A few years ago, I took my little boy to the Los Angeles Zoo on a sunny afternoon. A woman stopped to comment, "Your little girl is so cute." I thanked her and said, "By the way, it's a boy."

She was so surprised she could hardly speak. And I knew what caused her mistake: My boy had hair past his waist! I explained:

Traditional Jews often wait until a boy's third birthday before giving his first haircut. This is called "Upsherin" – a Yiddish word meaning to "cut off." The custom is first mentioned in "Sha'ar HaKavonot" by Rabbi Chaim Vital, the student of the great 16th century Kabbalist, the Arizal.

On his third birthday, a Jewish boy officially begins his Torah education.

The third birthday is a significant stage in the life of a Jewish boy. It is then that he officially begins his Torah education, and starts to wear a kippah and tzitzit.

On a developmental level, three years old is a key transition time. Until now, the boy was a baby – blanket, bottle, diapers. Now he is ready to move into the world of friends, school, etc. Cutting his hair at this time makes a strong emotional impression on the child. He knows that he is advancing to a new stage of maturity, and this helps him live up to the new role.

Interestingly, the Hebrew word for haircut, sapar, also means a boundary. The haircut sets a new standard of behavior; what was acceptable for a baby is now largely out of bounds.

Why Three Years?

The idea of three years as the transition stage derives from the mitzvah of orlah. The Torah says that if you plant a tree, all fruits which grow during the first three years are "orlah" – off-limits (Leviticus 19:23). Just as orlah fruit is off-limits for three years, so too we leave a child's hair alone during the first three years.

What's the connection? In various places, the Torah compares a person to a tree:

• "A person is like the tree of a field..." (Deut. 20:19)

• "For as the days of a tree, shall be the days of my people." (Isaiah 65:22)

• "He will be like a tree planted near water..." (Jeremiah 17:8)

Therefore, like orlah, we leave a child's hair alone during the first three years.

Why are people compared to trees?

A tree needs the four basic elements in order to survive – soil, water, air, and fire (sun). In a figurative sense, human beings also require the same basic elements.

Soil is where a tree needs to be firmly rooted. Humans also require a strong home base, where values and morals are absorbed, and which provides a supportive growth environment. Today, unfortunately, many trees are at risk of being blown down by the forces of media, materialism, and information overload. We need a "filter," a safe haven to return to and refresh. Home is the "soil" where we can be ourselves, make our mistakes and still be accepted, loved and nourished.

The Talmud (Avot 3:22) speaks of a person whose roots are numerous: "Even if all the winds of the world were to come and blow against it, they could not budge it from its place."

Both rain and Torah descend from the heavens and provide relief to the thirsty and parched.

Water is crucial as well. Without it, the tree will whither and die. The Torah is compared to water, as Moses says: "May my teaching drop like the rain" (Deut. 32:2). Both rain and Torah descend from the heavens and provide relief to the thirsty, giving zest and vitality to the human spirit.

The air contains oxygen that a tree needs for respiration, and carbon dioxide for photosynthesis. In an imbalanced atmosphere, the tree would suffocate and die. The Torah states that "God breathed life into the form of Man" (Genesis 2:7). The Hebrew word for "breath" – nesheema – is the same as the word for "soul" – neshama. Our spiritual life force comes, metaphorically, by way of air and respiration.

A tree needs fire (sunlight) to survive. Humans also need fire, symbolized by the warmth of community. People absorb the energy of peers, friends, family, neighbors and associates – and channel that into identity and actions. Essential Jewish observances are based on community, including the celebrations of birth until death. If we don't attach ourselves to a strong community, we risk being cast into the pale bleak anonymity of urban life.

In other words, a person is like a tree.

Spiritual Blockage

The term "orlah" appears in three different references in the Torah, regarding 1) fruits, 2) Bris Milah, and 3) the pursuit of truth. But what does the word "orlah" literally mean? And what is the connection between these three references?

The first reference, in Leviticus 19:23, is that fruits which grow during the first three years are classified as "orlah" and not eaten. Nachmanides explains that while the tree is yet immature, there is an excess build-up of fluids in the fruits which can prove harmful if eaten. Orlah, as defined by Nachmanides, means "blocked up."

The second, and perhaps most famous reference to "orlah," is the foreskin removed during circumcision (Genesis 17:11). The commentators explain that this orlah also refers to blockage – in this case a spiritual blockage. A Jewish boy does not receive the full measure of his soul until the circumcision is performed, and for this reason the Torah notes the consequence of "spiritual excisement" for any Jewish male who does not have a Bris Milah (Genesis 17:14).

(Since this reference applies only to boys, the third-birthday haircut is only done with boys. But on a conceptual level, it applies to girls as well – as women also recite the line in Grace After Meals referring to "the Bris which You [God] sealed on our bodies.")

Barriers of the heart prevent one from seeing the truth.

The third reference to "orlah" is when God tells the Jewish people to "remove the orlah from your heart" (Deut. 10:16). Here the reference is symbolic; the Almighty is exhorting us to pursue truth. Doing so requires removing that which prevents one from seeing the truth – the "barriers of the heart."

It is therefore fitting that the day of the young boy's "upshern" (when he symbolically leaves the category of "orlah" vis-a-vis his hair) is also the day that he traditionally begins his Torah education. For Torah study is the primary way to unplug spiritual blockage, and to remove barriers that prevent one from seeing the truth.

As his hair is shorn off, the young boy feels he is moving into a new stage. For this is his day to remove the barriers.

Upsherin: "How-to"

A Jewish boy's third birthday is a special event filled with meaning and activity. For the haircut itself, it is customary for friends and family to take a snip. The first cut is done at the front of the head, at the spot where the boy will later place his tefillin upon becoming Bar Mitzvah.

After snipping, people give the boy a blessing for success in Torah. It is also a good idea to take the boy to receive blessings from great rabbis. Some also have a custom to weigh the boy's hair, and then give an equivalent value in gold or silver to charity – in the merit that the boy should have success in Torah.

One custom is to weigh the boy's hair, giving an equivalent value in gold or silver to charity.

The first haircut is often styled to give the boy "peyos" – the sidelocks. This is a glorification of the commandment not to closely crop the hair on the sides of the head (see Leviticus 19:27). "Peyos" can be as long or as short as you'd like, providing they are not fully removed. Adults can fulfill this mitzvah by wearing sideburns down to the middle ear.

Upsherin day also includes learning the Aleph-Bet with the child. A beautiful way to do this is to get a plastic-coated Aleph-Bet card, and place a bit of honey on each letter. Then have the child lick the honey while saying each letter. This is so the Torah should be "sweet on his tongue!"

We also teach the child the verse: "The Torah was commanded to us through Moses, an inheritance for all the Jewish people" (Deut. 33:4). These are the first words a Jewish child should be taught to say, since this communicates how each Jew has a unique, personal relationship with the Torah.

In Israel, many boys get their first haircut on Lag B'Omer, at the tomb of Rebbe Shimon Bar Yochai in Meiron. It's an incredibly joyous scene as thousands of boys receive their first haircut there all in one day!