The Bregman Leadership Podcast
Episode 48

Caroline Webb

How to Have a Good Day


Can you decide to have a good day? According to Caroline Webb, author of How To Have A Good Day, you certainly can–and there’s a few tricks that can get you there. In her new book, Caroline combines neurobiology, psychology and behavioral economics into a practical guide to help you live happier and work smarter. Discover how to reduce anger with just a pen and paper, how to ask questions that get people out of “defensive mode”, and her best advice for ending your day–which might just be the secret to having a good day, every day.



Book: How to Have a Good Day
Bio: Caroline is CEO of Sevenshift, a firm that shows people how to use insights from behavioral science to improve their working life. Her book on that topic, How To Have A Good Day, is being published in 16 languages and more than 60 countries. She is also a Senior Advisor to McKinsey, where she was previously a Partner.


Peter: Welcome to the Bregman Leadership podcast. I’m Peter Bregman, your host and CEO of Bregman partners. This podcast is part of my mission to help you get massive traction on the things that matter most. With us today is Caroline Webb. She is a management consultant and executive coach. She spent many years at McKinsey, and now runs her own firm Sevenshift, showing clients how to use behavioral science to boost their professional effectiveness.

Caroline is an economist, a former McKinsey partner, and a practitioner. What I find so interesting is the melding of the science and the practice. Often we’ll speak to academics who are more on the science side, we can speak to consultants or leaders who are on the practice side. What Caroline does very very well is to match and marry the two in her accessible book, How To Have a Good Day, harness the power of behavioral science to transform your working life. How to use what we know and what we’ve discovered in the 21st century that is different maybe than what we knew 50 years ago, and how that should impact the way we lead our lives on a daily basis. Caroline welcome to the Bregman leadership podcast.

Caroline: Thank you I’m delighted to be here.

Peter: So how to have a good day, that’s in some ways both a mundane and tangible accessible promise, and a very lofty one. How many of us end our days going, “ah, that didn’t work out the way I wanted to.” It’s both very tangible and seems sometimes inaccessible. You base the book on three major, I’m going to call them discoveries, or insights, that we seem to have now in a way that we didn’t maybe 50 years ago. One from behavioral economics, the two system brain. One from psychology, the discovered defend axis, and one from neuroscience, which is the mind body loop.

I’m wondering if you can describe each of them briefly, and also why those three? Given how many discoveries we’ve had over the last half a century let’s say, why are these the three that should really govern the way we think about how we live our lives.

Caroline: Yeah, that’s a great question. Well as you say, I was attempting a rather grand synthesis of the behavioral sciences and thinking about what do we know from neuroscience, from psychology, from behavioral economics, that is really directly useful in our working lives. I was trying to pick out the three big ideas that I found coming up again and again and again in my work with real people, in real professional situations. The two system brain, just take the first one, is this very core idea that we have lots of complimentary systems in our brain, but there’s two important ones to know about.

One is the automatic system, which takes care of most of what we do from day to day, and is very fast, and is very heroic in shouldering the load of most of what we do. Then there is the deliberate system which is everything that we do deliberately. That’s our conscious brain that’s responsible for self control, for planning, and for reasoning. All that grown up stuff that you might find surprising in a toddler. The two system brain concept is that each of those two systems has pros and cons, has strengths and weaknesses, but we kind of behave as if we don’t really pay attention to those strengths and weaknesses.

Especially with the deliberate system, which is incredibly smart. It’s responsible for all of our creative insights and our smart decisions, but it’s limited in capacity. It can only do one thing at a time, and is comparatively slow, gets tired comparatively easily. If you understand that, about your brain, then actually a lot of what feels difficult at work becomes easier to understand. Then it becomes easier to imagine how you might create the conditions for you to be at your best, and for you to thrive. That’s the first concept.

Peter: Let me check something about that. When we see people, and we hear about flow. We see someone in their flow. Do they tend to be operating out of that first system, the autonomic system?

Caroline: Well flow is an interesting state, because you’re, I mean everything we do harnesses both our automatic system and our deliberate system. Flow is interesting in that it’s very explicitly describing a state where you’re doing both, because you’re doing something which feels very natural, and gives you a sense of ease, but you’re also stretching yourself. It’s also a challenging situation that you’re handling. Yes, it is, it’s actually a lovely demonstration of the fact that the automatic system is very powerful, and shouldn’t be dismissed as perhaps the illogical or stupid part of the brain.

Sometimes you read literature that says, oh we’re dumb, stupid, illogical animals, because of this automatic knee jerk system that we have. No, actually the automatic system is incredibly powerful and represents a lot of the things that feel very natural to us day to day. It’s just that when we think about stretching ourselves and learning new things and pushing ourselves, in a direction that typically we associate with high performance, we’re also engaging the deliberate system. We had to know how to do that in the best possible way, and leaders need to know how to create the conditions for other people to be able to have their deliberate systems function at its best.

Peter: That makes a tremendous amount of sense, and it’s also tremendously fun. I’m going to take two different examples. One is skiing, which I’ve done all my life, and I teach skiing and I’ve raced. The other is speaking. One, you would think is very very physical, the other very intellectual. But the truth is when I’m in either of those modes, I’m using every part of who I am to show up. When I’m skiing I’m completely and totally focused on what I’m doing in a way that I couldn’t even dream of multi-tasking.

It’s the same thing when I’m speaking. I guess there’s some moment when you’re really on the edge of what you do, and you’re doing it in a tremendously powerful way, and you’ve practiced it a lot, and you’re really good at it, and you’re challenged, you’re at your edge, that seems like you’re really operating on both the deliberate and the automatic process.

Caroline: Yeah, absolutely, and interesting that you mentioned the point about single tasking. When I think about the leadership implications in the work that I do, one very obvious one that flows from the two system brain, is that if you understand that peoples’ conscious brains, their deliberate system can only do one thing at a time, it becomes a little bit clearer why you might want to establish team norms around email and messages. That actually if people are being bombarded by emails all the time, it’s really very difficult for them to avoid multi-tasking.

We know that multi-tasking, because our deliberate system isn’t really able to do it, it makes us make between two and four times as many errors, and it slows us down. It makes us less creative. As a leader, getting clear on well actually when do I need a response to my email, and how can I encourage my team to go offline for periods of time, so that they can think clearly and do their best work. That can be really a distinctive edge in a way that your team operates, if you’re willing to embrace that as a manager or leader.

Peter: You’re saying that it’s really critical to be thoughtful about when we are engaging which system, because they are certain things we could do in certain systems, certain things we can do when we’re being deliberate, and certain things we can do when we’re being automatic. If we misuse them, that slows us down, and gives us errors.

Caroline: Yeah, and whenever our deliberate system is tired, our automatic system is more likely to be driving our decisions. Sometimes automatic decisions are totally fine. I mean if I’m trying to decide on a place to go for lunch, I don’t actually want to engage in a huge spreadsheet analysis.

Peter: Really because to me that often is my hardest decisions.

Caroline: It’s helpful that our brain also makes some of these more basic decisions every day. The tricky thing is that if you deliberately recognize that your automatic system is always going to want to take shortcuts, it’s job is to lighten the load on your brain. It’s always going to want to take shortcuts, it’s always going to be subject to what behavioral economists call hearistics, what the rest of us might call biases, where we’re just saying you know what, if it looks good, it probably is good. If this person looks competent, they probably are competent.

We jump to conclusions. Which is fine, for a lot of the time, but if you’re making a decision that really matters, you need to know that you’re going to be subject to groupthink. You’re going to be subject to anchoring, and confirmation bias, and all these sorts of things. They’re are actually some really simple routines that you can institute in your problem solving, and your team sessions, that really help you to get around those instinctive biases that our automatic brain introduces.

Peter: It seems like the whole concept that you have is let’s use our deliberate thinking brain in order to make decisions about when to allow our automatic brain to operate vs. when to really focus on our deliberate brain?

Caroline: That’s a good way of putting it. I mean fact is I think there’s a meta-theme across the whole book which is that sense of being deliberate. It’s recognizing that the more that we understand the reasons that we think, feel and behave the way we do, and indeed understand the reasons that other people think, feel and behave the way that they do, we can be far more conscious and deliberate about things that seem to be kind of random in our lives. We can be more mindful of the factors which drive high performance and drive low performance. A lot of things which seem to be imposed on us, actually become under our control once we understand a little bit of this behavioral science.

Peter: Let’s talk about the second principle in effect, which is the discover defend axis.

Caroline: Yeah, that’s a good example of the kind of control I’m talking about. It turns out that most people, when you see bad behavior in most people around you, it’s usually not because they’re a psychopath. It’s actually statistically unlikely that they are a psychopath. It’s actually far more likely that their brain has gone on what I call into defensive mode. The way it works is this, our brains are constantly scanning the environment around us for threats to move towards, to seek out, discover, and threats to defend against.

When we’re more focused on threats, we are running the risk of putting our brain on the defensive, which many people know of as the fight flight or freeze response. The thing that’s really important to know about that is that first of all, it takes almost nothing to trigger it. It can be something as minor as feeling that you’re being treated unfairly, or someone is stepping on your toes in a meeting. Anything which undermines your sense of competence, or autonomy, or sense of purpose. Fairness, inclusion, respect. These are kind of existential, but they’re strong enough that if they’re taken away from us, then our brain goes on the defensive.

The other thing to know about going on the defensive is that when your brain is in defensive mode, there’s less activity in your pre-frontal cortex. That’s where your deliberate system mostly lives. As a result of that, what that means is when you’re under pressure or when other people are under pressure, feeling stressed, they become less smart, and less wise. That is a hell of a shame. It seem that, it’s one of those things that becomes obvious when you think about that time in the meeting when someone put you on the spot, and you couldn’t think of the brilliant thing to say, but it comes to you two hours afterwards. That’s because your brain has gone slightly on the defensive through being put on the spot.

If you expand that out to thinking about people’s behavior in the workplace, so much of the knee jerk or short premised, or just generally kind of dumb or unpleasant behavior that you see, is a result of people’s more sophisticated brain, their deliberate system being very slightly offline.

Peter: I want to ask a question about the discover defend axis. When you’re in that moment when someone has triggered you and you’ve gone into defend, you’re acting in a way that you don’t even really love, and maybe you even recognize it.

Maybe your deliberate brain recognizes it, and goes, “I’m being aggressive with this person, I don’t want to be aggressive with this person, but I really don’t trust them, and the thing they said to me, they just said that to me, just made me so angry, and I know it shouldn’t make me angry, but I’m angry.” How do we remove ourselves from the grip that these triggers have? Over this weekend, I was staying at a hotel, and there was someone who was supposed to be very welcoming, because she was the innkeeper, and I was a bother to her. Like my very existence was a bother to her the moment I walked in.

I found myself so annoyed – I was nice to her – but there was very little that I could do to change my attitude. Which was one of anger and frustration, and I never want to stay there again. I was really kind of triggered and I acted nicely, but how do I change the feeling that I have, so that I can have access to the deliberate brain in a sense, so I could make smarter choices.

Caroline: Yeah, well I mean the first thing is you notice it. You recognize what’s going on. I mean I think it helps people to understand that actually, first of all this is a very natural reaction. We’re all experiencing these small threats, and these small triggers, every single day. Knowing that that’s what’s going on allows you to, it can be enough to allow you to notice, ah, right, I know this is what’s going on. Okay, and then ask yourself a question, what really matters most here? That can be enough for small triggers to get you back on track.

It’s actually funny, what you were just so eloquently describing there, about she was making me feel like this, and making me feel like that, because of this that and the other. One of the things that I love in the research is the power of asset labeling. The fact that if you take a pen and paper, and you write down how you feel, and why you feel that way, and then set it aside, research has shown that it reduces that state of alert. That state of being triggered. It gets you out of defensive mode in other words.

It’s one of the most strangely powerful things. If I get to the end of the day and I haven’t been able to move beyond the state of being triggered, it’s my go to technique for just writing it out. Sometimes then screwing it up in a ball, and throwing it in the trash. Makes it easier to sleep.

Peter: This might just explain why and how I write my entire blog. It’s actually very helpful to me.

Caroline: There are a ton of techniques that have been shown to reduce that level of activation. Distancing is another favorite. When you ask yourself what will I think about this when I look back on this in a year’s time. What would I argue, what would I say to a friend who’s in the same situation that I’m in right now. Anything which takes you out of the heat of the moment, and puts you [inaudible 00:16:43] some distance, has also been shown to reduce that defensiveness in your brain, and therefore allow you to think more clearly and be more of your best self when faced with an annoying innkeeper. Who is probably not a psychopath, who might be having a bad day. Who’s probably being triggered by something.

Peter: Right, and I think all of that is true. Where do we draw the line between distancing ourselves, and repression?

Caroline: Repression, it’s interesting, you definitely don’t want to be doing repression it turns out, because when we seek to repress emotions, it’s been shown it just doesn’t really work. If we’re annoyed, and we are trying to tell ourselves don’t be annoyed, don’t be annoyed, not only do we know that our emotions are strangely contagious. That if we feel stressed that that stress response is strangely transmissible, even when we’re not working with the person that we’re transmitting this to, even when we’re not even speaking to them. Actually suppressing had been show to increase the feeling of stress that you’re feeling. Perhaps because you’re trying so hard. That also gets picked up by the other person.

It’s far better to actually label how you feel. Then say okay, what’ll I do now, what really matters most. It helps to ask that kind of purposeful question, because purpose is inherently rewarding to our brains. What we’re trying to do after dampening the initial response, is get our brains more focused on reward than on threat. In other words get us back into discovery mode, rather than defensive mode. Purpose is a nicely rewarding thing to present as an alternative thing to think about to our brains. That’s why it helps to say, hang on, what really matters to me most here, and how do I take the first step towards that.

Peter: Tell us about the mind body loop.

Caroline: It’s interesting. We kind of are aware that our mind is connected to our body, and vice versa. I mean we know that if we sleep badly, that we’re really hard to be quite as hilarious and creative the next day. We know that our physical state has an impact on our mental state. Many people know about the research suggesting that staying fit and active helps you stave off dementia and other age related cognitive decline. Yet, what a lot of people don’t know is that the link is pretty immediate.

We can see lots of evidence that just a few minutes of physical activity, jumping abut, going for a brisk walk, can boost our focus and our mood, immediately. Not just in the long run, but immediately. I think this research is incredibly encouraging, because many of us know that we should exercise, but I think it’s a very different kind of equation to say actually, if I get up from my desk and go for a walk, and I don’t know, do some jumping jacks or whatever, that’s actually going to deliver immediate benefits to how I feel, and what I’m able to do.
I think that’s, that’s easier for the average person to contemplate, than to think, oh this is good for me in the long run.

Peter: It seems like the correlation or the connection is even deeper in some ways. Amy Cuddy has written beautifully about certain poses that if you hold them, your physical body actually permeates your emotional state.

Caroline: Absolutely.

Peter: Holding your arms up high in the air will change how you’re feeling. You may not even have to jump, you may not even have to leave the floor in order to get that kind of invigorated rush.

Caroline: That’s right. We know that when we are happy, we tend to smile. We know that when we are relaxed we tend to breathe deeply. We know that when we’re confident we tend to stand tall. It turns out that our brain and our body don’t really much care about the direction of causation. That doing any of those things in reverse will create a significant effect. When we smile, even if it’s a kind of lame smile, and we’re really kind of struggling to find something to smile about, it’s been show to boost our mood.

When we breathe more deeply, it’s one of the reasons that all of that sort of tradition of take a deep breath, when you’re stressed. Well it turns out yes, it does actually tell your body that somehow you can’t be breathing deeply if there’s a threat nearby. Therefore you start to relax, and the same goes for the power posing one that Amy Cuddy been so vocal and eloquent in explaining to the world. There’s a lot of evidence to suggest that this phrase, which some people love and some people hate, the sort of fake it ’til you make it, is really really powerful.

There’s an enormous amount of evidence to suggest that if we adopt the physical stances associated with being happy, relaxed, competent, that our brain thinks, all right, okay I better get with the program.

Peter: I want to pull all this together now, and you do this beautifully. In fact I was so delighted to see that you had an appendix C. Having read the entire book, the question left with me was: how do I actually pull this together. You do it beautifully in appendix C. I wanted to share this before asking you to expand on it a little bit. It’s how all of this works.

I was mountain biking over the past week. I was in a very difficult mountain biking situation. I was on a very technical single track trail, with a lot of rocks on it, and I was really on my edge. In fact arguably I was well past my edge. I realized in that moment I was holding my breath. I started to bring this methodology that we’re talking about into that mountain biking, and I started to deliberately breathe. I started to think about all these different things that I’ve read.

In that moment on my edge, and I’m thinking about Amy Cuddy, and I’m thinking about you, and Kelly McConical has written this beautiful book. She’ll be on the podcast talking about her book, the upside of stress. Which talks about how a change in your belief about stress actually changes the impact that stress has on your body. I’m biking and I’m intentionally breathing, and I’m lowering my shoulders, and I’m still in as chaotic and challenging a single track mountain biking course as I can handle, or maybe even a little beyond, and I’m thinking, okay this is good for me, because it’s stress that pushes me. I’m going to think of this as good for me.

I managed not to fall, but it very fundamentally changed my experience, and the whole point of your book, how to have a good day, is to say all of this research is interesting, and most interesting in its usefulness for how we live our lives. Whether it’s mountain biking, or whether it’s leading, or whether it’s working on a tough project with challenging colleagues. How do we, we’re living in a chaotic world, where we get pinged with emails and texts every 3 seconds. How do we bring what we know about science and translate it in a way that helps us to lead our lives more productively, more joyfully, in a more connected way with other people.

If you could leave us with a picture, drawing from all of these different pieces that we’ve talked about. How to structure a a day that allows us to take advantage of what we know, and live our lives most fully.

Caroline: That’s a nice invitation. Thank you. I mean I wrote the book so that you could dive in at any point. There’s a chapter on managing tensions, and there’s a chapter on conveying confidence, and so on. I did try and structure it so that you could keep it on your desk and dive in wherever you most needed it. There’s no doubt that you can rework your daily schedule to just weave in a lot of this stuff. For example, one of the things that’s most powerful for me at least, as someone who’s not a morning person by the way, always struggles with the morning routine, is the power of understanding how selective attention works, and setting intentions.

The way that that works is that because you’re deliberate system can only process part of reality, you’re filtering out a lot of stuff, all the time. What you tend to notice, see and hear consciously, is typically whatever matches what’s already top of mind for you. Which is how you can get out of bed the wrong side, and everybody suddenly, somehow seems to be a jerk. It’s not that they’ve become really awful, it’s that you’re noticing only the bad stuff, because your brain is deciding, oh you’re in a bad mood, so therefore the most salient, the most relevant thing for you to see, are anything that confirms that the world is a terrible place.

We’re constantly seeing only part of reality. How powerful is it to actually say, you know what, if I know that my starting point will determine what I actually see and hear, why not be more deliberate about my starting point. Actually taking, honestly it can take 15 seconds. Some people I know actually do it in a more involved way and they’ll take 15-20 minutes, and they’ll think about the most important things that are happening during the day, and what they want to have top of mind, so that it shapes their experience.

For me it’s often, I’m walking to my first meeting, I’m thinking okay, whatever I have top of mind is going to determine what I see. If I walk in and I think this person’s going to be a jerk, I’m going to see that they’re a jerk. What is it that I actually want to have top of mind. What’s my bigger goal? That will totally shape what I experience. That is probably the most powerful thing that I can do in the morning.

Then as you’re thinking about your tasks, there are, there’s lots of interesting work to show that, as I mentioned earlier on, we’re terrible at multi-tasking. What does that mean? It means that actually the more you can single task through your day, the quicker you’ll get your work done, and the better you’ll do it. Thinking about in practice, if you’d look ahead, what is the most important thing you need to do in the day, that requires most brain power, and how can you be totally focused on that. What would it take to remove distractions while you’re focusing on that.

That might mean you need to batch your email processing, 2 or 3 times a day, instead of 2 or 3 times a minute for example. The more you can think about single tasking and grouping together the tasks that are similar to each other, the less you’re asking your brain to switch from one thing to the next, and multi-task like crazy, which we know causes us to to be less smart, and less productive. Single tasking as much as possible.

There are so many Peter, I don’t know really where to go next. I think one other thing that I like to do whenever I’m starting a meeting, is to make sure that I’m asking some kind of positive question that puts everybody into that discovery mode that gets them less focused on whatever is threatening or challenging in the situation. Something that’s more positive. I might start by saying what’s our ideal outcome by the end of this meeting. It sounds kind of obvious but so often you just sort of plow in, and the more you can say what’s our ideal situation, what’s our first step towards that, the more you can frame difficult discussions with a positive question. The easier it is to keep people out of defensive mode and in high performance discovery mode.

A the end of the day, I mean apart from obviously being really attentive to the importance of sleep. I mean to the point of really restructuring my days to make sure that I’m getting enough sleep. Knowing the cognitive impact that that has. I always do something with my husband, we sit on the couch and we ask each other what were the good things that happened during the day. There’s an interesting reason for that. Several interesting reasons. One is that the more you think about good things the more that your brain looks out for them. The other is that there’s something in behavioral economics called the peak end effect.

It turns out that we, when we look back on the quality of a day, or actually a conversation or just any kind of experience, we don’t remember everything about it. We actually tend to rate the quality of the experience based on just two data points. One being the most intense moment, whether it’s good or bad, that’s what they call peak, and the end. You can’t always engineer the most amazing inspirational peak, especially if it’s not been a great day. You can engineer ending on a high by making sure at the end of the day you look back and think, okay, what went well.

Honestly sometimes it is really, we have to grit our teeth a little bit and say, well I remembered my umbrella. What a blessing. The fact that you end the day by reviewing what went well, means that you’re engineering a situation where you’re ending on a high. As a result, your day gets essentially stored in your memory banks as a better day. The way that we remember our days eventually becomes the way that we think of our life. That’s a few ideas.

Peter: I love that, and I think there’s a few things to underscore. I mean one is you’re really speaking very eloquently just about intention. Which is to be very intentional about how you’re going into an experience, and how you’re coming out of an experience.

Caroline: Exactly, exactly.

Peter: That’s what we have to do in our day, both at the beginning and the end. I have to say I’m actually both touched an inspired by the offhanded umbrella comment, because it’s so true. Which is that ultimately you can have whatever happens in your day happen in your day, but little things that are, hardly the most important thing in your life, but yet they seem to hold substance. Which is oh, I brought my umbrella, and it poured, and I actually walked home dry. There’s something that gave me pleasure about that, especially I’m not proud of this, looking at everybody else soaking wet.

It brings both humor, but also a sense of reality that we could be working on the biggest projects, and the most profound ideas, but our lives are built out of realities that are based in whether we brought an umbrella on a rainy day. That’s very true also.

Caroline: Yeah, and the whole reason for focusing on the unit as a day, was there’s a lot out there on how to do your greatest strategic thinking or how to pick the best possible next career step. Actually there’s not that much focus on the minute, the every day, the kind of, the [inaudible 00:32:13], the tiny steps that you take from one meeting to the next, from one task to the next. There’s so much in that that we can engineer to create a working life that is more enjoyable and more effective in every way. I hope that, I’m thrilled that you like those small steps, it’s definitely a book that’s full of those sorts of small steps.

Peter: Thank you. Caroline Webb, the book is How to Have a Good Day, harness the power of behavioral science to transform your working life. I would add to that title that it’s not just your working life, it’s your life life. Caroline you do really a beautiful job translating academic ideas into very real tangible on the ground actions, that we can take to live our lives more powerfully, more joyfully. I thank you for writing the book. Caroline thank you for being on the Bregman leadership podcast.

Caroline: Thank you so much Peter, it’s been a treat.

Peter: If you enjoyed this episode of the Bregman Leadership Podcast, please subscribe and leave a review on iTunes. For more information about the Bregman leadership intensive, as well as access to my articles, videos and podcasts, visit Thank you to Clare Marshall for producing this episode, and to Brian Wood, who created our music. Thanks for listening and stay tuned for the next great conversation.


  1. B”H
    Beautiful program, Peter!
    Caroline shines bright, so eloquent, informative and effective.
    Often we find that proven modern techniques have their roots in our holy, ancient traditions, a few of which were mentioned on this program.
    A commonly known one is the Jewish tradition to begin every day, literally the very first words as we awaken – by verbalizing our gratitude to G-d Almighty for returning our soul to our body, providing us with the opportunities of another day. Read all about it here:

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