[mmczaplinski]

Obviously, there is a tradeoff between the two ends of the spectrum that you've labelled travel and careerism...

Here is another tradeoff for you to consider: One between telling an inspiring lie in order to pick someone up and being brutally honest about their life choices.

If your "advice" is "you missed your chance, you're screwed", then that does not help anyone else either. Advice is as much about inspiring confidence and fostering a change in perspective as it is about dealing with the hard truths.