One of the simple explanations for the commandment to dwell in a sukkah on the Festival of Sukkot lies in the dual feeling that the experience creates.
On the one hand, there is the sense of exile, of leaving one’s house to dwell in a temporary structure, but there is also a feeling of recollection as we remember the exodus from Egypt.
In dwelling in the temporary structure of the sukkah, we give up all our bounty and abundance.
We return to the nation’s original condition, to the experience of wandering and deficiency, wherein there is only faith and hope for the future but nothing substantial in the present.
Indeed, if one can live temporarily in the wilderness and once again be a wandering, dispossessed exile, he can view his life in a different – joyful – way.
–Rabbi Adin Steinsaltz
From as essay published in 2013 by Rabbi Adin Steinsaltz