Caroline Webb, author of How to Have a Good Day, specializes in the application of behavioral science to the workplace and beyond. She is CEO of Sevenshift and a Senior Advisor to McKinsey and Company, where she was previously a partner.
Caroline recently sat down with world-renowned business thinker Whitney Johnson, author of Build an A-Team and host of the Disrupt Yourself podcast, to discuss little steps we can all take to have better days.
This conversation has been edited and condensed. To listen to Caroline and Whitney’s full conversation on the Disrupt Yourself podcast, click here.
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Whitney: So, you’ve told me you were a bit of a daredevil as a child, and you liked to write stories. What did you think you were going to do when you went to college?
Caroline: I wanted to be an astrophysicist. I was very deep into sci-fi and read everything that I could about black holes and the early beginnings of string theory and multiverse theory.
Whitney: Were there any particular books that you especially loved?
Caroline: Oh, I loved Carl Sagan. The truth is that the kind of science fiction that I most liked was less about natural science or technology—I was much more interested in how a society evolves. If you push an assumption to a limit and take it forward into the future, how does society [progress]? Of course, that was perhaps a clue that I was slightly more interested in people-science than I was in natural science.
So when I took a class in economics when I was sixteen, it blew my mind. I thought, “Wow, you can be rigorous about human stuff!” The whole course of my life changed at that point.
Whitney: Interesting! So that’s an interesting question you just posed. 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: Well, I didn’t think of myself as a risk-taker. I grew up in a modest, loving household, which meant that I didn’t have that financial security that sometimes helps people be bold early in their lives and go out on their own. What I did have was a clear sense that I liked learning. The thing that has guided me throughout my life has been this question of “What do I want to learn next?” If I push that to the front of my mind, then I’m a little braver and a little bolder in what I choose to do.
“The thing that has guided me throughout my life has been this question of ‘What do I want to learn next?’ If I push that to the front of my mind, then I’m a little braver and a little bolder in what I choose to do.”
Whitney: Okay, so [based on that guiding question,] walk us through the chronology of your career.
Caroline: I was a public policy economist for most of the 1990s. I enjoyed it, but realized that it was missing people, in some ways, [which was] my original interest in economics. So I thought, “How do I get closer to that again while playing to my strengths and figuring out how to bring more joy into my professional life?” I decided that management consulting would be a good way of working on organizational change and leadership, which was really what I was interested in.
So then I went to McKinsey, the consulting firm. McKinsey was surprisingly willing to let me play and build a practice focused on behavioral change, so I did that for quite a while. I was there for 12 years and was a partner in the organization practice.
Career number three actually started while I was still there. I was enjoying the intimate work that I was doing with leaders or their teams one-on-one. I thought I should probably get certified as a coach in order to do that properly, and after my training, I thought, “This is what I was born to do.”
Within McKinsey, I pivoted to focusing on individual effectiveness and doing much more coaching. And then I quit, wrote a book, and became an entrepreneur.
“How do I play to my strengths while figuring out how to bring more joy into my professional life?”
Whitney: Ambitious people want to disrupt themselves, to do something new, but also often don’t want to leave their current job. You did that really well at McKinsey. How did you get the buy-in to be able to play? Do you remember the process you went through to make that happen?
Caroline: Absolutely. I joined McKinsey in 2000, which was an interesting time to move from the public sector to the private sector, because it was right after the markets had all tanked. So basically nobody was getting staffed, because there just wasn’t enough work to go around. It was a very awkward, stressful situation. I just remember deciding that, instead of relying on the staffing process, I would just find out who was doing [a project that] sounded really cool and interesting, and I would leave them a voicemail.
Not everybody replied, but many people got in touch. I suppose they were perhaps charmed by my proactive outreach, even if what I said was a bit garbled. So, I got to do very interesting work from the beginning, which was a prize, not only because it was interesting, but because I was just staffed on anything at all when a lot of my colleagues were not. That was definitely one big eye-opener—you have to be clear about what you’re going after, and then be a little brave in reaching out for it.
“You have to be clear about what you’re going after, and then be a little brave in reaching out for it.”
Whitney: How did you make the decision to leave McKinsey and to write your book, How to Have a Good Day, and start on the path that you’re on today?
Caroline: It’s the same question that I started asking myself early on: “What do I want to learn next?” At McKinsey, the big questions were about building a bigger business, which is an exciting thing to do, but it wasn’t what I was most excited about. I was doing a lot of work showing clients how to use simple insights from behavioral science to improve their professional lives. After a session, they would often ask, “Can you give us a book as followup reading?” I would talk to them about my most cherished behavioral science books, and they would say, “No, I want the practical stuff—how you change your to-do list, how you have conversations, and so on.” I thought there was an opportunity to give people something that did not yet exist, a book that people could dive into at any point, depending on what they most needed that afternoon.
I considered trying to do it while I was still working at McKinsey, but I thought it might be time for a new adventure. It became clear that it was possible to have an arm’s-length relationship as a Senior Advisor. The best of all worlds, really—still part of the family, but with the independence to pursue my new passions.
This article originally appeared on Heleo.
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