I like the theme of authenticity but do not see the connection of having to make a choice to be popular or unpopular. Authenticity is what makes you who you are and defines your character, which you then use to define the world and society with which you interact, and not the other way around where the world and society defines who you ought to be. If its the former, then you are guided by your principles and values in making your choices and the consequences that come with them. If it’s the latter then you let the world and the society with which you interact influence your choices but are still personally responsible for the consequences. True authenticity allows us to pursue the best in ourselves irrespective of what the world thinks. In your reasoning one is also required to be judgmental between ‘popular’ and ‘unpopular’ and ‘authenticity and inauthenticity’ which are value judgements that are subjective and relative. I would feel very uncomfortable doing that. To answer your three questions; Five years from now, I would like to say that I was true to myself and my character. Ten years from now I would not really care what others say about me as long as I was true to myself, my values and principles. If I were to die today my last thought would be “I’m at peace with myself for being who I was.” John Wooden, known as ‘Coach’ who led the UCLA Basketball Team to record wins that are still unmatched sums it up quite appropriately when he said ‘Be more concerned with your character than your reputation because your character is what you really are, whilst your reputation is merely what others think of you.’
Thank you for your post and sharing and the opportunity to respond.