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by spikyman 729 days ago
A very short list:

* The trick is to set everyone's expectations low, especially your own. E.g.; Even for a relatively small project, make sure management understands that there is no way to guarantee a schedule.

* If you think a step will take x days, schedule 4x days. EXPECT 4x. Generally, EXPECT bizarre failures to fry your so-called "schedule."

* Simple, obvious steps that work initially will suddenly stop working, and likely near the project's end.

* At least one thing not obviously connected to your project will stall everything (e.g., an old switch, a DB update, something somebody band-aided with COBOL 40 years ago**, ad nauseam.)

* You will almost certainly have at least one hair-pulling interaction with the security team. Hopefully, you'll have someone higher up to help you.

**yeah, that happened.