How would you explain the contrast between the way Willy described his career and the real degree of his success?

Willy over estimated his career and success, but a lot of that was due to the fact that he never moved with the times. When he began is career as a saleman, he was perfect for the job....... when things moderized, he kept up with the old ways, and eventually he became a dinosaur of sales.

To hear Willy talk, you'd think he'd been the top salesman throughout his career. He may have seen the changes and realized his deficits (which might be the reason he couldn't stay on the road), but he always believed that his years of service would guarantee him loyalty. Unfortunately, when his boss retired...... the loyalty ended.