I used to think I was a genius because I managed to book a round-trip ticket from Hong Kong to Tokyo for $1,100 HKD. I felt like I’d beaten the system. I told everyone at the office. I was the ‘flight guy.’ Then 2019 happened—well, specifically, a rainy Tuesday in November 2019—and I realized that…
I lost $42,000 in three months because I listened to a guy with a blue checkmark on Twitter who told me that if I wasn’t growing, I was dying. It was 2018, a Tuesday in November, and I was sitting in a shared office space in Chicago that smelled faintly of burnt espresso and desperation.…
I remember sitting in a cramped, windowless conference room at a mid-sized logistics firm in Chicago back in November 2016. I had my resignation letter printed out on 32lb heavy cardstock (I used to think the weight of the paper communicated gravitas; I was completely wrong, it just made me look like a weirdo). I…
I spent exactly $4,180 on a freelance writer back in late 2019 to produce a series of “ultimate guides” for a side project I was running. By February 2020, the site was hitting 75,000 unique visitors a month. I was checking Google Analytics every hour, watching the real-time map light up like a Christmas tree.…
I once paid $4,200 for a software I opened exactly three times in six months. It was Salesforce. I felt like a “real” business owner because I had the same tool as Coca-Cola, but in reality, I was just an idiot with a credit card and a dream that automation would fix my messy habits.…
I woke up at 5:00 AM on October 14th, 2022, and I felt like I was dying. Not the dramatic, ‘call an ambulance’ kind of dying, but the slow, crushing realization that my brain had been replaced by wet cement. I had just finished reading The 5 AM Club by Robin Sharma, and I was…
I was at this massive tech mixer in Austin back in 2018—I think it was during SXSW, but the whole week is a blur of bad tacos and humidity—and I spent exactly forty-seven minutes locked in a bathroom stall at the Hilton. I wasn’t sick. I was just hiding. I could hear the muffled roar…
I spent three hours yesterday researching the best mechanical keyboard switches instead of finishing a project that was already two days late. I don’t even like mechanical keyboards that much. They’re loud and they make my fingers ache after an hour. But there I was, deep in a subreddit, convinced that the ‘thocky’ sound of…
It was October 2017, and I was sitting in the Hero Coffee Bar on Jackson Blvd in Chicago, sweating through my shirt. I was meeting with a guy named Dan. Dan was my first real hire, and he was failing. Not just missing deadlines—he was actively dragging the whole team down. But instead of telling…
I spent three hours last Tuesday trying to make ChatGPT write a scene where two people argue about a burnt piece of toast. It failed. Miserably. It made them sound like two HR managers resolving a conflict in a breakroom. There was no grit, no spit, no actual human resentment. Just a lot of ‘I…
