Given that the various sites in the stackoverflow world discourage questions related to career advice and soft skills, perhaps a new site for this kind of thing might be in order? Or is the thinking that there isn't enough interest for this?
If you think that's a good idea, you can head to http://stackexchange.com and create one yourself!
"Career Advice" would appear to be what you are wanting so it is out there. You may just not know it.
Consider asking such questions on The Workplace, which is "for members of the workforce navigating the professional setting". While it includes career development for professionals in general, there are of course lots of IT professionals there.
Another site that overlaps with IT careers is Project Management.
Warning: Programmers used to have questions related to this (as the name suggests). However, it is now restricted to "conceptual questions about software development". Some career-related questions are still on-topic ("freelancing and business concerns" related to software development), but general career questions should go on The Workplace. See the [career-development] tag (note that most questions are closed).
Really? You want:
Getting a little long on site addresses eh?
The Stack Overflow format is not well suited to discussions; it is designed to be oriented around questions and answers (that is, problems that are answerable).
General programming discussions are much better suited to somewhere like reddit.com/r/programming.
It's not that there isn't enough interest. Those sites remain tightly focused on their stated purpose.
- Stack Overflow - Programming Questions.
- Super User - Power User Computer-Related Question.
- Server Fault - Professional System Administration Questions.
"Questions related to career advice" are rarely within the scope of any of those tightly-focused topics. So, yes, they are discouraged.
Stack Overflow, for example, is about programming and programming-related questions. It can't realistically become a anything-of-possible-interest-to-programmers site without losing focus. "Anything of interest to programmers" covers way too much territory and runs the risk of becoming a Yahoo! Answers-style free-for-all.