Two Goofs Talk About Being Unemployable

Breaking down the best worst compliment I've ever received

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This is either the best worst advice or the worst best advice.

I kicked off this newsletter with a story about being unemployable. It’s a word I think about almost every day.

I’ve told the story before—I’m sitting at breakfast, I’m upset about work, my friend pulls out the term unemployable, and it lands hard on me. But where did he come up with it? And do others feel the same?

On the latest episode of Boss Barista, I talked to that friend! His name is Brandon, and he’s pictured above proudly displaying an Oreo bike he won at a raffle as a child.

In our conversation, I asked him about this moment—not the Oreo bike moment, but the moment he told me I was unemployable. I wanted to know where he first encountered the idea of being unemployable, and what about the stories I was sharing with him signaled I might be fighting an uphill battle.

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I’m still trying to grapple with what being unemployable means. I recently had a different conversation with a friend who warned me that using this term as a badge of honor might be a mistake. Everything about myself that I put into this bucket of being unemployable—being critical, not being afraid to speak out—are actually really, really valuable traits and I need to frame them as such.

Instead, he suggested the term “unemployable” might be placing the blame on me for the fact that a lot of people are shitty leaders and bad employers.

I don’t disagree—this whole newsletter is pretty much an ode to terrible leaders—but I still could never capture the feeling of being continually frustrated at work in the way that the word “unemployable” has. And it translates. When I use it around others, they know exactly what I’m talking about, even if they can’t define it themselves.

Me blowing out candles on my mom’s birthday cake. I’m a cute jerk.

So listen to this episode! Tell me what you think about being unemployable! If anything, Brandon is one of my best friends so this is a weirdly intimate episode of the show—which I love because I thrive off shared moments. I hope beyond that, you get a sense of what I’m trying to articulate. And you feel seen.

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