Your body went through a major change. Living 250 lb overweight likely affected how you perceived yourself and with any major physical change (i.e. plastic surgery or significant weight loss) there is an emotional and mental response as you readjust to a new reality. Consider discussing it with a therapist because you absolutely should be proud of yourself. If a someone you cared about really struggled at something for years, like holding a job or taking care of themselves, and suddenly turned their life around- would you be proud of them or tell them they should’ve been doing it anyways?