publicly about his mistakes.

His message to students was both powerful and sobering: how small compromises in honesty can snowball into destructive patterns, how easy it is to rationalize harmful decisions, and how essential it is to remain vigilant about truthfulness in even the smallest matters. At the same time, his story underscored the possibility of teshuvah – that accountability and change remain possible even after serious missteps.

Students continued to reflect on the assembly when they went to their advisory sessions. In small groups, they discussed what stood out to each of them from the talk and how the ideas connected to their own lives, such as the common temptation to make excuses rather than be upfront to avoid inconvenience, and how cutting corners is not as “victimless” as it may seem. The students were grateful to hear the surprising talk and will take this lesson with them into Yom Kippur and beyond.