Why I Quit a Job I Loved to Chase Freedom

When the system tells you to play small, choosing your dreams becomes the most radical act.

A week ago, I wrapped up my final day at a job I loved, a job that advanced my career, provided stability, and strengthened my skills. I spent a year as Associate Director of Advancement at Recess, and on paper, everything looked aligned: exciting work, professional growth, and financial security.

But here’s what I’ve learned about leaving a job you love: even when you succeed, you carry the system’s voice inside you, telling you to play it safe, to hold on tightly, to not want too much.