I have a very different model of financial planning than you do. I view spending money in exchange for time now as equivalent to spending future free time in exchange for present free time, as it increases the amount of time I will need to work until I can retire passively off of investment income. For me, retirement isn't some far out, dubious prospect, it's a very real thing that I have created a specific budgetary goal/timeline for. I can't generally trade free time for money in arbitrary quantities. I'm okay with trading time now for time later, because I don't think all free time should be valued equally. Free hours are worth more if I have more of them consecutively, don't have to go to work the next day, and when friends are available.
I think the value of free hours in general is much greater when I can elect to have a whole week of free hours, even if I don't truly stop working. Once one has retirement saved for, they truly can set their own hours, and if someone asks them to do otherwise, they retain the option to tell them to screw off. Not having a Sword of Damocles hanging over me is something I value highly.
I'm going to reply to my own post and expand on a couple more things. Let me know if it is considered better etiquette to edit even if it has been around for a few days.
The article just seems so...short sighted. Like, no doubt is trading money for time something we all do, but I don't think of it as virtuous or something to be sought out. I have a feeling most people err on the side of doing it too often, not too little.
One thing I think this article discounts is the idea that doing things instead paying to have them done often confers knowledge onto you ... (read more)
Here's an interesting post about calculating the value of your free time and why it might not be as simple as some tend to think.