This is one of the hardest psalms to outline, for it treats the problem of the righteous and the wicked plus the outcome of their lives in a back and forth fashion.  The outline I have made attempts to show the flow of this major theme.

I. The Wicked and Me (vv. 1,2).
II. The Lord and Me (vv. 3-11).
III. The Wicked and the Lord (vv. 12-15).
IV. The Wicked, Me, and the Lord (vv. 16- 22).
V. The Lord and Me (vv. 23-33).
VI. The Results (vv. 34-40).

Ellicott's Commentary has this to say: “The poet has one answer, and only one, for the questions handled so pathetically and profoundly in the Book of Job.  The happiness of the wicked cannot endure, and the justice of Jehovah will assuredly re-establish the right, punishing the godless and recompensing the patience and fidelity of the godly” (p. 139).  Other writers also recommend that we read Psalms 49 and 73 in connection with this one.

The opening point, “Do not envy the wicked,” is also a major part of the theme in Proverbs 24.

Do not be envious of evil men, nor desire to be with them;
For their heart devises violence, 
and their lips talk of troublemaking.  
Do not fret because of evildoers, nor be envious of the wicked; For there will be no prospect for the evil man; the lamp of the wicked will be put out (1,2,19,20; NKJ).

These verses from Proverbs 24 cover the basic themes that are explained more fully here in Psalm 37.  Let us now examine this psalm in order to see its answers for a problem that affects the faithful in every age, “Is there really a price to pay for being wicked?  Is there really a reward from God for living right?”

I.  THE WICKED AND ME (vv. 1,2). 

With regard to the evildoers, I am told not to fret or be envious. Since the Lord is saying that these are two things I might end up doing, I need to know what they are:

Fret:  “Incense not thyself”; to be inflamed or heated; to be angry or discontented (also in vv. 7,8).
Be envious:  A similar meaning; “burn with jealousy,” by comparing your position with that of evildoers (see Proverbs 3:31; 23:16; 24:1; Psalm 73:3).

I am also being told at the very beginning that the outcome is certain—they shall be cut down and wither—and it will be “soon”!

II.  THE LORD AND ME (vv. 3-11).

Since I am being tempted to focus on myself in light of the “progress” of the wicked, there are two major sections in the psalm where I am encouraged to view the whole picture and resist the temptations to be fretful and jealous.

At least four key themes are brought before me in verses 3-11.

Trust (vv. 3,4):  Lest I trust in any of the ways of the wicked, I am given the only real alternative: Trust and delight in Jehovah!  He can fulfill my needs and desires.
Commit (vv. 5,6):  If I am desiring that everything will turn out well, I must realize that it can only happen if I commit and trust myself to Him by making His way my way.  He will make all things well.
Rest (vv. 7,8):  Opposites are brought before me here.  Rather than fretfulness, anger, and wrath; I need to rest, wait patiently, and avoid the harm that fretfulness causes.  
Wait (vv. 9-11):  Since I have to “wait” for that which wickedness “promises” (and all of it is a lie); why shouldn’t I “wait” for what Jehovah promises (and all of it is true)?  Inheritance, defeat of the wicked, and abundant peace can be mine by proper waiting.

III.  THE WICKED AND THE LORD (vv. 12-15).

The “ways and means” of the wicked are now more fully exposed for me.

They plot (v. 12).  How can I allow myself to be envious of those whose “success” depends on plotting with gnashing teeth against me?
The Lord laughs (v. 13).  If the Lord can see the feebleness and futility of their ways, why don’t I see them through His eyes?
They draw the sword (v. 14).  Why shouldn’t I look carefully at the “helpless” state of their victims and stand tall for uprightness?
They meet their doom (v. 15).  Isn’t it fitting that their downfall will be at the end of their own swords?

Since the Bible regularly teaches (from Genesis 2 through Revelation 22) that “the wages of sin is death,” isn’t it wise to recall such descriptions as this one when I am tempted to give in, and give myself over to evil?

IV.  THE WICKED, ME, AND THE LORD 
(vv. 16-22)

In three brief statements, all three of us (the wicked, me, and the Lord) are considered.

We are considered in light of who has “little” and who has “a lot.”  If the only consideration is from an earthly view, it cannot be fair!  But from a heavenly and spiritual view, it is obvious that the faithful are wealthy and the evil are destitute.  God will uphold the righteous (vv. 16,17).
We are considered in light of “days.”  That is, “time will tell” the whole story.  God observes the persevering faithfulness of my life in evil times and famine.  He also promises that the seeming splendor of the wicked will perish as the beauty of the meadows or a puff of smoke (vv 18-20).
We are considered in light of the idea of inheritance.  The wicked is unfaithful with things that are not his, so he shall be cut off.  The righteous is the very opposite, and shall “inherit the earth” (vv. 21,22).  This was especially meaningful to Israelites in the era of the land inheritance in Canaan, and is applied spiritually by Jesus in the Sermon on the Mount (Matthew 5:5).

V.  THE LORD AND ME (vv. 23-33).

Five beautiful and motivating points are made here as the Lord appeals to me to be faithful to Him in all circumstances.

In verses 23 and 24, He speaks of my steps.  In His word, He teaches me what my steps should be (Ephesians 5:15-17).  Since the Lord delights in the path He has revealed, surely I ought to delight in it!  He will guide, support, and lift me up by His hand.

In verses 25 and 26, He speaks of bread.  He has promised to care for me in this life, and I can count on His promises (However, this does not mean that the righteous will never have hard times; see Luke 16:19-31).  Let me thank Him for His blessings and look to Him when blessings are not so plentiful.

In verses 27 through 29, He says, “Do.”  The simple action words of the Bible are constant reminders that I cannot inherit from the Lord unless I DO WHAT HE TELLS ME TO DO!  Commandment-keeping has always been the only way to please God!  Do I believe it?  Let me regularly read John 14:15-23; 1 John 2:3-6; 5:3 to remind myself that this is true.

In verses 30 and 31, I am reminded of words.  The righteous can be identified (in part) by the way they talk.  I must speak that which is wise and just.  I can only do this if the law of God is in my heart—then it will guide my steps as well as my words.

In verses 32 and 33, I am told that God will not allow me to be overcome.  He will not leave my sentence up to the hands of the wicked.

VI.  THE RESULTS (vv. 34-40).

Everyone’s life has many results.  Most of those results occur while we live.  But there is one result at the end of every life—what will my one result be?  Will it be heaven or will it be hell?

Three themes are brought before my soul as Psalm 27 is concluded.  All of these have to do with RESULTS.

Me, the wicked, and the land (vv. 34-36).  This lesson is frequently demonstrated in the Old Testament stories of the land of Canaan.  Often, the land was invaded and/or overcome by enemies because God’s people chose evil.  And even now, I often see how many bad results come to people who abuse their earthly blessings.
Me, the wicked, and the future (vv. 37,38).  “Mark,” and “observe” that the future of the upright is peace.  But, the future will be far different for the transgressors and the wicked.
Me, the wicked, and deliverance (vv. 39,40).  The fact that the wicked are lost is not stated, but it is clearly implied; for the righteous are those who have salvation, strength in trouble, help, and deliverance.

Do I trust in Him—or do I fret and envy about the wicked?

“Trust and obey”—this has always been the way.  Let me take this path and keep my affection on the promised result (Colossians 3:1-4).

    — Skip Andrews