Why hasn't money made me happy?

Rabbi Landau answers with a question of his own: “Why did you expect money to buy your happiness?” Money can buy a steak, “but it can't buy your appetite.”

“Money can buy a house, but it can't buy a home. It can buy medicine, not health. Money can buy a bed, but not sleep. You can buy a book, but not wisdom.” Shlomo HaMelech already warned us: “Better a meal of vegetables where there is love than a fattened ox where there is hatred.”

He calls it tragic that people expect “to fill a spiritual void with materialistic solutions.” So when we use dollars to plug spiritual holes, he says, don't wonder why it feels empty. You're not lacking money. You're lacking alignment.

Also answered in this teaching

Does that mean I should reject material things?

No. In A Soul at Peace, Rabbi Landau writes that the verse does not say to throw away the ox; it says to bring the love in. Money bought the house; now fill it with Shabbos, with conversation, with peace in the home, and with Torah.

Going deeper: Rabbi Landau's teaching, level by level

Surface claim

Money buys things, not what makes them worth having: a steak but not an appetite, a bed but not sleep.

Fear, vulnerability, or tension

A person can work hard, earn, and still feel empty, and wonder what went wrong.

Underlying need or longing

What people are really after is appetite, home, health, sleep, and wisdom: the life inside the things.

What may be behind it

Rabbi Landau names it plainly: trying to fill a spiritual void with material solutions. In A Soul at Peace he writes that money buys the vessel, but cannot reach the light that fills it.

Deepest human truth

You're not lacking money; you're lacking alignment.