Good Life Project - Jenny Blake: Pivot Your Life (It’s no longer optional)

Episode Date: September 5, 2016

Is it possible to optimize your career for money and meaning simultaneously? Or does one always take the lead?We explore this and more in today's conversation with author, career and business strategist and international speaker Jenny Blake.Jenny helps people organize their brains, move beyond burnout and build sustainable, dynamic careers they love. Her latest book, Pivot: The Only Move That Matters is Your Next One dives deep into how to methodically make your next career move by doubling down on what is already working. With two years at a technology start-up as the first employee, five years at Google on the Training and Career Development teams, and over five years of running her own business, Jenny combines her love of technology with her superpower of simplifying complexity to help clients through big transitions — often to pivot their career or business.We talk through her own personal pivots that lead her to leave the clout of Google, write her first book, find herself in NYC with a dwindling bank account and what she did about it when confusion, uncertainty and fear crept in. She even turns the tables on me to share some behind the scenes pivoting happening in Good Life Project.+++My book - How to Live a Good Life: Soulful Stories, Surprising Science and Practical Wisdom - is available now! It's a joyful, story-driven, engaging and eye-opening deep dive into what really makes a difference in your pursuit of a meaningful, alive and connected life. Click here now to download and read the first chapter for free. Hosted on Acast. See acast.com/privacy for more information.

As a kid, like I said, I loved playing business, but in this moment I realized I don't want to be CEO of some giant company someday. That's not my aspiration. And that was starting to be the first moments that I said there can be a different path. So I first met today's guest, Jenny Blake, back when she was working at a little company called Google. And she had the job that so many people thought, that's what I aspire to. That's how I know I've made it. Shortly after I met her, she left that job to go out on her own and really start her own business, become an author, a coach, a speaker.

And it was a huge move. And she has a new book out now called Pivot. And it's really kind of fascinating because what she's doing is reframing the idea of making these sometimes fairly substantial career shifts and saying, you know what, this is not actually a big disruptive thing that happens every once in a long while in a career anymore. This is your career. It's a constant evolution, or in her words, a constant pivot. So we spent some time sort of deconstructing this idea and how to navigate it, but also really looking at her personal story, looking at her journey, and what kind of gave her the fortitude to make some really big moves, and how that turned into a process for her.

Hope you enjoyed the conversation. I'm Jonathan Fields, and this is Good Life Project. The Apple Watch Series 10 is here. It has the biggest display ever. It's also the thinnest Apple Watch ever, making it even more comfortable on your wrist, whether you're running, swimming, or sleeping. And it's the fastest-charging Apple Watch, getting you 8 hours of charge in just 15 minutes. The Apple Watch Series X.

Available for the first time in glossy jet black aluminum. Compared to previous generations, iPhone Xs are later required. Charge time and actual results will vary. So we're going to jam a little bit on, there's a little thing that you're bringing to life as we're hanging out right now. But we've known each other for a long time now. And I knew you before you were actually rocking New York City, I guess shortly before. So let's take a step back in time. Actually,

let's take a bigger step back in time. We're hanging out, you have this awesome new book out called Pivot, which is all about making some pretty cool changes in your life, which you have done many times over. Take me all the way back. You grew up where? San Francisco and then Palo Alto, starting in seventh grade. Right. So I was kind of surrounded by tech. I even started a family newspaper when I was 10 called The Monthly Dig Up,

which is not unlike having a blog. My mom was really good about getting new technology. So we had one of those Apple IIe computers and I taught myself desktop layout software. And at first it was going to be the Sunday scoop, a weekly paper, but that was a little bit intense. So the monthly dig up, I would write about tech trends and interview family members. I remember when scanners came out, I wrote a front page article. At 10 years old? Yeah, 10, 11, and I did it every month,

and then I shifted to quarterly in high school until I graduated high school. I'm so fascinated by the mind of a 10-year-old that thinks that this is a cool thing to do. I don't. It was some combination of playing on the computer, creating something, and sharing. I've always been a synthesizer and a sharer. As you know, I geek out on spreadsheets.

I love making something complicated, simple, and then sharing it. And so even back in those days, I think I had, and I ran a little business. I'll also say that I loved playing business when I was a kid. So people had to pay like $5 a year for this subscription and that covered postage. Wait, so this was actually not, this was a legit business. I think that, you know, it started free, but then I, once color, xeroxing and printing, I mean, I'm sure it was out, but once that became accessible, I wanted a full four color spread.

It was printed on 11 by 17 and folded. And wanted a full four-color spread. It was printed on 11 by 17 and folded. And then, so there were production costs. Right, exactly. Especially like color printing method. Every page was like, it costs you real money. Yeah, exactly. And I would have an assembly operation in my living room and people, my family and extended family would comment that they looked forward to this every month. And it was how they kept in touch with what was going on. So what was your distribution at its peak? By mail. Oh, my distribution, maybe 50 at its peak, 50 households. That's pretty solid. Yeah. So that was kind of my blog before I ever had a blog. And then I studied journalism. I was eventually the editor-in-chief of my high school paper in Palo Alto.

And then when I got to UCLA, I joined the Daily Bruin, and I got so burnt out on it. And I hated having these deadlines. I hated that they would say, we don't care that you have a final. I was a news reporter. Front page, it's due in two days. And so I quit, and I thought never to return to journalism again and so it was kind of funny when five years later I became aware of blogging because I could finally resuscitate this right long it's like citizen journalism hobby yeah I and I want to go there but but I don't

want to leave Palo Alto behind yet because I'm curious about something you grew up in Palo Alto when you were 10 like around when was this? The sort of late 80s-ish? So 10 was San Francisco. Yeah, I'm trying to remember. I think we moved 1997. Okay. And I was in seventh grade. All right.

So you're in Palo Alto in like the late 90s, which is a really interesting time to be there. Tell me just a little bit about sort of what it's like to be there. It was wild. I mean, one of my good friends, her dad co-founded Sequoia Ventures. I mean, my mom was, she's still, 20 years later, the Stanford landscape architect. Just the kids that I grew up with were very, from very interesting parents and families. And the pressure was also very intense. And so, but I enjoyed it. By the time I got to college, it felt like college was easy compared to growing up in Palo Alto. Right. And for those who don't know, Palo Alto is sort of like the epicenter of what we now know as Silicon Valley. It's where so many of the biggest names in technology came out of these days. But it's also,

from the outside looking in, a lot has been written about the culture and the ethos of the town and how it is fiercely, fiercely competitive and comparative. Yes. And that, you know, it's, you know, if you're priced out, if you don't have a $10 million home or it's like it's so, so it's always, I've never known somebody who actually kind of like grew up, like spent a part of their formative years there. So that's why I'm curious. Yeah, it's not unlike New York where we were paying so much money to live in a kind of box, Eichler place. And, you know, no complaints. I really loved growing up there. experiencing these cycles of burnout starting in high school, of trying to get the right grades and do the right extracurriculars

and be a straight-A student at life. Was that coming from the inside out, or do you feel like that was coming from the outside in? Both, probably both, because I also have that personality type. I've had to work really hard not to just the need to please and to do well, but I also was ambitious. And I write about now helping people move beyond burnout because I then worked at a startup and then Google, and it was repeating the same pattern.

So it was not until I kind of stepped off that ladder when I was 27, around the time that we first met in person at least, that I was able to pull myself out of that cycle. Right. You end up taking this sort of maniacal drive. It's been part from the inside out and part installed from the culture you grew up in and going through these series, like hyper intensive things where you're completely and utterly all in and then burning out, it sounds like repeatedly. You were at one point, you were at Google. I think we first met back when you were at Google, right? Yeah. And I had read Career Renegade before we ever met in person.

And then I think I was at Google from 2006 to 2011. And the company grew from 6,000 to 36,000 in that window. And I remember meeting you in person for the first time at the Soho House in New York with cappuccino. And I just thought, this is it. This is my happy place. And if I'm sitting here with, I call him JF, if I'm sitting here with JF, having coffee in New York, I've done something right, and I've got to figure out more of it. And I'm probably, I was probably thinking, I'm like, wow, she works at Google. I wonder what that's like. Grass is always greener.

It's so interesting, though, because we all have, I've been thinking about and talking about this more probably lately. I'm curious what your thoughts are on it. You know, I think we all, there's something in us which tends to be wired to constantly compare ourselves to other people and to judge our success based on, you know, what we perceive to be other people's successes. Do you explore that at all? Is that part of your inner conversation? Definitely. By the time I was 24 when I first became a manager at Google, and by 25, 26, I had bought a condo, I had a car, I had the job. I had become a manager. And basically, all that was missing was insert husband and 2.5 kits because I had been operating on this sort of American dream checklist that I felt I was just programmed to pursue.

And then when my first book was coming out, and this was about 2011, I just stopped for a minute and I said, this isn't right. This isn't it. I had Sheryl Sandberg ran the part of the company that I was in for a few years while I was there. And I remember looking to her, we all admired her so much. But as I looked to her role, I thought to myself, I actually don't want to be some high level manager someday. I do not want to be in middle management. It was really stressful to me. I enjoyed the coaching aspect, but not the other parts of the job. And I realized that while I, as a kid, like I said, I loved playing business. But in this moment, I realized I don't want to be CEO of some giant company someday. That's not my

aspiration. And that was starting to be the first moments that I said there can be a different path. Yeah, well, especially again, reflecting on the sort of the culture you grew up in, it's like considered the idea of a different path, you know, it's sort of like, there's it was a famous line in the network where like who was it, Justin Trimilli playing Sean Parker, it was like, you know, like, do you want to start a laundromat or do you want to, you know, like build a company, the rules of the world and totally butchering the line.

But it's the idea of creating something that's smaller, more intimate, more hands-on is still so devalued by those in quote legit business that especially when you're working in this company, where, you know, like, so many people aspire, yes, to have your job or to have a role in this, they perceive this as like, this is the pinnacle of where you could work like this is where you go here. And you know, this is this is making it. Oh, yeah. And that was programmed into me starting my first day, all the way through those five

and a half years. My family was always so proud to say that I worked at Google. And peep friends, when I would say it at a bar, a party, or a networking event, would want to know all about it. And then I was running the Authors at Google program toward the end. And so my heroes, my author superheroes, those are my superheroes in life, would reach out to me, but only for Google. And I was just so worried that if I left, I'm going to fade into internet nothingness. I will not be interesting,

nor will anyone like you want to be my friend. And that was really scary to me. And I felt ridiculous for not being happy there. What's underneath that? I'm curious. Take me deeper into that. I think one of my values is being as helpful as possible to as many people as possible. And when I wrote Life After College, it was to fulfill that aim. That was my first book.

But almost right after it came out, I had this urge to move on. And I don't know what's behind. I love books. And I don't know, it's really weird to say this, but I love authors. I live for conversations with smart, interesting, thoughtful people who love grappling with big, complex ideas. And for some reason, I just had this urge to do something that fellow authors would really respect and be interested in. And so even when Life After College came out, I created this big book marketing spreadsheet, and that helped me get to know other authors.

And that was just this really nice byproduct of it. That was quite legendary. But I guess my deeper curiosity was, you mentioned that you were concerned that when you no longer had the association with Google, that all these people who all of a sudden were your friends and wanted to like hang out with you, that that would all fall away. That I think is my bigger curiosity of what's underneath that. I guess I just, you know, even for me to prop up my blog, I set up the website in 2005 and the blog 2007. It felt sort of weird to raise my hand and say, I have something to say. I have something interesting or unique. I felt really weird about positioning myself as any kind of expert. And then as I was thinking about leaving

Google, here was this thing that had given me so much of that social proof, if you will, that just by waving the Google flag, people wanted to talk to me and made shortcuts that were helpful. And I was just afraid that without that, who am I? And actually, this sparked a huge crisis of confidence after I left the company that's now the foundation of Pivot, of how to work my way out of it. Because I just felt like I became the girl who left Google. So I was still hanging my hat on Google's hook, even though I had tried to move away from it. And I had no clue what was ahead. And I just, I value big, original ideas,

to the extent that it's possible. I know it's hard for anything to be original these days. And I was just really felt aimless and lost and the most unhappy, just about that I've ever been in my life, when I didn't have that sense of purpose and clarity. And that was kind of triggered by you leaving. Two years later, the first year after I left, I was so hopped up on adrenaline of don't fail. Don't screw this up. Don't prove to everybody that they were right.

You know, I joke that leaving Google was like breaking up with Brad Pitt. You know, you really think you can do better than Google? Why on earth would you leave and try and make it on your own and move to New York, the most expensive city in the country or at that time? And so the first year was just trying everything I was seeing everybody else doing online and how to run a business. And I just sort of scrappily scraped together a living. And I was doing one-on-one coaching and career development programs at Google. So my pivot was doing those still just on my own. But then when that adrenaline

wore off and it was really time to, in your words, like lead a revolution, have something that I stood for. And what was I looking to? That's when I started pausing my coaching. You know, I was getting less speaking, and bank accounts started dwindling right down to zero. And now I had to figure this out. And it got to the point at the end of 2013, early 2014, where I didn't have the money to pay my rent in two weeks. And it was looking likely that I would have to leave New York and or get a job, if not both. And both felt soul crushing to me. So where do you go from there? Well, then I would just, I struggled for so long and this question of what's next.

And I came to one of two conclusions. There's either something wrong with me because I keep going through this question of what's next every few years and I'm destined to be unhappy the rest of my life and I really am that entitled millennial that everybody talks smack about or this is I'm not alone in this and this feeling is happening more frequently now to your question of where do I go in that moment of not paying the rent, that's, I found this grip inside. In that moment, I got so low and in my determination not to quit my business, I just said to myself, I have to figure this out. I have two weeks. What am I doing wrong here? And in that moment, I realized that I had been so focused on what wasn't working, what I didn't know, what I didn't have, that I was spinning around completely aimlessly. So in that moment, I said to myself, what on earth? Why have I not acknowledged everything that is already working that got me to this point?

Why am I so focused on what I don't have? It's the good old negativity bias. Yeah. And you write in your book about strength-based everything, strength-based planning and positive psychology. And so only when I looked at how I had already been earning income, I called all my past coaching clients. I asked them what I could create for them and with them.

I then rolled out a program and I started to climb my way back out of that. Yeah. It's so easy to get caught in that place because especially, you know, we start to play the woe is me meets I'm not competent meets I've been faking it the whole time. And now it's finally just hitting that I actually have been an imposter the whole time. Yes. Oh my gosh. I asked myself over and over, am I being delusional? Yeah. And I meant it in all seriousness. I really wanted to know if I was being delusional to think that I was cut out to do this on my own.

I remember a couple of years back, I sat down with Jerry Colonna, who's this awesome coach for mostly VC-backed founders. And I asked him, I was like, what makes you want to work with all of these people? And he's a former venture capitalist and just this amazingly soulful Buddhist guy. And his answer was something like, I love working with delusionally optimistic people.

That's awesome. Because to a certain extent, anyone who starts something, the odds are so much against any of us succeeding that on the one hand, you need a certain amount of rationality behind what you're doing. But on the other hand, I once saw research that asked a whole bunch of business people, successful business people down the road after they had always, you know, they've been successful for a while. Had you known how hard it would be, had you known what it would take from the beginning,

would you have done it? And the majority said no. Wow. So it's almost like there needs to be, there's this sweet, there's like a dynamic balance. There's like a sweet spot between sort of like delusion and rationality where you're constantly kind of dancing between them. You know, you've got to be,

you've got to believe that what everybody else says is impossible is possible. And at the same time, you've got to, you know, be willing to own the data as it comes in. Yes, yes. And that's, I mean, one of the hardest questions that I've, I'm curious how you answer this too, especially with what you write about and explore these days. The hardest questions I've been asked over and over and over is, how do you know when it's time to walk away? Or pivot? Or instead of saying, well, there's actually a lot that's right here, but the world has now shown me that you have to kind of shift a little bit. You have to adjust course rather than, no, actually the world is now

telling me it's time to shut it down, walk away and do something else. I know. It's so hard. I share, of course, lots of tactical things in the book, but ultimately I think this comes down to gut instinct. And that's where meditation and mindfulness practices and surrender, which you talk about in How to Live a Good Life, which I think there comes a moment where I had to turn it over to something bigger than myself. And I did not grow up a religious person at all. And if anything, it's almost cliche to say this, but if anything, in that moment, I just was like, I give up. I had stopped trying to be happy every day.

I started just praying and asking for equanimity. Please just let me wake up and just be okay. I give up on happiness. Fine. Okay. No problem. But give me some sense of peace. I felt too sensitive for my own life.

So that forced me to just say, I surrender this. And when I got really quiet, and I had been meditating that whole year. So I sometimes joke like, no amount of gratitude lists, meditation and yoga classes were doing the trick. I had done all the things and I still was in this position. So sometimes you're doing all the things and you still don't have the answer. But when I really tapped into my gut, my instinct, my intuition said, it's not time yet. This is a doorway for an even bigger mission on the other side. And so I think there are practical ways to

tell. I mean, you know, even in my case, why did my bank account get to zero? Look, was there a way I could have pivoted before that happened? You know. That's where I started to question things too. How long, how many more accounts do I drain before I do something differently? But every time I would calculate the ROI on my time of going and getting a full-time job, it was nuts. I could spend a fraction of that time just trying to get more coaching clients and be fine. And when I was afraid to quit Google,

I would often, my fear was, what if I end up in a van down by the river? And I would make myself also then ask, what if I earn twice as much in half the time? The Apple Watch Series 10 is here. It has the biggest display ever. It's also the thinnest Apple Watch ever, making it even more comfortable on your wrist,

whether you're running, swimming, or sleeping. And it's the fastest charging Apple Watch ever, making it even more comfortable on your wrist, whether you're running, swimming, or sleeping. And it's the fastest charging Apple Watch, getting you eight hours of charge in just 15 minutes. The Apple Watch Series 10, available for the first time in glossy jet black aluminum. Compared to previous generations, iPhone XS or later required, charge time and actual results will vary. And so in this moment where I really questioned, should I go get a job? Should I go back to Google? Should I ask them if I can work part time? But I thought, I can earn twice as much in half the time. If I'm going to be working 25 hours a week, and I put that focus into pulling myself out of

this business ditch, I'll fix it. I'll figure it out. And somehow you had the fortitude to say this is the time. But at that moment, because it's not like you were slacking off. No. Yeah. I really wasn't trying. We've known each other for a chunk of years now, and you remain one of the most maniacally organized, methodical, action-oriented people that I've ever met. I mean, your brain works in spreadsheets and action steps in a way that almost nobody else I know works. My brain absolutely doesn't work that way. So I can't imagine it's because you weren't

doing all these things. So it had to have been a matter of in that moment, you decided to do things differently. So how, like, what was the different? First, thank you for saying that. That's really sweet. I, integrity is a huge value of mine. So it has never felt right to run programs or do things where I don't feel 100% authentic and sort of grounded and it's truthful. So I've never been the type, I would rather let my bank account get to zero, the market programs I don't believe in, or run things where I didn't feel authentic running them. For example, I had done a build your business course because a lot of solopreneurs would come to me and want to quit their job and start their own business. But who the hell am I to run,

build your business when I'm sitting here dwindling to zero. So one thing I did differently, I just first of all said no to all this stuff that was making me feel gross. And because I'd been trying to do what everyone else was doing online, and that wasn't working for me. I would create, I loved creating programs. I loved teaching them. But when it came to marketing them, I would grind to a halt at my to-do list. And that was a red flag. The thing that I started doing differently was really analyzing what had worked to get me to this point, my book, my speaking, my coaching. And instead of trying to, in the book and pivot terms, I say turn so sharp as I had been doing, I went back a few steps and I said, I'm willing to do things that are not my longer term dream, but to build from where I already am. Instead of trying to come up with

a new direction from scratch. And so even just by going back to my previous coaching clients, that was an example of not trying to get new clients from scratch, but saying, this has already worked. In fact, all of you have already come to me before. So let's see how we can work together. And even creating that program alone bought me three more months of runway. Okay. And then, you know, I get this way. If I'm really stressed out

by something, whether it's book marketing or life after college, I left before my friends, I left school early. I'm determined not to have other people ideally have to suffer as much as I did. If I can somehow take my confusion and my inefficiency and my suffering and organize it somehow so that other people can have just 10% more straightforward of a process, especially around change, which can be so stressful, then I have succeeded. And so it's kind of meta, but simultaneously to pulling myself out of this mess was, I have got to fix this for all of us. And the reason the book is called Pivot is that I wanted something gender neutral and judgment neutral. Up until this point, I feel like we've called these

existential moments midlife or quarter life crisis. Those are your options. And yet I was having it every few years. And so it was really, it is really important to me to also change the language around this. And so that it's not a personal shortcoming. You're not delusional just because you've hit a plateau in your business or in your career and are ready for the next thing. That's actually a sign of success. Yeah. So it's not a crisis. No, but it feels like when we're not used to it. And also if you've got, I think the association is if you've amassed a certain amount of responsibility and bills and expenses and people are looking to you to provide some semblance of security in this moment, it feels like a know, and if you have limited financial runway, it feels like, okay, this is a crisis because I have constraints that are very real.

And so the brain says, like, red alert, red alert, red alert. Well, and your work has been so influential and a guiding light on certainty. And then you write in Good Life Project that at moments living the question gutted you. Yeah, still does sometimes. I mean, I wish I could say I was just, I've been meditating for a long time and I have a daily practice. But it's the nature of growth, you know, is that you will hit moments where you don't know what's coming next. And it's not because you're failing in the current. It's because you've sort of, you've hit a window. This is funny, when, you know, what we didn't talk about

is you also at some point became trained to be a yoga teacher. Yes. And there was, and in my distant past now, you know, I ran a yoga center in New York City and I taught for seven years and I trained hundreds of teachers. And what was always so interesting to me was that there would be a window during training where teachers would all come in and kind of be like, Oh, I'm really good. I've been practicing for years. And they're rocking and rolling.

Then about halfway through, they would fall off a cliff and realize that the body of knowledge and experience that is learnable is so much vastly larger than whatever the experience in the body of knowledge is that they currently have, that there were only one of two reactions to it. You know, once that light bulb happened, one was complete and utter devastation and paralysis, like, oh, there's so much more that I'm never going to be like anywhere close to mastering it. I'm always going to suck. I'm always going to be a newbie. So why bother? Or the other one was, oh my God, this is astonishing. I can do this my whole damn life and never run out of stuff to learn and grow into. And it was so fascinating to see who chose which path. You are the latter. But even you, who seems like I've known always as being almost like maniacally optimistic and methodical, you hit that point too where you were moving towards the other direction.

I didn't even feel like myself anymore. And I think because I had always been so clear and driven and I love working, it gives me a lot of joy. Part of the maniacalness is like the intrinsic joy I get from creating things just like you. And so when I wasn't creating, I just felt so lost. And, you know, I know all the cliches like, oh, you are not your work, you're not your job. But actually, I do feel my purpose on this earth is connected to my work. It's to serve through my work. And so I'm just going to put a stake in the ground and say it. Without it, no, I don't feel like myself.

And yeah, I don't know. I feel like the yoga teacher thing, I felt like I'd graduated kindergarten. Like once I finished teacher training, it was, if not preschool. And I wrote this book for people I call high net growth individuals. Some people optimize for money and we call them high net worth. But there's this segment of people, I'm sure like everyone who is listening to your show, who are high net growth, that the real aim is growth. And when our personal needs for growth are being met, we turn toward meaning and impact. And I call them impactors for short. And so yes, and you know, no one wants to be a starving artist. So ideally, when someone's pursuing growth, meaning and impact,

we also end up financially successful. But part of what this experience taught me and leaving Google was money is not everything and i am willing to go to zero i am willing to eat power bars i would i remember walking by restaurants in new york seeing friends inside laughing and i felt so sad like i was on the outside of the fish bowl because during this time a lot of friendships turned over as tends to happen during big life changes. And I was just so wistful, like, when can I afford to be in a restaurant again laughing with friends? And... So when could you? Yeah. So the amazing thing is by going back and doubling down on what was working,

I use the analogy of a basketball player that one foot is firmly rooted and grounded and that's in your strengths and experience and network. And then the other pivot foot can scan for opportunity. By the end of that year, this year where I didn't know how to pay the rent in January, I had tripled my income from the three years prior. It was the first year in my business. I hit six figures.

So the glorious thing was that it worked. And not just in a mindset sense, it worked financially. This pulled me out and I've been so much happier in my business since. And so the year following was still, I called it a hustle and flow was my theme. It was a lot of hustle. It was a lot, a lot, a lot of work. And then finally, I started to emerge from that darkness and feel that I had momentum on my side again. And so, it's really been in the last two years that I feel, you know, and I'm ready. I'm sure it's going to come back. But one of the things that I discovered when writing Pivot was that actually people are changing much more quickly than even I

thought. And that when we get better at this pivot process, the turns aren't so sharp. We don't get shocked by pivot points that we didn't see coming. And so my hope is this book has actually taught me how to be comfortable with uncertainty, running my own business as well, you know, is such an exercise in that. Yeah. And I, and I still agree about the, um, the frequency rate of making these, these pivots increasing. It's almost like it's a, it's a constant process, you know, rather than saying, okay, three years and now it's time to pivot three years. Now it's time to pivot and then two years. And then one year it's like, no,

you're just, I feel like I'm constantly, I mean, the name of my, like the center of my business right now is the name of the company, Good Life Project. The last word in the brand, like our registered intellectual property, has the word project in it. And it's intentional because it's a project, which almost gives me this cover to experiment and to do all these different things and try some of them. And some of them fail miserably and some of them succeed really well. But built into everything I do is just an ethos of nonstop experimentation and iteration.

And I am constantly killing stuff and constantly doing new stuff. This year is a huge year of transition for me. We're literally tearing down the business and rebuilding it almost from scratch. And I don't see it as a moment in time. I see it as a constant evolution. You said something that I want to revisit, which is you can either optimize for money or you can either optimize for meaning. Can you optimize for both at the same time in your experience?

Yes. I wrote a blog post called How to Optimize for Revenue and Joy. Commentatorial questions to me means taking two seemingly contradictory statements and combining them. We've, you know, a lot of business books now reference the improv technique of yes and, but essentially a lot of people that I speak with are afraid of making a change because they're worried about finances. So ask it as a question, how can I be financially successful and run my own business? You could get more specific. How can I earn 200 grand a year or a hundred grand a year

and run my own business and have freedom and flexibility in my schedule. And just asking the question starts to allow for more creative answers. I do think that for people who are high net growth by nature, they're willing to take a pay cut. They're willing to bootstrap a business. They're willing to make a horizontal move in service of that growth. And they're willing to take those risks, whereas other people are more either security oriented, or just straight up money oriented. And they're willing to build cat furniture in order to earn a living, you know, like or do something that just doesn't resonate on any internal level, but it makes money. And so that's not exactly who I'm

right thinking about. I guess, when I hear you say that, because this has been my experience, what I hear, here's what's filtering through to me, is my brain is saying you can't actually optimize for money and meaning simultaneously, that you're sort of constantly alternating between the two. It's like an upward spiral where you go hard into meaning and that spurs the next wave of opportunity that allows you to sort of unlock a certain amount of revenue, which then allows you a certain amount of freedom to then sort of lean back into meaning, and it creates this upward spiral. It's a real fascination of mine, because I'm constantly trying to figure out like, can I, and like what you were just saying is sort of like, it seems like there's this choosing between I mean, if you're going to bootstrap a business,

because you want complete control, and you want to just do the most meaningful thing, you're essentially optimizing for meaning and expression and alignment and hoping and praying that the money is going to come. And very often that's what then generates, you know, because it's so unusual, that can then be the thing that unlocks the revenue, which allows you to hire more people, which allows you to do more of the stuff that you actually only want to do that matters the most. But I'm suspect of the idea of being able to simultaneously optimize for both all at the same time. Maybe you can, but it's just both grow at a more moderate pace. I don't know. I totally believe you can. Maybe that's just my unfailing optimistic side. I call myself an optimistic realist because I also try and be real. Money, yeah, it doesn't grow on trees. But I actually think of it as tapping into the flow, these meridian lines of our life, and it's not easy to do. But I actually do think, like for me with Pivot for the last few years, I've been working on it, it'll be three years

from the time I first started mapping out the proposal to when it hits stands. And I have never felt more alive, more on purpose. And the money, yeah, you're right, you know, it's not there yet while I've been working behind the scenes, but it's the best shot that I've had yet. And so in a way, everything I'm doing, I actually think there is this confluence where it finally feels like they're not separate. I'm growing. I'm challenged.

I'm creating something that I hope will make a big impact and be really helpful. And it has motivated me to create all the business programs around it. Whereas before, I was not that motivated to create or launch the business programs because they didn't have meaning. Yeah, I think we're probably saying the same thing. Yeah, probably. I just always remind myself, we live in a nonlinear universe, time and space are constructs that I know in some ways. Yes, we're really sitting here on the couch, but I've seen enough wild things happen and enough serendipity and things that seem impossible that I really just try and eliminate the if-then

thinking of if I'm working on something I can't figure out, then money has to go on hold. Yeah. I also like the way that you framed the question when I asked you originally, because my question to you was, can you? And you came back to me and you're like, well, don't ask, can you? Ask, how can I? Which it primes your brain to just function in a completely different way. Can I is like your brain is just looking for a yes or no answer. When you say, how can I, your brain assumes the answer is yes, and then starts looking for mechanisms and pathways. And that happens in the background, just on autopilot. Like, you know, it's just running.

Now you've actually planted the question. And it's like, I don't know if your brain works this way, but mine certainly does. I plant a question, and then I just know it's there. And the answer generally, my brain is always working on it in the background, even when I don't think it is, and I'll be walking in the woods, and I'm like, boom. It's to that, which is not to prime yourself with the yes or no question, but to assume yes and then prime yourself with the question that says how. Yes. And let your brain work on that instead of just the yes or no. I think that's powerful. Well, thank you.

My dad and I call what you just described, we call it drop the bucket. So if there's a question you don't know the answer to, we just say, oh, drop the bucket. So if there's a question you don't know the answer to, we just say, oh, drop the bucket. And the bucket will go into the little wishing well of your brain, and it'll just hang out down there until it has the answer. And the bucket always resurfaces. So you just have to ask a good question and then drop the bucket. And sometimes I'll physically drop a bucket by putting a blank piece of paper on the back of my front door. I've even used idea paint to paint the back of my front door. Or for mapping used idea paint to paint the back of my front door or for mapping out the book, I did post-its and I stuck blank post-its, color-coded of course, on the whole back of my front door. And every time I was leaving the house, I would jot down ideas.

So you can drop the bucket by writing, how can I optimize for revenue and joy on the back of your front door? And every time you leave the house, add ideas. Yeah. So it's not a fixed thing. It becomes more fun. Yeah, I love that. I have to turn the tables on you. Mayday, mayday. We've been compromised. The pilot's a hitman.

I knew you were going to be fun. On January 24th. Tell me how to fly this thing. Mark Wahlberg. You know what the difference between me and you is? You're going to die. Don't shoot him. We need him.

Y'all need a pilot. Flight Risk. The Apple Watch Series 10 is here. It has the biggest display ever. It's also the thinnest Apple Watch ever, making it even more comfortable on your wrist, whether you're running, swimming, or sleeping. And it's the fastest-charging Apple Watch,

getting you 8 hours of charge in just 15 minutes. The Apple Watch Series 10. Available for hours of charge in just 15 minutes. The Apple Watch Series X. Available for the first time in glossy jet black aluminum. Compared to previous generations, iPhone XS or later required. Charge time and actual results will vary. For a second. Because we're talking about... It's like we're two people who like to ask questions.

No, but Jay, I can't, especially I think for everyone who listens to good life and to your podcast and read your work, you have pivoted your content. Like I just have to know, since we were just talking about me trying to answer the question, what's next as a self-employed person and a person who values ideas. Do you feel like you've gotten better from, let's say, figuring out career renegade to uncertainty to now how to live a good life? How do you land on that next idea? And do you feel like your process has gotten any smoother? I land on, so the ideas are generally just personal questions for me it's deep fascinations or personal questions or master requests and that's what drives me and then the hope that in some way

there'll be an intersection between that and something that will a way to express what i discover that will be of service to other people on a level that's valuable enough so that i can build something around it that allows it to be my living. Do you care if it connects to the previous thing? No. No? Mm-mm. Fascinating.

Yeah, I'll latch onto something for a couple of years. I mean, everything has for me. And the further I get into life, the more dots that I have to look back at and see how they all connect. And I'm now actually, literally just in the last few years, have started to see a lot more about how they connect. And I'm now actually, literally just in the last few years have started to see a lot more about how they connect. But yeah, there's for me, so there's, if you look at actually the three books that you just mentioned, there's an evolution, you know, Career Renegade was basically asking the question, if there's something that you're really curious about doing, and there's no clear conventional path to doing it, is there an unconventional way to maybe do it? And that was a question I had, you know, because I had very often the things that I am interested in, there's no clear conventional path to doing it. And then uncertainty was all about, you know, if you're wired so that

you have to create, and that process at the highest level requires living in a place of sustained and deep uncertainty to get the best, coolest, most innovative outcomes. And for most people that kills you. And for me, that really caused a lot of pain. Is there some way to train yourself to be okay in that space? Or are there are you either wired for it or you're not? And if there is a way to train, what's the how, how is it? And in fact, so that was a very personal question. And so to a certain extent, there is a broadening. So it started with specifically with career. It broadened out to creative work on the planet.

And now the next iteration for me is really, you know, the bigger question about like, how do you spend your time on the planet in a way which is good? So there is a common thread. But yeah, there's no intention to link them as I create stuff. It's really just following something that lights me up. I do think it's fun to reverse engineer past pivots. And anyone listening can do that. And what I find so empowering about that is being able to see, oh, I've done this before.

I have shifted. I have pivoted. And there was something in common. I wasn't starting from scratch. To me, that's very empowering. And actually, what I'm saying in I have pivoted. And there was something in common. I wasn't starting from scratch. To me, that's very empowering. And actually, what I'm saying in pivot is nothing new. I hope I give new tactics, but I'm not saying anything new. I'm saying you already have the answer.

You've already done this. Just let's put some language to it. But what you're doing, I think, is really important. And so maybe we'll just spend a little bit more time just more granularly on what you did. Because our brains work similarly in one way in that we're both really into pattern recognition. You know, taking big complex systems and distilling it into really simple frameworks. When it comes to actually creating processes around those, your brain goes to a place that mine is not even capable of touching.

So when you decided to actually take what you had figured out and turn it and distill it into a framework, and this essentially became a really straightforward model that helps people navigate this thing, which is not a crisis, but which is going to be an increasingly present part of every person's life. Yes. Well, you mentioned guiding questions and mine was, how do we more efficiently answer the question, what's next? And I had this basketball player thing that was the reason that I got out of my pivot, which was the one foot grounded and the other one scanning for opportunity. And then the third stage in the pivot method is pilot. And at first I thought, how does that connect to basketball? Because that was more for my Silicon Valley experience and at Google, which was all about be scrappy, launch and iterate, experiment.

I did 10% projects that later became my full-time role. Well, piloting is like passing the ball around the court. And then you can repeat plant, scan, pilot, plant, scan, pilot as many times as you need over months or even years before the fourth stage, which is launch. And that's when you have to kind of pull the trigger on something, quitting the job, starting the business. And so I kind of had this feeling of what had worked for me. And I'd been coaching people. I've been doing career coaching since 2008. So it's not like, oh, I had never worked with anyone. I had never helped anyone out of a pickle. In fact, I was always very helpful for my client. So it was very weird that I couldn't do this for myself.

And that's when I started to, I had a process that was many more stages, but there's this agile development quote I love. Each time you repeat a task, take one step toward automating it. And I thought, okay, how can I help automate this? You know, what's next? And so then I got the hypothesis and I teach this in the book too, the hypothesis around the pivot method. And it's these four stages. And so then I got the hypothesis. And I teach this in the book too, the hypothesis around the pivot method. And it's these four stages. And so then I tried to map it. And I did many, many interviews.

And I looked at people. And just the more that I could see through the lens of this model, the more I saw that it works. And it worked for me. And I wanted to make sure it didn't just work for me, but everybody else. And interestingly, the fourth stage used to be called leap. And then my editor and I, and she flagged it. We realized there's nothing leapy about this. I'm actually not saying, I used to say, take great leaps.

You know, my dad and I had a mantra like, oh, you can't cross the Grand Canyon in two small leaps. And we hear a lot about leaps of faith. And yes, certainly I think there are those moments in life, and they're very exhilarating. But I don't have that kind of constitution. I don't have that kind of risk tolerance. I don't have a second person in my household that's paying any bills. And so I wanted something that was also for people who are slightly more risk averse. And that's where we realized that the plant scan pilot, whether you're stuck on a

business plan, a project or a career move, helps reduce risk so that by the time you're launching, it's the remaining 10 to 20%, not some big shot in the dark. So it's more just take the next step rather than take a big honking leap into the abyss. Yeah, exactly. And I give a diagram in the book that I call the riskometer, which is that you're either in your comfort zone, If you've really hit a plateau and you haven't been answering the call, you kind of fall into your stagnation zone. The sweet spot for change is in the stretch zone. But when we try and turn too sharply, that puts us in our panic zone. And a lot of people, especially around career change and when money is in question, they feel panicked to the point of paralysis. They don't do anything or they're scanning for opportunities without being anchored in their strengths and what's already working. And so both in this panic zone is nothing's happening. And it's where I was ending up. And it's very hard

to think creatively from a constrained place of total panic and fear. And so the key here is take smaller steps, run smaller experiments, exactly as you talked about with Good Life Project, that even all the different streams that you run in your business, podcast, camp, the book, you know, everything is an experiment. And so no one has the pressure to be the one, the next big thing. And that was one of the mistakes that I made was waiting for that. Yeah. Although, I have to tell you, there's the upside to running constant experiments is that you get to distribute the load, the responsibility, the burden, the risk. At the same time,

when the experiments eventually start to lead you to having a deeper interest in one specific thing, and you start to develop a yearning to just go deep into that one and let everything else go, because you really just want to spend all your energy, not for life necessarily, but for like a solid chunk of time that causes its own other frustration. Because you've built a life and a living around diversified things. And yeah, and to a certain extent, that allows you to constantly experiment and scan and learn and grow. There comes a time where a lot of that experimentation starts to give you enough information for, not for everybody, but for certain people where it's like, at least for now, on hold or on hiatus for so many of those other things that were active parts of your contribution ecosystem before this. And that has its own agita attached to it. Well, that's why I asked you the question if you felt any impulse to have to connect your work. And I think something you talk about is the power of story.

So I think when that happens, I think of it like pilots and experiments are kind of, there's a bunch of racehorses at a starting gate, like we're at the Kentucky Derby, and we don't know which one's going to pull ahead. But what you're saying is eventually one does. And for me, certainly pivot, I've worked, I've poured three years into this. That's a huge, it's a risk because I don't know. I mean, I'll say I've enjoyed poured three years into this. That's a huge, it's a risk because I don't know. I mean, I'll say I've enjoyed every moment of it. So there's also enjoying the process here, but one, that's a big risk. And then two, kind of what you're describing, I call it project-based purpose that not everyone has a feeling of I'm on this planet for this reason, but for the next

few years, they have a project-based purpose. And I do think that even all those other experiments are not for naught. Sometimes, for example, in your business, you were doing good life video, and then you kind of pivoted it to a podcast. So the things can shift as the pilots inform the greater umbrella and the greater mission. But I think they have more in common than it feels. But yes, I do think there's adjective. I think it's actually really hard. I did a podcast for my show called Opt Out. And it got the most response almost of any of my shows because so often pivoting involves saying no to something

and usually something good. It's usually not something we totally hate, and that's what makes it challenging. It's saying no to something that's kind of working or worked so far. And then it's really hard if it, you know, and it's hard for me, you know, in my business, I felt like, am I biting the hand that feeds me by rejecting, let's say, life after college? And it's hard to know, you you know am i just killing the thing that got me here and is that a huge mistake yeah i it's a it's a constant exploration but i know i'm feeling the call a lot more to go narrow and deep and that's what a lot of is happening behind when you say

narrow and deep what do you mean to simplify and focus on a smaller number of things and put more energy into those. And that's a lot of what's happening behind the scenes now. Do you think we get better at spotting when to do that? I think the answer is yes and no. If you develop an awareness practice, over time I do think we get better at it because we develop the habit of zooming the lens out and asking, what's really happening here?

If you do nothing to develop that sense of awareness, I think you go through your entire life and never really pick up on what's going on. So, you know, and I've, God knows there's, you know, I'm still in what I would consider the very early days of my practice, but I do think it's probably helped me just more consistently pull out a little bit and kind of ask what's really happening here and what really matters and what doesn't really matter. You brought up your dad a number of times. Yeah. Tell me about him. He's a big creative collaborator. He edits my books many, many times. And he writes essays about evolution and how we kind of go back and forth about how evolutionary theory relates to pivoting.

And so it's just he's a great thought partner. We used to take my dog for walks and read the New York Times and talk about everything under the sun. And so I've learned a lot from him. He's an architect, but also a painter, songwriter, total creative. And then my mom has the really analytical, logical, they both have that, but it's just interesting. My mom's been at Stanford 20 years. My dad's the more wily, creative, entrepreneurial type. And so's been at Stanford 20 years. My dad's the more widely creative entrepreneurial type. And so I've tried to integrate both. Yeah, interesting. I kind of had that, but it's reversed.

Interesting. My dad ran a research lab for decades and decades and decades. And my mom was always much more of the artist. So I want to come full circle, I think. As we're hanging out here on my couch, it's kind of fun. The best. We're hanging out at a moment where your book is just out, and you're stepping fully into this new thing

and a whole new level. What's your greatest hope for the work that you've done with this? My greatest hope is that it's insanely helpful, that people read the book and they feel relieved, and that's an inner feeling, and then it works, that they make changes and stop taking pivots so personally and instead are just empowered to embrace the chaos and

uncertainty and fear and insecurity, all things that I know you embrace as well, and embrace those things and move forward. And so if that works, I think of myself like a book doctor, come to me with what ails you and I'll prescribe you a book. And I would love for pivot to be the book that people prescribe to their friends when their friends say, I'm bored or I'm stuck or I don't know what's next. And to being in the eye of the launch storm, my biggest mantra is just be a graceful messenger. I really feel success. I don't know. I feel like books take on a personality of their own and a dharma, a path of their own once they're into the world. I'm doing everything I can to help that be successful. And on some level, I have no control over any of the numbers or

metrics. And so my intention and prayer, if you can call it that, in my meditations is usually something along the lines of show me the way, put me to work. Like I'm yours, world, universe, divine flow, super consciousness. I'm yours. Put me to work. Show me the way. Show me what's next. And that's how I hope to go through this, which is a way of living at the edge of uncertainty. Because I'm also saying I have no clue what's going to happen. I feel that, you know, publishing a book is like buying a serendipity lottery ticket, or this other analogy that came to

me of like climbing a roller coaster, and it's kind of really nerve wracking. And I have no idea how this descent is going to go. I know it will be fun, but I don't know what's on the other side. And so to just be in that space and co-create from here with wherever this work is meant to go. So you go from developing a fierce methodology to total surrender? Yes. And that's the holding the paradox of hustle and flow. Name of this is good life project. I'm going to offer that term. Awesome.

What comes up? For me, living a good life is, I don't know who said the quote to serve is to live. That's how I feel. I know it may sound cheesy, but for me, living a good life is being as helpful as possible to as many people as possible and doing it with a sense of equanimity and grace and to, we talked about flow, but to lean into the flow of my life and not try and resist it. And what that probably means for me in practical terms is continue to embrace what seems like the dark side, confusion, fear, insecurity, that I want to become their cheerleader for those things only because I have

struggled with it so much. So the good life is welcoming and embracing all of it. The highs, the lows, the creation, the retreat, and ultimately in service of other people. Thank you. Thanks so much for having me and to everyone for listening. Hey, we love sharing real unscripted conversations and ideas that matter. And if you enjoy that too, and if you enjoy what we're up to, I'd be so grateful if you would take just a few seconds and rate and review the podcast. It really helps us get the word out. You can actually do that now right from

the podcast app on your phone. If you have an iPhone, you just click on the reviews tab and take a few seconds and jam over there. And if you haven't yet subscribed while you're there, then make sure you hit the subscribe button while you're at it. And then you'll be sure to never miss out on any of our incredible guests or conversations or riffs. And for those of you, our awesome community, who are on other platforms, any love that you might be able to offer sharing our message would just be so appreciated.

Until next time, this is Jonathan Fields signing off for Good Life Project. The Apple Watch Series 10 is here. It has the biggest display ever. It's also the thinnest Apple Watch ever, making it even more comfortable on your wrist, whether you're running, swimming, or sleeping. And it's the fastest-charging Apple Watch, getting you 8 hours of charge in just 15 minutes.

The Apple Watch Series 10. Available for the first time in glossy jet black aluminum. Compared to previous generations, iPhone Xs are later required. Charge time and actual results will vary. Mayday, mayday, we've been compromised. The pilot's a hitman. I knew you were going to be fun. On January 24th. Tell me how to fly this thing.

Mark Wahlberg. You know what the difference between me and you is? You're gonna die. Don't shoot him! We need him! Y'all need a pilot? Flight Risk.