Plenty of people on any pilgrimage have not been to confession in ten or twenty years. The priest knows this. It is why confession is scheduled every day and not left to chance, and why the first days of a Bold Pilgrim itinerary are deliberately unhurried.
Rome works for someone coming back because it is the whole Church at once: the big basilicas, the small neighbourhood churches with a Mass at seven in the evening, the madonnelle on the street corners. Assisi works because St. Francis's story is one of starting over at twenty-five with nothing. Lourdes works because the entire sanctuary is organized around mercy, and the Divine Mercy Sanctuary in Kraków was built for the message that nobody is too far gone.
You do not need to have everything sorted out before you go. Come as you are. The sorting out is some of what the days are for.
