I spent three hours in a text exchange with my mentee Kylen recently about education, politics, and war. We started with a reel about educated people skewing liberal and ended up in the middle of the Israeli-Palestinian conflict. Somewhere in between he used the word “misnomer” wrong, called peer-reviewed research propaganda, and asked me if I thought he was a paranoid schizophrenic.
It was one of the best conversations we’ve ever had.
For context, this is the same man who was given a USPS shipping link by my husband Brian, didn’t use it, told Brian he shipped via FedEx, and when Brian checked the tracking, it was UPS. He also ordered eggs Benedict for breakfast that week, left them on the counter for roughly eleven hours, and ate them for dinner like a man with nothing to lose. Hollandaise sauce, for those keeping score, is essentially a warm mayonnaise. Eleven hours. In what universe.
I need you to understand the full range of this person. He can text me an eerily sophisticated analysis of how technology is being weaponized to compromise the authenticity of our information systems, and he can also eat room-temperature hollandaise at 7pm and be genuinely surprised by the consequences.
Kylen is 33. He’s my podcast co-host, my assistant, and someone I consider family. He’s also a man who lost a decade of his life to a system that was never designed for him to win. Abuse, depression, friends lost to suicide, drugs, alcohol, screens, the manosphere. The kind of ecosystem that doesn’t leave you broken so much as rerouted. He was once considered the number one amateur beach volleyball player in the country. The talent and the discipline were always there. They just got buried. Some people would call him broken. I think he’s more wabi-sabi. The cracks are where the interesting stuff lives.
Sometimes I’m the person who corrects his vocabulary in the middle of a political debate, and I don’t feel great about the power dynamic in that, and I do it anyway, because love without honesty is just politeness wearing a costume.
Here’s what happened.
Kylen and I send each other links every day. Articles, reels, podcasts, whatever catches our attention. Then we talk about it. We compare what his algorithm sends him versus mine. We ask whether something is trying to pull us in a direction or whether it’s just interesting data worth exploring. It’s become our version of morning coffee, except instead of small talk it’s media literacy in real time.
So when I sent him a reel about research showing that highly educated people tend to skew liberal in their political orientation, it wasn’t out of the blue. It was a Tuesday. Decades of data. Pew Research. Nonpartisan, peer-reviewed, replicated. His response was immediate. He called the study “wildly inapplicable,” invoked technology and misinformation, and ended with “misnomer of the year goes to.”
The word he wanted was misconception, or maybe misattribution. A misnomer is when something is called the wrong name, like calling a koala a bear. I told him. Because I love him, and because vocabulary is a tool, and using the wrong one means your point doesn’t land the way you think it does. He later corrected himself to “misdiagnosis.” Closer. Still not quite. I told him I was filing it for the podcast and he took it with grace.
But the vocabulary was the easy part.
The harder part was what he did next. He built an entire counter-argument against a claim the research never made. He argued that the study was saying liberals are smarter. It wasn’t. It was documenting a demographic pattern. Educated people tend to skew liberal. That’s descriptive, not prescriptive. It’s the same as saying rural populations tend to skew conservative. It’s just data. But Kylen heard an insult that wasn’t there, constructed a rebuttal to the insult he invented, and then got offended by his own construction. I have done this. You have done this. We have all built a scarecrow in the yard and then gotten furious that it’s standing there.
And then I told him both things could be true.
The research could be real AND the information landscape could be compromised by technology. One is a demographic pattern backed by decades of evidence. The other is a systems-level observation about how we consume and process information in 2026. They’re not in competition. They’re layered. The more interesting question is how they interact. If technology is compromising the authenticity of our information systems the way he described, then who is most vulnerable to that manipulation?
He pushed back hard. He questioned the motives behind the research. He asked what purpose it served other than to divide. He compared it to propaganda dressed as science. He used the phrase “bias identifying as empirical evidence,” which is a pretty good line even if it was aimed at the wrong target.
And then he did something that stopped me.
He asked, “What do you see in me? Am I a nice guy who also has the makings of a paranoid schizophrenic?”
I put my phone down for a minute after that one.
That question is the whole story. Not because the answer matters, but because he asked it. He was checking himself. He was saying, I know I see patterns everywhere, and I know sometimes that’s insight and sometimes that’s paranoia, and I trust you enough to tell me which one this is. That kind of vulnerability doesn’t come from people who are doing well. It comes from people who are doing the work. There’s a difference, and it’s enormous.
That is what mentorship is built on. Not agreement. Trust. The kind you can’t manufacture and can’t rush. The kind that gets built one honest conversation at a time, including the ones where someone uses the wrong word three times and eats rogue hollandaise for dinner.
I told him what I see. Someone who is smart enough to see through things but still building the filter for when that instinct is protecting him versus when it’s keeping him from sitting with something uncomfortable. That’s not a flaw. That’s the work. And I told him I wrestle with the same thing, because I do. My instinct when something threatens what I believe is to put up the walls, not get curious. I’m just further along in learning to catch it.
Later in the conversation, Kylen sent me a video of Yosef Haddad, an Arab-Israeli journalist and IDF veteran, making a passionate pro-Israel case at a university debate. Haddad grew up in Haifa, volunteered for the IDF, and clearly loves his country. Nobody should take that from him.
But his experience being true does not make everything the Israeli government has done in this war right. Both things can be true.
So I walked Kylen through it. The coalition. The corruption trial. The money. The history of military occupation failing everywhere it’s ever been tried. Not because I wanted to win the argument, but because I wanted him to see that holding someone’s lived experience as valid while also questioning the system they’re defending is not a contradiction. It’s the job. I sent him the research to back every claim because you don’t get to demand citations and then offer none yourself. You don’t get to call something propaganda without reading the methodology. Critical thinking isn’t rejecting things that make you uncomfortable. It’s examining them especially when they do. I know this because I have rejected things that made me uncomfortable and called it discernment, and it wasn’t. It was just fear wearing reading glasses.
Kylen heard me. He didn’t agree with everything. He shouldn’t have to. But he stayed in the conversation. He asked questions. He admitted when he was wrong. He showed vulnerability that most people three times his age couldn’t manage. And he said something I won’t forget: “I love you too and I treasure this. This is exactly what I want to talk about and investigate and I appreciate you with all my heart for being someone I trust enough that I can do this with.”
I read that text sitting on my couch and I thought, this is it. This is the whole thing. Not the political arguments. Not the research links. This. A person who survived everything that was supposed to keep him small, sitting on the other end of a phone trusting someone enough to say “tell me what you actually see.”
The people who navigate this world with the most clarity are not the ones who simplify it into sides. They’re the ones who can sit with something uncomfortable, resist the urge to dismiss it, and still have the courage to ask what else might also be true.
I’m not trying to change what Kylen believes. I’m trying to expand how he thinks. That’s what I’ve always wanted for him. And honestly, it’s what I’m still working on for myself. I still catch myself choosing certainty over curiosity because certainty feels safer. I still want to be right more than I want to be accurate, and those are not the same thing, and the distance between them is where most of my mistakes live.
It’s a relationship you earn through honesty, through refusing to be comfortable, and through showing up for the conversation even when it’s hard. Especially when it’s hard. Especially when one of you has just eaten countertop eggs Benedict and the other one is trying not to scream.
Both things can be true. The person in front of you can be brilliant and struggling. They can be insightful and wrong. They can question everything and still need someone to question them back. They can make you proud in one conversation and make you question their survival instincts by dinner.
That’s not contradiction. That’s complexity. And complexity is where growth lives.
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