OK, the boots were bought, but anyhow I agree GuitarStv that a pair of boots were/might be a necessary purchase that should be considered on its own.
Ignore feelings of entitlement. Regardless whether it’s with employees, children or your own self, incentives should be used to incent the behavior and results that you desire.
If you want to give yourself regular milestones rewards, then one such reward might be “I will only buy a bottle of wine each time when my net worth increases by $5000”.
If you want to use big rewards then they should be for stretch goals, for example: Using $1K to go on a desired vacation if your savings reach $100K by Dec2015, when your budget/plan today has you tracking towards early 2017.