The Iggeres HaGra

By Rabbi Yair Hoffman

Few figures shine as brightly as the Vilna Gaon, Rabbi Eliyahu ben Shlomo Zalman zt”l (1720-1797). Among the many fascinating chapters of his life stands an unfulfilled journey—his attempted pilgrimage to Eretz Yisroel and the letter he wrote to his family while traveling to Königsberg.

In this deeply personal correspondence, the Gaon expressed his profound yearning for Eretz Yisrael, describing it as the “desired Land of Israel and the desire of Hashem, whose upper and lower realms yearn for it.” Despite his spiritual longing and physical journey, the Gaon ultimately returned home, stating with his characteristic humility that he had “no permission from heaven” to make aliyah.

But when exactly did he write it? The timing of this attempted journey remains a subject of scholarly debate. Dov Eliyach, in his comprehensive biography “The Gaon,” argues that the attempt occurred when the Vilna Gaon was approximately forty years old, during the winter of 1759–1760. The esoteric work “Kol HaTor” places the journey much later, in 1782.  Eli Eliyach presents a third possibility, positioning the journey in the summer of 1767.  This author, however, prefers the dating of Dr. Aryeh Morgenstern who suggests that the journey took place around 1778. His evidence to this is quite compelling, having delved into the archives of the Tzarist government – which only opened in the 1990’s.  Regardless, here is the letter in English translation – written for class I teach in Yahadus – a Yom Tov gify for those who care to print it.

Introduction and Reassurance

Dear Family,

I ask my family not to feel any pain over my departure, as you promised me. Please don’t worry—after all, what is there to worry about? People often travel far from home for years at a time – merely to earn money, leaving their wives alone while they wander in poverty. But I, thanks to Hashem, am journeying to the Holy Land that everyone longs to see—our people’s most cherished place, the Beloved Land toward which all heavenly and earthly beings yearn. Thus, I travel in peace, thank Hashem.

My wife, you know I’ve left behind our children who my heart aches for, as well as my precious books and comfortable home. I find myself a stranger in foreign lands. Indeed, I’ve left everything behind…

The Meaninglessness of Worldly Pursuits

This world is clearly full of vanity, every amusement worthless. Woe to anyone chasing empty things that bring no benefit.

Don’t envy another person’s wealth, for “riches are hoarded by their owner to his misfortune” (Koheles 5:12). “As he came from his mother’s womb, naked will he return… What did he gain by toiling for the wind?” (ibid. 14:15). “Even if he should live a thousand years twice over… all go to the same place” (ibid 6:6).

“Even if man lives many years, let him rejoice in all of them, but remember that the days of darkness will be many; all that comes is vanity” (ibid 11:8). “And of joy, what does it accomplish?” (ibid 2:2). Tomorrow you will cry for having laughed today.

The Futility of Honor and Pleasure

Don’t desire imaginary honor—it’s worthless. Time is treacherous, like faulty scales that elevate the light and lower the weighty.

The world resembles drinking saltwater: it seems to quench thirst but actually only increases it. No one leaves this world with even half their desires fulfilled. “What profit does man have from all his toils under the sun?” (Koheles 1:3).

Remember our ancestors whose love, desire, and joy are now lost, yet who face severe judgment for indulging in worldly pleasures.

What use are pleasures to someone destined for dust, maggots, and worms, when all enjoyments turn bitter in the grave as death is bound to every person?

What is this world, whose days overflow with vexation and pain that prevent sleep even at night?

Guarding Your Speech

Every word we speak will be judged; not even the slightest expression is overlooked.

I urge you to become accustomed to solitude when possible, as misusing the tongue is among the gravest sins. Our Sages taught: “These are things that people enjoy their fruits… and evil speech equals them all.” This is the most serious of all transgressions.

“All man’s toil is for his mouth” (Koheles 6:7). Our Sages taught that all one’s good deeds and learning cannot outweigh what emerges from one’s mouth.

“What is a person’s purpose in this world? To make oneself silent like a mute” (Chullin 89a). One must seal their lips as tightly as two millstones.

The Consequences of Improper Speech

The punishment known as Kaf haKelah, where the soul is bounced from one end of the world to the other, comes primarily from meaningless words. For each pointless word, a person deserves to be flung across the world.

This applies to mere unnecessary speech, but regarding forbidden speech—gossip, lies, mockery, oaths, arguments, and curses, especially in shul or on holy days—one faces far worse consequences.

The suffering from even one wrong word is beyond imagination, as no word is lost. Spiritual beings constantly record all that we say: “A bird of the skies may carry the sound, and some winged creature may tell the matter” (Koheles 10:20).

“Do not allow your mouth to cause your flesh to sin… Why should Hashem be angered by your speech and destroy the work of your hands?” (Koheles 5:5).

Practical Guidance for Daily Life

Arrange for others to purchase what you need, even if it costs more. “Is there a limit to what Hashem can provide?” (Bamidbar 11:23). Hashem feeds all creatures from the highest to the lowest, providing adequately for each one.

On Shabbos and holidays, speak only about absolutely necessary matters, and even then, be brief. The sanctity of Shabbos is immense—our Sages barely permitted even greetings on these days!

Honoring Sacred Times

Continue giving great honor to the Shabbos as you did when I was present. Don’t reduce your Shabbos expenses, since “a person’s entire sustenance for the year is predetermined from Rosh Hashanah to Yom Kippur, except for Shabbos and Festival expenses” (Beitzah 16a).

Raising Daughters with Purpose

I strongly urge you to guide our daughters carefully so no curses, oaths, deceit, or arguments come from their mouths. Everything should be done peacefully, with love and gentleness. I’ve left several Yiddish moral instruction books—ensure they read these regularly, especially on the holy Shabbos when they should focus exclusively on ethical works.

The Importance of Discipline

For curses, oaths, and falsehoods, be prepared to discipline them firmly without misplaced mercy, as parents will be severely punished for their children’s misbehavior.

Even if you consistently provide moral guidance which they reject, woe to your sorrow and shame in the World to Come. As written, “She defiles her father” (Vayikra 21:9)—in such cases, even a righteous man’s son becomes known as “the son of a wicked man” (Sanhedrin 52a).

Additional Guidance for Daughters

Take similar care to guide our daughters regarding gossip, proper blessings before and after eating, prayers, and proper intentions in worship.

Most importantly, they must not leave home unnecessarily. They must obey and respect you, my mother, and their elders, following all principles in the moral guidebooks.

Educating Sons for Excellence

Raise your sons on the right path with sensitivity. Pay for their education, even hiring a tutor to study with them at home. Don’t be stingy with the tutor’s wages, for a person’s yearly income is predetermined except for Torah study, Shabbos observance, New Moon celebrations, and festival expenses. I’ve left books for them as well. For Hashem’s sake, guide them kindly and attentively, always monitoring their health and meals, ensuring they have everything needed for their wellbeing.

Approach to Torah Study

First have them learn the entire Torah until they know it almost by heart. This learning must be done gently, not with pressure, as Torah is best absorbed when learned in a relaxed state. Reward them with coins and similar incentives.

Preparing for the Afterlife

Focus your attention on these matters, as everything else is futile. We take nothing from our labor except our burial shrouds. “Yet a man cannot redeem his brother… he cannot give a ransom to Hashem” (Tehillim 49:8), and “Fear not when a man grows rich… upon his death, he will take nothing” (ibid. 17-18).

The Illusion of Leaving Wealth

Don’t say, “I’ll leave my children means to acquire food,” for when you’re in the grave, who will tell you whether they maintain the wealth you leave? People are like grass—some grow while others wither. Everyone lives according to their destiny and Divine Providence. Children may even rejoice at their parent’s death.

When Reish Lakish died, he left his children minimal possessions, applying to himself the verse: “…and they leave their wealth to others” (Tehillim 49:11). Woe to those planning to leave wealth to their children, when the only benefit from sons and daughters comes through their Torah observance and good deeds. Their sustenance is predetermined.

The Merit of Women

Women merit eternal life by bringing their children to learn Torah (Berachos 17a). Our Sages said: “The most virtuous wife is one who fulfills her husband’s will.” These are words of the Living Hashem, so I trust you’ll follow everything I’ve written. Nevertheless, I strongly caution you not to deviate from my guidance. Read this letter weekly, especially before and during Shabbos meals, to avoid idle talk and gossip.

The Power of Gentle Guidance

I reiterate my request to guide our children primarily with gentle words that will reach their hearts, especially if we merit reaching the Holy Land, where following Hashem’s ways is essential.

Train them well, since perfecting speech and character requires consistent practice, which surpasses all other training methods. All beginnings are difficult, but afterward, one rejoices in having developed proper speech habits.

The Challenge of Self-Control

Even the wicked person knows they’re on a destructive path but struggles to change. This is humanity’s primary challenge—not following desires but restraining oneself with discipline.

Spiritual Self-Discipline

Until a person’s last moment, one must practice self-restraint, not through fasts or physical mortifications, but by controlling one’s speech and desires. This is true repentance and leads to eternal reward, as written: “The commandment is a lamp… the way to life is the rebuke of affliction” (Mishlei 6:23). This exceeds the value of all fasts and mortifications!

The Rewards of Restraint

For every moment of restraining one’s speech, one merits experiencing a “concealed light” beyond imagining. Scripture states: “Who desires life and loves days to see good? Guard your tongue from evil and your lips from speaking deceitfully” (Tehillim 34:13-14).

This atones for every sin and saves from suffering, as written: “He who guards his mouth and tongue guards his soul from troubles” (Mishlei 21:23). Also: “Death and life are in the power of the tongue” (ibid. 18:21). Woe to one who destroys themselves through ill-considered words!

Avoiding All Negative Speech

Refrain even from praising others, let alone dishonoring anyone. Why speak about others at all? “The mouth that speaks of strangers is a deep pit; those scorned by Hashem will fall there” (Mishlei 22:14).

The Value of Solitude

The primary protection against improper speech is solitude—don’t leave home unnecessarily. Even in shul, keep your stay brief. In fact, it’s better to pray at home since shuls inevitably expose one to jealousy, idle talk, or gossip. One will be punished for hearing such things silently. This is especially true on sacred days when people gather to talk—it’s better not to attend at all.

Warning About Graveyards

My wife and daughters should avoid visiting graveyards, as impure forces attach themselves particularly to women there, leading to troubles and sins.

Guidance for Daughters Regarding Shul

It’s advisable that our daughter not attend shul, where seeing beautiful clothes might spark jealousy and lead to harmful speech at home. She should instead immerse herself in moral teachings. Don’t become jealous of anything in this fleeting world where everything is vanity and illusion, “Though importance ascends to the Heavens… he will perish forever” (Iyov 20:6-7). “Strength endures not forever, does wealth last from generation to generation?” (Mishlei 27:24). Even existing wealth is futile and contemptible to sensible people.

The True Object of Envy

Envy only others’ fear of Hashem. She shouldn’t say, “How can I earn a share in the World to Come? I can’t do it!” for we’ve learned: “One may do much or little, provided the heart is directed toward Heaven” (Berachos 17a).

Charitable Giving

For Hashem’s sake, give one-fifth of all earnings to charity as instructed. Don’t give less, as doing so violates numerous commandments every moment and rejects the Torah, Hashem forbid.

The Supreme Value of Guarded Speech

The primary way to merit eternal life is by guarding one’s speech, which exceeds the value of all Torah study and good deeds. This is the meaning of “tranquil women” (Isaiah 32:9), because the mouth is supremely holy.

Ethical Study and Practice

Among my books is Mishlei (Proverbs) with Yiddish translation. Have them read it daily—it’s the finest moral guide. Koheles (Ecclesiastes) should also be read regularly as it reveals worldly vanity. Study other similar works too.

The Need for Application

But reading alone isn’t enough! Many read moral works without changing. Even those who study ethics lose their growth by going out among people, losing what they’ve gained.

This resembles sowing without plowing—wind scatters the seeds and birds eat them because there’s no protection. Reading moral works without application is like planting without a fence—everything gets trampled. Some plant on stone—comparable to a hardened heart where nothing penetrates, requiring the stone to be broken. That’s why I advised disciplining children who don’t listen. “Train a youth according to his way” (Mishlei 22:6)—a fundamental educational principle.

Torah Study with Pure Intent

I also urge my son-in-law to follow all this guidance, reading this letter to the children, and ensuring his Torah study is for heaven’s sake. For Hashem’s sake, become well-versed in Torah for its own sake, ignoring those who claim it’s unnecessary for children. On the contrary, “Train a youth…” It’s easier to remove an unripe nut’s skin before it hardens. Most importantly, studying for its own sake brings all blessings, as our Sages stated: “Whoever studies Torah for its own sake merits many things; furthermore, the whole world exists for his sake alone” (Avos 6:1).

Proper Conduct

Study Pirkei Avos (Ethics of the Fathers), especially Avos D’Rabbi Nassan, and Derech Eretz which precedes Torah study. Honor your mother-in-law (my wife) and your children’s great-grandmother (my mother) with great respect. Conduct yourself with politeness, gentleness, and respect toward everyone.

Honoring Elders

My beloved Mother, I know you don’t need my guidance, being exceptionally modest. Nevertheless, this letter should be read to you, containing words of the Living Hashem. I beg you not to worry about me, as promised. If Hashem wills that I reach Jerusalem, the Gate of Heaven, I’ll pray for you as promised. If we merit it, we shall all be reunited according to the Master of Mercy’s will.

Creating Harmony

I ask my wife to honor my mother as the Torah commands, especially as a widow whom it’s gravely sinful to pain even slightly. To you, my mother, I request that peace reign between you both, each striving to gladden the other with kind words—a great obligation for everyone. When judged, we’ll be asked, “Did you make your fellow a king over you?” showing we must graciously elevate others. Most of Torah aims to bring joy to humanity.

Final Plea for Peace

Even if someone acts improperly, forgive each other and live in peace, for Hashem’s sake. I ask you, mother, to guide my children with gentle words they’ll accept, and to supervise them. I instruct my children to honor you. Let there be no fighting or anger among you—resolve everything peacefully. May the Master of Peace grant you, my sons, daughters, sons-in-law, brother, and all Israel – life and peace.

Your loving Eliyahu, son of my Master R’ Shlomo Zalman, of blessed memory

The author can be reached at [email protected]