- You are experienced enough that the likelihood of you getting hired is higher than younger (less experienced) and older (more expensive) competitors.
- You are aware of your market value.
- You are confident enough to negotiate and get along.
- You have sufficient cushion to take the hit of not having a paycheck in case your job search takes longer than you expected.
- You know quite deeply how your industry operates.
I might update this as I go along.