I never have an issue getting from the ladder to the roof, but it's getting from the roof to the ladder that always scares me a bit. I'm always scared that when I put my foot on the ladder it will slide off or something. Though I've learned that trying to do it slowly is what makes it more risky. Best to just get into position then put both feet at same time while keeping the ladder stable from the sudden weight shift with my hands.
Speaking of roofs, just realized it's almost time to consider putting the Christmas lights back up. Seems I just took them down.