Meaningful Life Skills with Rabbi Simon Jacobson

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

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.

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.

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.”

If you could change one thing in your life, what would it be?
It’s an important question. But there’s an even bigger one: Is real change actually possible?
Our habits, patterns, routines, and the inertia of the status quo can hold tremendous power over us. We may want to change, but somehow find ourselves returning to the same place.
And yet, there are times when the energy for change is greater than usual—when we’re given the opportunity to transcend our past, access deeper dimensions within ourselves, and become who we were meant to be.
That time begins now.
The next 60 days are a journey—from where you are to where you can be. A journey of recognizing your potential and beginning to actualize it.
We call it the 60-Day Journey—the period we know as the High Holiday season. But rather than simply a season on the calendar, see it as an opportunity: a window to create real, lasting change.
Please join Rabbi Simon Jacobson for a timely and powerful discussion on how to access the dimensions within yourself you may have thought were beyond reach. Your next 60 days could change everything.