When will it become easier?
When you complete individuation and integrate the shadow.
Jungian Psychology
Psyche seeks wholeness through integrating unconscious material. Difficulty stems from rejecting shadow aspects. Recognize archetypes, achieve Self (not ego). Midlife crisis is developmental necessity. Active imagination plus analysis.
Practical Lever
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Shadow work. Dream interpretation. Recognize archetypal patterns. Dialogue with anima/animus. Individuation is lifelong project.
Related Perspectives
Advaita Vedanta
internal
When you realize Atman equals Brahman (Self equals Absolute).
Similar mechanism: internal
Buddhism (Theravada/Mahayana)
internal
When you extinguish craving (tṛṣṇā).
Similar mechanism: internal
Absurdism
Never, and caring about this question is the error.
Contrasting perspective: accept
Anarchism (Kropotkin)
After spontaneous mutual aid abolishes coercive hierarchy.
Contrasting perspective: external
Aristotelian Virtue Ethics
When virtue becomes second nature through decades of practice.
Similar timeline: Months to years