“My boss is killing me; I don’t know what to do,” Simon said, rubbing his eyes as he sat across from Jim at a restaurant eating lunch. “My boss is demanding, unpredictable and destructive. I’m on my first lunch break in a month, and I’m only getting this break today because my boss had to go to a parent-teacher conference.”
“I get it,” Jim said, holding his glass for a toast.
“Wait, don’t you work for yourself?” Simon asked.
“Yeah, but I’m my own worst boss,” Jim said as if this was obvious. “I spend all day telling myself things like you’re a moron, go do something. We could have more if you’d just get it together. Don’t buy a ukulele. Get ukulele lessons; you’re terrible at playing the ukulele. I don’t give myself any slack.”
“I can’t imagine bringing a ukulele to work,” Simon said, completely confused.
“Here’s what I do,” Jim said. “I find ways to trip up the boss. I ask him questions without an answer, so he has to think about them for a while. Some of my questions have included: Are we sure green is the best color for what we’re trying to do? What would therapy be like? What if we turned the business into a sticker business?”
“Who do you tell this to? Simon asked. “Your wife, an AI chatbot, another client?”
“No, just that voice in my head that gets words in during the commercials on the YouTube videos I’m watching,” Jim said. He looked at his phone and shook his head. “Well, the boss says I have to get back at it. Good luck, Simon!”