Sukkot: Finding Strength in Joy

You may find it hard to rejoice.
You may find it hard to dance.
You may be consumed with anxiety, watching the world unravel around us.

In these moments, you may ask yourself, “How can I truly feel joy in such a difficult moment?”

These are the feelings I’m grappling with too. In times like these, I’m reminded of a particularly vulnerable moment in my life, when my aunt passed away from cancer shortly before Rosh Hashanah. It hit me hard. I found it difficult to even think about celebrating the chagim.

In my moment of vulnerability, I reached out to my Rabbi, and what he shared with me has shaped the way I approach life, especially during Sukkot. He told me: “God is brilliant. Our actions and feelings are intertwined. Our feelings motivate action, and our actions nurture those very feelings. It’s a reciprocally reinforcing relationship.”

This simple insight changed everything for me.

Sukkot calls to us in precisely these moments. Not to ignore our feelings or pretend they don’t exist, but to lean into the mitzvot that are designed to give us strength when we need it most.

This is the beauty of the Torah’s mitzvot—they aren’t just rituals, they are designed to shape our hearts. The more we commit to these actions, the more they nurture us in return. And as we step into Sukkot this year, I want to invite you into this journey with me, one that’s deeply personal and yet universal.

The Triad of Sukkot: Blessings, Joy, and Shelter

Sukkot is more than a holiday; it’s a triad of themes that are as interconnected as they are powerful. Chag HaAsif, Zman Simchateinu, and Chag HaSukkot—the celebration of gathering, reveling in true joy, and feeling the trust in Hashem’s shelter—are not three separate ideas, but parts of a whole that shape how we live.

Chag HaAsif, the Festival of Ingathering, marks the end of the harvest season. But it’s not just about crops—it’s about “gathering” all the brochot (blessings) of the past year. What have we overcome? What blessings have we overlooked?

For me, this brings to mind one particular Sukkot early in my entrepreneurial journey. I had left the comfort of a salaried position to build something of my own. But as many entrepreneurs know, that decision comes with a lot of vulnerability. I was in a scarcity mindset, wondering if I had made the right choice. But that Sukkot, sitting in the sukkah with my wife, I found myself reflecting on how far we had actually come. We had gained skills, progress, and blessings that I hadn’t noticed in the daily hustle.

It was in the sukkah, under the stars, that I felt a shift—Hashem had been with us all along, even when I couldn’t see it.

What have you “gathered” this year? What blessings are there that you might not have noticed amidst the challenges?

Sukkot is also known as Zman Simchateinu—the Time of Our Joy. But how do you access joy when the world feels so uncertain?

For me, the answer lies in bitachon—trust. True joy doesn’t come from the absence of challenges; it comes from knowing that Hashem is guiding us through those very challenges.

As I mentioned, after my aunt’s passing, I found joy to be one of the hardest emotions to embrace. But I realized, through the action of rejoicing on Sukkot, that joy is a choice we can make. It’s not about pretending everything is okay—it’s about trusting that Hashem is with us through it all. The name of the holiday “Sukkot” tells us precisely this. The sukkah is fragile, just like many aspects of life. But in this fragility lies the eternal protection of Hashem.

Yes, life feels fragile. Yes, the sukkah is temporary. But Hashem’s protection is eternal.

In halachic practice, we are told to fulfill the mitzvah of sukkah by imagining our ancestors beneath the Ananei Hakavod—the majestic clouds that sheltered them at the time of the Exodus.

What would change in your life if you lived with constant awareness of this? How would you approach your challenges differently?

The Mitzvot of Sukkah and Lulav: Unity Through Trust

From this place of trust, we turn to the mitzvah of the Lulav, which teaches us about unity through diversity. The four species—lulav, etrog, hadassim, and aravot—represent different types of Jews. And yet, we bind them together as one, recognizing that our strength lies in our unity.

But here’s the thing: unity is hard to achieve when we are hurting. It’s difficult to love and accept others when we ourselves feel insecure. That’s why the mitzvot of Sukkah and Lulav come together. The sukkah shelters us, offering a space of security and true inner peace, and from that place, we can embrace others. The lulav reminds us that every Jew, no matter where they are on their journey, is a part of the whole.

How can you contribute to the Achdut (unity) of the Jewish people this year? How can you bring more love and connection into your family and community?

The Triad of Vivacity: Fully Alive

Where does this place us?

The Zohar describes that God, the Torah, and the Jewish people are one.

This isn’t just about stepping into the square of the sukkah, or closing a circle of connection. It’s about embracing the strength of the triangle—the living relationship between Hashem, Torah, and the Jewish people.

Just reading the word vitality makes me feel alive.

Rabbeinu Bachya speaks about the Triad of Vitality, where Hashem, Torah, and the Jewish People are all described as being “alive.” This isn’t just a nice metaphor—it’s the essence of life itself.

• Hashem is the living God, the source of all vitality.
• The Torah is called the “Torah of Life” because it not only guides us but breathes life into every moment of our existence.
• The Jewish People are described as a “living nation,” sustained through our connection to Hashem and Torah.

What does it mean for you to live fully alive, connected to Hashem, Torah, and the Jewish People?

I know I’ll be thinking about the millions of Jews around the world who, like me, are sitting in their sukkot, reveling in the joy of being in God’s close embrace. Leaning into this triangle through the mitzvot, drawing closer to God and our unique role in the Jewish nation.

What might that look like for you and your family this Sukkot?

Sukkot: The Climax of the Year

Sukkot is the climax of the Jewish year. After the deep introspection of Rosh Hashanah and the cleansing of Yom Kippur, Sukkot invites us to revel in who we are and to dream forward about what’s yet to come.

How has Hashem blessed you, and what new possibilities might you feel inspired to create for yourself, your family, and your community?

Questions for Your Sukkah

Here’s a recap of some of the questions I’ve shared. Use them to guide your reflections and conversations as you sit in your sukkah this year:

• Chag HaAsif: What “blessings” have you gathered this year? How has Hashem guided you through your challenges?
• Zman Simchateinu: How can you cultivate joy through trust in Hashem?
• Chag HaSukkot: What would your life look like if you lived with constant awareness of Hashem’s protection?
• Lulav: How can you contribute to unity within your family, your community, and the Jewish people?

May this Sukkot inspire you to live fully alive, gathering blessings, embracing joy, and uniting with the Jewish people in trust and love.

Chag Sameach!