Faith in Knowledge or Knowledge of Faith

"How do you know when taking a leap of faith in something is the right thing to do?"

This is the Great Paradox that is inherent in the intersection of the material world with the spiritual world.  How do you "know" "faith" in something is justified?
The real question is, "Which is greater, faith or knowledge?"  If knowledge is greater than faith, I need to "know" before I leap.  However, if faith is greater than knowing, that is what is required before I jump.

You've read this one:

Heb 11:1 NASB  Now faith is the assurance of things hoped for, the conviction of things not seen.

You can't "know" that  a leap of "faith" is the right thing to do.  If you "know" it, it is no longer "faith".  And, yet, no matter what premium we've attached to knowledge and rational thought in our enlightened age of reason, the reality is that it has little power to propel us into anything greater than where we are.  Only by faith in things unseen do we ever learn, grow, conquer, create - live really.  Knowing is limited to the material world and the five senses.  Faith allows us to transcend these to reach a place we have never been.  It doesn't negate "reality", but, simply puts it in its proper place.
The truth is that there is no place "where no man has gone before."  Oh, in the very literal sense there is in that no two situations are identical. I suppose, in that case, every "where" we go is unexplored.  But in a more practical sense, it is not about going to a place where no man has gone before as much as it is going to a place that I have never gone before.  Just because I don't have a road map doesn't mean there isn't one, or, as many people believe, that the place must not exist.
Faith is a conviction (the state of being convinced).  It is a term with strong legal overtones that carries with it the ideal that ample evidence has been presented to persuade us that "this" is the truth.  We "know" something to be true either because we have ample evidence through personal experience or because we have "faith" in the source of the information
You see, you can have a great deal of faith with very little knowledge, but you cannot have any knowledge at all without a great deal of faith.  In order to have knowledge, you have to have faith in your senses, memory, the consistency of experience and lawful order.  You must have faith that you can even "know" anything in the first place.  If knowledge is dependent on faith, then faith is greater.  If faith is greater than knowledge, then it is not necessary to "know" that "faith" is justified.  It is only necessary to know what our faith is in.
In the secular world, we should take the leap when it will lead to our growth and ultimate greater good or if it provides opportunity for someone else to do the same.  In the sacred, the question is, "Will this result in glory and honor to God?"
My faith is founded on God.  The ultimate source of creation and sustenance in our material world.  He is sine qua non (without which not), or that without which there is nothing.  My knowledge of Him is very, very limited, however, I am convinced to a very great extent through personal experience that He is more that I can even imagine and therefore completely sufficient.  As I continue to "leap", I accumulate more evidence of his all sufficiency.  When I leap amiss, I nearly always discover that my knowledge failed me.  But not my faith.
So, jump already.

For I know whom I have believed and am persuaded that He is able to keep that which I've committed unto Him against that day. KJV 2 Tim 1:12b