If educators are to educate they must be accorded some level of trust. Anthony Giddens claims that because trust is not easily created, it is now being replaced with "confidence" because this latter disposition is much easier to give and is more convenient. It is argued in this paper that this shift from trust to confidence stifles education because emphasis is placed solely upon qualifications and competence, and is neglectful of disclosing one's motives and desires--which are considered to be essential elements for relationships and communities which depend upon trust. Therefore, educators ought to seek to become more trustworthy by going beyond evidence-based practices and codes of ethics, towards articulating a developed personal philosophy of education outlining the ultimate end-purposes to which they aspire. Through such a philosophy, educators identify their ultimate desires and commitments and this self-disclosure can make trust-giving more likely. Demonstrated evidence of achievements and qualifications encourage confidence and this has some value. In addition to these artefacts of evidence, it is argued here that educators must also articulate what they actually "desire". This can be understood as John Dewey's virtue of "genuine interest" which he characterises as being wholehearted, persistent and impartial. For educators, this is often represented in our personal philosophy of education and because it is personal, it is also existential in the sense that it pertains to giving sense, meaning and purpose to all of our activities and way of life for which we are individually responsible and passionately committed to as professionals. As a consequence of being existential, our philosophy and our commitment to it has an intellectual and moral aspect and because it reaches to the very depths of our "raison d'être", it pertains to our passion as described by Søren Kierkegaard. This paper shall draw upon Dewey's notion of wholeheartedness and Kierkegaard's notion of purity of heart, to make the case that if educators embrace these in their practices, we may become more trustworthy.