How about Jesus himself then? He may not have been wealthy in material possessions, but he was often well-fed, and we find that in some settings - such as when Jesus was returning to Jerusalem - crowds praised and hailed him. And Jesus certainly laughed from time to time. So can we apply Jesus' statement literally as do many ecclesiastical interpreters?
No. Jesus is speaking metaphorically.
What Jesus meant by "rich"
What does it mean to be "rich"? Is richness only about money? And if so, does having $20 in our pocket mean we are rich? People in some parts of the world would consider that a lot of money, while others might see that as merely pocket change. How about having $10,000 in the bank? Again, some would feel that only having this in the bank is being poor, while others would see that as being rich. In other words, being rich is relative.
Rather, the word "rich" is being applied here to refer to someone who is focused upon their material possessions. Someone who prides themselves on being comfortable, and considers themselves wealthy and superior to others is being referred to here.
The opposite consciousness is not feeling we own anything. Everything is owned and controlled by the Supreme Being. When we are in such a consciousness, we feel that all our possessions are God's, and they exist to be utilized in His service.
What is wrong with laughing?
Likewise, there is nothing wrong with laughing. Laughter in a humble way, especially when we can laugh at ourselves, is a good thing. But when we laugh at others - say we think others are beneath us and we can laugh at them - is a different thing altogether.
Jesus is also using laughter metaphorically to refer to someone who feels they can stand above others and laugh at them.
That type of laughter is certainly not happy laughter. It is sad and empty because it assumes that we are better than others, and can make fun of them.
How about others speaking well of us?
This also goes for people speaking well of us. Jesus is not saying a person who is praised is condemned. But someone who seeks out the approval of others while feeling superior to others is. One who follows the herd to gain acceptance by others will often, ironically, be judgmental about those very same people they seek acceptance and approval from.
This actually illustrates the emptiness in such a consciousness. If a person is feeling superior to others, yet at the same time seeks the approval of others, then we can easily see that their seeking approval from others is a symptom that feeling superior is a consciousness of emptiness.
This is our disease, and why each of us fell to the physical world. We wanted to feel superior to others. We became jealous of God's superiority. So God set up an environment where we could pretend that we were each superior to others.
God allowed us to occupy these temporary physical bodies so we could pretend to be someone we are not for awhile. These things - our body, wealth, fame and so on - are real things, but the illusion they bring is that they are a source of happiness. The illusion is that they deliver fulfillment.
What is our real consciousness?
Our real consciousness - our spiritual identity - is one of humility. By nature, each of us is a humble caregiver of the Supreme Being and His associates. But because love and care require freedom, each of us also has the potential to reject our original nature.
Those of us who fell to the physical world and took on physical bodies rejected our spiritual nature.
Jesus is trying to re-introduce his disciples and students to their original consciousness. He is trying to show them their true nature. The word "woe" in these verses is taken from the Greek word οὐαί (ouai) which indicates denunciation. Jesus is denouncing the material, self-centered consciousness.
Why? Because this is not a consciousness that brings happiness. This is a consciousness that brings sadness.
It is not as if Jesus is going around denouncing everything - he isn't being some sort of fault-finder. In fact, here he is speaking directly to his students. What Jesus is doing is delineating between - or contrasting - a consciousness that brings emptiness and sadness from a consciousness that brings one fulfillment.
Jesus is saying that a consciousness that focuses on self-centered material wealth and comfort, superiority over others and seeking acclaim from others produces emptiness.
Spiritual wealth, spiritual happiness and spiritual love
And those who seek spiritual wealth, spiritual happiness and spiritual love will receive fulfillment as they humbly seek those things from the Supreme Being.
Seeking spiritual fulfillment does not mean artificial rejection of the facilities of the physical world. A person can give away all their possessions, fast for long periods, and become a hermit, but if the person's consciousness is in such a state that they feel superior to others, and they seek acclaim from others, then there is no spiritual benefit to their charity, fasting and hermetical lifestyle.
On the other hand, a person who lives physically comfortable, laughs with friends and gets praised by others may indeed be on the path that Jesus is discussing here if we do not place our need for happiness upon these temporary facilities. If we humbly accept that all those physical benefits are temporary and ultimately belong to and come from God, then we can see those facilities for what they are - and even use them in our service to God.
Such a person may be able to focus our life upon the Supreme Being, as we do not confuse our physical body and these physical things with our spiritual nature and our need for re-establishing our relationship with God.
This is Jesus' intention here. It is about the state of our consciousness, not the state of our bank account, our relative popularity, or even the lack thereof. It is about the focus of our lives. Our purpose. Our direction. Jesus clearly identified the humble consciousness we should ultimately seek:
"'Love the Lord your God with all your heart and with all your soul and with all your strength and with all your mind'; and, 'Love your neighbor as yourself.'" (Luke 10:27)