Does losing a paid customer always hurt more than missing a signup?

When we were free tracking new user signups was super exciting. But once we added paid plans seeing a customer cancel after a few weeks felt way worse than someone never trying the app at all.

Looking into cancellation feedback, most users aren't leaving because of missing features. They're leaving because the app doesn't naturally fit into their daily work routine.

Does that sharp pain of subscription churn fade over time, or do you just get better at fixing workflow gaps?