CBT ToolTalk

Strength of Struggle Q&A #30: “Why Am I Still So Insecure?”

2026-06-10

Q:

Dear Rabbi,

I have been plagued for years with self doubt and low self esteem. Although I have been a teacher for many years I still find myself obsessing over whether I succeeded and why a particular student left my class and feeling unconfident generally as I give over the material. This only leads to me feeling rejected and a sense of failure. I end up feeling more anxious and depressed particularly at certain times of the year.

Although I have been taking medication for anxiety, depression and ADHD it doesn't seem to do more than take a bit of the edge off.

I remain stuck in my childhood insecurity of feeling that I don't fit in, probably due to bullying when I was in my formative years of adolescence.

Not many people would even know because I generally carry myself with an air of confidence or humility.

In the meantime I'm suffering terribly inside. Any talks and therapy I go to feel like a band aid.

I learn books on Emunah but I remain stuck in my negative paradigm.

What would you suggest to help me move on, or at least make progress in this many decade battle I'm going through?

Thank you,

-Avi


A:

Dear Avi,

First of all, what you are describing is much more common than it seems.

There are people who struggle openly, and there are people who struggle privately. Sometimes the person who appears confident, capable, and successful is carrying around a tremendous amount of pain that nobody sees. People are afraid to reveal what is really going on out of a fear of what others may think or perhaps out of not wanting to deal with the discomfort of whatever is causing those thoughts and feelings.

You described this as a battle you've been fighting for decades.

When something has been with us for that long, we often assume it must be the truth.

If a person hears the same message for thirty or forty years, eventually it stops feeling like a thought and starts feeling like reality.

"I don't fit in."
"Something is wrong with me."
"I'm not enough."
"Everyone else is more confident than I am."

The problem is that repetition does not make something true.

It just makes it familiar, and then we treat that familiarity as our truth.

Many people who were bullied when they were younger unknowingly carry those experiences into adulthood. The hurtful words become internalized and eventually start sounding like our own voice.

A student leaves your class.

Most teachers might think, "I wonder what happened."

Your mind immediately turns it into evidence.

"Maybe I failed."
"Maybe I'm not good enough."
"Maybe people don't really value what I do."

The event is no longer the problem. The meaning attached to the event becomes the problem.

Emotional pain is not always from what is happening now. Sometimes it comes from an old wound that keeps getting reopened.

Like an old injury, many of the situations that trigger you today may simply be touching a wound that has never fully healed.

You also mentioned Emunah. Emunah is essential.

But sometimes people try to use Emunah to solve a problem that first needs compassion.

You can believe that Hashem loves you, that you are Hashem's precious child, and still struggle to truly feel it.

I wonder if part of your struggle is that you are still measuring your value through outcomes.

Did the student stay?
Did people appreciate me?
Did I perform well enough?
Did I make a mistake?

As long as self-worth is tied to results, life becomes exhausting because results are never fully under our control.

If you are up for the challenge, for the next thirty days, choose one situation each day that triggered self-doubt.

Write down two things:

1. What are the facts?

For example:

"A student left my class."
"I made a mistake during the lesson."
"Someone didn't respond to my email."

Just the facts.

2. What conclusions did I immediately jump to?

"I'm a failure."
"They don't respect me."
"I'm not good enough."

Then ask yourself:

"Do the facts actually prove that conclusion?"

Very often they don't.

Avi, after reading your letter, I do not see someone who has given up.

I see someone who has continued teaching, learning, growing, searching, and serving others despite carrying this struggle for many years.

That does not sound like weakness to me.

It sounds like real strength.

May Hashem help you see yourself with greater honesty and greater kindness. May He help you let go of old wounds and old stories, and allow you to see the strengths and gifts that have been there all along.