Our culture seems to think that the best way to build self-esteem is by never experiencing failure. Whereas in youth sports activities the winners used to be the only team to receive a trophy, today every participant receives a trophy, or a blue ribbon, simply for participating. As if mere participation was the goal to obtain rather than accomplishing something special together as a team. Our modern culture has adopted the mindset that everyone needs to be made to feel special and important regardless of how much effort has been invested or how much growth has taken place. In other words, you can feel good about yourself simply because you showed up. Just give it some kind of effort and you will be celebrated and rewarded because we don’t any child left behind. From all accounts, this approach has backfired. Rather than making everyone feel special, it has left no one feeling special. Rather than challenging our youth to persevere, grow, and pursue excellence, it has built a generation who either don’t feel much is expected of them, or who feel catered to as if that is the best they could do. In the book Generation iY Tim Elmore interviews a business owner who consistently hires young people for his company and asks the owner what one word would he use to describe this Millennial generation. The man’s response was the word, “Entitled.” This trophy kids generation has been raised to believe that what matters most is how they feel about themselves, and therefore the expectation they have developed is that the world should bend and shape to whatever it is that makes them feel good. The desire to make sure our kids had good self-esteem has instead produced a generation that is more self-centered than any generation prior.

Pride can show itself in one of two ways. The more obvious way is the person who boasts of his own greatness. The person who always makes the conversation about himself. The person who always has to one-up you when sharing stories. This person makes life all about himself as a means to prove he is better than others. However, there is a more subtle form of pride. This is the form that masquerades around like humility, but is in fact a false version of humility. This is the person who is always putting himself down, who is always in need of a compliment or being told he is good enough. This is the guy who feels he doesn’t measure up to anyone, who is the constant victim. This person is also making life all about himself, not to prove he’s better, but in hopes that someone else can him feel better.

With either form of pride, the root cause is ultimately insecurity. It is the fear of not being enough; not being beautiful enough, smart enough, talented enough, powerful enough, etc. It is the discontented soul that constantly screams at us that we’re not worthy of love or acceptance because of our very essence that causes us to either over inflate or over deflate our achievements. In response we either boast to make ourselves appear more lovable than others, or we mope in hopes that someone else will make us feel lovable at all.

Nope. Pride is an unquenchable thirst and hunger. The more attention and adoration you feed it the hungrier it becomes. Because the essence of pride is to say I have to do more to prove my worth, and because more is a quantity you can never satisfy, so pride will continue to drive you deeper and deeper into a place of despair because no matter far ahead you seem to get you always still feel way behind.

To boast in the cross is to brag about two things: first, it is to brag about your own inadequacies, your own failures, but not in a woe is me kind of way that is simply fishing for compliments. It is to brag in a way that acknowledges you don’t have what it takes to be awesome, to be loved by God. It is to look into the eyes of that voice that screams you’re not lovable and say in response, “Yeh, and what of it.” Second, it is to brag about the unconditional and unmatched love God has extended you, despite your failures, because Jesus has deemed you lovable. To boast in the cross is to put it, as Dr. Tim Keller put it, “I realize I am more messed up than I ever thought because Jesus had to die for me. But, I also realize I am more loved than I could have ever imagined because Jesus was glad to die for me.” Boasting in the cross is to acknowledge that I may not be lovable or acceptable based on anything I have done, or ever will do, yet I am unbelievably loved by the King of the Universe because Jesus has traded places with me.

It is in realizing what boasting in the cross means, that you can then stand firm in your position before God. You can know that no matter what anyone else may say about you, Jesus, the King of the Universe, the Most Important Being in Existence, has already affirmed you, loved you, accepted you, desired you, invited you in to be His. So, when others reject you, wound you, dismiss you, or seek to hurt you, you can look them in the eye and say, “There is nothing I have that you can take from me, so in response I can give all I have to you rather than needing anything from you.” It is the only way to love unconditionally, once you have understood how unconditionally loved you are. There is no insecurity because you know you are secure in the love of Christ. And, there is no pride because you recognize that the position you stand in has nothing to do with anything you have done, but in every way with what Jesus has done on your behalf.