QUESTION:
What is the difference between a healthy and constructive kind of fear or concern that one might fall into doing an aveirah (sin) versus an unhealthy kind of fear or concern which is not constructive? When does being afraid of not doing enough teshuvah become unhealthy? We find terminology in Tosafos Kiddushin 31a that a person should be “worried and pained lest he transgress and sin”, which seems to imply that a person should constantly be worried that he might do an aveirah and that it’s not just a small thing but a big concern that envelopes our life constantly.
ANSWER:
One needs to weigh out his thoughts carefully: What does Hashem want from me? After a person does that, he will become calm, because he becomes aware that his main fear is that he is afraid of going against Hashem’s will [and he has made himself concerned about doing Hashem’s will]. As it is well-known, the Brisker Rav had great yiras shomayim, but as soon as he finished doing what [he knew] Hashem wanted from him, he became very relaxed and serene.
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