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Just watched this frugal YouTuber Austin Williams break down which expensive things that are worth it, and honestly some of his picks hit different. Like, I always thought I was being smart buying cheap stuff, but then you realize certain things just pay for themselves long-term.
The one that got me was his take on where you live. Yeah, his rent in Atlanta is higher than a suburb, but he'd rather pay more to be in a walkable area with actual things to do. That tracks - being miserable in a cheap suburb sounds way worse than paying extra for quality of life. Same energy with his coworking space at $100/month. Sounds expensive until you realize it's breaking up isolation and actually making him more productive.
Also respect that he's not gatekeeping the expensive things that are worth it. Like, he'll drop $200 on a giant whiteboard for brainstorming, invest in prescription sunglasses instead of cheap ones that hurt his eyes, and yeah, he travels to 40+ countries. But he's also buying Target sheets for $60 instead of going overboard. It's about being intentional, not just flexing.
The self-employment thing resonated too - he's been doing it 2.5 years and while the taxes and insurance hit different, he says it's worth every penny for the character building. I'm starting to think the real skill isn't being frugal about everything, it's knowing which expensive things that are worth it actually matter to your life. Not all spending is the same.