The Truth About Why Most People Feel Stuck

Most people don’t even realize they’re trapped. They wake up every morning, follow the routine society expects of them, and chase the version of success they’ve been told is “right.” The job, the house, the vacations, the designer brands—it all looks good from the outside. But inside? Something feels… off.

The Illusion of Success

I once had a student, Jax from Queens, who was caught in this cycle. He was constantly comparing himself to his friends. If they got the latest designer sneakers, he needed them too. If they posted about luxury vacations on social media, he felt pressure to go somewhere just as extravagant.

Then one day, he stopped and asked himself a simple but powerful question:

“Do I even want this?”

That was the moment everything changed.

Jax realized he had been running a race he never even wanted to be in. He wasn’t chasing his own dreams—he was trying to keep up with someone else’s. And the worst part? It wasn’t making him happy.

That’s when we had a conversation about true success—not the kind that looks good on social media, but the kind that brings real fulfillment.

At CoolCantor Hebrew School, we emphasize personal growth and identity. Whether students are in Online Bar Mitzvah Lessons or working through their Bat Mitzvah training, I teach them to focus on their unique path, not someone else’s expectations.

The Crowd Isn’t Always Right

The truth is, just because everyone is chasing something doesn’t mean it’s worth chasing. The masses aren’t always heading in the right direction. If you follow the crowd blindly, you may find yourself lost, wondering why you’re not as happy as you thought you’d be.

Through Jewish Studies Online, our Weekly Torah Portion discussions remind students that standing out has always been part of the Jewish tradition. Think of Moses—he didn’t follow Pharaoh’s rules. He challenged them. Leaders aren’t the ones who fit in. They are the ones who dare to be different.

What Society Tells Us vs. What Actually Matters

Society says:
✅ Get the best grades.
✅ Go to the most prestigious school.
✅ Land the highest-paying job.
✅ Own the biggest house.
✅ Wear the trendiest clothes.

But true success is:
✅ Living with integrity.
✅ Finding a career you’re passionate about.
✅ Surrounding yourself with people who uplift you.
✅ Doing what brings you joy.
✅ Staying true to yourself.

I teach my students in Online Jewish Education and Bar Mitzvah Classes that their worth isn’t determined by what they own or how they compare to others—it’s determined by who they are and what they stand for.

How to Break Free From the Trap

If you’ve ever felt like Jax—constantly chasing what everyone else has but never feeling truly fulfilled—here’s how to break free:

1️⃣ Question Everything

If you’re chasing something, ask yourself: Do I actually want this, or do I just think I should want it?

So many people go through life chasing goals that weren’t even theirs to begin with. Maybe it’s becoming a doctor because your parents wanted you to. Maybe it’s buying expensive things because that’s what your friends do. But if you never stop to ask, “Do I actually care about this?” you could waste years going in the wrong direction.

2️⃣ Redefine Success for Yourself

What does winning look like for you? Not your friends. Not your classmates. You.

For Jax, he realized that true happiness wasn’t in luxury brands or impressing his peers. It was in being creative, pursuing his love for music, and spending time with the people who truly supported him.

For some, success might mean wealth. For others, it might mean having the freedom to travel, or making a difference in their community. You get to decide what success means for you.

3️⃣ Get Comfortable Being Different

If you always fit in, you’re not growing. If your choices never make people question you, you might not be making your own choices at all.

It takes courage to stand out. But when you stop seeking approval and start living authentically, life becomes so much more fulfilling.

4️⃣ Stop Comparing Your Life to Others

Comparison is a trap. The moment you start measuring your success based on someone else’s highlight reel, you’ve already lost.

Think about it: On social media, you only see the best moments of people’s lives—the vacations, the achievements, the celebrations. But you don’t see the struggles, the self-doubt, the disappointments.

Focus on your own path, not theirs.

What Jewish Wisdom Teaches Us About Authenticity

In Judaism Classes Online and our Weekly Torah Portion Study, we often discuss how Judaism encourages personal growth and authenticity.

Take the story of David and Goliath. David wasn’t the strongest, the biggest, or the most equipped warrior. He wasn’t trying to fit in with the rest of the army. Instead, he used his unique strengths—his slingshot and his courage—to win.

The lesson? You don’t need to chase validation. When you focus on your strengths and purpose, your moment will come.

Your Challenge

I want you to think about this:

1️⃣ What is one thing you chased in the past just because everyone else did? Was it a certain grade? A job? A material object? Did it actually make you happy?

2️⃣ Is there something you’re chasing right now just because everyone else is?

Take a step back and reflect. If it’s not what you truly want, give yourself permission to walk away.

Because at the end of the day, your life should be built around your vision. Not theirs.

A Final Thought

Jax from Queens realized that chasing someone else’s definition of success would never bring him happiness. He stopped comparing, stopped trying to fit in, and started pursuing what actually mattered to him.

You can do the same.

It’s not always easy to break free from the crowd. But the people who build incredible lives? They have the courage to walk their own path.

So what’s one thing you need to let go of today? Tell me in the comments. I’d love to hear your thoughts.

And if you want your child to learn these lessons early—about confidence, authenticity, and breaking free from societal pressures—CoolCantor Hebrew School can help. With Virtual Bar Mitzvah Lessons, Online Bat Mitzvah Training, and Online Jewish Studies Program, I help students develop not just knowledge, but life skills that will serve them forever.

Let’s build a generation of leaders who don’t follow the crowd—they lead it.