Why do I keep comparing myself to others and always lose?

You lose because you are comparing your inside to their outside — your fear and doubt against their edited surface. Say the envy out loud to God instead of dressing it as judgement; named, it shrinks. Then ask for two things: enough for your own life, and the ability to be genuinely glad for someone else, which is a skill, not a mood.

The old teaching is sameach b'chelko — to rejoice in one's own portion; the wealthy person, it says, is the one who is content with what is theirs.

From the sources “Be still before the Lord and wait patiently for Him; fret not.” — Psalm 37