Should I set goals that seem unrealistic?

Rabbi Landau answers yes: aim far higher than seems reasonable. “Every wealthy person you admire was completely out of touch with reality when they start.”

His point is about where you land. Someone who aims for billions may not reach billions, “but they at least got the millions.” Someone who aims for millions may land at a few hundred thousand, “which is still higher than the people who are being realistic.” Being realistic tends to fix your result low before you begin.

He grounds this in a saying of our Sages: no one leaves this world with even half of his desires fulfilled. Rather than reading that as a reason to want less, Rabbi Landau reads it as a strategy. If you will only reach half, make the whole as large as you can.

“So desire big,” he says, “and the same applies to everything in life. Always make it half of something massive.”

Also answered in this teaching

Does “no one dies with half his desires fulfilled” mean we should want less?

Rabbi Landau teaches the opposite. Since a person reaches only part of what he aims for, the lesson is to aim for something so big that even half of it is massive.

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

Surface claim

People who aim very high usually land higher than people who aim to be realistic, even when they fall short.

Fear, vulnerability, or tension

Aiming small feels safe. In A Soul at Peace, Rabbi Landau calls this a kind of “realism” that looks humble but holds a person back, fixing his “half” at a low level from the start.

What may be behind it

The Sages' saying that no one leaves the world with half his desires fulfilled is not a counsel of despair. Rabbi Landau reads it as a rule: what you achieve depends on what you aim for.

Deepest human truth

The same applies to everything in life, Rabbi Landau says, including serving Hashem. Make your aim so large that even half of it is something great.