Hey I just got an idea; put the "I could have gotten you more" guy in the back of your head and use him when you want a raise? It would be easier to talk to someone who already thinks you deserve/could get more than to someone you don't know exactly what they think?

I had a boss who was retiring and he said I was worth a certain amount and I stored that in the back of my head and the next job I applied for a year later (I'd been out on my own for a year, working for a contractor) I asked for less (and got it :-) but I've always remembered that and not felt bad, "knowing" I was worth more but just fear made me ask for less. Fear is an "external" thing to me, not part of me, just something I experience but my "worth" is greater.