Transcript | Episode 68 – Caroline Webb: Creating Opportunity

Transcript | Episode 68 – Caroline Webb: Creating Opportunity

2018-07-24T15:42:29+00:00July 24th, 2018|Transcripts|


Disrupt Yourself Podcast with Whitney Johnson
Episode 68 – Caroline Webb

Welcome to the Disrupt Yourself Podcast. I'm Whitney Johnson. I think, write, speak and live all things disruption. My guest today is Caroline Webb, CEO and founder of the consulting firm Sevenshift, and author of the book How to Have a Good Day.

Whitney:    Welcome to the podcast, the Disrupt Yourself Podcast. I am absolutely delighted to get to have a chance to talk to you.

Caroline:    Oh, likewise. I'm so thrilled to, to be here. Thanks, Whitney.

Whitney:    You've obviously got a lot of accolades, a lot of credentials, um, and I want to absolutely talk about those and dive into your work because I think our listeners will find them incredibly interesting. But I'd like to back up just a little bit and find out where you grew up and what did you like to do as a child? And I'd just like to hear a little bit of your origin story.

Caroline:    (laughs) What a lovely question! Well, I grew up in a small town on the south coast of England, as you can probably tell from my accent, that's where I hail from. And it was, uh, kind of near a lot of very pretty places but itself was not in itself a very, uh, you know, deeply interesting place. But it certainly, you know, gave me, uh, put my feet on the ground, let's say. And as a kid I was, uh, I-I, there were lots of things I liked to do. I really enjoyed being a little bit of a physical daredevil. Um, I like riding my bike with no handle bars down hills and, uh, my, my, while my-

Whitney:    Wow!

Caroline:    -parents watched. Yeah, with, uh, uh, with their hearts in their mouths.

Whitney:    And no helmet, right?

Caroline:    Well, of course not! No. This was the early 70s. I mean, somehow our brains didn't need helmets then. And actually later on in my life I, I went back to that moment and realized I had a little bit more of a risk taker in me than I had perhaps realized. I mean, I loved reading and writing stories. And I also really enjoyed, uh, make believe games that involved me organizing. And, uh, one particular thing I loved especially was to take all the shoes from everywhere in the house and set up a shoe shop which I would then organize and, you know, run. So, you know, I think there might have been some roots (laughs) of my entrepreneurial life now in that's, in those early years.

Whitney:    So, so, you, you grew up, you were a bit of daredevil as a child, you liked to write stories. Um, what did you think you were going to do when you went to college? Or did you even think you were going to go to college?

Caroline:    I was very certain that I wanted to be astrophysicist. Uh, I was very deeply into, uh, sci-fi. I, when I talk about writing stories actually, you know, over time, um, it was definitely a science fiction genre that I was writing more and more in. And I, I read everything that I could about black holes and, um … I mean it was early then, I mean, string theory and multiverse theory was really in, in play. But certainly there was some, some interesting speculation about what black holes might be. And I just remember being so excited about all of this.

I had no interest in actually being an astronaut but I really like the idea of working for NASA. So I was really full on course to do, I mean, I was doing double maths, physics, chemistry, which has a specific meaning to any Brit listening, but basically means a lot of science. And, uh, yeah, so that, that was what I thought I was going to do. Hey, ho. (laughs)

Whitney:    Well, you're doing the science part, just not the astrophysics.

Caroline:    Yeah.

Whitney:    Were there any particular books that you loved especially?

Caroline:    Oh, I loved Carl Sagan. Um, I-I-I read anything that I could get my hands on, uh, with Carl Sagan. And I think actually the truth is that the kind of science fiction that I most liked was less about, “This is, this is a really cool rocket.” I was much more interested in how does society evolve if you, if you push, uh, if you push one or two assumptions to a limit and you take it forward into, into the future, how does society evolve?

And of course that was perhaps a clue that I was slightly more interested in people science than I was in natural science. And th-, what happened was that I took a class in economics when I was 16 and it blew my mind. I just thought, “Oh, my goodness, you can be rigorous about human stuff! Wow.”

Whitney:    Mmm.

Caroline:    Whole course of my life changed at that point.

Whitney:    Interesting. So that's an interesting question you just posed. W-What happens when you take a specific assumption and start to play it out over time? What's one of those assumptions that you've played with and played out?

Caroline:    Oh, for myself, you mean?

Whitney:    However you want to answer the question.

Caroline:    (laughs) Well, um, I didn't think of myself as a risk taker. Um, you know, I grew up in a, in a modest, loving household. Um, you know, I went to, uh, not a, not a great school. Um, I didn't have that sort of financial security that sometimes helps people be very bold early in their lives about, you know, perhaps, uh, going out on their own.

But what I did have was a clear sense that I liked learning. And I think, you know, at every point in my … I'm probably on my fifth career and this point, and if I think about the thing that has guided and has, has been sort of this drum beat throughout my life it's definitely been this question of what I want to learn next. And that has been a guiding assumption that if I, if I push that to the front of my mind, you know, then I'm a little braver and a little bolder in what I choose to do next.

Whitney:    Interesting. So, all sorts of questions are coming to mind. I guess one questions is, is would people who knew you in, when you were 14 or 15 years old be surprised at what you're doing today? Are you surprised at what you're doing?

Caroline:    (laughs) Um, well certainly I think, you know, the, the shift from natural to behavioral science would be, you know, surprising to myself. I think that, that actually the people around me might not be all that surprised. It's an interesting question, though, because of course you don't know what you don't know. I'll have to post the question on Facebook and see what my old school friends say. (laughs)

Whitney:    It is an interesting question, right? Because, uh, th-the reason I'm asking is the way you just described yourself you said, “You know, we had a loving home, uh, you know, y-you, there was money and there was food on the table but not necessarily a lot of financial security” and you s-, just there was this implication that you're a little bit surprised at what you've been able to accomplish. Like, you wouldn't have necessarily predicted that-

Caroline:    Yeah.

Whitney:    -and yet what's been a driving north star for you is what can you learn next? And so I'm just wondering how you put those different pieces together?

Caroline:    Well, I, I think when you, when you come from a modest background of course, yes, I mean, you know, y-you, it's perhaps a little harder to picture yourself … I mean, certainly I would never have dreamt, uh, that I would have written a book that would be successful and, uh, you know, I don't think that I, I might have dared to hope that, uh, that I would be enjoying my, my work as, quite as much as, uh, I am. But I, I did have one horizon broadening experience that really, I think, gave me a sense of possibility.

I got a scholarship to an international school when I was 15. And it was very idealistic place, uh, the idea was to, you know, basically create, uh, peace-loving leaders of the future who (laughs) prevent their being, uh, world wars, uh, by taking kids from all sorts of backgrounds and smooshing them together. And, um, you know, it, it did naturally give me a real sense of, uh, horizon broadening. It did give me sense of, “Oh, actually, maybe I could make a difference in the world.” What that would be, goodness knows, right? I mean I certainly-

Whitney:    Mmm.

Caroline:    -wouldn't have expected exactly the trajectory that I've been on. But, uh, but certainly it gave me a sense that I almost had an obligation to try and make a difference in the world, uh, which is close to feeling that, uh, I might be able to. (laughs)

Whitney:    Yeah, it's su-, it's such an interesting question, isn't it? Where you look at, you know, and obviously you study this, but you look at, you're on one trajectory and then what, what are those inflection points that cause the slope of your line, you know, of your trajectory to steepen and just change?

Caroline:    So I, I had this very fixed idea that I was going to be a public policy economist and that, that was the way I was going to contribute to the world.

And then as I got further into classical economic, uh, policy work I became very frustrated with actually the, the, the dominant school of thought in economics, which was not at that time very behavioral at all. And so, uh, you know, I feel that I … I think I started to pay attention to the discomfort. I started to pay attention to the, the, the mismatch between my sense of duty and what I should be doing and what I was truly enjoying. And the reality was that I was always still enjoying, even when I was building these forecast models and (laughs) whatnot, you know, this is very technical stuff, I was always enjoying anything which had more of a people dimension to it.

And I, I think I just got better in my 20s at paying attention to that and recognizing that there was information in that and that I should figure out how to follow that.

Whitney:    So you mentioned a few minutes ago that you've had five careers? Seven careers? Did you say five or seven?

Caroline:    I, well, who knows right (laughs) I think maybe five. Five is reasonable.

Whitney:    So … Okay, so walk us through that, that, um, chronology. So you just mentioned your first job, it sounds like, out of college. Um-

Caroline:    Yeah. Uh, yeah, so I was a public policy economist for most of the 90s and I had some interesting jobs within that. I enjoyed it. Uh, but then I realized that there was something that I had originally been interested in economics which was that it was a people science and I thought where's the people? (laughs) So I thought how do I get closer to that again while playing to my strengths and figuring out, you know, how to bring a bit more joy into my professional life. And I decided that consulting, management consulting, would be a good way of working on organizational change and, and leadership issues, you know, really what I was interested in.

So then I went to McKinsey, the consulting firm and I thought I'd stay a couple of years and then maybe go back into some leadership role in public policy world again, uh, I say “leadership role” with quotes around it, you know, that would be the aspirational (laughs) the aspirational plan. And then, um, actually I, I found that McKinsey was surprisingly willing to let me play and build a practice which was pretty unusual within that firm, focused on behavioral change.

And so, you know, I did that for quite a while. I mean, I was there for 12 years, I was a partner in the organization practice. But the sort of career three actually started while I was still there. I-I just decided that I was really very much in joining the, enjoying the intimate work leaders coaching with their teams and I thought, “Oh, my goodness. I, I hope I'm doing any psychological damage. I should probably get, get qualified, certified as a coach in order to do this properly.”

So I went and, um, I got trained and I thought, “Oh, my goodness. This is actually what I want to do. This is the thing. (laughs) This is what I'm born to do. How did I not notice this before?” Um, and so within McKinsey I pivoted to really focusing on, uh, individual effectiveness and, and doing much more coaching. Um, and then I guess my fourth career, I quit and wrote a book. And then my fifth career is being an entrepreneur and, uh, building a business. Um, I think four and five were kind of in parallel. So there we are. They're the five so far.

Whitney:    So I, I want to talk about your current career, um, in just a moment. I … Before we do that I'd like to go back to McKinsey for, for a few minutes because one of the things I think people find is they say, they discover, “Okay, I want to disrupt myself, I want to do something new. And, um, I don't want to have leave my current job.”

Caroline:    Mm.

Whitney:    “Like, I really like this organization, I really like this company. How do I get buy-in for me to try something new, to play where no one else is playing.” And so could you go back and, do you have any memory, I'm sure you do, how were you able, you said that McKinsey let you play, but how did you get the buy-in to be able to play? Do you remember what steps or process you went through in order to, to make that happen?

Caroline:    Pretty vividly. Yeah, absolutely. I, uh, I joined McKinsey in 2000, which was an interesting time to move from the public sector to the private sector because it was about 10 minutes after the markets had all tanked (laughs) and I thought, “I've made a really smart, uh, career, decision.”

Whitney:    Mm-hmm (affirmative)-

Caroline:    Um, but, uh, you know, it was a, it was tough because, you know, uh, consulting firms around the world had hired a lot of new people and it was there, it was a step back for me, right? I mean, you, you talk about this in, in your writing, y-, it was definitely a step back to say, “You know what? I'm going to go in at the bottom despite the fact I've already had a first career and I'm really just going to learn my trade as a consultant.” And so it really felt like I'd, you know, (laughs) taken a few risks, let's say.

Um, and then I, uh, I-I noticed that basically nobody was getting staffed because there just wasn't enough work around and it was, uh, very, uh, awkward (laughs) uh, stressful situation. And so I just remember, it didn't even occur to me not to do this but I know that, I know that it was an unusual step to be taking. I decided instead of relying on the staffing process, the internal matching between, uh, uh, consultants and projects, I would just find out who was doing what that sounded really cool and interesting and I would pick up the phone to them.

And this was, uh, back in the day of, you know, people using voicemail a lot, so I would re-record those voicemails, you know, many times (laughs).

Whitney:    (laughs)

Caroline:    Yeah, you know, it's not cool to admit, right? But I, I would-

Whitney:    I think it's fantastic.

Caroline:    (laughs) Ah, the lost of art of the, of the perfect voicemail. So, um, yeah, I just, I left a lot of voicemails. And I, you know, not everybody replied but I got a lot of people getting in touch and I suppose they perhaps were charmed by my proactive outreach even if what I said was a bit garbled and, uh, and I got to do very interesting work from the, from the beginning, which, you know, was a prize, not only because it, work was interesting but because I was just staffed on anything at all, uh, when a lot of my colleagues were not.

So that was definitely one big eye-opener, I'm not very sort of self-promo-, self-promotion-y kind of person but, y-you have to be clear what, what it is you're going after and then be a little brave in reaching out for it.

Whitney:    So were you afraid to make those calls?

Caroline:    Well, of course I was a bit nervous. Yeah, absolutely. Um, but I will say again, you know, it never occurred to me not to do it. I thought, well, how on earth are they going to know I'm here? Um, I remember going to, uh, going to meetings to try and get staff on our project and there would be 20 associates trying, you know, vying for a place on this project. And I thought, “Well, this isn't going to work.” So, you know, it felt like a natural thing to do. It doesn't mean it was, you know, it doesn't mean it was easy.

Whitney:    Mm-hmm (affirmative)-

Caroline:    Um, but then l-later on after I did that coaching course, this is now flash for-, forward a long way. Um, I, I, I, it was really challenging because I thought, I can't be a coach at McKinsey, McKinsey isn't a coaching firm, oh no. I really like it here, I don't really want to take the risk of leaving. Um, and what am I going to do? How do I actually, you know, how do I deal with that? And it became very clear that, (laughs) actually the first step was going to be to tell everybody that I could you know, get two minutes with that I wanted to do more Executive coaching, and yes I know that's not what we do but you know, I wonder if?

And um, you know, that was just the kind of again, a slightly scattergun – not scattergun, that makes me sound a bit (laughs) unthought through. I mean I really reached out to everybody who would listen. And it worked out, you know, within three weeks someone came to me with uh, an opportunity to, uh, to actually teach some consultants how to be better coaches, which wasn't what I had in mind. But you know, but still it was great. (Laughs)

Whitney:    Right.

Caroline:    And then in three weeks uh, another senior colleague came to me and said, “You're the only other certified coach uh, that I know. So uh, we've got a huge engagement, which has 18 leaders that need coaching, I'll take nine of them and you take nine of them. And that was it, that was my practice up and running.

Whitney:    That's fantastic. What a great lesson. Um, thank you for uh, being willing to go back and look at that because I think there are a lot of really good, important learnings from your experience of figuring out how to disrupt yourself inside of an organization that you loved, you didn't want to leave. You wanted to stay there and so you, you created your opportunity. Fantastic.

Caroline:    Yeah. And you know, it might not have worked but it, it, I, I nearly didn't um, I nearly didn't you know, do this broadcast uh, message, of kind of going around and telling everybody about it. I thought, oh gosh, I'll have to leave. And then I thought well, what have I got to lose you know?

Whitney:    Mm-hmm. (Affirmative)

Caroline:    If I'm going to quit anyway I might as well tell everybody what it is I'm trying to do.

Whitney:    So you were surprised?

Caroline:    I was, I was. I really didn't think it was going to work out. I really thought that you know, that this was the end-game. Uh, and then I ended up staying for another six years or so at McKinsey, because I had such a great time (laughs) being effectively a coach while also being a partner, it's wo-, wonderful.

Whitney:    Hum. So how did you make the decision to leave McKinsey and to go and write this book, and start you on the path that you're on today? And I want to talk about the book that you've written, To Have A, How To Have A Good Day.

Caroline:    Well I think it's the same question that I started asking myself quite early on, which is you know, “What, what do I next want to learn?” And I think you know, to have gone further within McKinsey um, the big learning was about building a bigger business. And actually, which is entirely an exciting thing to do, but it wasn't what I was most excited about. Um, I had some threads of interest that had been dormant since I was a kid. About you know, for example, writing. I didn't (laughs) I did not think that I was going to write a Sci-Fi novel. So you know, but my sense of enjoyment at writing, yeah I knew it was bubbling around there.

And I also I, I was (sigh) doing a lot of work showing people, showing clients how to use really quite simple insights from behavioral science. So you know, Neural Science, Psychology, Behavioral Economics uh, to improve their professional lives. And what was happening was that they would say, “Oh, can you give us a book, as follow up reading?” I mean to be clear, not, no-, (laughs) not everyone, right? Most Executives are too busy to ask that question.

But they asked uh, uh, for a recommendation, and I would talk to them about my, my favorite, my most cherished behavioral science books. And they'd say, “No, the practical stuff that's about how you change your, you know, your to-do list. And how you have conversations and so on.” And I thought, ooh I wonder, there’s maybe a need here that I could fill. There's maybe an actual you know, opportunity uh, to uh, give people something that does not yet quite exist, and it has to be really accessible for super busy people.

So I, you know, I was thinking about you know, a book that people could dive into at any point, depending on you know, what they most needed that afternoon. And yeah, and that was where the genesis of the idea was born. And I did consider trying to do it when I was still working at McKinsey, but I actually thought um, I think really this might be the time for a new adventure. And I uh, I think once again I di-, I thought well, the obvious thing is to leave. I wonder whether there's any you know, anything here that I'm missing?

And it became clear that it was possible to have a kind of s-, arms-length relationship as a Senior Advisor. So you know, best of all worlds really, still part of the family but uh, you know, with the independence to pursue my new, my new passions.

Whitney:    So again, another important question I think a number of people will have, how did you negotiate that? That arms-length relationship that allowed you to write the book but still have a relationship with them, do some work, to not worry about cash flow? Any thoughts that you would be willing to share for people?

Caroline:    Well i-, it's interesting. I, I guess I, what I did was I asked myself what was the fear that I was experiencing. I had uh, I had resigned, so you know, to be clear, I knew what I needed and wanted to do. But I was still, I had six months to kind of wrap up my client work and gradually, you know, gracefully kind of exit without leaving anyone hanging. Um, and I, but I was you know, I was feeling fearful. I'd actually practiced for a year before, uh, introducing myself uh, you know, I don't know, at dinner parties or uh, events, conferences and so on, as not saying, “I'm a partner for McKinsey.”

And you know, just saying you know, what I do. What I actually do, which is you know, Executive Coaching, and, and Leadership Development.

Whitney:    I love that.

Caroline:    Yeah.

Whitney:    So you practiced for a year.

Caroline:    Yeah.

Whitney:    So you had your script of how you were going to introduce yourself, so you allowed yourself to have a new identity.

Caroline:    Exactly. I tried a few different things and I also I, I wanted to gather the evidence that life wasn't going to fall apart when I didn't have the big brand you know, to wrap around my head.

Yeah, so I, I tried that and the world didn't fall apart. I can still remember actually doing my first. I did a BBC radio interview and this was after I left McKinsey. And I was absolutely gobsmacked, because I thought that they would lead with Senior Advisor McKinsey. And they just simply said, CEO of Sevenshift, which is my company. And I thought, oh okay, it seems to be a real thing.

Whitney:    (Laughs)

Caroline:    (Laughs), So I've been practicing that a little bit you know, before I left. Um, but you know, there was definitely still this, oh my goodness am I really doing this? This is you know, oh! Um, and so I sort of interrogated that fear. And I, I said, “Well what is it that I'm nervous of?” And it was definitely a sense of losing a feeling of family and belonging and connection. And I'm an extrovert, so being on my own, you know, I knew that, that was going to be a, a new learning journey for me.

And so I thought well, what, what would be a way of squaring the circle? You know, what would be a way of somehow uh, (sigh) still having the benefits of that sense of the affiliation, while having the independence that I now you know, very much desperately want and need? And so I just started again you know, uh, I did prepare a little bit of a script. The first person I reached out to was a senior guy. And I said, “Look, how about if you know, uh, ye-, uh, do you think, you know, do you think that could work?” (Laughs)

So I, I painted the picture, um, was clear on what I thought the benefits were to both sides. And then um, you know, they said, “Yeah, I think that's fine.” And it was so weirdly easy, but I think I perhaps made it a little bit easier by painting the picture and describing how it could work.

Whitney:    What was your role?

Caroline:    My role, um, well it's this Senior Advisor role. And actually I hadn't even realized that there was actually a ca-, uh, there was a, a container for that role. It did exist, there was a title for that role of someone who's not on staff, but you know, provides uh, input from time-to-time. And um, (laughs) I mean I literally made it up, I thought I was making it up. I said, “You know, w-, I could be maybe a Senior Advisor.” And then it turns out later on that, that actually was a thing. And um … (Laughs)

Whitney:    (Laughs)

Caroline:    Uh, I didn't make it up. So uh, and now, they're really, really investing in the Senior Advisor program. And I will say, you know, most of my work, the vast majority like 98% of my work um, since leaving McKinsey, has been non-McKinsey. But i-, it's more that sense of connection and belonging I realized I needed and wanted.

Whitney:    Okay, so you've written a book, “How To Have A Good Day.” You wrote it two years ago. Um, I think you've talked a little bit about what inspired you to write a book, but talk to us about what inspired you to write this book specifically. And what are some of the highlights? What are some of the good take-aways?

Caroline:    Well I, I mentioned that this book in particular, came from the genesis of, of feeling that there was a need uh, to be met. I thought about writing a book (laughs) about the experience … Now you're going to laugh about this Whitney. Uh, about the experience of you know, quitting your job and making you know, making bold career choices. Um … (Laughs)

Whitney:    (Laughs) I like that idea, it's a very good idea.

Caroline:    I know. (Laughs) But I, you know, as I say, I was hearing, I was hearing a particular appetite for the sort of practical applications of behavioral science. So I had a sense that you know, there was a, there was something there. Um, and then you know, specifically what was happening throughout my caree-, I mean my ma-, many careers was that I saw how people could be in ostensibly good jobs. Really smart people, hard-working you know, apparently doing great. And actually from day-to-day they would feel quite worn down. And you know, certainly you know, if you asked them how often they really felt at their best, it was not as often as you know, you would hope or imagine, or you know …

It, it was really sort of, I mean you could say it's sort of dispiriting. But I thought, well if there are days when you are at your best, what would it take to recreate those, those days more often? And so I became over time, more and more interested in the everyday, that's more the small stuff. And in my coaching book so often you know, I would be engaged in a large-scale transformation, you know, helping to shift the culture in a company.

And so much of it would come down to the tiny habits of how you have conversations about things when they're going wrong. Uh, how you prioritize when there's too much to do. What you do um, you know, when, when there are ups and downs and how do you build uh, that resilience at the end of tough day. Um, this was the sort of thing that started to you know, be the focus of so much of my work, even with the most senior people. So I think that the second layer of where the book came from was that increasing in trust in the everyday.

Whitney:    So I took the quiz. And, by the way everyone, there is a quiz that you can take um, to assess how well you're doing at having a good day, and it gives advice. Um, so what are some pointers that you would provide Caroline, of how to have a good day? Just two or three.

Caroline:    You must be way off the charts on that quiz. (Laughs)

Whitney:    I'm not but I think maybe I might be under … Because I do, I thought, I think my score was 73, does that sound right?

Caroline:    That's pretty, yeah, that's pretty good. That's pretty good.

Whitney:    It’s pretty good.

Caroline:    Yeah.

Whitney:    I think I was maybe being a little hard on myself.

Caroline:    Hum.

Whitney:    Um, so it might have been higher, but anyway …

Caroline:    Yeah. (Laughs)

Whitney:    … That was my score.

Caroline:    (Clears throat)

Whitney:    Um, and so I haven't delved into yet. I'm actually excited to delve into it because I want to have even more good days …

Caroline:    (Laughs)

Whitney:    … Than I currently have, right? And so I would love for you to give people a few um, pointers or suggestions that you would make. Just so that they come away from this podcast and think, okay, Caroline said I could do these three things in order to improve my day. Besides buying your book of course.

Caroline:    Yes, yeah, oh of course, absolutely. Yeah, there were about a hundred uh, a hundred tips in my book. And as I say, it's very much guided by what you most need at any given point. There is something I do absolutely every day, which I will say um, has been I think uh, an incredibly strong influence on the extent, of which I've enjoyed my life. (Laughs) I think so, it, it's um, it's using something called The Peak End Rule. And the way it works is this, as uh, researchers have found that when you think back on the quality of um, a day, or an experience of any sort, we don't actually add up how amazing or how terrible each moment was.

What happens was-, is we, we remember what we code in our memory banks. It tends to be the average of the most intense moments, so the peak, whether it's positive or negative, and the end. And so, (Laughs) well you know, it's sort of like a, you know, (sigh) dumping a lot of the noise and just picking out two really salient, really important points of an experience to decide how much you enjoy it. And you know, they've, they've tested this in all sorts of really uh, creative ways. So it turns out people prefer colonoscopies if they're longer but they end with a less unpleasant bit. Because the, the end is that experi-, is that important.

There is this well-worn, very well established post of psychology intervention which is to, “Count your blessings, to think about three good things, thr-, three things that have happened that are good.”

Whitney:    Right.

Caroline:    And what I do is I, I take, I mean I, I tend to look across the variable sciences. I, you know, I know that, that's well established, very helpful for one’s general mental health uh, to do that uh, as much as possible. Boosts your well-being pretty quickly. Combine that with what behavioral economics says about the Peak End Rule, and then oh, okay, so the time to do it is at end of the day. Well actually, it's useful to do it whenever you want and whenever you can. But especially to remember to do it at the end of the day.

Because that's going to give you a tiny bit of a high at the end of the day, and it pulls up the average of how you remember the whole day.

Whitney:    Hum.

Caroline:    So yeah, that's, that's something I do. Uh, even if I can only remember some really small kind of poxy kind of little … You know, like I remember my umbrella. (Laughs)

Whitney:    Mm-hmm. (Affirmative)

Caroline:    You know, there are days when you're really having to think, what was good today? Um, but you know, it, it changes the way you remember the day. And uh …

Whitney:    So at the very end of the day you don't need to reflect on the low, because that's just there. Reflect on the high of the day. Okay, and then good things. Got it.

Caroline:    (Clears throat) Yeah.

Whitney:    Love it. So okay …

Caroline:    And a particular thing is you know, I, s-, I typically do that with my husband if he's around, and if not then I, I typically do it as I go to bed and I'm sort of lying there and … I often remember things I would have otherwise forgotten …Because your brain sort of filters out so much stuff. And you know, if you don't make an effort to remember it at the end of the day, then you know, you may, you may simply completely forget about it.

And then I think you know, if you end in that way … And then you also recognize that at the beginning of the day, that your brain is similarly selective about what you perceive. Not just what you remember, but also what you perceive, that you can't actually perceive everything that's going on around you consciously, it's highly selective. We have something called selective attention. And the way it works is that whatever is top of mind for you, tends to tell your brain, “This is salient enough, this is important enough that you should see things that match that.”

So you know, that's what happens if you buy a new car and then you see cars on the road that are the same model.

Whitney:    Mm-hmm. (Affirmative)

Caroline:    Uh, or if you dare to wear a new color and suddenly you notice everyone else who's wearing the same color. So we know that whatever is top of mind for us will drive what we seem to notice, when we're actually filtering out you know, a ton of stuff. It just allows us to kind of tell our brains, well this is what is important enough for me to see. Confirmation bias is another example of that. You know, if you have expectations that someone's going to be a complete jerk, then your brain will make sure that you see everything that confirms your right. And you might just miss the one moment where they are a bit less like a jerk.

And so being very, very deliberate about your starting point, your mental state as you go into uh, a meeting perhaps that you're not particularly looking forward to, or a conversation with you know, a family member that you might …family member that you might … think might be a bit tense, and just being… aware that what's top of mind for you, whether it's your goals, whether it's your attitude, is gonna shape what you perceive? Wow. You know? That's-

Whitney:    Mm (affirmative).

Caroline:    … It kind of sounds a bit new age-y almost, but it's- the science is really solid on this.

Whitney:    Yeah, and what's interesting, a-as you're talking, I'm thinking u-uh, that's why it's so important at the beginning of the day to do meditation, or to do a scriptural study, or to… to read, or listen to, um, ideas or people that are very positive because basically what you're saying is it's setting your filter for the day-

Caroline:    Yeah… yeah.

Whitney:    …What you're gonna filter for, what you're gonna emphasize, what you're going to remember, and… and so it's supremely important to do that if, in your words, you wanna have a good day.

Caroline:    Yeah, absolutely. So that's, you know, you asked for a couple. That's the start and the end of the day, and then there's-

Whitney:    Yeah.

Caroline:    … also a ton of … a ton of stuff in between! And I will say, I am not a morning person, so I s-I really struggle with any multi- morning routine.

So… you know, for me, the most I can really manage is, you know, get a post-it note, think about what's important in the day, decide what I wanna have top of mind as I go into that, be clear about what my real aims are, knowing that that's going to shape what I notice.

Whitney:    Interesting. Okay, very interesting. Any-any last tips that you wanna give before we move on?

Caroline:    Oh my goodness… I don't kno-wh-what … What-what's-what are you struggling with? What's something that you … that's going on in your life?

Whitney:    Actually I'm going to look at the quiz, I just saw one that says, “I'm able to handle everything that's on my plate right now”. Um, that's one that I think I do pretty well, but there's a lot happening right now, and so there's a piece of me that just thinks I can't sort of take any more stimulus, or stimuli-

Caroline:    Yeah.

Whitney:    … because I won't be able to manage it. What do you do when you start having cognitive overload?

Caroline:    Yeah, well, I think first of all it's great that you're noticing it, because I think a lot of people feel that discomfort and they're stressed without being able to pin down why-what's really driving it.

And… you're absolutely right, your brain can only handle a certain amount of information at any given time, so, uh if you overload it, then, you know, that will cause stress and it will actually, you know, hurt your performance.

I, I think the thing that's been really… transformational for me, there is sort of just understanding that every yes is a no to something else.

Whitney:    Mm (affirmative)

Caroline:    And (laughter), I mean there are whole books written on-on just that idea, um, and you know rightly so, because… you know you're the only person that's living your life, and you are going to do the best thing for the world if your brain is functioning really effectively.

And so… you know I do … I'm a little braver and bolder than I might otherwise be, knowing about that cognitive overload issue, in s-in parking things that don't need my attention right now. And, um, in being very clear with people what it is I'm saying yes to right now so that I'm open with them about the priorities that I'm setting and the boundaries that I'm setting.

And, you know, I feel there's something which I've… I still wrestle with myself, you know, I've still got, you know, requests coming in every day that make me feel stressed because I know I don't have the time to… to… to respond to them, but by, you know, w-doing what I call the positive no, which I've-I've always borrowed from William Ury.

Uh, by starting with warmth, then saying what it is I'm saying yes to, then saying that's why I need to say no, and then ending with warmth, “I've got a few dozen emails I need to send today” (laughter). Uh just to kind of reduce the load and clear some space, and, time for me to think-

Whitney:    So, do you have bad days?

Caroline:    Well, that's a really good question. I mean I do have days when things go wrong. Uh there's no question. I think I've learned how to… bounce back from them. Uh, I mean not least because every time I-something goes wrong now, I think, “Ooh I can use that in a speech or a story” (laughter).

Whitney:    (laughter)

Caroline:    Um, so you know, things go wrong. Um, but the question is how you deal with them, and how you…

Whitney:    Yeah.

Caroline:    … and I've got a lot of … a lot of tricks and tips in my, uh, you know that I-I take my own advice, and there's nothing in the book that I don't actually do for myself that was a filter… uh, for what I put in the book, so, you know.

I-I know how to… use distancing and labeling techniques to get me back in the moment and reduce my kind of… sense of absolute panic. Um, I know how to reframe after the fact so that I can, you know (laughter)… um, figure out what I can take from the experience, uh, a-and so on.

So, you know, th-of course there are, it's all about how you bounce back.

Whitney:    Yeah, it's so terrific to me that you … you, you know, since you are an expert o-at how to have a good day that, you know, to the extent that you're going to have any credibility you've got to be living it, and isn't it nice that you get to live something, or practice every day something so that people will know that you're walking your talk.

It allows you to really… or pushes you to really continually up your game, and I think that's really fun, and… and… and exciting for you.

Caroline:    Yeah a-uh-thank you. A-uh-I, I will say that, you know, I basi… (laughter). Any time I look at all… tired, or stressed, or, uh, you know, just grumpy, it is now in p-I mean, uh, you know, there's … people will always say, “So are you having a bad day, Caroline?” (laughter)

Whitney:    Oh, ouch. Ow-

Caroline:    Gotta laugh, you gotta laugh, but it is true-

Whitney:    (laughter)

Caroline:    … I do have the techniques that allow me to bounce back quickly, and so, you know (laughter).

Whitney:    So…it… you know, uh, you mentioned a few minutes ago that there were some books that really had inspired you when you were first starting coaching and you hadn't yet written your book yet and you would say, “Well read this book”, or “read this book”.

Caroline:    Mm (affirmative)

Whitney:    Then you realized that, in fact, you needed to write your own book. What are some of those books that had really inspired you, and perhaps continue to.

Caroline:    Well, uh, there was um… Obviously Predictably Irrational. I think that was, uh by Dan Ariely, that was um… a real eyen-eye opener, to me, because he wrote in such an accessible way, and… suddenly this field of behavioral economics, you know, was something that… uh, was generating a-it-an-you know, a really broad audience.

That really gave me… first of all I was excited, because I thought it was a great book. Secondly, I thought, “Oh, right, okay. So you  actually-you can take this stuff out into the world, and, you know, you can… um, have nonspecialists read, and understand, and-and use this stuff”. It was a huge inspiration to me. And then of course, uh, Thinking Fast and Slow.

Whitney:    Mm (affirmative)

Caroline:    Um… by Daniel Kahneman, I mean, you know that was sort of the master work, so to speak. Um, and then before that I would say Nudge, right? I mean Nudge, by Cass Sunstein and Richard Thaler, you know, was pro-perhaps the first book that said, “Look, this … this behavioral science can be made incredibly useful in very meaningful ways”.

Um, and uh you know, those three books, they really did give me a sense that there was, uh, an appetite… uh for the practical application that, you know, that-that-that was something that much inspired me on my path.

Whitney:    So, where can people find you?

Caroline:    (laughter) You mean apart from sitting in my delightful office in New York City?

Whitney:    Exactly. Apart from that.

Caroline:    Um… yeah. Uh, so, th-I have a website called, and it is, uh “dot co”, not “dot com”, 'cause there are apparently millions of Caroline Webb's in the world.

Um, so Caroline There's lots of articles and podcasts, and there's the quiz that you mentioned already. Um, thank you so much for taking that, and um… you can sign up for an incredibly, um.. ex- (laughter) – extremely occasional newsletter. Um, and uh, yeah, there's lots of resources there, there's a discussion book for the, uh, a discussion guide for the book, a-and so on, so that's probably the best place to go. Caroline Webb dot co. And of course I'm on social media; Facebook, a-and-and Twitter.

Whitney:    Got it. S-So what- so Caroline, as we start to wrap up, what are you… excited about right now? What are you working on, what are you, um… yeah, what're you excited about?

Caroline:    Well, uh, some of it is steady-state excitement. So I, I love my clients, I love having a range of clients, so I always try and have some clients in the private sector and the social sector, and… you know, I love going on the journey with them. Uh, that I'm just never gonna stop. I think I'll still feel like that, you know, in… uh, 40 year's time. Um, if I'm still around, and um …

But the thing that's new is that I am really trying to think about how to build out the workshops that are around the themes in the book, because, you know everything in the book came from 15 years of actual practice, and… running workshop with, uh, with groups of people and-and-and coaching them.

Um, but what's happened since the book has been out is that there are repeating themes in what people're asking for, and so I thought, “Well, what about if I… stopped making it so artisanal? And-and-and custom and craft, uh based every single time I was asked for a workshop?

And how could I get a little bit more polished in the materials I have around, uh, those workshops… uh, whether they're on, you know, generally how do you apply behavioral science to be a better leader, or be a better… uh, human being, or… you know, how do I boost my resilience, how do I handle overload, how do I… um… harness diversity?

So these workshops are… uh, going live, uh, kind of almost as we speak. There's a website called, “How to Have a Day- How to-How to Have a Good Day dot com“, and um that is a big new venture for me. So we'll see how that goes. Big-big new experiment. And-

Whitney:    So you're-so you won't be delivering all the workshops yourself. So you're basically in the process of scaling … you-you mentioned earlier you'd written a book, but now you're figuring out how to become an entrepreneur, and build… a thought-leadership platform.

Caroline:    There you go. Right, exactly. And, you know, initially it is me running the workshops, but uh… you know, eventually yes, I will be teaching other people to… to run them, and uh, yeah. Big new venture. New s-curve, to use your language.

Whitney:    Yeah, exactly, a new s-curve, and it's so exciting. So you… so you write, you speak, do you-are you thinking of writing another book or are you just building out this IP? It sounds like there's so much to plumb here.

Caroline:    Yeah, thank you. Um, I am a practitioner first and foremost. Y-you know I … the book came from 15 years of work, uh, actually doing the work, and so, you know, I'm, you know … I-that's how I see myself. I see writing as one channel for-for, you know, reaching… reaching people. So, I don't know, there might be a b-you know maybe in ten year's time I'll write “How to Have a Good Night”.

Whitney:    (laughter) That's good, I love that. And with that, we will say thank you so much, Caroline Webb, for joining us on the Disrupt Yourself podcast. I have learned a lot about… how to have a good day, how to, um, be able to navigate inside of an organization. It's been incredibly valuable, and I think that people will, um… will find our conversation incredibly useful to them as they're trying to build out and disrupt their current version of themselves, and-and have a good day in the process.

So thank you again, and, um, and uh-it's been a pleasure having you, Caroline.

Caroline:    Thank you so much. You're such a great host.

I loved Caroline’s guiding principle — ‘What do I want to learn next?’ Asking this question allows you to pull energy away from fear into the wonder of something new.

Whether you want to ride downhill without handlebars, or jump to a new learning curve inside your current employer, Caroline provides a playbook. When she started at McKinsey, and wanted to get staffed, she left voicemails for people telling them she was interested. It sounds so obvious. But we don’t do it. When she wanted to coach–she thought that’s not going to work, I’m going to leave, but why don’t I at least throw it out there. She stayed six more years. When it really was time to leave, she suggested she become an advisor to McKinsey. And they said yes. This is how you play where other people aren’t playing.

Practical tip: If you want to get good at something, start thinking about it, talking about, rehearsing it as if you are already good at it. Not only because public accountability is a good thing, but because words have a physical property to them. Words said aloud come alive.

Thank you to Jaime Dubei for leaving our review of the week on Amazon. Here’s what she said about Build an A-Team.

As a school principal, this book was invaluable. It helped me to think about where my teachers and staff are on their S curves. I would like to see my staff's answers on the learning curve diagnostic so I can better make decisions for the overall organization and the individual people within it.

Jaime, please email us at and we’re going to send you a copy of Caroline Webb’s book.  For those of you that haven’t read Build an A Team yet, and you’d like to try before you buy, you can download the first chapter at

Thank you again to Caroline Webb for being our guest, thank you to sound engineer Kelsea Pieters, manager / editor Macy Robison, content contributors Emilie Davis and Libby Newman, and art director Brandon Jameson.

I’m Whitney Johnson

And this is Disrupt Yourself.