Listening For Its Own Sake
במדרש אשרי אדם שומע לי בשעה ששמועותיו לי כו'
In the Medrash: "Fortunate is the man who listens to Me" (Mishlei 8:34) — at the very moment that his hearings are directed to Me, and so forth.
The Medrash darshens the pasuk in Mishlei to mean that a person's good fortune is bound up specifically with the moment that his listening is directed toward Hashem.
פי' כי אין הכוונה אל השכר שיהי' לו מכח השמיעה
The explanation is that the intent is not to the reward that will accrue to him by virtue of his listening.
The Sfas Emes clarifies that the verse is not promising some future reward earned through listening.
רק האושר והתהלה הוא בשעה זו ששמועותיו לי
Rather, the fortune and the praise lie in this very moment, when his hearings are directed to Me.
Instead, the happiness and praise are found in the act itself — the very moment a person directs his attention to Hashem.
כמ"ש במשנה יפה שעה א' בתשובה ומעש"ט בעוה"ז מכל חיי עוה"ב
This is as the Mishnah states: "Better one hour of teshuvah and good deeds in this world than all the life of Olam Haba" (Avos 4:17).
He brings the Mishnah in Avos as a proof that a single moment of teshuvah and good deeds in this world outweighs all of Olam Haba.
שעה הוא רצון וזה עצמו ג"כ פי' שמוע תשמע להיות השמיעה עיקר המכוון שלא לשם דבר אחר
"Hour" denotes ratzon (a moment of favor), and this itself is also the explanation of "if you will surely listen" (Devarim 28:1) — that the listening be the essential aim, not for the sake of anything else.
The word "hour" hints at a moment of ratzon, and this is the meaning of "shamoa tishma" — that the listening itself be the goal, done purely for Hashem and not for any ulterior motive.
וזה בשעה ששמועותיו לי לשמי
And this is "at the moment that his hearings are directed to Me" — for My sake.
This is precisely the avodah of directing one's hearing to Hashem for His sake alone.
וממילא נמצאין לו כל הברכות לכן כ' ובאו עליך כו' הברכות כו' והשיגוך משמע בהיסח הדעת וכ"פ בספורנו ע"ש
And as a matter of course all the berachos are found to come to him; therefore it is written "and there shall come upon you... the berachos... and they shall overtake you" (Devarim 28:2), which implies that they come when one is not even thinking of them, and so the Sforno explains as well — see there.
Once a person listens for Hashem's sake, the berachos arrive on their own, unsought — which is why the pasuk says they "overtake" you, coming when you are not focused on them, as the Sforno also explains.
וגם והי' לשון שמחה להיות האדם שש ושמח בשמיעתו לש"ש:
And likewise "and it shall be" (vehayah) is an expression of simchah — that a person be glad and rejoice in his listening for the sake of Heaven.
Finally, the word "vehayah" expresses simchah — that a person should be filled with joy in serving and listening to Hashem for the sake of Heaven.
Summary: The Sfas Emes explains the Medrash on "Fortunate is the man who listens to Me" to mean that a person's true fortune is not a future reward earned through listening, but the very moment in which he directs his hearing toward Hashem. He proves this from the Mishnah in Avos, that one hour of teshuvah and good deeds in this world surpasses all of Olam Haba, since "hour" denotes a moment of ratzon — and so too "shamoa tishma" teaches that the listening itself must be the essential goal, done purely for Hashem's sake and not for any other purpose. When a person listens in this way, the berachos come to him as a matter of course, arriving unsought, which is why the pasuk says they "overtake" him. The word "vehayah" further teaches that one should serve and listen to Hashem with simchah, rejoicing in the avodah itself.