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Re:Ask HN: Senior devs: what are some tough programming prob... by jacob9706 on Friday November 09, 2018 @03:15PM (#18417557)
Legacy code is always frustrating. I had to pick up Delphi at one point to fix a bug in an application who's only job was to relay specific windows messages (essentially a broker).

5 sold days getting the environment setup (every dependency had to be in the PATH), 20 min to make the change then another 3 days getting the installer build environment setup.

Re:Ask HN: Senior devs: what are some tough programming prob... by jacob9706 on Friday November 09, 2018 @03:23PM (#18417631)
But don't conflate tough with what frustrates people. I spent 2-3 years designing and building 3D CAM software that presented MANY challenging problems from abstracting platform API's to optimzing toolpaths for cost effective manufaturing.

Not once did I get frustrated with the learning or implemention process. The frustration in a sr devs life (in my experience) usually comes from uper management putting "really cool" features on the back-burner to never be seen again.