Many fields explore the origins of leadership qualities, with Galton’s (1874; 1869) ‘nature vs nurture’ contention being the central point of conjecture. Contemporarily, Galton’s (1874; 1869) ‘nature versus nurture’ contention has been re-imagined as ‘personality versus expertise’. Although contemporary literature attempts conflating terminology specific to either personality and behaviour, the phenomena remain distinct (Bass, 1990; Beebe, 2010; Burns, 1978; Cattell, 1943b; Kania & Richards, 2012; Stogdill, 1974; 1948). Moreover, Theory X and Theory Y conflate leaders who maintain willing fellowship and those who can compel others to follow. With regard to personality and expertise literature, as well as McGregor’s (2002) Theory X and Theory Y, Ladkin’s (2008) philosophy-based ‘leading beautifully’ paradigm is discussed. Following which, a new ‘leading beautifully’ model is proposed emphasising willing fellowship’s role in leadership, as well as leaders’ inherent ableness to perceive harmonious forms. It is proposed that all individuals are born potential leaders, psyches expressed through personality which predicts their situation-based leadership (Duke, 1986; Ladkin, 2008). Ultimately, leaders with greater mastery of leadership will become better leaders, but inherently all individuals may lead.