Meaningful Life Skills with Rabbi Simon Jacobson

The 42 Journeys of Life – Part 4: Middle Age
The Quiet Question of Midlife: Is This All You Are Meant to Be?
How do you reach the Promised Land?
Each of us carries dreams, aspirations, goals, and a vision of the life we hope to build. We all seek success, fulfillment, happiness, and purpose. But what is the path that leads us there? Is there a map for navigating life's twists and turns?
The Torah's answer is yes.
Before the Jewish people entered the Promised Land, they traveled through the wilderness, passing through forty-two distinct journeys. These journeys were not merely historical events; they are the blueprint for every human life. Each of us must travel our own wilderness, facing challenges and setbacks, triumphs and breakthroughs, moments of uncertainty and moments of inspiration.
In this fourth installment of our seven-part series, The 42 Journeys of Life, we arrive at the pivotal stage of Middle Age—the season when many begin to hear the quiet but persistent question:
"Is this all I am meant to be?"
Having traversed the first twenty journeys—the formative years of childhood, the excitement of growth, and the early challenges and struggles that shape our character—we now enter a new chapter. A chapter of reflection, reassessment, and deeper self-discovery.
Every stage of life brings its own lessons and opportunities. The key is to recognize where you are on the journey, understand the unique challenges of that stage, and learn how to navigate them with wisdom and purpose.
Join Rabbi Simon Jacobson as we explore the next phase of the wilderness journey and discover how every step, every challenge, and every transition is part of a greater path—leading us toward our own Promised Land: the fulfillment of our mission and the actualization of our deepest potential.

Life is a journey. In fact, the great mystic the Baal Shem Tov teaches that each of us travels through 42 distinct journeys in the course of our lives. The 42 journeys the Jewish people traversed in the wilderness, as recorded in the Torah, are not merely ancient history; they are a map of the human soul and a mirror of our own life's voyage.
Every stage, every twist and turn, every ascent and descent, every triumph and setback is part of a larger choreography. When you begin to see your life not as a series of disconnected events but as a purposeful journey, patterns begin to develop and it starts to make sense. The challenges do not disappear, but your ability to navigate them is transformed. You recognize that every step, every encounter, and every obstacle carries within it an opportunity for growth and discovery.
In Part Two of our seven-part series, The 42 Journeys of Life, we continue the expedition. Having explored the first five journeys—the formative years in which our identity begins to take shape—we now enter journeys six through twelve, where we begin to develop the tools to confront adversity and discover our inner strength.
Please join Rabbi Simon Jacobson for Part Two: The Forces That Try to Break You Before You Become You—an exploration of the early challenges that test us, shape us, and ultimately reveal who we are meant to become.

In the second year [of the Exodus], on the 20th of the second month, the cloud rose from the Tabernacle of Testimony. The Israelites thus began their travels, [moving on] from the Sinai Desert [until] the cloud came to rest in the Paran Desert. This was the first journey at G-d’s word through Moses (this week’s Torah portion – 10:11-14)
Thus began the 13th of the 42 journeys through the wilderness. After the Jewish people camped at Sinai on the first of Sivan 2448, they remained there for close to a year (exactly 10 days less than 12 months), until the 20th of Iyar 2449, when the cloud rose, signifying the time to move on.
After the Torah elaborates on the events that transpired from the time the Jews arrived at Sinai on the first of Sivan 2448 (in the chapter Yisro in the book of Exodus), through the building and erection of the Temple on the first of Nissan 2449 (the latter chapters of Exodus), through the entire book of Leviticus and the first two and a half chapters of Numbers, the Torah resumes the story and begins to relate the series of journeys traveled by the Jewish people in the wilderness. The rising of the cloud in this week’s portion is essentially continuing the story where it was left off at the end of Exodus, when the cloud first descended on the Tabernacle.
As we now begin to read the story of the long and tedious journey, we bring you the first installment of a new series from Rabbi Jacobson, that outlines the psycho-spiritual 42 journeys that each of us go through in our own lives.

Jack, Charles, and Henry — three successful business colleagues — go out on a rowing trip. One is a financier, another a high-tech executive, and the third a prominent attorney. As they row across the water, Jack suddenly falls out of the boat.
Charles and Henry panic. They stretch out their hands and cry, “Jack, give me your hand! Give me your hand!” But Jack doesn’t respond.
Then Charles changes his words. “Take my hand!” Immediately Jack grabs hold, and they pull him to safety.
Henry turns to Charles, puzzled. Charles smiles and says, “You have to understand — Jack doesn’t know how to give. He only knows how to take.”
And that raises a profound question for each of us: Are we takers, or are we givers?
It’s not an easy question. We live in a world driven by survival, competition, and self-interest. We are conditioned to believe that the more we take, the more secure and successful we become.
But perhaps the opposite is true.
Perhaps the tragedy of being a taker is not only what it does to others — but what it does to us. Because when you only take, you never truly discover who you are.
Giving is not weakness. Giving is the ultimate expression of strength. It is the way we actualize our deepest potential. A giver is not defined by what they lack, but by what they possess within — the ability to contribute, to nurture, to illuminate, to transform. The more you give, the more you become.
Please join Rabbi Simon Jacobson in this vital discussion and discover: How do we move from being consumers of life to creators of life? From takers to givers?
And that makes all the difference. That change of attitude and direction -- from the inside out, instead of the outside in -- changes everything.

Do you believe in love that lasts forever?
It’s a beautiful idea—the language of films and novels. We all long to find that one person we can love endlessly. But is that truth, or is it just a dream? After all, everything in this physical world changes. It ages, it fades, it comes and goes.
So what makes love different? Why would love be the exception?
This is not just a philosophical question—it shapes everything. The choices we make, the commitments we’re willing to fight for. If everything is temporary, how deeply do we invest? Why give ourselves fully to something that won’t last?
And yet, we can’t let go of the idea. Something in us insists that love can be eternal.
So is it real—or is it illusion?
The answer depends on one thing: what do you mean by love?