The Wisdom of the Long Short Road: Finding Purpose Through Struggle

Rabbinic parables are uniquely complex and multi-layered stories that contain many levels of meaning—some levels intentionally hidden. While those unfamiliar with the framework may not notice the hidden insights, they may easily grasp a moral lesson from the surface. There is something for everyone.

The Setup

When Midrash¹ appears in the Talmud, it is known as Aggadah, which means "story." Some consider these to be the 'soul' of the Talmudic literature.

The particular Aggadah below comes from tractate Eruvin 53b, and is part of a discussion on the laws of eiruv. Eiruv (עֵרוּב) means 'merging' and largely focuses on the laws that govern boundaries for carrying items on Shabbat. However, like many Talmudic stories, this one transcends its legal context to offer moral and spiritual wisdom.

It goes like this:

The Long Short Road

Once, Rabbi Yehoshua was traveling when he reached a fork in the road. A young boy was sitting there. The rabbi asked him, “Which way leads to the city?”

Pointing—and perhaps cryptically—the boy answered:

“This road is short, but long.
That road is long, but short.”

Perhaps focused on the word "short," Rabbi Yehoshua took the "short but long" way—only to find himself blocked by gardens, orchards, and other obstacles. He was forced to turn back.

When he returned to the fork, he asked the boy, “Didn’t you say this was the short way?”

The boy replied, “Yes, but it is long.”

Understanding the boy's message, the rabbi kissed him on the head and praised him for his wisdom—this time, setting out for the long but short way.

There are multiple elements to draw from this story.

1. The Illusion of Shortcuts

Our world of duality never fails to give us options, sometimes difficult choices. This is by design.

No matter what we're trying to achieve, whether it is getting healthy, acquiring wisdom, financial security, or spiritual growth—we will always be given similar choices: a long, more winding route, and a shortcut.

But as my Rabbi always reminded me, "There are no shortcuts in life." This is what the Talmud is teaching us: that the longer path may be the truest route to fulfillment.

There is good reason for this. The trials we will face on the “long" road serve a greater purpose. They often build wisdom, resilience, and sustainable spiritual growth that prepare us for the next level.

2. Gardens and Orchards

Notice how the story tells us Rabbi Yehoshua was blocked by gardens and orchards that prevented his progress. Gardens (גנות) and Orchards (פרדיסין) are multi-layered metaphors of their own.

Gardens can represent the Garden of Eden, and sometimes the world itself. The same can be said of Orchards, but these have another meaning, as well. Orchards are often a metaphor for Pardes², the esoteric levels of Torah wisdom.

We find this idea in the famous story³ of the Rabbis who tried to enter the orchard (pardes), a metaphor for mystical knowledge. Most of them failed.

The lesson for us might be to slow down. There is much to uncover for those willing to invest the time, effort, and humility.

Those who rush to attain Biblical wisdom, without having built the proper foundation, may fail to understand it properly. This is why Torah learning will take all of us a lifetime.

Those looking for “shortcuts” in spiritual growth—mystical experiences without grounding—often find themselves lost or overwhelmed.

It is the slow but steady approach that builds a pathway that leads somewhere enduring. The road that seems longer is the road that actually gets you there.

This is also backed by data. Neuroplasticity tells us that deep change in the brain happens gradually and through methodical repetition. Not instantly.

3. The Soul

Lastly, this story, told by Rabbi Yehoshua, actually comes as the final in a series of 3 other stories. A chazakah. Rabbi Yehoshua recounts the three times he was defeated, once by a woman, a girl, and also a boy.

In this, the parable of the boy is part of a larger sequence of parables that combine to form a bigger picture. This, too, is seen in the Gospels, where a consecutive series of parables form the constellation of an overarching message.

Anyhow, later Kabbalists⁴ have noted hints in the text that indicate that these stories may correspond to the levels of the soul. The story of the woman represents the Neshamah⁵; the story of the girl represents Ruach⁶, and the story of the boy the Nefesh⁷.

Through this lens, the rabbi's initial choice of the “short and long” road reflects the soul’s temptation to follow the desires of the Nefesh for quick results, perhaps driven by worldly, or lower goals. Being blocked by the orchards represents the humbling need for development that the soul requires to make it to its destination.

The blockages may also represent the natural fences created in our world where enlightenment cannot be achieved by brute force, but through purification and discipline.

Though there is much more to uncover, this is where I will leave the story for now.

The paradox is that shortcuts are an illusion. Often it is our trials that teach us the most, and our failures that become the most transformative. The journey is the destination, and it is the slow and steady road that will be worth it in the end.

Notes:

¹ What is Midrash?

² Pardes, Jewish Hermeneutics

³ Chagigah 14b

⁴ See Ben Yehoyada commentary on Eruvin 53b

⁵ Neshamah - Soul Series Part 3

⁶ Ruach - Soul Series Part 2

⁷ Nefesh - Soul Series Part 1