(condensed from Ein Ayah, Shabbat 6:15)
Gemara: When one puts on his shoes, he puts on the right shoe first and then the left shoe. When one takes off his shoes, he takes off the left shoe first and then the right shoe.
Ein Ayah: One should, on a regular basis, raise the realization that there is a difference in levels among matters of his daily life. This is a means to enable us to understand the difference between that which is lofty and that which is lowly. One should come to realize the advantage of that which is of a high level and is connected to true honor over lowly and despicable things in the world of external matters. That in turn will train us to choose good over evil and greatness over pettiness.
It is not that only matters of prominence must exist in our world; we need all different sorts of tools in our lives. However, we should internalize that there is a difference between one and the other. It is true that our physical side is not as important as our spiritual one, but our body is also the setting in which spiritual things find outward expression. Therefore, in the physical realm, as well, we should prefer powers of more prominence to those of lesser prominence and efficacy.
Hashem created man in a proper manner, and, therefore, it is for good reason that he granted greater strength to his right side. Actually, it is because the right side is more fit for the useful inclination toward the goals of life that he needs to accomplish. This shows that life is not formed by disjoint unfocused parts. Rather life is set according to the divine foundation for a lofty and specific purpose. The powers in a person’s life are more recognizable in his right side.
When one prepares himself to act, including by putting on shoes, which allows him to walk powerfully and freely, it is proper for the right foot to be ready for action first. Since there will be a need for other parts of his being to take part in his activities, as is regularly the case, the left foot should then be prepared as well to enable him to function. This should not be done not in an uncontrolled, unplanned set of actions without a clear purpose and decision-making process, where there is no difference between big and small. Rather, it should be done in a wonderfully thought out process and with the desire for holiness, which stems from a divine idea that realizes that there is a correct way to go about life. This includes giving precedence to the honorable and powerful right side.
The time comes when one has to limit his ability to act. This is when he needs to cease activity to enable the replenishment of his strength. This, in turn, is needed when the prominence of the left side, which represents weakness, has spread too much and has weakened the right side. Because of man’s tendency toward exaggeration and dangerous actions, he needs breaks in his activity, as both a respite for the spirit and for the body. Therefore, while the preparation for action, represented by putting on one’s shoes, begins with the right side, the ceasing of activities, represented by their removal, begins with the left and then continues with the right. The break returns the strength of spirituality to its place by withholding the tumult of the system of activity. Then his spirit is able to elevate itself back to its potential and to a connection to the divine light. He then becomes a healed person and a new being. “New in the mornings, Your trustworthiness is great” (Eicha 3:23).