What I Learned About Confidence from Officiating Jewish Weddings in Toronto”

By Cantor Ben Silverberg

Jewish Wedding Officiant | Confidence Coach | Cantor & Life Mentor

⸻

It was a cold November morning in Toronto when I got the call. Mark and Anna, a beautiful Jewish couple deeply connected to their heritage, were planning their Jewish wedding ceremony and had heard about me—Cantor Ben—not just for my voice or services, but for the soul I bring into every moment.

As we sat down over coffee near their chosen Jewish wedding venue, I immediately felt their warmth. They wanted more than a cookie-cutter ceremony. They wanted a Jewish wedding celebration that would feel sacred, modern, and deeply personal. They had explored both traditional Jewish weddings and modern Jewish weddings, but neither fully captured what they were after: a ritual that reflected who they were becoming, not just who they had been.

As someone mentored by a great Jewish wedding Rabbi, I had been blessed to learn the Jewish wedding customs that go back thousands of years—the chuppah, the ketubah, the hora, and Jewish wedding music that lifts the soul. But what I’ve come to understand is that these traditions are only the starting point. What makes a wedding truly Jewish is intention. It’s about showing up with heart, humility, and hope—which is exactly what Mark and Anna did.

But this isn’t just a story about a Jewish wedding in Toronto.

It’s a story about what happened years later—when Mark and Anna’s son tried out for rep hockey… and didn’t make the team.

⸻

When the World Says “Not This Time”

Mark called me that day. Not as a cantor. Not for Jewish wedding services or a baby naming ceremony. Just as a friend.

His voice was low.

“Ben,” he said. “He worked so hard. He trained. He sacrificed. And… they cut him. Now he’s sitting in the back seat, quiet. He says it’s fine. But I can tell. He’s asking himself, ‘Am I just not enough?’”

That moment? That’s the defining one.

Not when your child wins—but when they don’t, and they wonder if it was all for nothing.

It reminded me of Joseph in the Torah. Remember him?

Joseph wasn’t chosen. He wasn’t celebrated. He was betrayed, thrown into a pit, sold into slavery, and jailed for a crime he didn’t commit.

Rock bottom.

But here’s the lesson I teach my students—whether in my confidence coaching, Jewish baby naming services, or Jewish wedding rituals:

Your effort is your identity.

Not your trophy. Not your score. Not your approval letter.

⸻

Confidence Isn’t Built When You Win—It’s Built When You Rise

Joseph didn’t wait to be rescued. He rose from the shadows by leading with integrity. He solved problems. He kept showing up. He used the tools he had instead of fixating on the ones he didn’t.

And that, my friends, is exactly what I teach in my life mentorship and officiant work.

Whether I’m guiding a couple under a Jewish wedding chuppah, or welcoming a child through a Jewish newborn ceremony, or standing with a family during a Jewish baby naming celebration, the message is the same:

💬 “Your value is not defined by public recognition. It is defined by private resilience.”

I told Mark to hug his son—not with pity, but with pride.

Because showing up with effort in the face of disappointment? That is leadership. That is Jewish strength. That is character.

⸻

The Hidden Torah in Rejection

In Jewish wedding planning, we speak about the ketubah—the contract. But the real contract is the one you sign with yourself.

To keep showing up when the world doesn’t clap.

To choose kindness when others don’t.

To be faithful to your effort, not just the outcome.

This is the Torah lesson woven into every Jewish baby naming ritual, every Jewish wedding vow, every soul I’ve stood beside during a Jewish wedding reception or Jewish newborn ceremony.

⸻

Why I Do What I Do

Mark and Anna came back to me a year after their wedding.

They asked me to officiate their baby naming ceremony Jewish-style for their daughter. They remembered how I made them feel at their wedding: seen, supported, and sacred. And they wanted that for their child.

That’s the power of a Jewish wedding cantor. Not just to sing—but to witness.

Not just to guide—but to believe in people when they’ve forgotten how to believe in themselves.

Whether it’s a Jewish wedding dance, or a Jewish baby naming invitation, or just a quiet moment after your child didn’t make the team—rituals are about remembering who you are.

⸻

Final Thought: From Pit to Purpose

If your child didn’t make the cut this year—know this:

✨ You are not raising a follower.

✨ You are raising someone who will lead when no one’s watching.

✨ You are raising a modern-day Joseph.

I’d be honoured to stand by your family—whether for your wedding, your Jewish baby naming ceremony, or your journey through life’s beautiful highs and humbling lows.

Because confidence isn’t a talent. It’s a teaching.

And teaching it? That’s my calling.

⸻

Let’s build confidence, community, and Jewish soul—together.

If you’re planning your Jewish wedding in Toronto, or seeking a Jewish baby naming officiant, I’d love to hear your story.

Message me today.