This paper focuses on the shadow side of philanthropy. The paper analyses some of the areas practitioners in the philanthropy sector should apply their minds to and avoid in the journey of building a progressive philanthropy ecosystem that works to serve the aspirations of those who give with good-will and those who receive the good-will gestures.

In the analysis on the dimensions that sometimes cast a shadow on giving, the paper shows that this produces mistrust, frustration, exploitation, abuse and misfortune among several other negative ramifications. In this paper we shall point out areas where challenges and excesses exist for purposes of supporting boundary-setting actions in the practice of philanthropy.