The Accreditation Council for Graduate Medical Education is transitioning to a competency-based system with milestones to measure progress and define success of residents. The confines of the time-based residency will be relaxed. Curriculum must be redesigned and assessments will need to be precise and in-depth. Core anesthesiology faculty will be identified and will be the “trained observers” of the residents’ progress. There will be logistic challenges requiring creative management by program directors. There may be residents who achieve “expert” status earlier than the required 36 months of clinical anesthesia education, whereas others may struggle to achieve acceptable status and will require additional education time. Faculty must accept both extremes without judgment. Innovative new educational opportunities will need to be created for fast learners. Finally, it will be important that residents embrace this change. This will require programs to clearly define the specific aims and measurement endpoints for advancement and success.