Meaningful Life Skills with Rabbi Simon Jacobson

Do you have commitment issues?

These days that phrase has become almost a cliché. A convenient excuse. You hear it all the time—serial daters saying, “We’re together, but don’t expect a commitment. I have... commitment issues.”

For some, commitment feels like a burden. Like a noose around the neck. “Why tie myself down?” they say. “I need an exit strategy. I want to keep the back door open.”

I once met a guy who told me—proudly—that h...

Would you consider yourself a humble person?

Most of us would agree that humility is a virtue—something noble and worth aspiring to. And for good reason. A humble person coexists peacefully with others. Humility allows for flexibility, for yielding. It builds bridges and fuels healthy relationships. Arrogance, on the other hand, breeds conflict, distance—even abuse.

So why is humility so rare?

Some may challenge the very premise and a...

Is resilience something we’re born with—or is it something we learn? Why is it that when life throws challenges our way—setbacks, failures, disappointments—some people bounce back faster, while others struggle to find their footing? Is that strength hardwired into them, or is it something we can all develop?This question touches every one of us. No one is immune to pain—be it a broken dream, a betrayal, or a deep personal loss. We ...

Do you feel like your life is chaotic—especially lately, with all the disruptions and upheavals?

Uncertainty seems to be the new norm, throwing us off balance, leaving many of us feeling confused, even overwhelmed.

Chaos can be disorienting. Sometimes it shakes us to the core. Other times, it gnaws at us quietly—we compartmentalize, minimize, escape. At best we work around and try to cope with chaos. But the inner turbulence remains.

...

How do we make sense of the turbulence and upheavals shaking our world today? Just glance at the stock market — a mirror of our times, swinging wildly with volatility, reflecting trade wars, tariffs, and global conflicts from Gaza to Ukraine. President Trump, in many ways, personifies this era of disruption.

But disruption is not inherently negative. The question is: how do we understand it?

Because one thing is certain — unpredictab...

We all seek healing from psychological and emotional wounds like childhood abuse, trauma, abandonment, and loss. These wounds create fears and insecurities, and undermine our trust, inhibiting us from reaching our potential. Often, we turn to destructive behaviors for relief. Addictions of all sorts may result from the deep void in our psyches. How many hours of therapy are spent, how many medications are ingested -- all attempting...

Frederick Douglass famously said, "It is easier to build strong children than to repair broken men." Can we even begin to estimate the staggering cost—financial, emotional, and societal—of fixing broken adults? Therapy, medication, addictions, ailments—endless attempts to numb the pain of fear, insecurity, dysfunction, trauma.

Imagine how much could be saved—how much suffering could be avoided—if we focused on building str...

Would you sign a contract without reading it? Would you make a serious commitment without first understanding the details and implications?

Most people would instinctively say, Of course not! First, we understand—then we act, then we commit.

And yet, the great paradox of life—the true secret to deep, lasting, and eternal connections—is precisely the opposite: commitment before full understanding.

This was the defining moment at Sinai,...

We speak much about freedom—but are we truly free? Bob Dylan famously sang, “Gotta serve somebody.”

You may be an ambassador to England or France,
You may like to gamble, you might like to dance.
You may be the heavyweight champion of the world,
You might be a socialite with a long string of pearls.

But you’re gonna have to serve somebody, yes indeed.
You’re gonna have to serve somebody.
Well, it may be the Devil or it...

How much of your potential have you actualized?

That’s actually a trick question. Because the real question is: Do you even know how much potential you have? You can’t measure what you've actualized until you first recognize the vastness of your inner reservoir—your treasure chest of talents, skills, and gifts, both inherent and acquired.

This touches on a fundamental truth: each of us is blessed with unique abilities, shaped by ...

What is the secret to true happiness? Is it simply a matter of having positive experiences while avoiding pain? If that were the case, why do we see people who have endured immense suffering radiate joy, while others, blessed with easier lives, remain bitter and despondent?

Real happiness is not about escaping hardship or pretending challenges don’t exist. It’s not frivolous joy or denial. True joy emerges not despite pain, but alon...

What is holding you back from living up to your greatest aspirations, your dreams, your ideals? What is stopping you from actualizing your full potential? Is it fear? Bad luck? A lack of skills or motivation? Or perhaps it’s all of the above? Maybe there are even deeper, unseen forces—subconscious patterns, societal pressures, or past experiences—blocking your path without you even realizing it.

One thing is certain: Each of us year...

Are you a leader or a follower? Many people assume they aren’t born leaders—that leadership requires ingrained charisma, courage, and wisdom, while they need guidance and direction from others. But is that really true?

We all need mentorship, education, and teachers, but does that mean we must conform? Following guidance is one thing—losing your individuality is another. Leadership isn’t about commanding the masses; it’s about in...

Do you ever feel like life is a masquerade—constantly switching masks depending on where you are, who you're with, and what’s expected of you? At work, at home, in social settings—always performing, always adapting, living up to others’ demands.
And then you pause and wonder: Where am I in all of this? What part of me has been lost?
We live in a world where inauthenticity has become the norm. We're not just talking a...

I came across a cartoon recently: two people sitting at a bar, and one asks the other, "Do you remember when you stopped caring?"

It struck me deeply and made me think; how many of us truly care? Care about others, care about events in the world... And not in a superficial way—curiosity, sensationalism, or a passing interest—but really care. When someone is in pain, do we feel it? Whether it’s a loved one or a stranger, d...

We often find ourselves living in the moment, consumed by its immediate demands and emotions. But true wisdom lies in stepping back and seeing the bigger picture—connecting the dots, identifying patterns, and gaining a bird’s-eye view. This perspective not only enriches our understanding of life but also empowers us to bring greater meaning and direction to the details of our daily existence.
Yet, it’s not easy. Living in the mome...

As we welcome the New Year, one of the most pressing questions -- and modern-day dilemmas -- is: how can we sustain our New Year’s resolutions? Whether it’s losing weight, launching a new project, mending a relationship, or breaking a habit, the resolutions we make often struggle to last beyond a week—sometimes even a day.

This year, the New Year aligns with the final day of Chanukah, when we light all eight candles of the menorah...

With the recent, bloodless fall of the oppressive Assad regime in Syria and the arrival of the holiday of Chanukah, it's impossible to overlook the striking parallels between events of millennia ago in Syria and those unfolding today. These connections offer profound lessons for our personal lives and the world at large.What did Syria symbolize in the time of the Maccabees, and what does it represent now? What can we learn from th...