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William Guthrie explains that one may lack assurance due to a failure to rightly understand what true faith entails.

Guthrie begins with the paradox of saving faith: It is both impossible for one to obtain, and it is simultaneously an easy thing.

The impossibility of faith is seen in that faith must begin with God:

No one can come to me unless the Father who sent me draws him. John 6:44.

Leaving aside whether the Father in a manner draws all after a manner ( as taught by Wesley, see, e.g., http://gbgm-umc.org/umw/wesley/walk.stm, “The grace or love of God, whence cometh our salvation, is FREE IN ALL, and FREE FOR ALL….”),  or God draws only the elect (the “Calvinistic” position, see, e.g., http://www.gty.org/resources/questions/QA86  ), all agree that true coming to God in Jesus Christ begins with the act of God.

Paul thus writes, “For it has been granted to you for the sake of Christ that you should not only believe ….” (Phil. 1:29).

Yet, at the same time, saving faith is an easy, as Paul writes elsewhere:

6 But the righteousness based on faith says, “Do not say in your heart, ‘Who will ascend into heaven?’ ” (that is, to bring Christ down) 7 “or ‘Who will descend into the abyss?’ ” (that is, to bring Christ up from the dead). 8 But what does it say? “The word is near you, in your mouth and in your heart” (that is, the word of faith that we proclaim); 9 because, if you confess with your mouth that Jesus is Lord and believe in your heart that God raised him from the dead, you will be saved. 10 For with the heart one believes and is justified, and with the mouth one confesses and is saved. 11 For the Scripture says, “Everyone who believes in him will not be put to shame.” Romans 10:6–11 (ESV)

To drive home the point, Guthrie compares the content of true with faith with things which would be difficult matters to believe, such as: I am not required to believe that I am elect, or that God loves me in particular. Such things would be difficult to believe, because such things would require belief in things which I could not know. Saving faith merely requires the belief in things which can be known.

Guthrie then addresses another paradox, or perhaps an irony. For the flippant atheist, asserting that God loves me in particular or making other statement about God’s undisclosed intention is easier than believing that I am a sinner in need of a savior.