Where the author and I differ is that I don't always believe "spending more" is the key. More appropriately, spend where it matters. As a corollary, don't spend where it matters as well.
"1. Chasing more and more money is not a route to happiness. You shouldn't try specifically to acquire more money in the hopes that it will make you happy but rather, once you have money, think carefully about how you can use it to increase your happiness.
2. Using money to buy the wrong things (often: things which are popular, things which other people desire, things which require much manual upkeep or worry - see #3) does not result in happiness.
3. People often use money to buy things which they then spend time worrying about, rather than purchasing things which allow them to worry less."
The main argument is that it's not a good idea to be frugal just for the sake of being frugal - both extremes of materialism and the opposite are an unhealthy relationship with money or possessions. Buying better things isn't because "you're worth it", but because in some areas it will genuinely make your life a better experience. It's about evaluating all the circumstances and making the best decision rather than applying one credo constantly and repeatedly.
The key thing is, if you care about the experience you give yourself, it will be easier for you to give the same level of experience to others -- and they more likely than not will appreciate it.
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.
I don't see how that's a healthy attitude. I'm probably on an extreme end of the spectrum as I'm pretty minimalistic and don't have many possessions but those I do have are typically of higher quality. I don't buy those things because they make me feel like a better person, that I'm worthy of the higher quality things, or that I deserve them but rather because they generally don't cause me pain. Isn't that why we here on HN try to build high quality software? To solve and cure some kind of pain? I appreciate when a product does that so I'm willing to pay for it.
Qualifying your worth based on what you choose to purchase is short-sighted, physical goods no matter their quality deteriorate in usefulness and lustre with time. Experience, knowledge, and human relationships are enduring. Therefore I reject any notion that a person's worth is valued by the quantity and quality of their possessions.