"I'm in with the 'In Crowd,' boast an old popular song, "I go where the 'In Crowd' goes." This catchy tune is still being remade today (recently it was on a TV commercial), becasue it gives voice to the desire to be popular, admired, a little envied, hip. To be, not "holier than thou" but "cooler than thou."
As an antidote to this desire, Jesus offers us a warning in today's gospel. To follow in his footsteps, he explained, often involves being out of step with the world. As his disciples, we are to think differently, and act differently, from the world around us. In other words, we may not always be "in" with the "In Crowd." This is what Jesus means- at least in part- when he speaks of losing ourselves, even if we've gained the "whole world." In other words, if we confirm ourselves to the world- the "In Crowd," we risk losing ourselves in the process.
Jesus' invitation to daily take up our cross and follow him may lead us to being at odds with the world, and the world as a result may in turn consider us odd. To follow Jesus is not necessarily to "go where the 'In Crowd' goes." Jesus was "rejected," and we may find ourselves rejected too- at least by the "In Crowd." But when all is said and done, that's okay. We may not be "in." But we will find ourselves, and have true life.