In this chapter, the authors cover the confidence dilemma and overcoming ‘imposter syndrome’, being determined yet patient, to partner or not to partner? and To plan or not to plan, and how good is good enough? Levels of confidence stem from a blend of intrinsic and extrinsic influences. Intrinsic influences include personality, values, self-image and personal qualities. Confidence is seen as an important attribute when starting up a new business – with a positive view of life being essential. The authors illustrate how a lack of confidence and imposter syndrome manifested in some of their interviewees’ stories and how they coped with it. They share some of their views to inspire others on how to overcome or at least mitigate or perhaps mask a lack of confidence. Interestingly, the best advice on confidence came from those who had learned the hard way by developing coping tactics or outgrowing it.