How much you strive to impress someone should be directly proportional to how much you admire them and their importance in your life. Your close friends, your family, your valued mentors – you absolutely should try to impress them! That’s part of their role in your life. If they’re noble people, then they’ll be impressed by nobility, and that will cause you to strive for good qualities and noble deeds.
That means don’t waste time trying to impress people you don’t admire, even if it feels like in the short term you’ll get something. The cost will be high as you pursue foul works to impress foul people. And certainly don’t waste time trying to impress people who can’t even observe you – don’t think “oh, my favorite celebrity would love this!” They won’t.
Want a good compass for life? Do good deeds, and watch who becomes impressed. Grow closer with them. And then impress them more. The virtuous cycle will carry you far.
The Opportunity Machine 