Who are the "holy ones in the land," and why would I connect to them?
Verse 3 is one of the hardest lines in the psalm, and the commentators do not agree. The words are "the holy ones who are in the land, and the mighty ones, all my desire is in them." Who are they?
Rashi (the classic commentator, France, died 1105) says they are righteous people who are buried in the earth, who walked before God in truth. The good that comes to the speaker comes for their sake. The Midrash on Tehillim agrees about the timing. It says God does not call the righteous "holy" until they are placed in the ground, because until the day a person dies, the urge to do wrong still presses on him. Even Avraham, Yitzchak and Yaakov, it says, were not called holy until they were buried.
Radak (Rabbi David Kimchi, Provence, around 1200) reads it differently. For him the holy ones are living people. Walk in the footsteps of the holy people you meet on your way, he says, and learn from what they do. He points to a teaching in the Gemara that "you shall fear Hashem your God" includes awe for Torah scholars.
Ibn Ezra (a Spanish commentator, 1100s) notes that "holy ones" usually means angels, which is why the verse had to add "in the land." For him it means holy people here on earth, and "all my desire" means that all his wish is to be like them.
The Tikkun HaKlali uses this verse too. The short paragraph said before the ten psalms (by Rebbe Nachman's followers; it names him) ties the reader to the true righteous of our generation and to those who rest in the dust, "holy ones who are in the land." It names both.
So the sources give two answers: righteous people who have died (Rashi, the Midrash), or holy people you can meet and learn from now (Radak, Ibn Ezra). The words do not settle it. In both, the speaker wants to stay close to people who are better than he is.
Rashi, Radak and Ibn Ezra on Tehillim 16:2-3,Midrash Tehillim 16:2,Pesachim 22b,Tikkun HaKlali, opening paragraphVerse 4 sounds like a curse. Is this psalm wishing pain on people?
Verse 4 begins: "Their sorrows will multiply, those who rush after another." Read fast, it sounds like David wishing pain on his enemies. The commentators do not all hear it that way.
Rashi takes it as a wish spoken to God: may the sorrows multiply of those who deny You and hurry to worship other gods. The speaker then refuses to join them. He will not throw blood to an idol, and will not even say the names of their gods.
Radak calls a different reading the correct one. David will cling to the holy and mighty ones, and the sorrows of the people who rush after other paths, away from the ways of Hashem, will multiply. Radak ties the sorrows to the road those people chose. He adds that offerings brought along with wicked acts do not help. They harm, as Mishlei says: the offering of the wicked is an abomination.
The Midrash on Tehillim hears something else. In one version, David asks God about Jews who died in a generation of persecution, rather than give up their faith: "You multiplied sorrows for them." God answers by reading the next words of the verse. Did they lose anything? Their blood is dearer to Him than offerings.
So there are at least three readings: a wish (Rashi), a warning about where those roads lead (Radak), and a cry over people who suffered for their loyalty (the Midrash). The sources do not choose one. In each, the verse goes on with a refusal: "I will not pour their offerings of blood."
Rashi and Radak on Tehillim 16:4,Mishlei 21:27,Midrash Tehillim 16:3"I place Hashem before me always." Who can actually do that?
Verse 8 is the line most people know from this psalm. The Rema (Rabbi Moshe Isserles, Poland, 1500s) wrote notes that are printed in the Shulchan Aruch, the main code of Jewish law. He quotes this verse in its first law. He calls it a great principle of the Torah and of the way righteous people live.
The Reishit Chochmah prayer tells his picture of a person standing in front of a great king, and what that does to how he acts.
That still sounds like too much to ask all the time. Radak begins: "in all my ways I will remember Him." He compares it to something that is always in front of a person and never leaves his eyes or his mind. He then quotes the Rambam (Maimonides, Egypt, died 1204) on "at my right hand": it is like your right hand, which you never forget for an instant because it moves so easily.
The Gemara uses the verse for prayer. Rabbi Shimon the Pious, a sage of the Gemara quoted by Rav Chana bar Bizna, says that someone who prays should see himself as if the Divine Presence is standing opposite him. On the same page, the verse is also read as a law for a king, who carries a Torah scroll with him, made like an amulet and hung on his arm.
The word in the verse is tamid, always. These sources each give a way to try it.
Rema, Orach Chaim 1:1,Radak on Tehillim 16:8,Sanhedrin 22a