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Retire the trapping question
Why “How good am I?” keeps confidence fragile, and the better question to ask in its place.
A new paradigm for authentic self-esteem
“How good am I?” “What is the next right thing to do?”
This is not another book about feeling good about yourself. It replaces the question that keeps confidence fragile with the one that sets you free — a practical, Torah-based path from judging who you are to mastering what you do.
Hardcover · 162 pages · ArtScroll Series
About the Book
Confidence built on the question “How good am I?” is always at risk. It rises and falls with success, failure, and comparison, so each day becomes a verdict on your worth. The harder you chase the answer, the more fragile the answer becomes.
The Self-Esteem Trap offers an entirely new paradigm. Rabbi Moshe Don Kestenbaum shows how the modern preoccupation with self-worth quietly reflects the workings of the ego — and how a Torah-based understanding of the self points to a better way. The path out is not to score higher on the old question, but to retire it.
In its place comes a single, freeing question: “What is the next right thing to do?” This shift moves you from judging who you are to mastering what you do. It turns each moment into a clear, doable step, steadies you when results swing high or low, and builds confidence that is durable rather than fragile.
Written by a mechanech who has spent his career close to parents, teens, and students, the book is concise, considered, and built to be practiced — not just read. It speaks to anyone whose confidence still rises and falls with the scorecard, and to anyone seeking a wiser, freer way to live and to grow in avodas Hashem.
Inside the Book
Concrete, teachable moves — not slogans — drawn from a Torah-based understanding of the self.
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Why “How good am I?” keeps confidence fragile, and the better question to ask in its place.
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How to hold your inherent, unearned worth apart from the daily ups and downs of results.
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A practical method for turning self-judgment into a single, doable step you can take now.
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How comparison quietly erodes self-esteem, and how to leave the ranking behind entirely.
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How the preoccupation with self-worth reflects the ego, and how to see it clearly for what it is.
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A framework for confidence that does not depend on the next achievement to stay standing.
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What to do when results come in low, so a setback stays a step and not a sentence.
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Simple, repeatable habits that turn the shift from an idea into a lived way of acting.
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For mechanchim, parents, and teens: how to bring the reframe to those in your care.
The Book’s Journey
A map of the movement the book makes — from naming the trap to living free of it. These describe the journey; they are not verbatim chapter titles.
Seeing how “How good am I?” runs the day, and why it can never make confidence steady.
How worth becomes a running tally, and how comparison and the ego keep the tally alive.
Retiring the trapping question and taking up the one that turns judgment into action.
The concrete moves that make the reframe durable — worth held apart from performance.
Carrying the shift into real life, relationships, and avodas Hashem, day after day.
Look Inside
A hardcover made to be returned to — clear typography, generous margins, and a calm, considered layout.
Specifications
Own the Book
Order the hardcover direct from ArtScroll, the publisher — the surest way to get your copy.
$22.49 $24.99 list