Simon Jacobson is addressed in the correspondence of the Lubavitcher Rebbe, Rabbi Menachem Mendel Schneerson, as a dedicated Chassid involved in communal activities and outreach, particularly relating to the observance and inspiration of fellow Jews.
The Rebbe's letter to Simon Jacobson (dated 1 Teves, 5712) responds warmly to a report Jacobson sent regarding a Yud Tes Kislev gathering, a significant date in the Chabad calendar. The Rebbe expresses appreciation for the update, though he notes it was somewhat general, and emphasizes the importance of translating good resolutions made at such gatherings into concrete action, quoting the teaching, "Not study is the main thing but action." The Rebbe encourages Jacobson to continually remind and motivate participants to fulfill their commitments and to use future gatherings as opportunities to inspire further observance.
The Rebbe also references a teaching from Chassidus, highlighting the responsibility not only to purify oneself but also to inspire and uplift others. He blesses Jacobson with success in these endeavors and expresses anticipation for further good news from his activities.
In a postscript, the Rebbe addresses a specific question from Jacobson regarding his interactions with Jews in various countries, including those who are not yet fully observant of Torah and mitzvos. The Rebbe affirms the longstanding Chabad approach of not distancing such individuals but rather drawing them closer to G-d through gentle words and acts of kindness. He cautions that while outreach should be done with care and without compromising one's own standards ("one should not lower oneself to the other's level, but rather elevate the other"), it is important to extend a helping hand—even a far-reaching one—when needed. The Rebbe assures Jacobson that this approach, when carried out with the proper caution, is successful and is the path that should be followed, expressing confidence in its positive results.