Why are the Goblets Upside Down? 
In his drawing of the Menorah, Maimonides drew the "cups" that were on the base and branches of the Menorah as upside-down cups (Maimonides writes that the goblets "had wide mouths and narrow bases"; in the drawing, the wide end of the goblets face downward). This detail seems, at first glance, inconsistent with the principle explained in the Talmud that when performing a Mitzvah with an object, it must be held or placed in its natural position:
Ḥizkiya said that Rabbi Yirmeya said in the name of Rabbi Shimon ben Yoḥai: With regard to all objects used in performance of each and every one of the mitzvot, a person fulfills his obligation only when the objects are positioned in the manner of their growth. One must take the lulav with the bottom of the branch facing down, as it is stated with regard to the beams of the Tabernacle : "Acacia wood, standing" (Exodus 26:15), indicating that the beams stood in the manner of their growth.
Why then were the cups of the menorah upside down?
The answer must be that, at least in the context of the Menorah, the cup's natural position was not to receive and contain but rather to pour and share. The purpose of the temple in general, and the Menorah in particular, was not to create a sanctuary of light and inspiration for the temple itself, but rather to "pour", shine, and influence the rest of the world.
Perhaps we can apply this lesson to our own lives. There is a built-in tension regarding our metaphorical "goblet," our defined personality, talents, and skills. Are we a goblet that "receives" or one that "pours"?
Within each of us, there are two opposing drives. On the one hand, we want to self-actualize, to achieve and enjoy a degree of success, recognition, meaning, and significance. On the other hand, deep within our souls is the desire to transcend itself, to submerge within something greater than ourselves. As the Tanya explains, the Torah refers to the soul as a candle because just as the fire surges upward as if to escape the wick, so too does the soul seek to escape the confines of its independent existence and "unite with its origin and source in G‑d, blessed be He, who is the fountainhead of all life. Though thereby it would become null and naught, and its identity would there—in its source—be completely nullified, with nothing at all remaining of its original essence and self, this is its will and desire by its nature."
Perhaps the Menorah's lesson is that we need to create a goblet which receives and contains our success. Yet, the ultimate purpose of creating a vessel which "contains", why it matters to us to accomplish and to feel significant, is in order for us to "pour", to share the blessing with others. In the final analysis, our desire to be significant is itself part of the greater transcendence because the reason we crave to be a goblet that "contains" is in order for our goblet to "pour" and "share".
Adapted from the teachings of the Rebbe, Lekutei Sichos 21 Terumah 3