Learning to Trust Yourself Again

When Dovid first walked into my office, he looked like any other young professional. Polished, polite, and pleasant. But beneath his composed exterior was a mind in turmoil. Dovid was plagued by what he called “decision regret.” It didn’t matter if it was big or small — buying a car, choosing a yeshiva, or even which tie to wear to a wedding — every decision came with a follow-up avalanche of self-doubt.

“When I make a decision, I feel good about it for a minute,” he told me. “But then I start thinking, ‘Maybe I was too emotional. Maybe I missed something. Maybe this will blow up in my face.’ And I start obsessing over it.”

This wasn’t the first time I had met someone struggling with Generalized Anxiety Disorder, but what stood out about Dovid was the way his self-doubt eroded his confidence and drained his energy. He was constantly replaying decisions in his mind, as if he were on trial in his own court of law, presenting evidence for and against his own judgment.

Over the weeks that followed, we worked together on identifying the underlying beliefs behind his anxiety. Dovid had grown up in a home where perfection was quietly expected and mistakes were quietly punished. The unspoken rule was: get it right the first time, or don’t try at all. It wasn’t hard to see how that early messaging had evolved into chronic self-doubt.

Then one session, something shifted.

“I have to say,” Dovid said, cautiously optimistic, “I haven’t been spiraling like I used to. The regret attacks... they’re not really coming anymore.”

This was progress. He still struggled with occasional hesitation when making a decision, but the internal panic had noticeably quieted. He shared that while buying a used car the week before, he felt some doubts after the purchase. “But I didn’t unravel,” he said. “I kept telling myself, ‘You made the best decision you could with the information you had.’”

To help solidify this insight, I invited Dovid to revisit a past decision that had caused him distress: the choice to leave a previous job. At the time, he had felt confident it was the right move. But a few months later, when his new job presented unexpected challenges, he began to torment himself. “Why did I leave? Was I impatient? Was I running away?”

In session, we slowed things down. I asked him to walk me through his mindset when he originally made the decision. As he retraced his thought process, he recalled details he had forgotten: the toxic work environment, the lack of growth, the way it was affecting his health.

His eyes widened. “I completely forgot about that. I was so focused on what went wrong afterward that I forgot why I even left in the first place.”

Exactly.

We discussed how regret often isn’t about what we did — but about forgetting why we did it. When the discomfort of the present clouds our memory, we assume our past self acted foolishly or impulsively. But often, we made thoughtful choices based on the best information we had at the time. Remembering that context is a powerful antidote to regret.

We also spoke about giving ourselves the benefit of the doubt. Just as we’d tell a friend, “You did what you thought was best,” we can learn to offer that same compassion to ourselves.

For Dovid, this wasn’t just about making better decisions — it was about healing a fractured sense of trust in himself. And as he rebuilt that trust, he began to walk through the world with more confidence and less fear.

Sometimes the most important decision we can make is to believe in the one who made it.