There is a moment many of us recognize. You look at your PTO balance and realize you have not taken a real break in months. Maybe it feels risky to step away. Maybe you worry about the pile waiting when you return. Or maybe rest has become one more thing you have to manage. In this conversation, we unpack the quiet pressures around taking time off, the habits we pick up from teams and past jobs, and the small ways we learn to give ourselves permission to rest.