It's helpful to tell people that they are in uncharted territory and can't rely on running on autopilot even if you don't have a new map to give them. Whether they can make their way or not is unclear, but the first step is just making sure they understand that they're now in a place where they need to make their own way and can't fully rely on existing maps. Otherwise they might not even realize they need to start asking "am I doing the right thing right now" by themselves.

You can cultivate good taste by intentionally taking in a lot of information about what's in the field, and what you like and what you don't like about it. This could be commenting on elements of film, fashion, photography, but it can also be having a sense of what you like to see stylistically in a contract, in a framework, or in corporate culture.

I recall reading an interview about a legendary developer, and the majority of the interview was not focused on his coding decisions or the structures he built, but it was about a notebook that he kept with voluminous notes about what was good and what wasn't. That notebook is a materialized version of 'taste', and it's certainly something almost anyone could put together with enough effort and time.

The author's answer was:

> But if I had to summarize it in one sentence, it would be that taste comes from practicing the skill of research, keeping your focus always on identifying what works and what doesn't.

Instead of following general guidelines, focus on figuring out what works and what doesn't in each specific situation. Keep doing that for many years, and your taste will develop. Remember that you are training your intuition, not developing a set of exact rules.