Meet Jane: She is happy at her current position as an executive assistant at XYZ Shipping Company. She loves her boss and, through regular performance reviews, she feels that her boss is happy with her work. Together they have set up a long term plan for Jane to keep her challenged and interested in her current role. She gets along with all her co-workers and is completely happy with her compensation package. How often should Jane update her resume? How often should you update your resume? The answer is constantly.