Meaningful Life Skills with Rabbi Simon Jacobson

By Rabbi Simon Jacobson

Join Rabbi Simon Jacobson, an embodiment of inclusive spirituality and wisdom, as he examines life & offers a comprehensive blueprint of the human psyche. Discover how to live a truly happy and me... more

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The podcast currently has 442 episodes available.

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Number 1: Sukkot: When Joy Takes Over
Joy. What a beautiful word. Is there a word more joyous than joy?Imagine living with a sense of happiness and joy—not just in fleeting moments, but as a way of life. For many of us, that sounds almost impossible.When we’re young, we’re idealistic. But then life happens. We get hurt. Dreams are dashed. Promises go unfulfilled. We experience loss, disappointment, frustration, even betrayal. And suddenly, the idea of living with continuous joy can seem naïve.Of course, we all have moments of happiness: the birth of a child, a wedding, a graduation, a celebration, a success. But those are moments. What about something deeper? Something that isn’t dependent on what happens around us?Can a person actually cultivate a life of joy?It may surprise you to discover that the answer doesn’t necessarily lie in external circumstances. The deepest source of joy may be found much closer to home—in the very depths of our soul, in a reservoir of meaning and vitality that is always there, even when it becomes buried beneath the noise and challenges of life.And this brings us to Sukkot, the holiday of joy—the time of our rejoicing.But here’s the question: Can joy be cultivated? Can we actually do something to become more joyful?And the answer is yes.Please join Rabbi Simon Jacobson as we explore the deeper secret of joy—and discover how to access that reservoir within us. And without using the word guarantee, I can assure you: by the end of this journey, you’ll have something to smile about.
September 24, 202634min
Number 2: The Return That Takes You Higher
We all have regrets. Mistakes we wish we could correct. People we may have hurt and would like to ask forgiveness from. Moments and situations we wish we could go back and change. But how do we truly repair the past? There is the familiar concept of repentance—atonement, asking forgiveness, making amends, changing our behavior, healing relationships, and rebuilding trust where it may have been broken. But Judaism offers us a deeper concept, especially at this time of year: Teshuva—return. Not simply repentance. Not simply regret. Return. Which immediately raises the question: Return to what? Teshuva means reconnecting with something deeper within ourselves—a place that existed before the mistake, before the transgression, before we lost our way. Are you at heart a sinner or a saint? There is a radical difference between remorse over the past and returning to who you truly are. And that is the secret: Teshuva isn't simply about damage control; a band-aid fixing past wrongs. It’s about reclaiming your essence and thereby transforming the past and allowing it to propel you forward. A liability can become an asset. A mistake can become a source of wisdom. Even a fall can become the catalyst for a higher ascent. So what are we returning to—and how can that return take us higher? Please join Rabbi Simon Jacobson for this timely and important discussion: The Return That Takes You Higher
September 17, 202627min
Number 3: The Power to Begin Again. Rosh Hashana and September 11
The 25th anniversary of September 11th this year coincides with Rosh Hashana. What can we learn from this powerful convergence? Every one of us remembers exactly where we were on September 11, 2001. I remember it vividly. I went to the rooftop of my office building in Brooklyn and saw the two towers smoking—already struck, already devastated. Nearly 3,000 people lost their lives. Lower Manhattan, the heart of the world’s financial center, seemed to have been destroyed beyond repair. The Twin Towers’ shocking collapse inflicted such trauma that many wondered if we could ever recover. But it wasn’t only the buildings that were shaken. The American psyche was shaken. The threat of terrorism, which had seemed so far away, had suddenly arrived at our doorstep. No one knew what would happen next. There was confusion, fear, uncertainty. September 11th fell on a Tuesday, just days before Rosh Hashana. I remember spontaneously writing a heartfelt article titled, “Today the World Trembles. Today the World Is Born.” It was inspired by the words of the Rosh Hashana prayer: Hayom harat olam—today the world trembles and is born. The world certainly trembled that day. But, at the same time, the world was also being born. Twenty-five years later, look at Lower Manhattan. What seemed irreparably shattered was rebuilt. Not simply restored, but transformed—rising again in ways few could have imagined. Its population has tripled, social life is thriving -- the neighborhood has come roaring back, making it the envy of other U.S. downtowns. And that raises a profound question: What is the secret of rebuilding after destruction? This isn’t only a question about cities and buildings. It is a question about each of us. We all experience moments when our own “towers” come crashing down—loss, disappointment, failure, confusion, emotional pain. Sometimes life can leave us feeling that something has been destroyed beyond repair. How do we rebuild? How do we grow through the pain rather than simply survive it? How do we transform what happened to us into something that strengthens us? Perhaps this is one of the deepest messages of Rosh Hashana: the power to begin again. Every year, we are given the opportunity not merely to turn the page, but to create a new beginning—to rebuild, renew, and become something greater than we were before. Please join Rabbi Simon Jacobson for a special pre-Rosh Hashana program on September 11th as we explore The Power to Begin Again—the power to turn trembling into rebirth, destruction into rebuilding, and a new year into a new beginning.
September 14, 202627min
Number 4: From Reflection to Renewal. Looking Back with Gratitude, Moving Forward with Purpose
Every healthy organization, every company, every living organism needs moments to stop and take stock. How are we doing? What worked? What didn’t? What can we learn? What needs to be repaired? And most importantly: How do we take those lessons and create a better future? This time of year gives us that opportunity. It is a season of reflection, introspection, and soul-searching. But true reflection requires two essential ingredients. First, accountability—the courage to look honestly at our lives. To acknowledge what we’ve been blessed with and express gratitude, while also having the honesty to recognize what needs repair and where we can do better. And then comes the second step: renewal. We cannot remain trapped in the past. Reflection is not about looking backward for its own sake; it is about looking back so we can move forward—with greater clarity, purpose, and intention. Please join Rabbi Simon Jacobson as we mark this important milestone in our lives: From Reflection to Renewal: Looking Back with Gratitude. Moving Forward with Purpose.
September 03, 202625min
Number 5: You Don’t Have to Search for G-d—He’s Already Near
One of the most universal questions human beings have ever asked is: Where is G-d? Where and how can I find Him? From the beginning of history, people have searched for answers—in books and debates, in songs and poetry, even through wars fought in G-d’s name. Recently, I asked one of my young grandchildren, “Where is G-d?” He answered, “G-d is invisible. He’s everywhere.” Is that the answer? Perhaps we need to revisit our very understanding of G-d and where His presence can be found. Perhaps the deeper truth is that we don’t have to search for G-d at all. He is already here. The question is: Are we open to letting Him in? Please join Rabbi Simon Jacobson for this vital discussion as we explore the timeless teaching of the Kotzker Rebbe, who, when asked, “Where is G-d?” answered: “Wherever you let Him in.”
August 26, 202634min