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Lesson 041 · posted Thu Sep 10 2026

Regret a Road Not Taken?

What Judaism says about the path you're on: five ideas, each with its source.

5 things Judaism can teach us about the path you're on. The other road was never yours. This one is. And it's being directed.

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  1. 1

    Man plans. God directs.

    ה׳ יכין צעדו
    “A man's heart plans his way, but the Lord directs his steps.”Proverbs 16:9

    Proverbs 16:9. You planned the other road. The steps you actually took were being directed. The verse does not cancel the plan. It says the plan was never the whole story.

  2. 2

    God sent me ahead.

    שלחני אלהים
    “God sent me before you to preserve life.”Genesis 45:5

    Genesis 45:5. Yosef, sold by his brothers, thrown in a pit, jailed for years, says this to the men who did it. The worst road of his life turned out to be the one that fed a nation.

  3. 3

    Your steps are established.

    מצעדי גבר
    “The steps of a man are established by the Lord, and He delights in his way.”Psalm 37:23

    Psalm 37:23. Not the destination. The steps. The one you are taking today counts, and the verse says it is being enjoyed.

  4. 4

    Plans for your welfare.

    מחשבות שלום
    “I know the plans I have for you, plans for welfare and not for harm, to give you a future and a hope.”Jeremiah 29:11

    Jeremiah 29:11. Said to people in exile who had lost the road entirely. The promise is not that you get the old road back. It is that there is a future on this one.

  5. 5

    Everything has its time.

    יפה בעתו
    “He has made everything beautiful in its time.”Ecclesiastes 3:11

    Ecclesiastes 3:11. In its time. Not in the time you had planned. The road you did not take had a time too, and it was not yours.

The other road was never yours.

This one is. And it's being directed.

Save this for a 2am what-if, and send it to someone living in the past tense.

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Sources

Art on the slides: Constant Troyon, Road in the Woods (mid-1840s) · Auguste Renoir, A Road in Louveciennes (ca. 1870) · Salomon van Ruysdael, A Country Road (1648) · Salomon van Ruysdael, Ferry near Gorinchem (1646) · Alfred Sisley, The Road from Moret to Saint-Mammès (1883–85) · Alfred Sisley, The Road from Versailles to Louveciennes (probably 1879) · Edmond-François Aman-Jean, The Outskirts of a Village (ca. 1880). The Metropolitan Museum of Art, open access.