Let's dive in! :-)
1 Then Jesus spoke to the crowds and to His disciples,
2 saying: "The scribes and the Pharisees have seated themselves in the chair of Moses;
3 therefore all that they tell you, do and observe, but do not do according to their deeds; for they say things and do not do them.
"Seating themselves in the chair of Moses" is a way of saying that these religious leaders were trying to get others to recognize them with the ultimate status, prestige, and authority. To put this in modern terms, it's someone putting himself in the chair of the Pope or Billy Graham.
In what ways do you seek to be above any others, whether that be in status/prestige or in authority over them?
These religious leaders were also hypocrites, demanding that others obey enormous sets of rules that they themselves couldn't even follow.
Are there things you judge other people for doing, yet also struggle with yourself? Or, is your issue comparing sins - thinking that what you do wrong is "less bad" than what others do?
In this case, Jesus told the listeners to follow the teachings of the religious leaders, I think likely because of the reasons Paul referenced in 1 Corinthians 8, limiting the freedom in Christ you know you are entitled to so you don't offend others. (There may be other reasons in this specific case, as well.) But motivation is key here - we don't want to become just like the Pharisees in the process! So, we should constantly keep humility at the forefront of our minds.
Are there situations where you've gone along with something you considered legalistic or unnecessarily restrictive to avoid offending people, then began to get comfortable with it and expect others to live the same way? (I'm not talking about things that really were wrong to begin with and you came to learn that.)
4 "They tie up heavy burdens and lay them on men's shoulders, but they themselves are unwilling to move them with so much as a finger.
We've already talked about the hypocritical legalism aspect of this, but another application to modern life I've seen has to do with effort. I've seen situations where some people look like they're really involved in a ministry or project, but really just be organizing and delegating. Now, sometimes, this can be a genuine manifestation of the gift of administration, but other times, it can be a very, very bad thing where someone wants all the credit for doing little of the work.
Does what I've said above strike a chord with any aspect of your life?
5 "But they do all their deeds to be noticed by men; for they broaden their phylacteries and lengthen the tassels of their garments.
Phylacteries and tassels were both accessories to religious garb in Ancient Israel (they're still used by some Jewish sects). So, big phylacteries and long tassels both said "Look how religious I am!" in two ways: They were more cumbersome, making the wearer look more sacrificial, and their size simply drew the eye.
Although the specifics have changed, this problem still runs rampant in the Church today. Sometimes a person who doesn't normally wear a cross necklace for themselves will suddenly wear one just to look extra religious for others. Or someone who rarely prays to God on their own will be asked to pray over a meal on a religious holiday and go over-the-top with something more like a KJV-stylized speech than a conversation with God. Of course, there are many, many more manifestations of this.
Matthew 6:1-6 has much to say about this topic, as well.
What aspects that you associate with your faith would you not do if no one else was around and it was just you and God?
6 "They love the place of honor at banquets and the chief seats in the synagogues,
7 and respectful greetings in the market places, and being called Rabbi by men.
8 "But do not be called Rabbi; for One is your Teacher, and you are all brothers.
9 "Do not call anyone on earth your father; for One is your Father, He who is in heaven."
Once again, this is far too applicable to the modern Church! I cringe when I hear a religious leader insist on being called "Reverend so-and-so" or "Pastor so-and-so" or "Dr. so-and-so." Someone in this person's congregation choosing to call them "Pastor so-and-so" doesn't normally strike me as an issue, since it's naming their spiritual gift and the leader himself did not request to be called that - but in virtually any other situation, I see it as flying in the face of these verses.
Even calling a pastor "Pastor so-and-so" doesn't sit totally okay with me if it's prevalent in a congregation, but for another reason: the clergy-laity divide. Basically, I don't like anything that separates the "official" clergy/ministry team/whatever you want to call it from what is considered the congregation. We all have spiritual gifts, and are all intended to use them at church gatherings, so the concept of official clergy is highly unbiblical (see my extensive exploration of spiritual gifts here) (verses 8-9 get at the fact that all believers are equal, as well). So, if we call someone with the gift of pastoring "Pastor so-and-so," should we call someone with the gift of celibacy "Celibate so-and-so" or the gift of poverty "Willingly-Poor so-and-so" or the gift of tongues "Tongues-er so-and-so"??? But anyway... :-) This paragraph is more my views that I base on the Bible, and is not something I'm claiming to be taught directly in Scripture.
If you're involved in some sort of ministry, do you make a point to mention that as part of your identity when meeting people, or love it when other people bring that up?
(One little side-note about verse 9: That's not saying you can't call your dad "Dad," or even that you can't consider the person you brought you to Christ your "father/mother in the faith" - Paul calls Timothy his son, for example. But what this is getting at is elevating some religious leader to an overly high status, so that it becomes a form of idolatry.)
11 "But the greatest among you shall be your servant.
12 "Whoever exalts himself shall be humbled; and whoever humbles himself shall be exalted.
These final verses are a message we have heard over and over and over and over in Matthew. That repetition reveals that it's a major issue! And the many times we've encountered it through Matthew in multiple different contexts, and have seen multiple modern parallels to those contexts, further demonstrates how critical it is to constantly keep this in mind.
Image credit: "The Synagogue in Florence, Italy" by Toksave. Wikipedia. Used by permission.