The Empathy Problem

I made a mistake in empathy that cost me tens of thousands of dollars.

It wasn’t a case of bad customer service or a botched partnership. It was something a lot simpler: I didn’t understand how people read blogs.

I thought people read blogs as I did, subscribed to only a few, with the queue of unread posts mostly empty. When I stop regularly reading a blog, I unsubscribe. And, I typically pay more attention to my 10-12 RSS subscriptions than my email inbox which can get hundreds of emails each day.

But it turns out I was wrong. First, people pay more attention to email. I get more email response for my newsletters than blog comments, despite having only a fraction of the subscribers. Second, few people purge their RSS subscriptions, meaning email gets read and RSS does not.

Because I didn’t understand people, I spent the first four years of my blog emphasizing RSS. And based on my subscription rates, I likely paid the price in tens of thousands of subscribers and dollars.

Empathy Missteps: Why We Fail to Understand People

I made a mistake in empathy: I failed to understand how people think.

Although we routinely think of mistakes in empathy as being grossly insensitive, that’s not the case. My bias towards RSS wasn’t because I didn’t care about my readers. It also wasn’t because I lacked common sense (although in hindsight, it is certainly obvious).

The real problems of empathy are both subtler and far more costly than we imagine. We all remember the dates than went badly because of poor communication. But we can’t remember all the relationships that never even began because we didn’t see the opportunity.

The empathy problem pervades more than just relationships. Design, programming, sales and even writing an email are all informed by our ability to connect with how people think.

I’ve noticed most empathy failures fall into one of two categories (assuming you’re actually trying to understand the other person):

  1. Believing other people think like you, when they don’t.
  2. Not understanding how you actually think

My story was a clear example of the first case. Of course, if most people actually used RSS as I did, then my strategy would have been spot on. I often skim emails, but I read nearly every post in my reader or I unsubscribe.

My failure of empathy was in using myself as the model for others, when that model was broken.

In the second case, you have an idealized version of how you think and act, but it doesn’t fit reality.

As a writer, I’ve had to deliberately train myself to understand that almost all people skim when reading. This feels unnatural because, after spending so much time writing, you believe people will hang on your every word. Good writers are able to divorce themselves from their writing and see their work as a bystander would.

Both these cases make empathy difficult: being a lousy example and not understanding your behavior even when you are.

Improving Empathy

If the problems of empathy are so costly, how do you fix them?

A good first rule of thumb is to watch what people do, not what they say. I’m always skeptical of any polls that rely on people’s stated opinions. Stated opinions are biased, we reveal ourselves in our actions.

A perfect example was a post I wrote about adding a subscription popup to the bottom of this website. The vast majority of comments were negative, which I completely understand (I don’t like seeing them either).

But that doesn’t mean they don’t work. I went from a couple new subscribers each day to 20-30. That’s a tenfold increase with no noticeable impact on traffic.

This doesn’t mean that the original dissenters were wrong (I was one of them). Usability is important and I’m still trying to make the popup more user-friendly. However, some people must find them useful otherwise there wouldn’t be a nearly 1000% difference in results.

I believe behavior is a better model because of the second case of empathy failure: people don’t really understand their own actions. We view ourselves as largely rational, smart, deliberate beings. But our actual thought processes are a lot more impulsive and easily biased.

Look for Attention Asymmetries

Another good heuristic is to be on the lookout whenever you’re paying more attention than the other person.

When I’m writing a sales letter, for example, I’ll spend hours trying to pick the correct words when the person reading will only invest a minute or two to read. This means it’s easy to miss the most obvious information and focus on details the reader doesn’t care about.

Writing an email to a person who gets tons of email is another example. They may only have a couple seconds to skim the email to see if it’s worth a response.

Dealing with asymmetries of attention requires a lot of testing and a thick skin. Because the investment is so lop-sided, the casual mistake is to infer too much, not too little. I’ve made the mistake in the past of assuming a sales letter failed because the product was doomed, or that an email garnered no response because the person was disinterested. It may be simply that the subject line was off.

Learning Empathy

We usually view empathy as something instinctive. It’s something you’re either good at, or you’re not. But, I’d prefer to see it as something that is trained with experience.

This means the only surefire way to be more empathetic is to interact with people constantly. I believe most of the subtle, yet costly, problems of empathy stem from not spending enough time interacting with the people you’re trying to understand.

The problem with empathy is that we don’t believe it’s important enough. We invest hundreds of hours trying to get results—in business, in relationships, in life—but less time trying to deeply understand how other people think and feel. But if those results come from other people, ultimately empathy is what we need most.

  • Violaine

    I really like your post, especially the importance you attached to empathy as a mean to understand other people.

    As you said, we invest a lot of time trying to get results. But, according to me, human relationships cant be seen in terms of results. Human beings are complex and we can all be irrational and impulsive at some time or another. Therefore, in order to understand human nature, as you said previously, we need to interact constantly (preferably with people who don’t think like ourselves). And the amount of time spending interacting does not necessarily mean we will get a result at the end. However, we have to keep in mind that understanding people is a goal in itself.

  • Marshall Jones Jr.

    I like how you broke this down into two problems: assuming people think like you do and not really understanding how you think. It’s so simple… but one of those things I need to remember more often.

    And then great conclusion on working around these problems:

    “I believe most of the subtle, yet costly, problems of empathy stem from not spending enough time interacting with the people you’re trying to understand.”

    -Marshall Jones Jr.

  • Life Exceptional

    Yes, I think you are making a very important point. It is also clear that listening to feedback is vital to improving your interactions with the world. But as you point out, you have to be careful and listen to what that feedback really means. But also use yourself as feedback. Try to notice how you respond to things you read and emails you get, and why.

  • Marcin

    And make sure you aren’t just observing people like you for traits that you think are good, and people unlike you for things that you perceive as bad. It’s comforting to act or think like a Nobel laureate, but somewhat confronting to identify with a bum.

  • Seth Czerepak

    I think this is such an imporant point where you say:

    “2. Not understanding how you actually think”

    Self-awareness is one of the first things I teach. You have to have a clear picture of where your perceptions and assumptions end and the world around you (and those in it) begin.

  • ah

    one of my strange feeling is that when our things are getting smooth, we tend to be less empathy. Only when things not getting well or experienced some very bad luck in the past, people usually became more empathy to others……

  • Michael

    Empathy, oh Empathy! I agree with ah, right above. We tend to start improving all of our virtues, including empathy, when we are at a low point in life. When we have been humbled, we act humbled, usually. We care more about others because at the bottom, the only thing we can do is hold out our hand and hope someone will help. In order to attract others to help us, we need to know more about them to form a genuine bond to justify their investment in us.

    I like how you summed up empathy failures into 2 main categories. One, as a little bit of autism, and two, as a little too much idealism. And, I also enjoyed how you believe empathy can be learned. It’s kind of like in the Patch Adams movie, where he encouraged everyone to talk to strangers, pick up the phone and dial wrong numbers, etc.

    Do you think there are any skills or virtues that CANNOT be learned but rather we are either born with it or we are not??

  • Steve

    “….the only surefire way to be more empathetic is to interact with people constantly…” – you hit the nail on the head there, Scott.

    The current fashion (in the UK at least) seems to be for organisations to decentralise operations and disperse staff into a loosely affiliated network of remote workers. I’ve watched the relationships and effectiveness of individuals and teams change each time this happens. In each case there’s a marked deterioration where emails and teleconferences predominate and are not balanced by regular face-to-face contact. Videoconferencing is often an ineffective half-way house with its limitations (indirect eye contact, jittery movement in a low-quality link and an urgency to ‘get to the point’ rather than socialise). We’re social animals (albeit some more than others). An on-line presence is no replacement for interacting in-person with peers, colleagues and friends to maintain an understanding of what makes them (and you) tick. If anyone finds the above sounding familiar but finds in-person meetings impractical, try this work-around: Schedule a daily ‘watercooler’ videoconference; kick back with a coffee and open a free discussion for 20 minutes. You may see a marked improvement both personally and in your relationships with others…

  • Scott Young

    Violaine – Yes, I agree. Empathy is a good end-goal to have, not just as a means to something else. However, even if it is an intrinsically worthy objective, it’s also incredibly useful.

    Michael – I don’t really see things as being completely learnable versus completely innate; it’s a spectrum. Empathy obviously has innate components to it that make some people great at intuiting others’ minds and others lousy at it. But to the extent there is a learnable component, I think that’s worth exploring.

    ah – I would agree. Broader life experiences also inform our empathy. Those who haven’t suffered can’t fully appreciate suffering in others.

    Marcin – Idealism definitely pollutes the intuitions of empathy. We see ourselves as being better than we actually are, so we expect such perfection in others.

  • Paola

    Definetely, people don’t know what they want. Your experience about pop-ups is a suitable example. Most say they don’t like pop-ups, but, if you use them, subscriptions increase. It’s both not-logic and not-surprising.
    When it happens, what do you think about it? Do you think that people don’t know what they want, or do you think that people choose what they don’t really want, just because it’s easier to say “yes” than “no”?
    When I say “no”, sure I can change my mind, but usually I think first, than answer, and once I’ve said “no” it’s no, unless something important change in the conditions. Most people say “no”, but that “no” has no meaning at all, because they act the opposite way. I’d prefer if they just said “I don’t know”.
    But, you know, I need much much exercise in “empathology”!

    Cheers, thanks.

  • Scott Young


    Part of it depends on when you’re asking the question. If I’m asking whether you like popups, and you’re already subscribed to my website, of course they seem annoying.

    But for a one-time visitor who might otherwise forget the site, they are a helpful way to keep getting the content.

  • Alice Hive

    I think the best strategy is to test, test and test. As you said, just asking people often doesn’t give us the answers we’re looking for. We rather have to oberve how they behave.

    So: Test something new, observe how people behave, learn from it.

  • Lou

    Well, yeah, obviously they’re annoying because I’m getting pop-ups again and again that I’ve already seen and taken the one-time advantage of. It would make more sense if there were a mechanism that tells the site that I’ve already subscribed / don’t want to see the pop-up ever again. But I’m guessing you would have done that already if it weren’t more trouble than it’s worth to you. But generally, unless I’m going through a bunch of your articles at once, I don’t have to seen the pop up more than once a week, whenever you have a new post.

    But I do like your point about empathy, although it’s kind of weird to start off your post talking about how you lost thousands of dollars and then title this an “empathy problem.” 😉 Understanding others is obviously not necessarily anything to do with empathy, as it can always be used for entirely selfish purposes. Empathy means not just understanding, but identifying with.

    What I like about it is how it makes me just think of interpersonal relationships. Often we don’t know how to create healthy, or ideal, relationships because we’re too stuck in our own heads. We don’t bother to ask what that person’s perspective is. We’re too buy worrying about whether they’re judging us or giving us what we want. If we worried about what they want, they’d actually be more likely to not judge us and to give us what we want.

  • Scott Young


    Definitely. I’m working on making the popup better. Right now it shouldn’t display any more than once in a month, since the cookie it sets lasts for 30 days.


  • Kitty

    I found this a thought-provoking article, however, I’d like to point out that “empathy” is not really the right word for “figuring out how other people (or you yourself) think.” Rather, it is about the capacity to understand and have compassion for how other people are FEELING. Understanding how other people THINK has more to do with good listening and observation skills and the cognitive ability to analyze and classify what you discover when you use them. It may seem a minor point, but I share it because I think being able to differentiate thoughts from feelings is an important aspect of a self-aware, critically thinking person.