Choosing to surrender free will

סוכות זכר לענני כבוד.

Sukkos is a remembrance of the Clouds of Glory (Ananei Kavod).

The mitzvah of sukkah recalls the protective Clouds of Glory with which Hashem surrounded Bnei Yisrael in the wilderness.

ומהיכן זכו בני ישראל לענני כבוד.

And from where did Bnei Yisrael merit the Clouds of Glory?

The Sefas Emes asks what Bnei Yisrael did to deserve this surrounding protection.

בזוה"ק זכרתי לך חסד כו' לכתך אחרי במדבר כו'.

In the Zohar HaKadosh: "I remember for you the kindness… your following after Me in the wilderness…" (Yirmiyahu 2:2).

The Zohar grounds the merit in the verse praising Bnei Yisrael for following Hashem into the uncharted desert with trust.

וכלל הענין ע"י שהכניסו עצמם תחת מלכותו ית' כי אחר יציאת מצרים יראו לנפשותם שלא יפלו שנית תחת ממשלת הסט"א.

The principle of the matter is: through their bringing themselves under His Kingship — for after the Exodus from Mitzrayim they feared for their souls, lest they fall a second time under the dominion of the sitra achra (the "other side").

They earned the Clouds by actively placing themselves under Hashem's rule, motivated by the fear of slipping back under the control of impurity from which they had just been freed.

ולכן אף כי הבחירה ניתן לאדם עכ"ז יש גם לזה בחירה.

Therefore, even though free choice (bechirah) was given to a person, nevertheless even this itself can be chosen.

Although every person is endowed with free will, one can use that very freedom to make a higher choice about how to use it.

שבוחר בכל נפשו שלא להיות בבחירתו.

That he chooses with his entire soul not to be left to his own choosing.

The highest exercise of free will is to choose, wholeheartedly, to surrender one's own independent choosing.

רק בוחר בהנהגתו ית' שינחנו באורח מישור.

Rather, he chooses His guidance, that He should lead him on a straight path.

Instead of relying on himself, a person chooses to be led by Hashem's direction, asking Him to guide him on the upright way.

וכדברים אלו ג"כ אחר ימי הדין ר"ה ויוהכ"פ שבנ"י נקיים מהחטא.

And matters such as these apply also after the Days of Judgment — Rosh Hashanah and Yom HaKippurim — when Bnei Yisrael are cleansed of sin.

The same dynamic of surrendering one's own choice plays out each year right after the High Holy Days, once Bnei Yisrael have been purified of their sins.

צריכין ג"כ לבחור בהנהגתו ית'.

They must likewise choose His guidance.

Fresh from the cleansing of Yom Kippur, they too must actively choose to be led by Hashem.

והוא ג"כ בחי' תשובה.

And this too is an aspect of teshuvah.

Choosing to subordinate one's will to Hashem is itself a form of return.

ומקודם הי' תשובה מיראה.

And earlier it was teshuvah out of fear (yirah).

The teshuvah of the Days of Awe is driven primarily by fear of judgment.

ועתה היא מאהבה ע"י שרואין חסד ה' שמחל לנו וטהרנו מן החטא.

And now it is out of love (ahavah), through seeing the kindness of Hashem, that He forgave us and purified us from sin.

By the time of Sukkos, the return is motivated by love — born of seeing how Hashem mercifully pardoned and cleansed us.

עכ"ז שבין אליו ומבינים שאין לנו מקום מעצמינו רק לחסות בצלו ית':

Even so, they return to Him and understand that we have no standing of our own — only to take shelter in His shade.

The culmination is the sukkah itself: recognizing that we have no independent foothold and our only place is to take refuge in Hashem's protective "shade."

Summary: Bnei Yisrael earned the Clouds of Glory by choosing to place themselves entirely under Hashem's rule after the Exodus — the highest use of free will being to choose to surrender one's own choosing. This same movement recurs each year: after the fear-driven teshuvah of Rosh Hashanah and Yom Kippur cleanses us, Sukkos becomes a teshuvah of love, in which we recognize we have no independent standing and our only true place is sheltering in Hashem's shade.