Why is it that when someone chooses not to follow conventional paths—like pursuing a Masters or PhD, having children or a traditional job—and instead lives differently without glorifying their struggle and challenges, people/society often dismiss it as taking the ‘easy path,’ while glorifying conventional struggles as more valuable🤨?

Yes because most people believe that the path of life  they have chosen is the best or the only true path. Besides every life has its own struggles and challenges. There is a tendency in most people to think that theirs is the most challenging circumstances. But each life brings its own challenge. The more unconventional one’s life, often the challenges are greater. But since the typical person has not faced them he does not understand it. 

Thus, for example marraige brings its own challenges but so does living singly brings its own, though different kinds, of challenges . People leading a householder’s life think that living life in an Ashram is easy. But those living in an Ashram think the other way round. It is because of the natural egocentric viewpoint to which we are prone. The grass seems always greener on the other side of the fence.

Affectionately,

Alok Da