Question: What’s the difference between pride & self-esteem?
Answer:

“The Gospel shows us that we are more sinful and flawed than we would ever dare admit and yet – at the same time – in Christ we are more loved and accepted than we ever dared hope.”
Spiritual health would be to believe both of these things about ourselves. God’s love in acceptance is not based on our worthiness but on the worthiness of Jesus. This security gives us a humble confidence that self-esteem never can never produce. For more on this, read Tim Keller’s article on the Centrality of the Gospel.
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