So why is it a challenge to love ourselves?
I'm pretty sure it is because we have a wrong idea of love. We only know love through the lens of our ego.
This fake love for us is separating. It makes us special at the expense of someone else. That's why judgment plays such a role. Because we have to know where we are on the continuum of specialness. When we feel like we are higher than others then we feel good and when we feel like we are lower than others then we feel bad.
Don't believe me on this? Walk into a fitness club where all the men or women are 10x fitter and hotter than you and walk into a fitness club when you are the youngest/hottest one there. How do you feel? Point made?
Real love is abundant. Inclusive. Connected. It doesn't have to be special at the expense of someone else. It is special because of its own qualities.
It is why real love for ourselves is never arrogant.
So why does it matter?
I don't think we can love other people without love for ourselves. Love for others without love for ourselves produces burnout. Resentment.
Real love is expansive. I believe it is the reason Jesus says to "love the Lord your God with all your heart, soul, mind and strength and love your neighbor as yourself." A love that encompasses our heart, soul, mind, strength, God, ourselves can't be viewed as linear neither horizontally (in that we have to get from point A to point B) nor vertically (greater than/less than). Instead it is 3 dimensional like some great pool we can swim in sharing the water with all and being immersed in our very being.