...Exegesis, anyone?

While reading Matthew 16:24-25 or Luke 9:23-24, where Jesus is saying "take up your cross and follow me...," I always just blew right past it. "Yeah, yeah, take up cross, gotcha." But a few months ago, while reading this, I realized - or rather wondered - to what extent Jesus was saying this.

As we current-day, 21st century, American (Gentile) Christians read these passages, we know what it means - Jesus took up his cross and died for our sins, so we need to, likewise, take up our crosses and daily follow him sacrificially. Yeah, good. But when Jesus was saying these words to his disciples, he hadn't died on the cross yet. And he was telling these Jews to take up their crosses?! Crosses certainly weren't a symbol of God's love and mercy to believers at that time – and weren’t an example of the sacrificial work of Jesus--yet. They were...the crudest, most grotesque, and vile of all punishments of the day. They were used as a mockery and to make an example of foul criminals along the road.

BUT

A couple weeks ago, my pastor in a sermon instructed us to "read the Gospels backwards," to keep in mind the end while reading everything preceeding the end of each book, as that is what each of the four books is pointing to from the beginning - ultimately when Jesus the Christ would be sacrificed as the Spotless Lamb... So in doing so, it would seem to completely obliterate this deliberation.

I'm just curious if the mind-set of the disciples in hearing, and those reading these words, "back then" would have any influence on how we should be reading the words currently...

Now Jesus had just been telling them in the few preceding verses that he was facing impending suffering and death, but that he would be raised again on the third day. He may or may not have said explicitly anything about a cross, but either way, Peter wasn't too happy about the prospect as it was, forgetting his place as disciple and rebuking Jesus, his rabbi.
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As was characteristic of the day, there were multiple rabbis running around Israel, thus there were multiple disciples of other rabbis. (As an aside - when I was little, I thought the word 'disciples' was to be strictly adhered to as followers of Jesus...I always thought it scandalous that John the Baptist had disciples. Ha.) Arduous work went behind being able to even become a disciple of any rabbi and when the sufficient amount of schooling and learning had transpired, and students had "interviewed" with a rabbi they admired, if said rabbi wanted to accept them to be one of his disciples, he would say the words "Follow me." Thus began the journey of close pursuing and copying of the rabbi. Everywhere he went, everything he did, his disciples desperately wanted to go and do. A saying of the time was "May you be covered in the dust of your rabbi." Meaning, may you follow so closely, the dust being kicked up by his sandals cake to your Bible-time dress thingy with a sash...or whatever they wore back then.

All that to say, when Jesus says "take up your cross and follow me...," was he specifically using those words to invoke their recollection of him calling them to be his disciples and to say, 'as my disciples, you'll be following me to death - one even of humiliation and suffering, as you should expect, even pursue by way of denying yourself to come after me'?
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Any thoughts either way on this? Should the history and setting be considered while reading these words or since we already do know what happens, should we be reading these words as already "knowlegable" of the end? Hmm...