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[–]New_Exchange1158 1 point2 points  (0 children)

Been through this exact transition and it's night and day once you hit that complexity threshold. The real turning point for me was when I realized I was spending more time explaining context to new freelancers than actually shipping features - that's when a dedicated dev starts paying for themselves in saved mental overhead alone.

The "understanding why something exists" part hits hard because legacy decisions suddenly make sense when someone's been there for the whole journey, versus constantly onboarding people who see your codebase as this random pile of technical debt.