Wait, What?!
A few weeks ago, sitting across the table from my daughter who was earnestly working on a Lego Buckingham Palace, I noticed a Bluesky post about OpenAI’s plans to put ads in ChatGPT. The news wasn’t a surprise to me, devoted listener of The Vergecast that I am. But knowing that Lola despises ChatGPT, I threw the conversational ball in the air.
“So it looks like they’re going to roll out ads in ChatGPT,” I said.
“Why would they do that?” she responded incredulously.
“They need to figure out how to make some money.”
Her reaction was classic “Wait, what?!” Her face twisted through the various expressions that coincide with having a cascade of reasonable assumptions shattered by the facts.
Her reasonable assumption was that a product that had become a household name and a company that was worth half a trillion dollars had to be making metric crap tons of money. I explained that while they do generate revenue, OpenAI loses a few billion dollars every month. She was appalled.
The "Wait, what?!" expression twists deeper into indignant confusion, and I realize that this whole-ads-in-ChatGPT thing only makes sense to me because I have a pretty good idea of how venture capital (and enshittification) work. In order for her to make sense of unexpected news, I needed to share my mental model with her.
To help her make sense of this, I attempted to explain venture capital. I’m not sure how much of that landed—cynicism isn’t her first language—but she understood enough to ask some good questions. Eventually, the conversation took us in a direction that caused the focused expression on her face to morph into something more impish.
I explained that companies that take on massive venture capital investment go under because they can’t just have a “healthy” business; they need to be blockbuster successes. She told me, a bit self-consciously, that she often finds herself quite amused when people who confidently and selfishly cause harm to others wind up in trouble themselves.
“Oh, that’s schadenfreude!” I said.
Schadenfreude, delight in another’s misfortune, was of course the next topic to make sense of. We tossed around example after example of instances when we’d felt schadenfreude. When she told me about her feelings of schadenfreude initially, she was acknowledging a sort of internal or emotional “Wait, what?!” moment. By putting a name to it and assuring her everyone experiences it from time to time, I was able to help her make sense of those emotions.
“Venture capital” and “schadenfreude“ were both intellectual frameworks—mental models—that I passed on to her as tools she could use to make sense of future “Wait, what?!” moments. The next time she hears about a company that appears to be wildly successful making odd decisions about how to make money, she’ll think “Ah, that’s venture capital at work.” And the next time she feels the creep of guilt mixed with snide delight at someone’s unfortunate turn of events, she’ll say to herself “Ah, that’s schadenfreude!”
A "Wait, what?!" moment occurs whenever our assumptions or expectations come into conflict with reality. When the clear front-runner loses the election, when a lucky break actually materializes, when the headline seems absurd but the evidence bears it out—these are times when what we thought we knew is, in an instant, proven to be otherwise. These moments can be small surprises or life-altering shocks. They can be merely incidental or matter a great deal.
I always start with the assumption (almost) everything happens for a reason—not in a metaphysical sense, but in the sense that events are the result of complex systems. If my reaction to an event is “Wait, what?!” then that’s a sign that I should learn more about the system that generated that surprising outcome. To be clear, I’m not talking about determinism or fate; my assumption is a heuristic, a mental rule-of-thumb, that triggers my curiosity about what the mechanics of a situation really are.
Using words like “systems” and “mechanics” make this sound like a technical process that gets applied in certain technical situations. But I use this process to make sense of all sorts of phenomena. Social interactions that strike me as strange, emotions that seem detached from reality, and even my own habits (or lack thereof) are opportunities to learn about the systems that create them.
Of course, making sense of one’s personal “Wait, what?!” moments is a powerful enough habit to adopt. But making sense of another’s “Wait, what?!” moment can create instant connection and build credibility. None of us have all the mental models or theories to make sense of the deluge of “Wait, what?!” moments that contemporary life and work triggers. We realize the incredible power of sensemaking together when we pool our mental resources, share the systems we know well, and seek out new understanding in the way others think.
The internet has supercharged our ability to trade mental models and make sense of new situations. Yes, there’s a ton of crap on TikTok, Instagram, and YouTube, and no shortage of conspiracy theories masquerading as honest sensemaking. But there are also incredible communicators that have made it their business to help us make sense of the unexpected. There are newsletter writers, video creators, and podcasters who help us put names to phenomena and map systems to outcomes: Jamelle Bouie, Anne Helen Peterson, Michael Hobbes, Matt Bernstein, Mia Sato, Nicole Holliday, and on and on. Some are exclusively “new” media creators. Others have ties to long-standing media institutions.
How many of your favorite newsletters, channels, or posters help you make sense of the world? My guess is that it’s most of them. They might not look like Serious Sensemakers. They might be comedians or interviewers or just people who seem to be hanging out online. But there’s something in their delivery that gives you a firmer grasp on the world around you. That’s why they’re your favorites.
Making sense of the unexpected is an incredibly compelling way to make media. Big or small, consequential or incidental, making sense inspires that feeling so many of us could use a bit more of: relief.
The good news is that you’re already a pro at making sense. Whether you do it for your kids, your colleagues, or friends, it’s part of why they trust you. The only difficulty is that most people don’t know what they’re doing when they’re making sense of the unexpected. They just do it.
In casual conversation, that’s great! But if you’re making a podcast episode, filming a video, or writing an article for an audience, familiarity with the sensemaking process can take your work from good to great.
I’m kicking off my 8-week workshop series, Making Sense, on March 24. This program walks you through the sensemaking process and takes you step by step through applying it to a media-making project. By the end of the 8 weeks, you’ll have made significant progress on your project and have an effective process you can use over and over again to create more compelling content.
Turn “Wait, what?!” moments into compelling communication and content. Learn more about Making Sense!
