Box of Crayons Blog


Jenny Blake on What’s Next for Me

jenny_blake_headshotI met Jenny Blake when she worked for Google, where she was doing internal coaching and career development and helping manage Authors@Google. She left Google in 2011 to launch her first book. Then, interestingly, Jenny spent a number of years experimenting, figuring out what it meant to run her own business and create her new career, which is why it’s so perfect that she’s written this new book. It’s called Pivot: The Only Move That Matters Is Your Next One. You can also follow her on Twitter @Jenny_Blake

So, join us as we discuss:

  • The fear of the unknown.
  • How test piloting a pivot will help answer “the three Es.”
  • One of the biggest hidden secrets of pivoting internally.
  • The biggest mistake people make when pivoting.And much, much more.

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Full Transcript

Michael:   I met Jenny Blake when she actually worked at Google. She was—one of the many things she did there, she was in charge of the Authors@Google series where, you know, authors come in, they speak to a Google crowd, and somebody has to organize that. And I knew—I was in California, so a friend of a friend had introduced me to Jenny and she hosted me. We got to hang out. And so, it’s been fun to watch her for the last six or seven years.

So what’s happened is this. She actually left Google in 2011, which is a big thing. She launched her first book and then, interestingly, spent a number of years kind of experimenting and trying to figure out what it meant to run her own business and create her new career, which is why it’s so perfect that she’s written this new book. It’s called Pivot and the subtitle is The Only Move That Matters Is Your Next One. And it’s really about when you’re thinking about a career change, whether it’s been thrust upon you or whether you’re working for a big company and you’re, like, “I need to get to the next level because I’ve kind of plateaued,” or whether you’re an entrepreneur going, “What’s the next project?” or whatever it might be, what Jenny’s done is she’s combined her experience at being the co-creator of the Google Career Guru Program with her own experience of shaping and forming her own interesting career, and really brought it together in this book where she suggests there are four stages to really thoughtfully, mindfully, successfully creating and launching your own next step for your career, whatever that might look like.

So, we get into this. We don’t cover all the four steps, just because there’s a third step that I was really intrigued with and we kind of went deep on that. But I do hope you’ll enjoy this conversation with me and Jenny Blake. Jenny Blake, author of Pivot: The Only Move That Matters Is Your Next One.

Alright, Jenny, so I’ve been praising you in the introduction, but here’s the thing: I know your mother’s unimpressed by you, still unimpressed by you, by your decision five years ago to leave Google. Why would you leave Google? But I’m guessing it’s part of the inspiration to where you’ve got to now around writing this wonderful book, Pivot. Let’s go back there. What was that thing that made you step away from Google, which is one of those cool companies that kind of lots of people aspire to work for?

Jenny:       As much as I loved my job there, I felt like by the time I left, it really was a ‘perfect on paper’ role. I was doing internal coaching and career development and helping manage Authors@Google so I could bring in amazing people like you.

M:              Right.

J:               And yet, still I felt like on a day-to-day basis, I was working in my zone of genius probably 30% of the time. I was doing a lot of emailing and PowerPoint strategy decks and meetings and the work that I really loved, being in the classroom or coaching, was getting to be a smaller percentage of my work. And then simultaneously, my side hustle, I had been building a website since 2005 and now had a book coming out in 2011. That was ramping up, so I was also feeling the physical signs of burnout coming on again, which I had had previously in my time there. And I just realized I can’t do both for much longer. I’m going to—I was at a fork in the road. I’ve got to pick one, and I knew that not ever trying to do my own thing, that’s what I would regret more than leaving, even if I failed.

M:              You know, the book is called Pivot and then the subtitle, The Only Move That Matter Is Your Next One, and it’s really helping people think about what’s the next career step. But you know, one of the things that just must come with this is just the familiarity and the comfort of what’s known and the discomfort and the fear of what’s not known, and that sense of, “God, what if I make a bad choice here? What if I take a leap and I, you know, leap off a cliff or leap into a wall or it doesn’t work?” Let me talk right at the start, which is around how do you help—and in the book, what guidance do you give around managing this sense of anxiety and fear that must come up whenever you’re about to take that leap into the unknown?

J:               The first thing is to recognize that, and I didn’t fully comprehend this, is that career changes in particular seem to threaten our most fundamental needs on Maslow’s hierarchy of food, clothing, and shelter.

M:              Right!

J:               Because we worry that if we make the wrong move, we will no longer be able to provide for ourselves and we’ll end up in a van down by the river. I thought that leaving Google was terrifying. I thought that that was the scariest thing I had done in my career. But actually, it was two years in when I hit another plateau and I was asking, “What’s next?” My bank account balance started to dwindle down to zero, and this time I didn’t have a steady paycheque to fund that exploration. Well now, the fear of not being able to provide for myself was very real and much more so than the decision of leaving Google because I was watching my savings account just get drained as I struggled with this question.

And so, that second—and it was not even my second carer pivot, but that was the time where I finally threw my hands up and said, “This is unacceptable, and if we’re all going to have to ask and answer, ‘What’s next?’ we’ve got to find a better way to do it.” And knowing and honouring the fact that career change does bring up so many fears for people, and that you’re human if you’re feeling hesitant to make a change.

M:              Well you know, you and I have known each other since when you were at Google, and so I’ve kind of hung around and watched the post-Google Jenny Blake and the things you’ve experimented and the things you’ve tried with, and it’s awesome that your, you know, let’s say, inspiration is when your past makes sense, and it feels like a lot of that is woven into this book.

And the pivot method that you talk about has four main steps: planting, which is kind of getting ready; scanning, which is checking out what’s ahead; piloting, which is experimenting; and then the launch, that leap. And I want to go to stage three, that piloting piece, because I know that over the last four or five years, you’ve actually done quite a lot of piloting, so tell me what—expand on what we mean by piloting and what the lessons have been for you around how do you pilot successfully.

J:              Piloting is really fun. This is all about small experiments. Typically, when people are at a pivot point in their career, and they contemplate—you know, in the old model of the career ladder you’re making these big, scary leaps from one rung to the next, and there’s a lot of pressure. But if we can instead run small experiments first, it takes that pressure off and it helps us test the waters of a new direction, and this is very similar to the mindset that we had when I worked at Google. It was the mindset of launch and iterate, get scrappy, and also much lauded in the press, Google’s 10 and 20% projects.

So if you think about that in terms of your own career, and you have kind of an itch or a call in a new direction, what’s a small pilot that you can run in 10% of your time? So, without going all-in right off the bat that will help you understand what I call the three Es: do I enjoy this new direction, can I become an expert at it, and do I want to, and is there room to expand? So if you’re self-employed, are there more clients in that market where that came from? Or if you’re working at a company is there room for you to do more of this internally? And so, pilots, a good pilot, will help us answer those three Es.

And then if you run several pilots concurrently, you can think of them almost like racehorses at the starting gate of the Kentucky Derby: usually one will start to pull ahead, and then that’s how you know, “Okay, this one’s got real momentum and I’m going to double down on it now.” And in doing that, we reduce risk for that ultimate stage of launching.

M:              Oh, this is great. So actually, one of the things that this brings out for me as I think about it is, you know, the term “pivot” as I understand it, I mean, I know it’s got kind of sporting characteristics as well. In fact, you talk about a basketball metaphor about pivoting in basketball to change direction. But the way it kind of hangs out most frequently as I see it is kind of in the context of Silicon Valley and startups and it’s like, “Oh my God, my startup isn’t working. We’re going to pivot, change direction, and try and recreate our startup.” And I ask, I set that up, just to say is this a book really for people who are in that entrepreneurial phase or can you pivot within a kind of more traditional career structure?

J:               I’m glad you brought this up because I see pivot as a mindset and a skill that we can all get better at. And some pivots are within our current role or business, and it’s really a tool for just answering, “What’s next?” So it doesn’t have to be always—you know, some pivots are smaller turns or even, again, within our current setup, and some are sharper turns, bigger pivots. And one of the biggest differences—because originally, my question that guided so much of this book was startups are so agile, they’re changing all the time given automation and outsourcing and everything that’s happening in our economy; how can people be that agile? And what I realized in writing Pivot is that startups use the word as almost a sign of failure, like you’ve failed at the initial strategy and now the business has to pivot.

M:              Right.

J:               But when it comes to our careers, for people who want to be really agile and for people who just love learning and growing and making an impact, we are going to get impatient. And pivots are actually a product of our success. When we hit a pivot point or a plateau, it’s not that we’ve failed, it’s just this natural plateau in our growth cycle where now it’s time to look ahead and plan.

So I love that you brought that up, and to answer your question more succinctly …

M:              Yes.

J:               … one can apply this even within a project, not just huge career moves.

M:              Alright, I love that. So it’s kind of got that scalability at a project level, at a career level in a more traditional organization, say, and then, of course, in that, well, maybe more startup or more entrepreneurial level it can apply as well. Let me take you to the middle one of those, in that more traditional organization, because I think folks listening to this podcast are often in that place. Can you give me some examples of, you know, for that stage three, the piloting stage, where you’re doing small experiments? What does that look like? Because I can—you know, if I’m trying to start a side hustle, to use a phrase I picked up from Pam Slim.

J:               Yeah.

M:              And, “I’m going to try coaching a few people on the side. I’m going to start writing a blog, or I’m going to start my bondage company on the side on the Web.” You know, all of that I can understand, but how do I do it within the context of a bigger company?

J:               This is one of the biggest hidden secrets of pivoting internally. And when I was at Google, I trained over 1,000 people and I was there while the company grew from 6,000 to 36,000, so I really—because I was training so many, they would come to me. These Ivy League grads that would come in for entry-level jobs and then of course get bored doing customer support and want to pivot internally. So my big passion is not—it’s a misconception that I’m really saying, “Oh, quit your job tomorrow! Everyone should just pivot willy-nilly!” No, I really want to help people pivot before they leap outside of the organization. And so, I’ll give two examples.

One, in my case, I was doing AdWords product training when I first started. And you know, I didn’t want to talk about how to place analytics tracking code for the rest of my career. So I started, on nights and weekends, I went to coach training as a result of a coaching session I had through a leadership program. Well, then I asked to join this 10% project. I had this vision. I wanted drop-in coaching to be as easy to schedule as a massage. So I joined this task force. Well, it was only a year and a half later that a career development team was formed, so when a role opened up I was perfectly positioned to take it because of my pilots of going getting training outside of work and starting that project.

Another example, Seth Marbin started a 10% project called Google Serve. He wanted all Googlers to volunteer during the same week, modelled after something he saw at Timberland. There was not a full-time role to be doing that, but each year the program grew and grew and grew, and Seth later pitched a role and he’s now managing Google’s volunteer outreach full-time.

So, the key within organizations is don’t wait until there’s a full-time, open role. That’s usually not going to be the case. But if you can start something small and build it and test it and prove the viability, it can often grow into something bigger over time.

M:             Alright, Jenny, here’s this interesting middle bit that I like to do: three questions to ask the good people I get to interview, and the first is this. What’s the crossroads you came to; what’s the decision you made, that when you made it seemed to make all the difference?

J:               For me, leaving Google was a tough decision, but what really changed my trajectory was recognizing that as a self-employed person, the biggest mistake I made was focusing too much on what wasn’t working and what I didn’t know and what I didn’t have. So it wasn’t until I could go back and actually look at my strengths and what was working and how I had gotten business in the past. That’s when things really started to turn around.

M:              Oh, that’s a great insight. I love that. Alright, second question. Whose work has influenced your work? I mean, it might be a writer. It might be a boss. It might be just somebody you hang out with. But whose work has influenced your work?

J:               Other than Michael Bungay Stanier?

M:              Yeah, other than that well-known person.

J:               Okay, fine.

M:              Yes.

J:               Nassim Taleb wrote a book called Antifragile: Things That Gain from Disorder, and the subtitle alone says it all for me. I loved his book and I love the idea of thinking of ourselves not just as resilient, that when setbacks occur we stay standing, but, as Nassem Taleb calls it, antifragile. We actually grow from chaos and uncertainty and disorder, and I just love that, so he’s been very influential.

And on the exact opposite side of the spectrum, Tosha Silver wrote a book called Outrageous Openness that she first self-published, and then it became an absolute runaway hit, and her book is all about surrender. And what I really loved is that as methodical as I am and as left-brained as this new book ended up being, Tosha’s message about when we really get stuck, we can surrender it, we can turn something over to the universe, our inner guidance, our inner wisdom, whatever you believe in, and ask for help and say, “Please just show me the one next step.” And that mindset, combined with some of the more tactical, action-oriented ones, has been extremely helpful and beneficial to me over the years.

M:              I love that. I love that what you’re pointing to is that kind of paradox between control and letting go and how they both matter. They both kind of coexist as a powerful way forward.

J:               Yes, and I see meditation—so I’m going to cheat and just throw in a third book, that 10% Happier by Dan Harris.

M:              Yeah. Oh, great book, yeah.

J:               It’s such a great take on meditation and mindfulness from a, quote, “fidgety skeptic.” So, because mindfulness and meditation, it actually helps me be more focused and strategic. Maybe you’re not supposed to say that, but it’s true. So I find the combination of those two things is really powerful.

M:              Fantastic. Okay, third and final question. You know, part of the heart of Box of Crayons is about helping people and organizations do less good work and more great work. Great work, the work that has more impact and the work that has more meaning. So how do you consider your great work right now?

J:               For me, beneath the projects or the output, I have this passion to help people embrace fear and insecurity and uncertainty. I see them as doorways of opportunity. I don’t see them as the enemy or something to be crushed or smashed or destroyed or conquered. I see them as signs that we’re on the right track. And so, to the extent that I can help people feel less alone, more human, and more okay that these things are present as we strive to do great things and great work, then I’ve done my job.

M:              Perfect. Alright, Jenny, let’s get back to the regular interview. Let’s say that you’ve done this work, you’ve done this piloting, you’re experimenting, you’re getting a sense of what matters to you, what lights you up, what kind of ticks off those three Es that you talked about; you can get all of that information and you can get to the edge and you still have to leap. There’s still that moment where you have to go from one state to the next state. How do you help people find the courage to take that leap rather than to scuttle back from the edge?

J:               Well, interesting note on nomenclature, my editor and I, I used to call the fourth stage “leap,” but then we realized that if someone’s really applying the steps in the pivot method effectively, it’s not a leap nor should it be. So we actually took out all mention of the word “leap” or “jump.”

M:              A-ha!

J:               And instead, it’s called “launch” because the biggest mistake people make when pivoting is not doubling down on their existing strengths, interests, skills, who they know, what experience they already have. So the biggest—so the way to do that, you know, we didn’t exactly talk about those first stages, which is no problem.

M:              Yeah.

J:               But what I want to highlight is that when you are really grounded in what’s already working and where you want to end up, then your scanning for different experiments to run is much more focused, the experiments are more focused. And so, in repeating that process, plant, scan, pilot, plant, scan, pilot, over and over, you reduce risk to the point where when you’re ready to launch, it’s kind of just the remaining 10 to 20%. It’s not a blind leap, nor is it a leap of faith.

M:              Right. Right.

J:               And so, at that point, a lot of people ask, “How do I know when I’m ready to launch?” You’ll know when you’re ready to risk failure, however you define failure. I joke that I wrote this book for high net growth individuals and that we don’t have FOMO, we have FONT, fear of not trying.

M:              Right.

J:               So, eventually you get to the point where you more regret just standing still and not taking action. And often, when people do that, they end up getting pivoted one way or another.

M:              Yeah. What happens if you come to that moment, you launch, you take the big stride because, you know, suddenly you got to that point of going, “I would rather try this and risk failure than not try it,” and it still doesn’t work? Because, you know, when I look at my career path, I landed this awesome first job out of university in the world of innovation and creativity, then I moved to a—I did all this work around what’s next for me, kind of not quite as rigorous and thoughtful a process as you lay out in the book, but you know, there was work done. And I’m like, “Great!” Found this organization, moved to it: less good than my first company. I was like, “Oh …” So then, I did work for them for a while. Finally, I moved to my next company after that: even worse than that.

J              Oh, man.

M:              I was on this kind of series of—you know, I’m like, “Man, my career path is getting increasingly boring, conservative, and less effective.” How do you help folks make that failure useful rather than just depressing?

J:               Well first, I’m curious. From you, looking back, were those worse and worse experiences …

M:              Oh, classic coaching move. I know what you’re doing, Blake!

J:               I know! But it’s really fascinating because this is a very interesting example you’ve just shared. So I’m curious: do you think, looking back, there was a purpose behind those? How did they serve your trajectory? Because on their face, it would seem they were failures or the wrong move somehow.

M:              Yeah. So, good questions. So you know, moving from innovation to the world of change management, I had a thing I wanted to pursue which is, so we kept inventing these things and they never seemed to really work. I mean, they were great ideas but somehow they went into organizations and died. So I got more interested in that kind of larger-scale change management. What does it take to make change happen within an organization? And I learned that at this organization. I got to play at that kind of larger scale of organizational design and change management, even though the job itself was less exciting and in some ways I had more failure in the work that I did.

And then the job after that, it actually happened right after I moved from Boston, where I lived at the time, up to Toronto. We originally had flights out of Boston on 9/11, and so I had another job lined up, and that kind of vanished in the rubble of 9/11. So, I got this internal change management job where my thinking was, “So, this will allow me to put the theory I know and I’ve used as a consultant into place as an internal practitioner.” And the problem was most organizational change projects either fail or they don’t work very well, and I was connected to a failed change management project so I just went down with that particular ship.

J:               Mm-hm.

M:              Even though, you know, I’m a big one for your scars are your stories and your stories are where …

J:               Mm-hm, yes.

M:              You know, as they say, wisdom enters through the wound, so that’s where you kind of become a smarter person.

J:               Yeah. Well, what you just shared is also a great example of sometimes pivots are actually comprised of several smaller pivots. And I see this a lot: when somebody wants to do—a lot of times, people know what they want two or three moves out. Even though I say the only move that matters is your next one, if they happen to have a vision like, “I want to be a self-employed author/speaker/coach/podcaster extraordinaire running a consulting practice some day,” well, maybe either that’s too sharp a turn from where they are now. So in your case, what’s really interesting is you pivoted industry and then job role and then job role again to kind of give you—to, like, build the path towards where you are now. And so, one way to think of this is like a parallel parking job. Sometimes pivots, you got to kind of wiggle in there to get it right.

M:              That’s interesting, yeah.

J:               And so, even what seems like … I had, Michael, I had so many people, when I interviewed them for this book, and I went to fact check a year and a half later and they just said, “Don’t bother putting my story in the book: I pivoted again,” and it just had the tone of failure. “And don’t bother.” But the funny thing, and at first it was a couple months in and only a few people said that. By the time I went to fact check, almost every single person had moved again and said to me, “Don’t bother putting my story.” So it got to the point where I had to make a note in the book like, “P.S., I couldn’t even keep up with these people. This is how often pivots are occurring, some by choice and some by circumstance.” So even what we typically view as failure tends to bring us additional data that helps inform the next move after that, hence the subtitle.

M:              And you know, it’s interesting when you think about it. When I think through what you were just saying, when I was working for that very first company, I remember having a clear moment of insight walking to work one day going, “I need to run my own company at some stage,” without having the slightest idea of what that even meant or what I would do or any of that. I didn’t have an idea. I just went, “You know what? I need to be my own boss at some stage.” And maybe this is a very sophisticated way of finally getting a job that sucked so badly that I had to go—I mean, they fired me in the end—that I had to go off and start my own business because, you know, it was only be getting fired from a terrible job that I finally had the courage to actually go and do that.

J:               Yes, and I hear so many stories like that. And I don’t mean to make light of getting fired because it can be very shocking, but there was nobody that I personally spoke with who said they wished that didn’t happen. Everyone who I interviewed, they said, “I’m so glad. That really kicked me into the new direction and I wouldn’t have had the courage to do it on my own.”

M:             You know, Jenny, I was just talking to a corporate client of mine and they were very proud of how they framed it as an entrepreneurial culture within their business, and that’s influencing this next question, which is around, you know, there are some people who’ve just got some hustle. They’ve got some entrepreneurial spirit to them, and I can see them picking up your book and going, “Yeah, this is kind of confirmation and advice and suggestions to help me do what I already do better.” And there are some people in this world who go, “I like to play it safe. I like more certainly. I like more comfort.” Are there words of guidance to people who are perhaps a little less wired like you and me who are kind of that more entrepreneurial, ‘what the hell,’ ‘take the leap’ sort of people, and who are feeling threatened by this whole idea of pivoting?

J:               Definitely. I share in the book a riskometer, a way to test your risk threshold, and that we have a comfort zone, works fine, a stagnation zone where you’re kind of more bored or physically uncomfortable, stretch zone where you’re engaged and challenged, and then a panic zone. So this isn’t meant to put anybody in their panic zone, and I’ll say I thought I was the last person to be cut out for entrepreneurship because my risk tolerance is pretty low and I was really concerned about finances. I have this fierce inner CFO that was like, “You’re an idiot! You know, how can you leave all this money on the table.” And it …

M:              That’s just your mother, isn’t it?

J:               Well, yeah, my—so when I was writing the book, I thought my mom having seen me be relatively okay for the last five and a half years, I thought she would say, like, “Yeah, looking back you did the right thing.” And she says, “No, I still disagree with your choice to leave when you left. I don’t—I wouldn’t have done it that way.” And yet, I wouldn’t have done it any differently. And even when I was eating power bars for dinner because money was so tight, I never once regretted my decision to leave Google.

So for the people who, yeah, your risk threshold feels lower, everyone’s is different. So that’s, again, where the small experiments, just toggle yourself, you know? If you feel yourself in your panic zone, ask, “Okay, how can I break that down? What’s the one next step that I can take or that would put me back into my stretch zone?” And I just encourage you not to live in the comfort zone. And so, just find that place.

And whenever I’m coaching with people, let’s say around ideal income, I always ask for three numbers—and this will apply to any moves you make, not just money—but what’s your minimum needed, what’s your nice to have, and what’s your job out of bed with glee? And the reason, as a coach, that I ask those three is I want to give them brackets because people will often say something that’s safe, but if I ask for those three they get to express all sides of themselves.

M:              Right.

J:               You know, what feels stretchy and edgy? What feels gleeful? And what feels the minimum? And so, you can kind of do that with any next move. What’s safe? What’s stretchy and edgy? And what’s like a dream? You know, even if it’s a snowball’s chance in hell.

M:              That’s perfect. Hey, Jenny, incredibly, our time is all but up. So for people who—and again, we have barely touched on this. I kind of—you know, there’s four stages and really a fifth stage if you want to take this into organizations and help drive career planning within organizations (inaudible) stage. And I got kind of hooked into the pilot stage because that feels really interesting to me, but it means that we barely scraped the surface or the depths of this book, so people are going to be clamouring for more. Knowing that they can find the book on Amazon and in bookstores and the like and you’ve got a ton of wonderful press, but where can they find more online about you and about this book?

J:               Sure. There’s a whole toolkit that goes with the book as well. That’s all at And then I also have a podcast. You can search for it. It’s called Pivot Podcast. If you search with Jenny Blake it will come up because there’s quite a few Pivot Podcasts out there in the world.

M:              Right, so Pivot Podcast, Jenny Blake.

J:               Yeah.

M:              Starring such lucid people like Michael Bungay Stanier as well.

J:               As yourself. That’s right.

M:              You were kind enough to interview me when we launched our book about six months ago.

J:               Yes, that episode is one of my favourites: “How to Tame the Advice Monster,” so I encourage everyone to take a listen.

M:              So, there’s the website. Jenny, are you on Twitter or LinkedIn or any of that stuff?

J:               Yes.

M:              Do you want people to know about it? Yeah?

J:               Absolutely. I’m on Twitter @jenny_blake and I also have a personal site,, and you can find me on LinkedIn and Facebook, too.

M:              Perfect. Jenny, it has been a pleasure.

J:               Michael, thank you so much for having me. And a huge thanks to everybody for listening. It’s an honour to be on the show and to be walking these pivot paths together all these years, so thank you so much for all of your guidance over the years as well.

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