What does 'blessed' mean?
The word “blessed” - translated from the Greek word μακάριος (makarios), which means to be "blessed" or "happy" - imparts Jesus' confirmation that this is a state that brings joy.
While some versions of the Bible translate "Blessed are the poor in spirit" to simply “Blessed are the poor,” the Greek word πνεῦμα (pneuma) - which means according to the lexicon, "the spirit, i.e. the vital principal by which the body is animated."
In other words, Jesus is not speaking of being financially poor. "Poor in spirit" is distinctly different than "poor" - indicating a lack of material wealth.
What does 'poor in spirit' mean?
It is describing the state of humility.
To be "poor in spirit" means to have a general disregard of oneself and have given up on their various concoctions - their ideas for happiness and their speculative philosophies.
This contrasts what we see today throughout the physical world: We see practically everyone is in a state of thinking we know so much. We think that we are so great that we can figure it all out. For most of us, this begins with our thinking that if we just get this thing or that thing - whatever our next desire is - we will become happy.
And for those who become philosophical, we think that our own mental speculations about the spiritual world are sufficient.
This essentially boils down to pride: We think we are self-sufficient.
Many of today's self-help gurus like to promote pride as the solution to all sorts of psychological issues: They recommend "self-love" and feeling that we can do anything we want to do. They recommend we need a dose of "I am incredible" and we will be fine.
This idea of self-confidence leads to the notion that we can figure out God with our mind. We don't need anyone telling us about God, because we know it all.
This is ignorance.
The fact is, we are not all-powerful. We are not all-knowing.
The reality is that our mind is only a storage device for the impulses that come in from the senses and the nervous system. It is not all-knowing. Our mind is like a computer hard drive. It stores what is fed into it.
And what is fed in is from the senses - the physical world. Thus the mind has no entrance into the spiritual realm because the spiritual realm is not perceived by the physical senses. The senses have no entrance and therefore the mind has no entrance into the spiritual realm.
Actually, our spiritual consciousness is covered over by the mind's concoctions. This prevents us from seeing even who we are beneath these physical bodies and physical mind. The mind is simply a product of our physical condition.
The pitfalls of self-esteem
Just consider our condition in the physical world: Our first nine months in this body are spent closed up in the cocoon of the womb. After several months, we emerge from the womb in pain - crying and gasping. Throughout our childhood we deal with life's frustrations, pains and insults as we try to cope with other children, our parents, and the general demands of the world. We deal with the ‘growing pains’ of peer pressure, school, and the demands of our family, versus our inclinations for freedom and independence.
As our bodies rise to adulthood, we find ourselves having to cope with struggling to maintain jobs, finances, spouses, family and everyday aches and pains. Life becomes serious in adulthood, and survival is tantamount. We begin to slave away at jobs with little future, and take care of children who have no idea what it takes to maintain them. As we grow older, our bodies become diseased and painful.
Our supposed ‘golden years’ are anchored in the aches and pains inherent in temporary bodies with a limited lifespan. Our teeth begin falling out. Our bones begin to ache. Our muscles weaken. Our eyes become progressively blind. Our hearing begins to fade. Our memory begins to falter. All of these elements make for a downslide into death.
At the time of death, whatever wealth or assets we have accumulated - including our name, reputation and status - all disappear. In one instant - after a lifetime of struggles to accumulate them - they are snatched away at the time of death.
So where is the "greatness" in such a condition?
Where is the "all-knowing" and "I can do anything" in this scenario?
And what did all that confidence and self-esteem get us? Nothing.
The reality is that the various hopes and dreams we might have about becoming happy in the physical world through the acquisition of fame, wealth, family and so on are simply that: dreams. They are illusions. These things do not bring happiness. These things only bring more emptiness. They only bring more sorrow. Why?
Because we are not these physical bodies. They are simply vehicles we drive temporarily. It is like a driver wanting to relieve his hunger by filling up the car with gas. Because the driver is not the car, filling the car with gas will not fulfill the driver.
In the same way, because we are spiritual in essence, physical things cannot fulfill us.
Rather, these physical bodies and this physical world facilitate learning.
Yes, this world and this temporary physical body were designed to teach us. But only if we are ready to learn.
Humility is needed to learn and grow
Now consider what can be taught to a person who thinks they know it all, compared to someone who is humble. The know-it-all doesn't think they need to learn anything. They think they are just fine. So they learn little.
But the humble person is capable of learning because they are not so proud of what they might know already.
One might compare it to a cup. If the cup is full, nothing more can be poured in. But a cup that is empty can be filled easily.
In the same way, a humble state allows a person to learn about spiritual life.
Should we at some point realize the futility of attempting to find happiness in the world, we may become depressed or frustrated with our existence. We might even realize that this world is not a place of happiness after all. We might realize that the world was meant to challenge, test and teach us rather than supply us with comfort and happiness. It is at this point that we become “poor in spirit.” We in effect, give up on chasing around all our concoctions for happiness.
When we realize the futility of trying to be happy in the material world, separated from God, we are ready to begin our re-entry into the “kingdom of heaven.” The 'kingdom of heaven' Jesus is referring to is the place where loving service of God is the primary activity, and pride and self-centeredness have no place. It is the world where love replaces greed. It is the realm where our lust for 'mammon' (or materialism) is replaced by a thirst for pleasing God. It is a world where we are truly happy because we are loving and serving our Best Friend and Soul Mate, the Supreme Being.
Re-entry into the kingdom of God doesn't come with just an intellectual realization. It also comes as a result of us arriving at true humility. True humility is the realization that our self-centered nature has created our separation from God, and that we do not have the power to change this nature alone. We need His help.
Only in this condition can a person truly take shelter in the Supreme Being and allow Him to guide us. Once we understand that we have no strength of our own, and we need our relationship with Him in order to be happy, we are equipped to enter "the kingdom of heaven."
In this state - after we give up our self-importance and our hopes and dreams for this temporary physical world and these temporary physical bodies - we become ready to return home, back to our relationship with the Supreme Being.