Guess I've always been old 🙃 YSK: properly fitting shoes are comfortable immediately. "You need to wear them in before they're comfortable" is something impatient parents tell their kids when they're tired of school shoe shopping, then the kids grow up believing it and tell their kids...
Ageing is realising shoe comfort matters. I used to wear pointy formal shoes for work, but upgraded to Doc Martens. Now realised they're too heavy and got some Skechers. Old.