The present chapter focuses on creativity and its potential role in overcoming fear and tolerating ambiguity. Both fear and ambiguity are known to be deterrents of entrepreneurial decisions. In this chapter, entrepreneurial decision-making is discussed as a part of strategic and cognitive process, Creative Aerobics (CA) is introduced as a strategy for enhancing creativity, and finally the key role CA can play in overcoming fear and negotiating and tolerating ambiguity/uncertainty to enhance entrepreneurial decision-making process is discussed. This chapter presents a conceptual model mapping the relation between creativity, fear, ambiguity and entrepreneurial decisions. Review of conceptual and empirical literature in the field was adopted as a methodology to bring forth the possibility of the relationship model. The chapter also emphasizes the need for creativity enhancement and presents CA as a strategy to enhance creativity. CA, a four-step ideation system, can help entrepreneurs generate multiple ideas/solutions in quick succession.