I Infiltrated the Corporate Caste System (And You Can Too, But You’ll Hate It)
When I was 25, backpacking through Europe, I stayed at a hostel. Other Americans found out I was from Mississippi. They didn’t say anything directly, but the vibe turned fast. It was like I’d walked in with a shotgun and a Confederate flag. They had already decided who I was: probably ignorant, probably backward, probably racist.
Never mind that I was in Prague to visit the Franz Kafka Museum. That didn’t matter. I said “Mississippi,” and that was enough.
I ended up hanging out with Australians the whole time. They were just like, “Cool, man. That’s where the blues is from, right?”
That experience showed me how quickly people judge based on a label. It wasn’t about who I actually was. It was about what they thought I was. And once I noticed it, I started seeing it everywhere. Especially in corporate life. Especially in tech.
The more someone tried to sound important, the less substance there usually was.
I worked at a tech company once, split between New York and San Francisco. Leadership wasn’t built. It was recycled. Everyone just hired each other from their old jobs. It wasn’t a company. It was a clique with a Slack login. The titles were bloated, the org chart was a mess, and nobody actually did anything. Everyone just spoke in corporate acronyms: OKRs, KPIs, MQLs.
Every time I asked what something meant, they’d explain it, and I’d realize I had already been doing that for years. I just didn’t know it had a fancy name.
I had a manager who was the embodiment of startup fluff. When there was a minor conflict on our team, we brought it to him. His response was, “You two should work it out yourselves.” I remember thinking, isn’t that literally your job? You’re not a life coach. You’re a manager. Why are we solving your problems?
Leadership in these places isn’t about leading. It’s about avoiding responsibility while collecting credit. Work gets delegated to contractors. The people at the top put their name on the results. It’s not leadership. It’s theater.
Also, it’s a caste system. If you’re in the right circle, you move up. I watched a coworker completely screw up communications with our community multiple times. Then they got promoted and got a raise. Got a senior title. Like, what?
I once recorded an interview with our CEO and a woman from a trillion-dollar financial firm. They stood there name-dropping Ivy League schools and talking about how their kids shared dorms with the children of celebrities. They didn’t acknowledge anyone in the room. No eye contact. No hello. Nothing. It didn't feel like they were just ignoring people. They were reminding us that they could.
Most of these companies that were once built on innovation or talent aren't anymore. They’re now zombies abandoned by their founders and propped up by nepotism, branding, and layers of middle management. They hire their friends, invent titles, and spend entire workweeks justifying their own jobs. When teams grow, they slow down. They stop building and start maintaining.
I saw this even back in college when I worked at FYE, you know the CD store. We had to rearrange the store five times in one year because some regional middle manager wanted to “align with seasonal marketing priorities.” It didn’t help customers. No one asked for it. It was just busywork to justify a salary.
That’s what middle management does. They create work to feel useful. They add steps to look important. They don’t build anything. They just get in the way of people who do.
Meanwhile, my fiancée cleans houses. Real work. Work you can see. But the moment people hear that, they reduce her. At least sometimes that tells me how she feels. But she works harder than most people in glass buildings ever will. She built a life with her own hands. And still, when people hear “house cleaner,” they act like that tells them the whole story.
And yes, I’m complaining. Because it's bullshit. It’s not about skill. It’s not about results. It’s about optics. It’s about who you know, how well you speak in a meeting, if you align with the right politics, and how many acronyms you can drop into a Slack thread.
I grew up in an environment where you show up, figure it out, and get it done. You don’t rename basic tasks to sound smarter than everyone else. You don’t throw money at a problem just because it’s easier. You use what you’ve got. If it works, it works.
The whole system felt like something I infiltrated from the outside. That’s because I did.
And if there’s one thing you should know about folks from Mississippi, we can smell nonsense from a mile away. And there’s a lot of it out there.
Also, if you actually want to succeed in that world, don’t listen to me. Play the game. Smile in meetings. Learn the lingo. Dress the part. Build the LinkedIn persona. Because some fresh-out-of-college kid with a Facebook internship handed to them by their dad is probably going to get the job over you, no matter how good you are, if you don’t.
Anyway, I’ll be updating my LinkedIn to say “executive" and "senior" on as many things as possible.
Thanks for reading.