Video from Father Spyridon
"Let’s begin with what Jesus didn’t mean. Many people interpret “cross” as some burden they must carry in their lives: a strained relationship, a thankless job, a physical illness. With self-pitying pride, they say, “That’s my cross I have to carry.” Such an interpretation is not what Jesus meant when He said, “Take up your cross and follow Me.” When Jesus carried His cross up Golgotha to be crucified, no one was thinking of the cross as symbolic of a burden to carry. To a person in the first-century, the cross meant one thing and one thing only: death by the most painful and humiliating means human beings could develop.
Two thousand years later, Christians view the cross as a cherished symbol of atonement, forgiveness, grace, and love. But in Jesus’ day, the cross represented nothing but torturous death. Because the Romans forced convicted criminals to carry their own crosses to the place of crucifixion, bearing a cross meant carrying their own execution device while facing ridicule along the way to death.
Therefore, “Take up your cross and follow Me” means being willing to die in order to follow Jesus. This is called “dying to self.” It’s a call to absolute surrender. After each time Jesus commanded cross bearing, He said, “For whoever wants to save his life will lose it, but whoever loses his life for me will save it. What good is it for a man to gain the whole world, and yet lose or forfeit his very self?” (Luke 9:24-25). Although the call is tough, the reward is matchless..." from the article: What did Jesus mean when He said, “Take up your cross and follow Me”?