"And you shall rejoice in your holiday…"  In three separate verses the Torah directs us to be happy on Sukkot, giving the holiday its secondary name, "The Time of our Rejoicing".  The concept of happiness, however, is hard to define.  What does the mitzvah of "simchat yom tov" entail?   Is Hashem commanding us to feel an emotion?   Is that something we can control?  What if we happen not to feel joyous on the holiday?

Rashi explains that joy is indeed an emotion, but that the verse is not a command but a promise.  Hashem is not demanding that we be joyous, since that might not be subject to our will.  Rather, He is promising us that we will feel that way on the holiday.

A second approach suggests that happiness is cognitive in nature.  The Torah specifies that we should rejoice "before Hashem", suggesting that the mitzvah must be done with Hashem in mind.  Happiness, thus, might refer to recognizing Hashem as the source of the good we have been given and being happy in our lot.  Sukkot is set during the harvest season, a time in which many actually forget Hashem, and instead attribute their successes to themselves.  As such, it is an appropriate juncture in which to pause and reflect on the true reason for our joy and blessings, and thank Hashem who has provided for us.

The Rambam notes that the obligation of joy in the Torah speaks of both an individual's own family and the Levite, widow, orphan and sojourner.  According to him, part of the way in which we rejoice is to make others happy.  We must not only enjoy the gifts we have been given, but also give of our gifts to others. True happiness is not internal, but external.

The above approaches are not mutually exclusive, and in fact might even complement each other.  When we recognize the good we have been blessed with by Hashem, we naturally want to share with those less fortunate than ourselves.  Hashem promises that if we do so, He will continue to give us an abundance of good so that we may serve Him in happiness.

With wishes for a Chag Sameach and Shabbat Shalom!