I'm almost convinced that rather than working on our weaknesses first, I think what works is knowing who we are in Christ first and foremost, and I don't think an average Christian actually does know who they are in Christ, creating an 'insecurity' of a different kind.
For starters, it's most beneficial for us to know that we're fearfully and wonderfully made, that we're so loved that Jesus would leave 99 sheep (who can stand together) than let that one get lost without any hope of ever finding their way home; that Christ died for us knowing that we'll make mistake after mistake in life, yet Jesus' love remains, for us, ever the same.