The me who teaches basic English composition to freshmen is extremely unhappy with this gospel passage.  The opening and closing sentences fit together, but the body is only a series of good but superficially unrelated single or double sentences: no topic sentence, no paragraph to provide context and hence deep meaning.... 

The me trained in literature, however, sees how Luke has brought together a number of related ideas and strung them into some insights on discipleship.  Several of these items simply address the question of prudence: do you have the resources to commit yourself to such a pursuit or not? 

Other parts, however, and especially the opening lines of this passage and the final line, most forcefully indicate that becoming Christ's disciple means a complete dedication of self, an abandonment of all other attachments and involvements, and this goes far beyond the realm of prudence.  Anyone who is willing to follow Christ must absolutely and completely entrust himself or herself to Him, let Him dictate what the proper attachments are, and let Him take care of his or her well-being. 

When Jesus speaks of bearing the cross it seems a little anachronistic: He cannot know that He will Himself carry a cross --- can He?  Or see that the lot of a true Christian is counter-cultural, sometimes even within the Church and even to the point of persecution?  Jesus tells us that such persecution is part of the life of His disciples and so (think about it!) His gift to them, His calling them forth to a challenge and a growth and a surpassing of self in their gifting Him in return....

Prudence cannot dictate our lives here, or we will have to admit that we are not following Jesus with all our hearts.  On the other hand, we will never be completely faithful to Christ, never as generous in our gift of self as we might wish and pray and work to be.  No one in this world, with the exception of Mary, has ever been able to live that absolute dedication of self to Christ in the absolute manner that they hope to do.

But if we follow Christ we are never right up with Him, never in any way His equal, but with Him we do not have to worry about that, about perfection, only about loving and serving Him as well and as generously as we can every day, as imprudent as that might be....