In this essay, I critique and critically reflect upon two questions derived from Action Ideal VIII of the MayDay Group: "We commit to understanding the wide range of possibilities and the limitations that technology and media offer music and music learning." Before we can address the "how," it is necessary to know the "why," which I offer here. This includes questioning dichotomies based on beliefs that either no longer hold true and/or are based on a presumptive fallacy--first, that making music in the 21st century is an "either/or" proposition--i.e. one either makes music acoustically or digitally but not both, and second, an implicit belief that hands-on acoustic face-to-face music making is always preferable to making music digitally--either by one's self or with others through technological mediation--for various reasons. I conclude with a discussion of the impact that corporate power on the Web has and continues to have on music making, and by extension, music learning, in the 21st century.