My friend Paula was asking advice on a situation that was giving her a little bit of anxiety; for which, I suggested that a particular fear needed addressing (which one not being relevant here), along with some other points.  She responded: "You seem fearless.  How does that feel to feel fearless?"  Here's how I answered:

How does it feel to not fear a speck of dust on the other side of the planet? It just doesn't matter.  How does it feel to have gotten past some particular fear?  Empowering.  How does it feel to realize that all fears don't really matter?  The smile that comes across your face has the most wonderfully high and sweet vibration—expanding into all beauty—freeing you.  Now go watch some Matt Khan and read my “Soar” writings.  — John Æonid

Note that this is not a claim that I am utterly free of fear; I'm not.  Nor is it a claim that fear has no purpose; fear does have a purpose.  But, this is to hint at how fearlessness should not feel special, but getting past it should—recognizing that fear need not be any more important than the function it performs to keep us alive.  Fear beyond that which keeps us alive is about things that need not matter at all, and there are ways around subjecting ourselves to fear that is useless. And, getting in the habit of setting aside unnecessary fear, along with the development of the associated skill, creates a growing sense of empowerment. Also, tip of the hat to Byron Katie and Eckhart Tölle as well.