A man goes to his rabbi and tells him, “I’ve been miserable for years. My business is failing, my children don’t call, my knees hurt. What should I do?”
The rabbi says, “The Torah commands us to be happy on Sukkot. It’s a mitzvah.”
The man says, “Rabbi, that’s wonderful news. When’s Sukkot?”
The rabbi replies, “In six months.”
The man says, “Perfect. I’ll suffer till then.”
Well, Sukkot is almost here, so his six months are up. And it raises a real question. The Torah tells us, v’samachta b’chagecha—“you shall rejoice on your festival” (Deuteronomy 16:14). That’s not a suggestion but a mitzvah. We are commanded to be happy.
That raises an obvious question. How exactly does one command an emotion? Happiness isn’t a light switch. It’s not something you can will into existence by decree. It rises and falls with our circumstances—a good day at work, a phone call from a child, a difficult diagnosis, a broken relationship. So how can the Torah simply legislate a feeling?
I think the answer is this: The Torah isn’t commanding us to feel happy on cue. It’s telling us that if we seek it in the right places, joy is to be found, built into the very structure of the festival and waiting for us to discover it. Sukkot doesn’t manufacture happiness out of nothing. It points us toward where real happiness actually lives.
There’s an old story about a couple in a shtetl in Eastern Europe. He was a Talmudic scholar, always buried in his books. She was the breadwinner, running a small trading business. Twice a year, there was a great fair in the nearby city, where she would buy goods wholesale and bring them home to sell at a profit. And that, essentially, was their livelihood.
One year, the fair was in the big city, and she asked her husband to come along and help her. He agreed. They arrived in the morning, and he went off to shul to pray, promising to meet her at the market the moment he finished. But once he began praying, he didn’t stop. And once he was done praying, he opened his Gemara and was gone. He became utterly absorbed in the Talmudic tome, the hours melting away—market, wife and purpose entirely forgotten.
When she found him that evening, furious, he offered her this philosophical defense. “Tell me,” he said, “why did you need me at the market?” “To help me buy the cheese and the goods.” “And then?” “Then we’ll sell them.” “And then?” “Then we’ll have money.” “And then what?” “Then we’ll buy more goods and sell them, and have more money.” “And then?”
She paused. “And then ... we’ll be happy.”
He replied: “Why do I need to buy and sell, and buy and sell, to be happy? I was happy already—there in the study hall, over the Gemara, in prayer. You want to chase happiness through the market. I already found it for free.”
The “pursuit of happiness,” when you think about it, is a strange phrase. Chase happiness directly, and it slips further away.
Happiness isn’t a destination you arrive at after enough transactions—enough money, enough acquisitions, enough achievements. It’s a byproduct. It blossoms naturally out of a life lived with meaning—a life that’s right in the eyes of God and right in the eyes of other people.
It shows up, uninvited but welcome, when the life underneath it is worth living.
There are countless examples of people who have all the money they could dream of, but still find joy elusive.
A wealthy husband who never spent much time with his wife discovered that she was, not surprisingly, quite miserable. When he eventually realized that she was unhappy, he asked, bewildered: “What do you want? A new house? Diamonds? Name it, and it’s yours!”
She looked at him and said, “Keep your house. Keep your diamonds. Just get me a lawyer. What I really want is a divorce.” Money, evidently, was never the problem—and it was never going to be the solution.
I think of my own grandfather’s sukkah when I was a boy. It was a patchwork of old doors and mismatched window frames, each a different color and held together more by hope than craftsmanship. By any objective measure, it was shabby. But step inside, and there was radiance, warmth—something you could feel but not quite explain. Somehow, the heavenly cover was sheltering and warming us in its embrace.
Compare that to the palaces so many of us build today—vast homes with every conceivable luxury, made of granite, marble, glass. It reflects outer opulence, but all too often, inner poverty. A strange emptiness sits in the middle of all that comfort. Warmth doesn’t scale with square footage.
I live in South Africa, and I’ve watched people who have next to nothing—some without even shoes—dancing, singing, toyi-toying with an unmistakable joy. No house. No money. No shoes. And yet there they are, dancing with joy.
Sukkot is called Z’man Simchatenu, the “Season of Our Rejoicing,” because it teaches us exactly where joy comes from. Not the size of the sukkah, but what fills it. Not what we own, but what we live by: Shabbat, our traditions, our Torah and mitzvahs, the values handed down from a grandfather with a rickety sukkah and a scholar too absorbed in Torah to notice a marketplace.
Keep the commandments. Live a life that means something, with people and purpose. Raise your children in this spirit, and no matter what the outer trappings look like, happiness—quite naturally, without ever having to chase it—will come.
