woman covering her face with her hands

How to Feel Bad About Yourself

Too much self-satisfaction is dangerous.

Is believing the best about yourself always a virtue?

The greatest religious figures are often those most convinced of their inadequacies. A man once approached Rabbi A.J. Heschel and said “I love my family, I pay my taxes, I keep a good job. What do I need to repent for? I am a pretty good person.” Heschel replied, “Good for you, but the same is not true of me. I am always thinking the wrong thing, saying the wrong thing, doing the wrong thing. I need God, and I need to repent.” Somehow I believe that the goodness of Heschel outshone that of the more self-satisfied gentleman.

What is it to have a sense of sin? Mordecai Kaplan gave an excellent account: “The best we can do” he wrote, “is generally much better than we actually do. To be troubled by that fact is to have a sense of sin.” We could use more of that sense; paradoxically, sometimes believing one is not so good makes us better.

Rabbi David Wolpe’s musings are shared in My Jewish Learning’s Shabbat newsletter, Recharge, a weekly collection of readings to refresh your soul. Sign up to receive the newsletter.

Discover More

Parashat Vaetchanan: Prayer and Pleading 

Life is not simple, and prayer is more than just pleading.

Kiddushin 82

Butchers, bakers and candlestick makers.

Kiddushin 64

Deathbed confession.