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Aspirational clothes are very valuable if they fuel the fire of the more fundamental aspiration, which is to do the work necessary to be able to fit into them. If they're not contributing to that, they possibly can get in the way. Courtney Carver has something called Project 333 and I think this helps a lot of people. The best dressed people have the simplest wardrobes.
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Listen to the best highlights from the podcasts you love and dive into the full episode