Don’t Overthink It

The question we should be asking ourselves isn’t what’s next? Understandably, everything’s so fricking weird, we want to understand what’s going to happen next. What’s the next shoe to drop? Is AI going to take our jobs? Is it going to liberate us forever? Is the American political situation going to revive itself? Is it going to get even worse than it is right now?

The kind of change that we’re dealing with now is so massive that I don’t think we can answer that question. And I think the better question is, what can I do now?

The training that a lot of us have is that we analyze first and then act, that we figure stuff out and then decide what to do. And that’s OK. But I think now the only way to figure out what the hell’s going on is to try stuff and do stuff. And I think in that stumbling way in the dark, when we just start doing things, we might be able to figure out what’s going on. But just sitting there and analyzing. OK, let me just think through what’s going to happen next, is a fool’s errand. I’m really convinced of that.

Our default setting, and I think it’s a very deeply embedded default setting among smart, accomplished people, is to do more. We’re going to add something. We really have to overcome that. We don’t have to necessarily abandon that all the time, but we have to be much more ambidextrous about how we solve the problem. We have to recognize that sometimes you want to add. But you also have to think about what we want to take away.

One of the reasons for feeling overwhelmed right now, in my view, is that we’re always adding and never subtracting. And this is one reason why you see sort of steps in this direction with things like, on this phone here you can put limits on how much you use social media. That’s a little bit of a subtraction. You can stop your notifications. Those are small steps in a world where we’re feeling overwhelmed.

This is an idea that’s been around for a while, sometimes it’s called a stop doing list, it’s something I’ve done myself for a few years now. You think hard about what are some things—I like to make it three, just because I think three is always a good number—three things that waste your time, distract you, divert your focus. Think hard about those things, but also memorialize them, write them down.

There’s a power to writing things down. Keep a list of things that you shouldn’t do and post it, like in the way that you keep your to-do list in view. So I’ve done that, and it’s been really helpful to me to do those kinds of things. And it begins ever so slowly to begin to think a little bit more subtractively.

One of the most important ones on mine is don’t answer email first thing in the morning. As silly as that sounds, it’s really transformative, because that’s what I want to do. Because you get it there, it’s there waiting for you, you know you can do it, and you get that quick hit of satisfaction. Boom, one down, two down, three down, four down, got rid of him, five down, six down.

But it’s never the most important thing I have to do that day. I’m much better off saying, what’s the most challenging or most important thing I have to do that day and take an hour to do that first. And that’s been really helpful to me. But it’s harder to enforce if it’s this theoretical thing that you know you should do rather than something that is this admonition staring you in the face at your desk.

Doing small things actually matters a lot. A lot of times we try too hard to come up with big, comprehensive meta-solutions, which are sometimes valuable. But in this case, just doing small things, getting a little momentum, trying some stuff, making some progress is really important.

There are all kinds of ways to stay motivated. I think day to day, one of the most important things is to pay attention to the progress you’re making. We have pretty good evidence that making progress on a day-to-day basis is the single most motivating thing that we do. We like to make progress. It feels good to make progress on meaningful things, but we don’t always see it. So once again, it’s a matter of coming up with a routine, a ritual that allows us to notice it and memorialize it.

It’s an exercise in noticing as well. If I were to say to you, “Here’s your assignment for tomorrow. I want you to notice people doing kind things for each other.” You’ll notice that in a way that you wouldn’t have before. So if I say to you, “Start noticing the progress you’re making because you’re going to have to record it at the end,” you start noticing more the progress that you’re making. The bang for the buck is really powerful on that one because it doesn’t cost you anything.

Many of us are doing it wrong.

It’s a little bit disconcerting given how much time and treasure inside of organizations is devoted to feedback, when we have evidence starting 30 years ago that it doesn’t have that much of an effect on performance. The reason it doesn’t have an effect on performance is that we’re doing it wrong. What the research tells us is that you want to give feedback that is timely, that’s super important. I don’t think that’s any great insight.

If you’re coaching an athlete and she’s shooting a free throw and her form is off, you don’t tell her the next day, you tell her in the moment.

So if we think about if [feedback is] timely, individualized, non-punitive, and then also forward-looking, what that distills to is the best feedback is actionable. And a lot of times we over-index on positive or negative. And we obsess, “Oh, you know, I want to be honest, but I don’t want to be cruel. Or maybe I can sandwich the bad stuff into the good stuff.” I think that’s a diversion. What we want to do is, can I give you feedback that is actionable? Can I give the feedback that’s actionable and that captures everything? Actionable feedback is forward-looking, it is individualized, it is non-punitive, it just helps people get better.

Regret is useful if we treat it right. It is inherently part of being human because everybody has regrets, everybody has moments where they look back and they wish they had done things differently, hadn’t done certain things, and it makes them feel bad. That’s actually really important, that it makes you feel bad. It’s one of the most common emotions that human beings have. But if you think about it, we have this very common emotion that makes us feel bad, and that sort of feels like, wait a second, what’s wrong with us? Why are we so messed up? And we’re actually not messed up at all. Because it’s adaptive, it’s stuck around evolutionarily for a reason.

I think the problem is, especially in America, contemporary America, we’re just way over-indexed on positivity. I mean it, honestly, I think that we’ve been sold a bill of goods. We’ve been told that the way to lead a good life, be effective, etc., is to be positive all the time and never be negative, to always look forward, never look back. And that’s just bad advice. It’s unscientific.

What we should be doing with our regrets, then, is not ignoring our regrets. Some people just ignore their regrets, and other people get captured by them, they wallow in them.

What we want to do is we want to think about them. We want to look at them as signal, as information, as data. And when we do that, we have all kinds of evidence that it helps us become better negotiators. It can help us become better problem-solvers. I talked a little bit about some cognitive biases today. It can help us avoid cognitive biases. It can help us find more meaning in life. It’s a teacher, but it’s a teacher only if we treat it right. We don’t run away from it.

It’s like a knock at the door, right? So somebody comes and knocks at that door right there. What can I do? I can say, “I don’t hear anything.” Or I can say, “Oh my God, a knock at the door, this has got to be the worst thing ever,” and I go hide underneath that table. Or I can say, “Hey, what’s up? What do you need?” Just like look it in the eye and say, “What are you telling me? Oh, that’s what you’re telling me.”

When we think about our regrets, when we just stare them in the eye, it’s a transformative emotion. But we haven’t been taught how to do that very well.

I did this big quantitative study, where we surveyed about 4,500 Americans on various dimensions of regret. The reason that the sample was so big was to look for demographic differences in regret. There weren’t very many. I’m still surprised by that, how modest these demographic differences were on race, on religious belief. But the one difference was on age, and it was massive.

You can have two kinds of regrets. In the broad categorization of regret, you can have regrets of action: I regret something I did. I bullied somebody, I regret it; I cheated on my spouse, I regret it. Or regrets of inaction: I didn’t ask somebody out on a date; I didn’t tell my grandfather that I loved him, and then he passed away.

What sticks with us over time are these inaction regrets. Young people, people in their 20s, had about equal numbers of regrets of action and inaction. But the older people got, the more they had more inaction regrets than action regrets. And it was just endless. By the time people get to their 60s, 70s, and 80s, it’s 3-1, 4-1. It’s so clear to me that over time, what people regret is what they didn’t do. Because when we have regrets of action, we sometimes will make sense of them. We can find a silver lining: I shouldn’t have married that guy, but at least I have these two great kids.

We had a lot of regrets in the database of bullying. You have people who [said], like, “I bullied somebody 25 years ago, but I found them on Facebook and I called them up and apologized to them.” So you can make amends. But the inaction regrets, they stick with you.

That’s part of it. Part of it is the unknown. But part of it, particularly for things like boldness, is that people look back on themselves and they’re not necessarily conjuring, oh my God, everything would have been great if I had asked that person out on a date or if I had gone on the trip. But they look back and say, “Why didn’t you just step up and do it, what’s wrong with you?” We look back on our former selves and say, “What were you so scared of?”

It is applicable to all people, but the reason I chose sales is that all people are salespeople. That’s one of the ideas in the book.

We did a piece of research, 10 years ago, 12 years ago, asking people what they do all day and trying to recategorize what they do all day. And we found that people are spending enormous amounts of their time persuading, influencing, convincing, cajoling. They don’t have to be in sales, they could be a teacher. A teacher is persuading people. Managers are persuading people. Doctors and nurses are trying to get people to change their behavior and so forth.

That’s one reason the book is called To Sell Is Human. It’s part of what human beings do, it’s part of what human beings have always [done]. It’s just that it’s become monumentally more important.

I wanted to write a book about sales per se, because I felt like it was getting a bad rap, big time. I was writing about other kinds of business stuff a couple decades ago, back when there were things called magazines. I did a fair amount of long-form magazine journalism on business. And some of the smartest people I met were salespeople. Yet among my smarty-pants friend circle, they look down on that. And it’s like, wait a second, I don’t understand this, why do some people look down on sales? They’re really astute and they’re really effective and they’re nothing like the stereotype. That’s why I wanted to do that.

I had an inkling that all of us are selling a lot and that sales had changed. I wanted to understand what people actually do all day, which is selling. But I didn’t want to hide entirely behind words like influence. I wanted actually to put a fine point up and say, “Hey, listen guys, we’re all selling all the time, whether we like it or not.” And selling is not this dirty, horrible thing, especially now. Salespeople could take the low road—we have experience as buyers when salespeople take the low road when there was information asymmetry. But now there’s less and less information asymmetry, and it makes it very different.

EWELL: Directly from the book: “When buyers can know more than sellers, sellers are no longer protectors and purveyors of information. They’re the curators and clarifiers of it—helping to make sense of the blizzard of facts, data, and options.”

Theoretically, AI also clarifies and curates information. Do you think salespeople being curators and clarifiers will change altogether?

I think it has a bigger effect on more direct customer service, because in customer service there are a lot of questions that are repeated. It’s probably going to have a bigger role on lower-ticket sales items. But for higher-ticket sales items, I think it becomes another accompaniment. In the same way that a salesperson or even a doctor would have to deal with someone coming to them with a stack of Google printouts, now they’re going to come saying, “ChatGPT told me this and Perplexity told me this and Claude told me this.” And [the salesperson is] going to have to say, “OK, here’s where they got it right, here’s where they got it wrong.”

A lot of times what you’ll see if people are using these large language models for these kinds of inquiries is they sometimes ask the wrong question, and the salespeople know how to ask the right question. I don’t think it replaces that contextual curatorial function. I think it forces them to up their game, though.

Oh, that’s a good question. OK, three things that are on my desk.

So, not much significance of the big rubber ball band, except that I use rubber bands and I need a place to hold them. And it also gives me something to bounce around. I don’t know where I got that. I think actually somebody gave that to me. Again, just to share more about the seedy details of my personal life, I really like rubber bands, I really like Ziploc bags. I think those are such ingenious tools. Forget about large language models, rubber bands and Ziploc bags are awesome.

What else is on there? I have this thing that one of my daughters made in preschool. You know those clips that you use to fasten a big thing of paper. Imagine the black part of that. So that’s the base. And in nursery school, they made this thing where they took a photograph of my daughter Eliza from the front, and then a photograph of her from the back. Then they laminated it and stuck it in one of those things. It’s like a little figurine of her from the front and the back. And so I have that on my desk, too.

The other thing I have on my desk is a stuffed doll. It is a stuffed doll of Charles Darwin, who is one of my heroes. Because he went against conventional wisdom. He was someone who wasn’t a scholar, who made a big contribution to the world of ideas. I designed my office in Washington behind my house, in part based on his office. There was an exhibit in London maybe 20 years ago of his office. He had this office where he looked out on his yard, essentially. So I got a garage office, and I was like, “Oh, you know what I want to do? Let’s knock this out and have a window and I can have like a Darwin-like office.”