If getting what I want makes me worthy, what does it mean when I want something I can never have?
If getting what I want makes me worthy, what does it mean when others have more than me?
If getting what I want makes me worthy, what does it mean when others have less than me?
If you could isolate the positive, useful aspect -- "I got what I want, and therefore I'm a worthy person" -- then there would be nothing wrong with it. It's good and useful to believe you're a worthy person. Unfortunately, your brain has a certain capacity for logic (even if you're not an engineer or programmer type of person :-P) and you can't prevent it proceeding from that benign intention to its ugly logical reflection. It's logically a zero-sum game, and some of the logically "neutral" effects (assuming a rich person is more worthy than a poor person could be seen as logically neutral) are not really neutral because they are unjust.
There's even the spite angle - I buy a crappy screwdriver, it breaks, I swear at it, I feel better. That's a payoff too. So its complicated.
> So what if they’re $100. Unless you’re some sort of foot messenger, you only need to buy one pair a year.
Or buy $30 shoes that last 2 years and are subjectively just as comfortable. Maybe if you're a foot messenger you need better shoes (or go shoeless), maybe if you have bad feet or a bad back you need expensive shoes with Dr. Shoels. Another example?
> Buy scented candle or some potpourri and a stack of washcloths for your bathroom counter. It smells awesome and you feel great when you grab a fresh towel to wash your face every day.
I hate that crap. My point is that people have different utility functions.
I think what he was saying was more like: if the difference in costs is smaller than the appreciated gaining in life comfort, then do it, spend the money in the expensive one.
The point being, don't be cheap if not being cheap can make your life better.