Hey Rabbi,

Before I started this whole Shabbat and Kosher thing, I had no idea how guilty I was supposed to feel. Then I discover there’s also say-your-daily-prayers and talk-only-nice-about-other-people and say-a-blessing-before-you-eat and a whole slew of other things to feel guilty about. Now I see myself failing almost every day, accelerating sometimes to a speed of one failure per minute.

This is getting really depressing. At times, I feel this whole halacha thing is not designed for happy-go-lucky wannabes like me. Can I get a modified, personalized version, with allowances for failure and perhaps even some down-time for guilt-free living?

—Gill T.

Hi Gill,

Okay, here’s your personalized version. It comes with:

  • Unlimited failure permit, as long as you pick yourself up afterwards and keep on trying.

  • Zero-tolerance for feelings of guilt, inadequacy, failure and remorse, except under controlled, clinical conditions.

  • Incremental, sustainable adoption of Jewish practice in all but the most crucial areas.

And that's not just your individualized program—it's everybody's.


Mitzvahs are not guilt-fertilizer. Mitzvahs are the ultimate celebration.

Because mitzvahs are not meant to be guilt-fertilizer. Just the opposite: Mitzvahs are the ultimate form of celebration. A mitzvah means you’re connecting with the Infinite Creator of the Universe on a deep, personal level. Halachah means you’re changing the world for the good. What’s more worth celebrating than that?

And there’s irrefutable proof: When you first became obligated in all this they made you a party—your bar or bat mitzvah event. If mitzvahs aren’t for celebrating, then why the party?

The earliest Torah source for that party happens to be the Zohar, where we are told to make a feast just like a wedding, to celebrate that we get to do mitzvahs.1 Proof that doing mitzvahs is a happy thing, not a do-it-or-get-zapped thing.

Now, imagine you’re making this wild bar mitzvah party with all your friends who brought a whole pile of gifts—and there’s one nudnik there standing next to you and kvetching, “What a lousy party. Your voice cracked in the middle of the Haftorah and your speech put even the rabbi to sleep. The sushi smells rotten. Your Aunt Monica didn’t even bring a gift. And your friends probably don’t even like you.”

You’ve got one of two choices: Throw the guy out, or stay far away and ignore him. And when the party is over, get your money back for the sushi.

That’s exactly what you do with guilt. Even guilt over serious, grave messups. Take the advice the of Baal Shem Tov and tell it, “Guilt, I have no time for you right now. I am too busy celebrating my mitzvahs, celebrating life and just getting stuff done. I know I messed up, I said I’m sorry, and I trust with perfect faith that G‑d has forgiven me. But you are distracting me from serving my Creator with joy—and what kind of a dumb life is that, doing all this stuff without celebration?”2

And then, one day before Yom Kippur, or sometime when you’re inspired enough and want to go even higher, you cry a little over the messes you’ve made and resolve to do even better from now on.

Success By Failure

The secret behind success is knowing how to fail.

Get this straight: The secret behind success is knowing how to fail. Failures are people who fail once. Successes are people who fail thousands of times—and pick themselves back up each time. Like little kids learning to walk. Like Babe Ruth, who held the world record for home runs—and also held the record for strike-outs.

If basketball's your game, here's a quote from Michael Jordan: “I've missed more than 9,000 shots in my career. I've lost almost 300 games. 26 times, I've been trusted to take the game winning shot and missed. I've failed over and over and over again in my life. And that is why I succeed.”

There’s a reason it works that way: Everything in the world—whether it’s energy, matter, a journey or a story—moves in waves. Wherever there’s a crest, a trough is on its way. To surf those waves, you have to learn to travel the troughs just as well as the crests. When you're little, you're good at that. When you grow older, your ego doesn't let you anymore. Drop the ego, admit you're fallible like the rest of us, and allow yourself to experience success.

And that’s the way it works with mitzvahs, too. As the Baal Shem Tov put it, “It’s not the bite of the snake that kills, it’s the poison.” The bite is the failure. The poison is the kvetching voice telling you what a failure you are.

Why is that voice saying those things? To make you into a better person? To get you to do more mitzvahs? Absolutely not. There's only one objective behind its strategy, and that is to get you depressed enough that you'll give up on the whole thing. And yours seems to be succeeding.


Guilt is the gateway to depression, and depression is the gateway to surrender. Celebration is the gateway to transcendence, higher and higher without end. When you're happy, you ride high above every obstacle and all the good things in life become so much easier.3

Don’t stop to talk with a snake. Boot it out of the party. There will be a time to clean up the mess. But why waste a good party arguing with a party-pooper?4