Variety: Matthew 21v31

Truly I tell you, the tax collectors and the prostitutes are entering the kingdom of God ahead of you. (Matthew 21:31) 
Blessed are the poor in spirit (Matthew 5:3)
Your life is now hidden with Christ in God.(Colossians 3:3)

Richard Rohr explores how chasing success is one of the greatest temptations we face. The things that Jesus cared about, such as powerlessness and humility, instead become our shadow.   
Our shadow self is any part of ourselves or our institutions that we try to hide or deny because it seems socially unacceptable. The church and popular media primarily focus on sexuality and body issues as our “sinful” shadow, but that is far too narrow a definition. The larger and deeper shadow for Western individuals and culture is actually failure itself. Thus, the genius of the gospel is that it incorporates failure into a new definition of spiritual success. This is why Jesus says that prostitutes and tax collectors are getting into the kingdom of God before the chief priests and religious elders (see Matthew 21:31).  
Our success-driven culture scorns failure, powerlessness, and any form of poverty. Yet Jesus begins his Sermon on the Mount by praising “the poor in spirit” (Matthew 5:3)! Just that should tell us how thoroughly we have missed the point of the gospel. Nonviolence, weakness, and simplicity are also part of the Western shadow self. We avoid the very things that Jesus praises, and we try to project a strong, secure, successful image to ourselves and the world. We reject vulnerability and seek dominance instead, and we elect leaders who falsely promise us the same.  
I can see why St. Francis of Assisi made a revolutionary and pre-emptive move into the shadow self from which everyone else ran. In effect, Francis said through his lifestyle, “I will delight in powerlessness, humility, poverty, simplicity, and failure.” He lived so close to the bottom of things that there was no place to fall. Even when insulted, he did not take offence. Now that is freedom, or what he called “perfect joy”!   
Our shadow is often subconscious, hidden even from our own awareness. It takes effort and life-long practice to look for, find, and embrace what we dismiss, deny, and disdain. After spending so much energy avoiding the very appearance of failure, it will take a major paradigm shift in consciousness to integrate our shadow in Western upwardly mobile cultures.   
Just know that it is the false self that is sad and humbled by shadow work, because its game is over. The true self, “hidden with Christ in God” (Colossians 3:3), is incapable of being humiliated. It only grows from such supposedly humiliating insight.  
One of the great surprises on the human journey is that we come to full consciousness precisely by shadowboxing, facing our own contradictions, and making friends with our own mistakes and failings. People who have had no inner struggles are invariably superficial and uninteresting. We tend to endure them more than appreciate them because they have little to communicate and show little curiosity. Shadow work is what I call “falling upward.” God hid holiness quite well: the proud will never recognize it, and the humble will fall into it every day—not even realizing it is holiness.