If you're playing within your capability, what's the point? If you're not pushing your own technique to its own limits with the risk that it might just crumble at any moment, then you're not really doing your job.
He didn't want me to become a musician, he wanted me to be a doctor, because he said singing was too hard.
A song must move the story ahead. A song must take the place of dialogue. If a song halts the show, pushes it back, stalls it, the audience won't buy it; they'll be unhappy.