It was October 14, 2022, around 3:15 PM. I was sitting in my home office—which is really just a corner of my bedroom in Chicago with a desk I bought off Craigslist—and I was feeling…
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October 2018. I was sitting in a Taco Bell parking lot at 9:30 PM, shoving a lukewarm Cheesy Gordita Crunch into my face and crying. Not a cute, cinematic single-tear cry—a full-on, snot-running-down-my-lip breakdown. My…
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I saw a guy on LinkedIn yesterday with ‘Senior Prompt Engineer’ in his headline. He had 12,000 followers and was selling a $97 PDF of ‘secret hacks’ to make Claude 3 Opus sound more human.…
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I once watched a grown man eat a bowl of Grape-Nuts at 2 PM exactly three feet away from my left ear while I was trying to debug a legacy payment script. If you’ve never…
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I was sitting in a windowless conference room in 2019, working for a mid-sized tech firm called CloudScale. The CEO was standing in front of a PowerPoint slide that just said RADICAL TRANSPARENCY in 72-point…
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I spent $1,400 on a logo for a business that didn’t exist. It was October 2018, and I was sitting in a cramped Starbucks on LaSalle Street in Chicago, vibrating from too much caffeine and…
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I spent three years of my life trying to be the world’s leading expert on a specific type of freight auditing software that no longer exists. It was 2014. I was working at a mid-sized…
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I once spent an entire Tuesday—October 14th, 2019, to be exact—organizing my inbox. I was working at a mid-sized logistics firm at the time, and I had convinced myself that my mounting anxiety was purely…
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I saw a TikTok last week that made me want to hurl my MacBook into the neighbor’s pool. It was a guy showing off a $25 ‘mouse jiggler’ he bought on Amazon so his Slack…
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I once spent four days—96 hours of my life I am never getting back—trying to fix a database migration for a “free” project management tool. We were a small team, maybe twelve people at the…
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