Matthew 6:1-6,16-18 can be broken up into 4 sections:
Concerning "acts of righteousness":
1"Be careful not to do your 'acts of righteousness' before men, to be seen by them. If you do, you will have no reward from your Father in heaven."
Concerning giving to the needy:
2"So when you give to the needy, do not announce it with trumpets, as the hypocrites do in the synagogues and on the streets, to be honored by men. I tell you the truth, they have received their reward in full. 3But when you give to the needy, do not let your left hand know what your right hand is doing, 4so that your giving may be in secret. Then your Father, who sees what is done in secret, will reward you.
Concerning prayer:
5"And when you pray, do not be like the hypocrites, for they love to pray standing in the synagogues and on the street corners to be seen by men. I tell you the truth, they have received their reward in full. 6But when you pray, go into your room, close the door and pray to your Father, who is unseen. Then your Father, who sees what is done in secret, will reward you.
Concerning fasting:
16"When you fast, do not look somber as the hypocrites do, for they disfigure their faces to show men they are fasting. I tell you the truth, they have received their reward in full. 17But when you fast, put oil on your head and wash your face, 18so that it will not be obvious to men that you are fasting, but only to your Father, who is unseen; and your Father, who sees what is done in secret, will reward you.
To follow my train of thought, please now read my spreadsheet on Matt 6:1-18.
What stood out to me especially is three types of hypocrisy. The first and most obvious is what Jesus describes the hypocrites as doing: actively seeking the praise of men through their deeds instead of seeking the Father's reward. (side note: He doesn't contrast their hypocrisy of doing "righteous deeds" to seek man's praise with doing righteousness for the sake of doing righteousness in some disinterested way. He instead contrasts hypocrisy with the right way: still seeking reward, but from the Father not from men. I tell you, I'm sold on "The Weight of Glory" and Christian Hedonism, not because C.S. Lewis and John Piper are so smart, but because they just explain well [in my opinion] what the Bible already teaches.)
Anyway, the first and most obvious hypocrisy is seeking the praise of men through these deeds. This, I am regularly guilty of in other areas, speaking of things I would not otherwise have said, but in such cases people think I'm smart, or spiritual, or suffering, etc.
The second hypocrisy would be to read these three passages in Matthew and go obey Jesus to the "T". For example, I might refrain from announcing my giving with trumpets, but I still seek the praise of men by "accidentally" making my "secret" giving known. Or I might avoid praying prayers on street corners, but I find ways to make sure a friend knows how long I prayed in private in my room. I might know better than to disfigure my face, but I wash it so well, people have to ask me why. Ok, maybe we're more subtle than that, but we find ways to slip in indications that we are doing "acts of righteousness." This is the obvious quintessence of Phariseeism; following the command to the "T," while missing the entire point.
It would seem then, that the solution is to follow the principle behind each of the three acts of righteousness. But even in following the apparent principle lies another danger of hypocrisy. This hypocrisy is the third, and in my opinion, most subtle (and therefore most dangerous). It consists in seeking out the apparent principle (and so convincing yourself you're not a Pharisee), and making that the rule to live by (and so remaining a Pharisee).
Here's an example: Let's say I'm fasting and I read that I should wash my face and avoid disfiguring it. Moreover, I realize I would just be a Pharisee to merely do those things while still finding subtle ways to let others know I'm fasting. So, I recognize a principle, namely that I should not let anyone know I'm fasting by any means whatsoever. And so I heed my newfound principle. The hypocrisy here is that my so-called principle turned out to be just another rule, and I've ended up being a Pharisee after all. I've missed the driving principle that unites the three examples of righteous acts Jesus describes, and I've settled for a "principle" which only applies to fasting (namely "don't let others know you're fasting").
I have learned that this third hypocrisy CANNOT be defeated by trying to come up with all possibilities of subtlely making known my otherwise secret deed and then not doing any of those possibilities. For sin always finds a way I haven't thought of. Rather, this error can only be overcome by truly seeking the reward the Father gives (whatever that be) and counting His reward of greater worth than the praise of men (cf. Hebrews 11:26). If we seek the praise of men, it will be our FULL reward (meaning no reward from the Father). So, the apparent driving principle behind Jesus' three examples is not "don't let others know your 'act of righteousness'" but rather "seek the reward the Father gives instead of the praise of men" (cf. John 5:44).
I'm realizing that when we draw out the driving principle Jesus is getting at, we are so free to follow that principle, we might even "disobey" the example in obedience to the principle. Examples might entail the following (these may be poor examples, but you can probably come up with better ones): After examining his heart to see if he's seeking the Father's reward and not man's praise, a pastor might flat out declare to his congregation that he is fasting and praying about some particular need in order to lead by example and so encourage others to do likewise or similarly. In such a case, the Father's reward for this pastor may even consist in his congregation's obedience, besides the reward that awaits him after the Judgment. Another example might be praying on a street corner in an atheistic society (unlike the religious atmosphere of Jesus' day), where there is no praise from men, only insult, but with the result that people observing see miraculous prayers answered (maybe even healings in their presence).
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It just so happens that last Tuesday at my young guys Bible study (which at this point contains one other guy, but he is very interested in it) we went over Matthew 6:1-18 as we've been working our way through the Sermon on the Mount. I am in agreement with what you have said and I wanted to throw in some extra support from the Sermon on the Mount itself.
First, when we were studying I mentioned that I think "do not let your left hand know what your right hand is doing" means not only don't do it to to be seen by others, but do not do it to be seen by yourself. Do not be overly conscious of your own good deeds, do them but don't think about them too much. It is all too easy to either be proud of yourself for having done well, or to worry endlessly (and uselessly) about whether your motives were perfectly correct.
Second, when we finished going over that section I had us immediately go back and read Matthew 5:16 "In the same way, let your light shine before others, so that they may see your good works and give glory to your Father who is in heaven." At first it looks like Jesus has flatly contradicted himself, but if you look more closely the motives don't contradict. Both fit with "glorify God and enjoy him forever." The valid motive for doing your "works of righteousness" in private is to do it for God and to enjoy God("And your Father who sees in secret will reward you"). The valid way to do your "works of righteousness" in public is to do it for the glory of God through demonstrating God's goodness and righteousness publicly.
Well, that's my take on the passage and I think it is basically your take on it but with different words.
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