Diving into the Deep End
How do you get someone else to care about what you care about?
One question has dominated my work for over 15 years now. It’s a question that often starts with tactical concerns about marketing or sales or product development, but the core of it is much more fundamental than any of that. It’s a question that’s as relevant to the small business owner as it is to the scholar or middle manager or community organizer:
How do I get people to care about what I care about?
That’s it. After all, there is no silver-bullet social media plan, no door-knocking strategy, no magical meeting agenda that produces results if the message at its heart doesn’t resonate with those receiving it. Communicating effectively is never a matter of yelling louder or repeating a message more times. Nor does it matter how many beautiful sentences you construct or what ingenious metaphor you use to explain yourself. This has always been true, but in the age of algorithmic distribution, the margin for error when it comes to resonance is vanishingly small.
The trick, if we can call it that, to getting others to care about what you care about is to care about what they care about. That’s the essence of persuasive communication, marketing strategy, and political organizing. However, it’s also the step in the process that's almost universally forgotten or rushed through. We assume we know what our audience cares about, but we don't verify our assumptions. So what we often have is really a fun-house mirror version of the thing we want them to care about.
This essay is in roughly four chapters. In the first chapter, I assure you that getting attention is actually (relatively) easy—even if few of us are willing to do what it takes. In the second chapter, I explain why paying attention is really difficult, with the help of my favorite French philosopher. In the third chapter, I've got a story about getting my teenage daughter to watch a movie explaining esoteric financial products. And in the final chapter, I'll share a little idea I've been referring to as the Swimming Pool Theory of Communication. Click on any of those chapter links to read that section specifically.
If you care about getting others to care about what you care about (and I know you do), this one is for you.
1. Attention is Easy
Related to “How do I get other people to care about what I care about?” is another question: How do I get attention for my work? My ideas? My movement?
Attention, argue many philosophers, economists, and sociologists, is a scarce resource. I don’t disagree, but in some ways, attention is more available and accessible than ever. We willingly cede our attention to whatever our devices deliver. It doesn’t take much to distract us or suck us into the feed. So it should follow that getting attention is pretty easy.
What’s more, we know what kind of content algorithms select for maximum distribution. We may not like it, but we know what gets the views. We know that content that promises money, beauty, and sex tends to do well. Even more of a sure bet is content that stokes outrage and righteous indignation. And in a pinch, copying just about any “trend” (i.e., a structural or aesthetic meme) will likely get eyeballs on your creative work.
Content distribution algorithms are like little instruction manuals written exclusively in the language of context clues. Once you learn how to read the signs, the instructions reveal themselves.
For example, if I wanted to start a TikTok channel for my cats, I’d look at what formats seem to do well in that space. I might notice that there are a number of creators who do some riff on “Reasons [ my pet ] expressed [ something ] this week.” I don’t know who originate this format but the two channels I’m most familiar with feature videos with the titles “Reasons my husky got mad at me this week,” and “Things that annoyed Waffles this week.” These videos tend to be sarcastic montages that highlight pets with, shall we say, big personalities.
This would be a great format for my cats since they also have big personalities. So I might try out “Junk my cats entertained themselves with this week.” It would mostly be videos of them playing with earplugs and string.
It’s no guarantee that my cat content will go mega viral. But simply following the algorithmic breadcrumbs other creators have left for me would give me a strong shot at garnering initial attention. Now, if you’re thinking that just copying what other people are doing sounds uninteresting, maybe even déclassé, I get it. Many of us don’t want to do the things that make it easy to get attention. Maybe we see that path to virality as an affront to our own creativity, ideas, or signature swagger.
Strategically, you might also clock that following the algorithmic breadcrumbs is rarely a good way to garner the kind of attention that leads to long-term investment, whether in your product, idea, or movement. Harnessing a meme can help your content go viral, but it doesn’t build sustainable momentum. To do that, we need a different kind of attention, the kind that generates genuine curiosity and care. And as we’ll see in the next chapter, that curiosity and care must start with us.
Whether for a product or a politician, the attention one attracts only goes so far. You can buy a fraction of my attention with an ad, but you can’t make me care about, let alone remember, what was advertised. No, the issue isn’t attracting attention in its current commoditized form; it’s connection, resonance, caring about the real needs or desires of the people you’re trying to communicate with.
2. Attention is Hard
Getting access to others’ attention is (relatively) easy, but paying attention to others is exceedingly difficult.
Our attempts at connection are so often thwarted by navel-gazing. The performance of modern life and the suffocating sameness of algorithmically-mediated interests coat our true concerns in a thick varnish of obfuscation. Add to that a dizzying whirl of competing responsibilities and fiddly paperwork obligations, and it’s a wonder that we have the energy to forge intimacy with anyone.
Outside the intimate sphere we (hopefully) cultivate with close family and friends, there is a tendency to instrumentalize our interest in others. That is, we pay attention because what we learn becomes a tool for getting what we want. That sounds callous, but I mean it neutrally. Honest persuasion and, ideally, mutually beneficial ends are at the core of how we live together. Or, as Dan Pink put it in the title of his 2012 book, "to sell is human."
The trouble here isn’t so much that we use what we learn about others to further our own interests. It’s that our own interests often make it next to impossible to learn anything true about others. We read others through our own concerns and have to work hard to see beyond our own expectations.
The French philosopher Simone Weil explored this problem through her work on attention. Weil saw attention as an intimate process, an exacting spiritual discipline that few attempted, rather than a passive awareness everyone contends with. So yes, giving our attention to others is work, but Weil argues it is not a "muscular effort," not the steely focus, intent listening, or brow-furrowing activation of every empathic neuron we possess.
Instead, Weil explains that the hard work of paying close attention is a "negative effort." Instead of trying to pour ourselves into the attention we give to others, she argues that true attention requires us to pour ourselves out. The work is in emptying our minds of our own concerns, values, and motivations so that we can be fully present to the reality someone else shares with us.
Weil relates attention to the way we read the world around us. Reading, as Weil defines it, is the simultaneous recognition of circumstance and meaning. It’s a constant, reflexive, and subjective process. Even if you and I share an experience with the same situational details, we’ll interpret it differently based on all sorts of other factors that are necessarily different between us. When I truly pay attention, when I empty myself of my own concerns and experience, I can start to read the world a little more like someone else does.
This is the crux of understanding what someone else cares about. If we can only read the world as ourselves, we’ll only ever see what others care about through our own filters. Without a concerted negative effort, we'll mistake what we think someone else cares about for what they actually care about.
In a marketing or communications context, this distinction between what someone actually cares about and what I think they care about becomes clear. For example, between 2023 and early 2025, Uber rolled out “teen accounts” that allowed kids between 13-17 to get rides on their own. As someone who grew up in the '80s and '90s, the idea of making it easier for your kid to get into a stranger's car seemed deranged. But sure, I can see the 2020s logic of it all.
During this time, Uber ran an ad depicting a mom at work receiving updates from her daughter at a dance competition. When the competition was over, giant trophy in hand, the daughter requested an Uber, and the mom tracked her progress in the app. The mom’s expression shifts from mild anxiousness about her daughter’s performance to a victorious smile and accompanying fist pump. We see no sadness or regret at having missed her daughter’s big event.
At least, that’s how I remember the ad. I can’t find it for the life of me!
Uber’s bet is that parents care about their kids getting to and from events and get-togethers safely and independently—even if they can't leave work. But this bet belies what Uber cares about: filling cars with more paying riders. It also says something about our attitude toward work, but that's a different story.
Whatever marketing team came up with this cursed ad (and really whatever product team came up with the idea in the first place) didn’t employ the negative effort required to ask what a parent actually cares about. Of course, a parent cares about their child's safety on the way to and from an event. But what they really care about is being there. A kid riding in an Uber alone is almost always a compromise. It’s the best (I guess) of a bad set of options. No shame on anyone who uses Uber for Teens—but suspect that it’s not your ideal solution.
This Uber ad seems bleak and dystopian despite (or perhaps, because of) the brightly lit smiles that fill every frame. It’s a complete misread. A more honest version of this ad would acknowledge the conflicting feelings—the disappointment alongside the joy. That’s asking a lot from an ad, of course; nuance isn’t typically the purview of 15-second ad spots. However, even an ounce of nuance, of real attention, can turn a dud of an ad into something that really connects with its audience. Despite (or perhaps, because of) their abundant resources, billion-dollar companies struggle with the negative effort required to understand what their customers actually care about.
Hopefully, you're not a marketer at Uber. You're not shilling a '90s parent's worst nightmare to satisfy stockholders. Your task is to communicate something less ick-inducing, but that doesn't mean your subject is easier to get people to care about. So let's look at an incredibly successful and ridiculously difficult example of connecting with what an audience cares about: The Big Short.
3. The Big Short
A few weeks ago, I suggested to my daughter that we watch The Big Short—the 2015 Oscar-winning film based on Michael Lewis’s book of the same name about the 2008 financial crisis. I didn’t have an agenda; I just thought she might like it if she was willing to give it a chance. Luckily, the promise of Ryan Gosling and “Michael Scott” (i.e., Steve Carell) was enough to pique her curiosity—or at least give in.
Directed by Adam McKay (Anchorman, Talladega Nights, etc.), the movie ping-pongs between dramatized events and breaking-the-fourth-wall explainers by Gosling, Margot Robbie, Selena Gomez, Anthony Bourdain, and more. It’s a fire hose of complicated financial information and grating personalities. What I’m trying to say is that it’s a lot to take in all at once. But its humor and pacing encourage you to pay attention.
My daughter, born right between the failure of Bear Stearns and the collapse of Lehman Brothers, got sucked in. We paused the movie a dozen times so she could ask for clarification. She exclaimed, “Michael Scott!” every time Steve Carell reappeared. When the credits rolled, I asked her what she thought: “It was good! I liked it!” Her reaction seemed genuine, but I thought I should check in with her again the next day. “I really liked it,” she told me, “But I’m not sure I understood what was happening.”
The reason it’s hard to understand is that it’s really hard to understand. Yes, the financial instruments involved are esoteric, and the seemingly unending string of not-quite-conspirators is convoluted. But really, the neglect, ignorance, and greed at the heart of the story are practically incomprehensible if you’re not old enough to order a beer. I think it takes a certain amount of experience in the “real world” to accept that there are systems that reward the kind of behavior The Big Short centers on. And even then, I think many of us have a sort of moral perception filter that makes it difficult to accept that such wanton selfishness exists.
Anyhow, I knew my daughter lacked foundational information that would make the movie more accessible—how mortgages work, the economic risks created by financialization, the perverse incentives of the stock market and derivatives trading, etc. But I also knew that Lewis and McKay are both brilliant communicators and storytellers. They make cultural products with people like my daughter—interested in politics, class, and systemic injustice—in mind, albeit with another decade or more of life experience behind them.
The Big Short—both the film and the book—is an effort to demystify a major economic event. It uses story as a medium of accessibility. The conceit at the heart of its critical, popular, and educational success is that there is no comprehensive, play-by-play historical or economic analysis that would fully explain what led to the 2008 collapse. The Big Short neither attempts a straightforward recap of events nor waters down the details.
By telling an engaging story with compelling characters, The Big Short makes us care about the various financial instruments that reckless traders threw giant wads of cash at. To tell the story properly, Lewis and McKay argue implicitly, we need to understand certain details we’d never care about otherwise—details that were purposefully obtuse: “Bond market terminology was designed less to convey meaning than to bewilder outsiders,” writes Lewis.
My daughter may not be able to explain the difference between a mortgage-backed security and a synthetic CDO (I certainly can’t), but the next time she encounters a story about Wall Street, she’ll be able to jump into the deep end a little faster and tread water with more confidence. Michael Lewis has made a career out of this type of communication, the kind that takes what people already care about—great stories and meaty questions about the world—and uses it to convey incredibly complex information. His work is not without faults, but his technique is time-tested, repeatable, and portable.
Lewis's technique is a good example of what cultural theorist Stuart Hall described as the process of encoding. Hall's theory begins with the idea that all of reality is mediated; that is, how we experience the world is always filtered through language, image, metaphor, mental models, etc. To communicate meaning, we first encode that meaning as a message using our various tools. Then we share that message with the receiver, who must decode it to arrive at their own understanding of the meaning.
This process happens constantly and without awareness that it's happening, so long as the message sender and the message receiver are working from similar "frameworks of knowledge." The more the sender and receiver differ in their frameworks of knowledge, the more conscious the sender should be in how their message is encoded. Otherwise, we end up thinking that the message means something different from what was intended.
One of the reasons that Lewis is so good at conveying complex information is that he's working with a framework of knowledge much closer to that of the receiver of his messages than, say, an economist, Wall Street analyst, or major league baseball manager would have. Lewis makes it his job to decode messages conveyed by experts and then re-encode them with a more familiar set of signs for his audience, who can then decode them again with relatively less loss of meaning. And when I say he's made this his job, I mean that—this process takes significant work.
In the next and final chapter, I'll bring this back around to how you communicate what you care about.
4. The Swimming Pool Theory of Communication
I'm going to assume you are some kind of expert—someone with special training, information, experience, and/or interests that make the framework of knowledge you're working with markedly different from that of your audience. In other words, on one level or another, you care about different things from the people you're communicating with. I'll also assume that your expertise, broadly defined, led to trouble communicating with your audience, again, broadly defined. You've struggled to get them to care about what you care about. You've suffered from the "curse of expertise."
The “curse of expertise” is a cognitive bias that leads an expert to forget that what’s transparently obvious to them is opaque and confusing to others. Experts use language, heuristics, and mental models that non-experts don’t have access to. And that’s fine if you’re, say, an economic historian writing a scholarly article on the causes of the 2008 financial crisis for the American Economic Review with an intended audience of other economic historians. But not if you’re Michael Lewis—or any other creator sharing with an audience of laypeople.
There’s a similar issue that we might call the “deep end problem.” Experts and deep thinkers get used to swimming in the “deep end” with other experts and deep thinkers. When they go to communicate with a broader audience, they get frustrated that either very few people are willing to dive into the deep end with them or that they need to “water down” their ideas to reach those in the shallow end. They perceive a choice between the integrity of their ideas and the siren song of mass appeal. This is a false distinction.
Swimming is swimming whether you do it in waist-high water or where your toes can’t touch the bottom of the pool. You can preserve the integrity of ideas even when presented to an audience who isn’t yet accustomed to thinking in the deep end. It’s not the novice swimmer’s responsibility to throw caution to the wind and try to stay afloat in deep water. The expert must always remember that an enthusiastic novice has the capacity to become a confident swimmer if provided with the right technique and support. The novice isn't lesser than the expert nor do they lack the capacity to swim in the deep end; the novice is simply different from the expert.
Stuart Hall's theory of encoding and decoding is helpful here because it represents the sender and the receiver of a message as equal. The sender's encoding process may be based on a different process the receiver uses to decode, but neither is better, smarter, or more sophisticated than the other.
Intellectual integrity and accessibility are not mutually exclusive. Experts—at least those who want to share their ideas with broader audiences—are responsible for learning and sometimes creating the techniques and support that allow one-time novices to dive into the deep end with confidence. And that’s quite difficult.
To do it, we have to employ Weil's negative effort and get curious about the knowledge and experience that our audiences use to decode our messages. If we can use their frameworks and, ultimately, what they care about to encode our message, we can more effectively communicate what we want them to know.
Every day, we communicate with people who don’t care about the same things we care about. The set of variables that includes my motivation, experience, knowledge, and anxiety is unique. So is yours. Any time I send an email, attend a meeting, go to the grocery store, or talk to another mom at a sporting event, I’m talking with someone who doesn’t care about the same things I care about.
Most of the time, we don’t think about this at all. The people I talk to regularly don’t have the same set of variables governing what they care about that I do, but the overlap is substantial. When we interact with people whose variables overlap far less with ours, the chances of misunderstanding are substantially higher. For a variety of reasons, we often misjudge the similarities between sets of variables. We assume that the person in front of us or reading our email or answering the phone cares about roughly the same things we do because they have roughly the same set of variables we have—that is until one or both of us realize that we are not on the same page at all.
To avoid these misunderstandings and move others to see things as we do, we need to take on their values, mental models, and knowledge frameworks when encoding our messages. Hopefully, you've noticed that that's exactly what I've tried to do here. I attempted to encode a message about effective communication within a question that I've heard in various forms from many people who are reading or listening to this: How do I get people to care about what I care about?
If you're still here, I think you got (at least part of) the message.
