Questions for the Soul: Building a Cheshbon HaNefesh for Elul

By Aaron Mandel

There is a particular kind of tiredness that arrives in late summer. The year has gone somewhere you cannot quite name. You meant to be a steadier, gentler, more honest version of yourself by now, and instead you are mostly just here — carrying the same short temper, the same unfinished apology, the same quiet ways you have let yourself down. The Days of Awe are coming, and you sense that you are supposed to do something about all of it. But where do you even begin? “Examine your life” is not an instruction. It is a fog. What you need is not a mood. What you need is the right set of questions.

That instinct is older than you. The Mussar tradition called this work cheshbon hanefesh — an accounting of the soul — and it treated it not as a feeling to summon but as a discipline to practice. The classic Mussar manual Cheshbon HaNefesh by Rabbi Mendel of Satanov gave it the shape of a ledger, drawing on the call of Lamentations to search out our ways and return. What follows is a way to build that ledger for yourself: a set of honest questions for the weeks before the Days of Awe.

What an accounting of the soul is actually for

Before you ask anything of yourself, it helps to know what kind of work you are doing. An earlier classic, Bachya ibn Pakuda’s Duties of the Heart, devotes an entire treatise to “examining the soul,” and it opens by slowing the reader down. (Duties of the Heart, Eighth Treatise on Examining the Soul, Introduction:2) The point of that pause is worth keeping: the accounting is not a single dramatic verdict but a subject with parts, something to be understood before it is undertaken.

The first of those parts is simply definition. (Duties of the Heart, Eighth Treatise on Examining the Soul, Introduction:3) A cheshbon hanefesh is not self-criticism, and it is not the vague guilt that floats up at this time of year and then dissolves. It is a deliberate reckoning — a turning of attention inward to see, plainly, where you have been spending the currency of your days. The merchant who never opens the books does not thereby stay solvent. He only stays ignorant of whether he is.

The areas a thorough accounting covers

A real accounting is broad. The Mussar tradition organized it around a list of middot, character traits, so that you are not examining one favorite failing over and over but touching every room of the house. Duties of the Heart itself frames the work as covering several distinct matters, including the question of how widely it should range and how many ways a person should bring himself to such a reckoning. (Duties of the Heart, Eighth Treatise on Examining the Soul, Introduction:5)

So spread the questions out. Ask about your speech: where did your words cut, exaggerate, or quietly diminish someone this year? Ask about your patience and your anger, your generosity with money and with time, your honesty in small things, your diligence in what you owed others. Ask about humility — not the performance of it, but whether you could be wrong without it costing you your peace. The aim is not to find one large sin to feel terrible about. It is to see the whole pattern of a year, trait by trait.

Wrongs toward people, wrongs toward God

A thorough accounting also distinguishes between whom you have wronged, because Jewish teaching does not treat all repair the same way. The Mishnah in Yoma draws the line cleanly: transgressions between a person and God, the Day of Atonement helps to mend; but transgressions between a person and their fellow are not mended by the Day until you have first appeased the one you hurt.

This single distinction reshapes the whole exercise. It means your accounting must produce two different kinds of resolution. Some lines in your ledger you can take only to God — the prayers you skipped, the gratitude you withheld, the way you let your inner life go untended. But other lines have a name and a phone number attached. The friend you went cold on. The family member you spoke about unfairly. For those, no amount of solemn reflection on the High Holidays substitutes for the harder, smaller act of going to the person and making it right.

The questions that surface gratitude and growth

If your accounting only ever hunts for failure, you will not last the season, and you will not see yourself truly. A person is not only their debts. So write the other questions too. Where did you grow this year, even a little? What did you do that was quietly good and that no one praised? What were you given — health, a kindness, an ordinary Tuesday that held no catastrophe — that you forgot to be grateful for?

The psalmist’s own self-examination is not only an audit of guilt; it is an invitation to be fully seen, in the hope of being led somewhere better. To pray search me and know my heart (Psalms 139:23) is to ask for examination as a gift, not a sentence. Let your ledger have a column for that. The honest soul is not the one most fluent in its own shame. It is the one willing to see all of itself — the growth alongside the failure — and to be led, as the psalm continues, in the way that lasts. (Psalms 139:24)

From honest questions to concrete resolution

Here is where most self-examination quietly fails. We name the wrong, we feel the weight of it, and then we mistake the feeling for the fixing. But guilt is not teshuvah. The Rambam, in his laws of repentance, is exact about what completes the turn: it is not enough to confess and regret; one must resolve in his heart not to return to it, and call upon the One who knows all hidden things to witness that he will not do this thing again. The proof of repentance lives in the future, not in how badly you feel about the past.

The danger in the meantime is not cruelty toward yourself. It is delay. The Mussar masters knew this temptation intimately, and Mesillat Yesharim sketches it as a small comic dialogue with the eternal procrastinator. Tell him to set out, and he answers: (Mesillat Yesharim 9:23) Reassure him the way is short and the teacher near, and still: (Mesillat Yesharim 9:24) There is always one more reason the door might be locked, one more lion on the road, one more better week to begin. The accounting you keep deferring is the one you never actually make.

So turn each honest answer into one small, sayable resolution. Not “I will be more patient” — that is a wish — but “this week I will not raise my voice at the dinner table.” Not “I will be a better friend,” but the name of the one person you will call. There is a quiet dignity in the way Scripture marks the close of real work in this very season: (Nehemiah 6:15) A broken-down wall, rebuilt in a fixed number of counted days, finished in the month of Elul. Your cheshbon hanefesh is that kind of work. Counted, finite, and meant to be completed — not perfectly, but actually.

The year is not asking you to become someone else before the Days of Awe. It is asking you to sit down honestly with the person you already are, to open the books gently, and to write down one or two true things you will do differently. That is enough to begin. That has always been enough to begin.

Published by Higgayon Press. For questions of halacha, consult a qualified rabbi.