Jenny Blake on Saying "No" to Something Good, Free Time and Pivot | The Pathless Path Podcast

[00:59] Paul: Welcome to The Pathless Path. I'm Paul Millerd, and in this podcast, we examine the invisible scripts that run our lives and dare to imagine new stories for work and life. Today I'm talking with Jenny Blake. So excited for this conversation. We just finished recording for her podcast. I think we're both people that get a lot of energy out of conversation, so we're crazy enough to do two podcast back to back.

Uh, Jenny is the author of 3 books, uh, Life After College, Pivot, and Free Time. Uh, she runs what she calls a heart-centered business. Resonates so deeply with me. I love that. And one of her goals, her core goal, is helping people come alive through the pursuit of big ideas. There's so many overlap on our ideas, and I'm so pumped we're diving into each other's work I am so excited to have this conversation today.

Welcome to the podcast, Jenny.

[01:54] Jenny Blake: Thank you, Paul. Me too. I'm so happy to be here. I also was underlining and hearting so many things in your beautiful book that I felt like, how are we not friends until now? And then secretly, that's why I even have a podcast at all. I figure if we're going to have a conversation, why don't we just hit record, publish it anyway?

So you have the same logic there too. I love it.

[02:19] Paul: The question— yeah, so the question I always start with are, what are the stories and scripts you grew up with around what you were supposed to be doing as an adult to be seen as a good person in society?

[02:31] Jenny Blake: It's so interesting because I grokked a lot of these scripts just observing the adults around me. My parents were pretty encouraging to follow my interests. My mom did have certain rules, like if we started a sports team, we could not quit halfway through the season. So there was a strong ethic of not quitting things, that's for sure. I was always doing little creative projects at home, but I was also very centered around money from a young age. I could see that the fights that my parents did have were often around money, and I saw how hard my parents were working full-time to provide money for for my brother and I, like to pay for our lives.

And so even at 8 years old, I started saving birthday money. Like, you know, talk about the marshmallow test, just like who puts, when you get tiny little sums of money as an 8-year-old into a bank account instead of spending it. But I was always kind of, I think I had more of a scarcity mindset until I knew what that word even meant, of acquiring money, saving money, hanging onto money, figuring out how to get money. So I started babysitting really young. I started a family newspaper. I worked at a local newspaper when I was in high school.

Even in college, I would get paid to go to class by taking lecture notes. And so I was just always, I would say that was one of my driving scripts was getting, saving, holding onto money. And therefore what comes with that is trying to get the right grades, get into the right school, get the right job, advance quickly at that job, and don't do anything to disrupt the money cart, to put it bluntly.

[04:10] Paul: Were there any phrases that stand out? I always find people have certain money phrases, like people have said, oh, we're not the kind of people that can earn money, or we'll never have enough, we need to save our money, don't take out debt, all these things. Were there any phrases that stand out?

[04:26] Jenny Blake: One that I'll never forget, my mom said to me, you should always know how to support yourself. It was really serious. It was like, you should never be in a position where you're reliant. Now I'm filling it. She just said it really simply and bluntly. But I think growing up as a young woman, it was like her generation was one of the earlier ones where in her profession, landscape architecture, women were even in the office at all.

And so I grew up very convinced that I never wanted to stay in a relationship or a job because I couldn't afford to leave. And so I think that was also part of my obsession around money was also independence. I was very afraid of losing independence if I had to stay in a bad situation because of the money. So I've always— the entrepreneurial efforts were also redundancy plans, like always have 5 ways that I know how to make money. I even one time posted 3 completely different ads on Craigslist for HTML CSS tutoring, babysitting, and home organizing. Just to see which ones like took off.

And it turns out the HTML tutoring for small business owners like did the trick. But I was like always making sure that I had the money to make decisions in my life.

[05:42] Paul: I— this is such a deep script, especially in the US. I mean, that's what I know best. And I, I think some of these scripts make sense for previous generations. I think we were a less prosperous country. There were less opportunities for a lot less people. But it's sort of gotten baked in that, like, money is the point of life.

And I think sometimes I wonder if this was true for you. If you start thinking that way, right, then it becomes hard to look at a relationship as something other than like something that can fit into a certain way of living money-wise and work-wise. How, how did you revisit those scripts as you got older?

[06:25] Jenny Blake: Well, I had so much fear. I mean, I again resonate with so much of The Pathless Path. My loudest voice when I was thinking of leaving corporate was, what if you go broke? So I joke, I call it my inner CFO, and it was so loud and strong. And many people in my actual life reflected that value as well. Like, I think sometimes the kind of funny way the universe works is that whatever our inner critics are, there will certainly be people in our life who are even close to us who show up and say those things verbatim, almost reinforcing or stress testing.

Are you gonna listen to that fear? And then I just, at some point I thought, God, I'm spending all this energy saying, what if I fail? What if I fail? What if I go broke? Like so much obsession around losing money that I could at least add in, not that I could ever remove the fear, but I could add in, at the time it was, what if I earned twice as much in half the time? So, okay, what if I go broke?

Sure, that's not, that fear's not going anywhere. Or what if I earned twice as much in half the time? And now looking back, I think that's even a form of cognitive behavioral therapy where you do thought replacement. I didn't have that language or that, I didn't go to therapy or anything. I just, started to ask myself, why not? And another thing I'll say is that even though I always had all these little projects, I never thought of myself as entrepreneurial.

I didn't think that I was cut out to work for myself. I'd always been such a good student and a people pleaser and a rule follower that I genuinely did not think I could make it outside of that environment or even that I would be happy. Like, even my dad, who's self-employed, said, well, what about all the friends at your job, you know, or like all these social connections? And everybody had these reasons of what I would miss. But I started to just plant the seeds of possibility. And just like you, there was some point where I was willing, finally, for the first time in my life, I realized I am willing to spend every penny of my savings to try.

And I had 6 months of savings, and finally, I just, got burnt out enough and frustrated enough that I said, all right, 6 months, that's it. If I do this 6 months, I don't earn a penny, and I need to go back and get another full-time job somewhere, I will. But at least I will go to my deathbed knowing that I tried, and that I tried while I was young and I had less responsibility, relatively speaking.

[09:01] Paul: I love that so much. It's so similar to my story. I felt like I had no other option than to sort of bet on myself, but it took me so long to get there because I had models of that behavior of being self-employed or being entrepreneurial around me. Everyone was centering their life around employment. And when I left, it did trigger so, so much fear. But I did have some like small moments where I'd meet people doing different things.

And so as background for the listeners, you, you went to UCLA. You graduated in 2006, you ended up working for Google. I'm wondering, that period, the early, the 2000s, were there different influences you started to see around you that started to plant those seeds of possibility?

[09:51] Jenny Blake: Well, actually, prior to Google, I left UCLA. I had done 2 years. I was ahead in 2 majors because I also did a 4-year planning spreadsheet to a T of how efficiently I could get through school. Not how much I could learn, not how much I could enjoy it, just how fast. And I left at the start of my junior year to work at a startup in Palo Alto with one of my professors. It was a political polling company that later got acquired by YouGov.

That was my first break with what everyone else was doing because my friends all said, what are you doing? Like, these are the best years of your life. They were still partying and taking finals and having fun together. I was even in a sorority. They're living together, they're roommates, they're going on trips together. And I exited all that.

I moved home alone midway through college to work full-time. So I think a lot of people were like, what on earth are you doing? But it felt like this unbelievable opportunity. And I was the first employee at that startup, and I stayed for 2 years as it grew to 30 people. So I experienced a lot. I learned a lot.

I later went back for one semester in 2005 to graduate with my class. But I had become sort of alienated by my own doing. But like, I was now an outsider to those friend groups. I just hadn't been there. And that's when I kind of just realized, okay, I'm a little bit more on my own. I'm on my own path.

And I had to figure out adulting before the rest of my friend group, before everyone else that I knew who was my age, whether from high school or in college. And so that's actually what sparked me setting up my first website. And then on the professional side at the startup, one of my many hats was managing our AdWords accounts. So by the time I hit a plateau at the startup, once again, I felt like, is this stupid to leave? I think it's always hard. I say this in Pivot, I quote Stephen Gross, he wrote a book called The Examined Life that is so beautiful.

He says, all change involves loss. And for me, what's always been the hardest thing about change, especially when I'm choosing it, is saying no to something good. Usually it's, I mean, that's if you're lucky. Sometimes we get pivoted or we get catapulted onto a Pathless Path where we can't see what the next steps should be or could be. But for me, the hardest part is always when do I say no to something that I would otherwise should feel really privileged to have? And so it was only magnified 10, 20x working at Google where when I was starting to hear those whispers that maybe this isn't for me or forever, or the grind of so much email and meetings was just like sandpaper to my soul.

I just knew that I wasn't doing my best work when I was kind of felt trapped by all that. I felt like, what right do I have to walk away from this when so many people I know would kill to be there. And I even had a mentor who had her own coaching business on the outside that when I told her I was thinking of leaving, she said, oh, well, is there any way you can put in my resume? 'Cause I'd love to have your job. And so like, it made me really scared. Oh no, like if I leave and she even wants my job, what hope is there for me if I make the decision to go?

[13:10] Paul: I love that so much. And I think we have the tendency to tell these glorious stories like, oh, I hated my path and I, marched onto the new path, I still miss being really good at my job and being super deep in work in the consulting environment with really smart people. Now, that didn't happen continuously, and it was often out of my control. So that, that's why I like working on my own better. But I do miss that, right? I felt good about myself.

I was doing good work. My clients liked it. It was fun at certain points, and that part of me is gone. And I've had to sort of mourn the loss of that identity, the good and bad parts. And it's hard. And I think I sort of have this vision of life or this understanding of life is you sort of have to keep reinventing yourself.

If you read throughout history, all the people that seem to thrive into later age always keep blowing up their life, right? And my question is, if we're going to change more than we expect, how do I continuously blow up my life? And you got a taste of that so early. And I often think that's a blessing, going off script early, because you start looking at things different. Whereas a lot of people graduate college and they just transition into doing what everyone else is doing, and you can kind of get lost in that.

[14:38] Jenny Blake: Definitely.

[14:39] Paul: I'm wondering what were the best parts of working at Google? I imagine the first 2 years were pretty fun. I mean, like, 2006 is such a cool time to be joining Google.

[14:51] Jenny Blake: Oh, it was amazing. I was in a training role too, so I trained over 1,000 people that year. I was often their first, one of their early points of contact coming in. I was teaching people how to support the AdWords product. And so, like, just the other day, someone brought me in to do a Women at Google 16 years later, and it was someone in one of those training classes. So, I mean, that was super exciting.

I love technology just like you. I was starting a minor in computer science if I had stayed in school, but I always loved computers and building things with computers. So working within Google, which was just this incredible hub of innovation and technology, I loved it. I loved feeling like I was at the epicenter of so much innovation, like to use a cheesy Silicon Valley term. And the people were really interesting and bright. And yes, of course, it creates a really fast-paced, sometimes untenable work culture, but it was so exciting to be part of it.

And I learned so much. Like, it was the best business school. I feel like those 5 years was a business school I could never have paid for, and I got paid to go. And what's surprising, and I tell Googlers this who are thinking of leaving, you have no clue how many skills you've gotten that you're going to apply on the other side. And working within the context of Google, the bar is so high that leaving, anything I ever did or have done after has felt easy in comparison. So like, even the ways I work, the efficiency, the how I communicate, there I learned to launch and scale global programs and think in scalable terms and how do you implement things at such a vast reach that those are skills that I'm taking with me to this day.

But to your point, one thing I miss that you do get in corporate is feedback, for better and for worse. So sometimes as an entrepreneur, I'm now 12+ years in, I don't know what I'm doing wrong. I probably have blind spots other than the market will tell you by not buying your stuff or reading or whatever, listening. But I also don't know what I do well. So sometimes I don't think there's anything special to what I do or how I think until someone else or a few people give me that feedback and they say, "Oh, I've learned so much," or, "That's interesting. You should write about that or talk about that." And so I find that on both sides, it's really important having friend tours, as I call them, and people to give feedback and insight and talk things through because that part of it can feel kind of opaque.

And I can get lost in my thoughts or my own insecurities without clearly seeing what's there.

[17:33] Paul: At toward the end of working at Google, you were there for 5 years. Was it a bigger pull to want to go away from Google or was it a bigger pull to run towards that new path? Because I know you had been experimenting on the side. You were doing this book launch and you were doing a lot. But what was the bigger pull? Was it wanting to run away or running towards something that was really more powerful?

[18:02] Jenny Blake: My driving consideration was that at that time, the work I was doing could reach 33,000 Googlers. That's how big the company was. But my mission has always been one-to-many and to be as helpful as possible to as many people as possible. People. At some point, I started to feel like, again, spending probably 80/20— 80% of my time doing admin meetings and emails, and maybe 20% of my time creating programs or facilitating the things that really gave me a lot of energy, where I felt I was creating things, even in that corporate context. So at some point, I just kind of ran the numbers, and I thought, I can, I can reach X number of people here, or I can try my hand and try to reach more people on the outside.

And because my first book— I had kind of— was an early blog-to-book story. Because my first book was coming out, I also realized there was no way I could do both. So, I asked for a sabbatical. I got a 3-month leave. I genuinely didn't think— I wasn't trying to do that just so I could quit. I just needed a minute to think and to give this book launch its proper due.

And within 1 week, first of all, I didn't even It was 2 days after the sabbatical started and I was on a plane to South by Southwest to launch the book. So, I didn't give myself any break. Yes, burnout was happening, like, as, you know, as it's all happening. But I very quickly realized a week in, this is a full-time, this is a full-time thing, like, following. So, it really was a pull toward my own projects, I would say, more so than just needing to leave the aspects I didn't like.

[19:40] Paul: Did anything else emerge in that sabbatical?

[19:45] Jenny Blake: Well, let me think about that. I realized, I mean, I was having a lot of fun. I got my first coaching client, Alex Budak. He was just a guest on the Pivot Podcast and we talked about him pivoting into professorship, but I only told him now, like 10 years later. By the way, you were my first client. You gave me hope that I could make it on my own.

And like, we were very pivotal in each other's lives, but I never wanted to tell him that because I think I was afraid he would think, well, what the heck was I doing being your first client, like hiring someone who's so new to the scene? Um, but that felt really good. Like, so about halfway through the sabbatical, getting one paying client was proving, okay, I'm not earning zero. And I very quickly realized that if I spent 40 hours a week just trying to figure out how to pay the rent, I could easily do that. So I think sometimes this fear, oh no, what happens if I leave? How will I make money?

You don't realize how much bandwidth gets freed up creatively, strategically, energetically. And after this period of being a couch potato, cuz I really needed to unwind, suddenly my life, my work, I had my full creative faculties that I could put toward this very simple number, paying the rent. And all of a sudden I went from having like 20 confusing OKRs that I was responsible for every quarter and juggling and having a hard time prioritizing. And some of them I didn't even believe in to having one, pay the rent. And like, it really is not rocket science and it doesn't take 40 hours a week to figure out how to meet that minimum monthly net. And so especially I think again, what people don't realize making the transition, is how much of your life force gets unleashed that you can then apply to that one question.

And then in later years, of course, as you know, Paul, it became not just how can I earn twice as much in half the time, but now with joy and ease for the highest good of all involved. 'Cause I'm not just about, oh, how much money can I make and still be miserable? That's not interesting to me.

[21:55] Paul: Yeah, this is such an interesting point. I talk to so many people that are in jobs And they have this conception of the world that is centered around a salary and employment. And their idea is, well, I can't leave without sort of making what I'm making now. I need to replace my life. The thing is, what often happens is that people tap into this creative energy, this different sort of excitement about exploring possibility that it seems you unlocked in that sabbatical. That they then go, oh, I'm willing to just break even and it's going to make it easier.

And I'm now spending instead of 20% of my time doing the work that matters to me, I can spend 100% of my time or 50%, and you're still spending more on the things that matter to you. And playing that game can actually have more upside over time or at minimum just be worth fighting for. And I sort of went through the same thing. It was like, oh, if I can make $35,000 a year after quitting and I was making $150,000, I could do everything I wanted to do and that would buy me time to figure things out. And I often sense that making $1,000 on your own is worth $100,000 for a company. Because 1,000 on your own basically tells you, oh my gosh, I did this on my own.

I've like competed in the market and people are paying me for stuff. Is that how you felt with that first consult, first coaching client?

[23:34] Jenny Blake: For sure. And then over time I've also realized that there's a really good feeling when you spend that time to create assets. So one of the reasons that no matter how low I've ever gotten in my business, I never ultimately went back to get a job to hold me over is that I couldn't really stomach the idea of creating assets for somebody else's business. Like, I would so much rather wait it out, struggle, struggle through, but, but all my time and energy going into— again, when I say assets in my business, even creating a registration process for a new coaching client is an asset. It's something that once you create it, You don't have to create it again, and it makes everything easier and smoother and saves time. Creating a book.

I have 3 books now, 2 podcasts. Those are assets. Every podcast episode is an asset. So I've also been very disinterested, and I've been off social media for a long time, even though it built the early days of my social, my, um, entrepreneurial career, because I felt that I was not creating assets. You are, like, your tweets are really thoughtful and interesting. I had stopped doing it that way.

And so I'm not interested in just creating clutter and noise for someone else's business, but certainly not for my own. So one of the insights that I've had over the years is that every course I create, every sales page, which I call an invitation letter, it feels good to spend the time on things that can serve you and serve your future self. And so in the beginning of an entrepreneurial journey, I do think, you know, always people kind of say don't trade time for money, but you kind of have to. Like, that's how you learn. You, you talk to people, you work with them, you learn what you like, who you get energized working with. But over time you can start to realize, okay, for me, I'm always asking, well, what can I learn from this that I can share back out?

Because it kind of bugs me from a— talk about a systems perspective, but I don't like when valuable information or templates or things live in secret. Like, to me, what completes the process of something, especially something I struggle with, is being able to synthesize it and share it back out, just like you did with your decision to turn down the two-book deal with a traditional publisher. Some— it feels really good to go through something and then share about it so that other people can learn and maybe save themselves some time and anguish. So that's the other piece that I just— I'm just not interested in I'm not doing that for anyone else. And I know that if I spend enough time and effort building assets for myself, I'll be so much better off for the long term rather than just taking money to ease the pain in the short term.

[26:16] Paul: It also ties into this thing you talk about, serendipity as business strategy. So speaking of sharing all my reflections on self-publishing and that, I've had, I had the CEO of Eight Sleep reach out to me this week based on my tweets. He's like, hey, I'm thinking of writing a book, want to learn more about self-publishing. And I've had a couple other people who are like names people know. It's pretty wild how this happens. And this, this often drives me to share because it's like, one, I love sharing ideas and putting them into text and kind of crafting and challenging myself to figure things out for my own, but it's also sort of a thing that I don't get a lot of energy drain from social media.

So it's like fine for me to do this, but it does also create serendipity. What are some of the most interesting ways serendipity has emerged for you?

[27:16] Jenny Blake: Well, how are we here right now? Because in my private BFF community, we had a thread. Oh, I remember. Okay, this connects to transparency and serendipity. Somebody asked me the numbers of something about royalties, and so I actually uploaded to BFF my royalty statement, which I had never done. The full royalty statement, which publishers act like this is the most secretive document, and agents as well.

Everybody thinks somehow this should be like highly classified information. Okay, so I upload that.

[27:47] Paul: I also post the numbers. Did people say not to share this?

[27:50] Jenny Blake: Yeah, there's a really weird vibe of like, I can't remember who has said it, but it's this feeling that it's— I don't know. I don't know why it feels so classified. And someone had published— Jane Friedman has a publishing calculator so you can crunch the numbers of traditional publishing and self-publishing and we can put it in the show notes. I'll give you the link. But I laid it out. I laid out exactly what my royalties were, how much I was earning, how much— how long it would take me to earn out the advance.

but also how much I had earned through Pivot on the backend, which over the course of 6 or 7 years was $2 million. Like, pretty amazing. So even though I did go traditional for my second book and not for my third, you know, there's, there's up, there's, there's pros and cons and like I was just laying it out. And then Al wrote in the comments, oh, you might also appreciate Paul Millerd's take. And he linked to your post. So then all of a sudden I read that, I say to Al, who is this guy?

Al puts us in touch. We've now— this is our third conversation, you know, and that's, that's an example, I think, yes, of serendipity, but also generosity, which I know is a value of yours, and transparency. And I feel like part of serendipity, as I say in Pivot, is making yourself discoverable. Like Bluetooth devices, it does help if you put yourself in discoverability mode somehow, some way. And even though I don't like doing that, for me, social media feels like death by a thousand attention cuts. So I make myself discoverable with ideas or templates or conversations on my two shows, books.

Those are, you know, I like really deep, long-form type work, for better or for worse. It doesn't always serve me that I'm so stubborn about that. But if you can put yourself out there, especially in ways that are vulnerable or transparent, that I think also serves as such a beacon for the right kind of people to just attract like for you, the Eight Sleep guy, to just reach out out of nowhere. And it's my favorite thing to have these serendipitous moments occur as a result of giving first or leading that way.

[29:55] Paul: Yeah, and I think this is something that's not easy to see, right? We, we talked on your podcast about sort of what Justin Walsh calls shiny outcome syndrome. So we see other people's outcomes and we think we want that. But we often don't know what game people are playing. We don't know the messages they're sending behind the scenes. We don't know the generous acts people are making.

And you, you understand after a while, like, I've really always tried to give away so much and I share everything I'm learning and people start to trust me. I've also said continuously, if you want my book, I'll email it to you for free. I'll send you a copy in the mail for free. And I know you do this too. And it creates moments of delight, but it also taps into what Kevin Kelly has written about, about 1,000 true fans. So you don't need to be on social media because other people are gonna rave about you and talk about you, right?

Thank you for saying that. Like Al, Al, for example, is going to shout you out. Right. And you are intentional. You do have your community and those people are on social media. You do have your podcast, so you have ways of reaching people, but you don't need to be on everything, especially if you are really on this sort of like path that's true to yourself.

I sort of think there's a magic to tapping into what really matters to you. And when you do that, crazy stuff starts happening. As you've leaned more and more into your true path, I think "Free Time" is really sort of your bold proclamation of like, this is what I'm about. Have you noticed that things sort of emerge even more organically than in the past?

[31:47] Jenny Blake: Yes, and there's a couple things I wanna say to this. One, it is really important to me, especially with something as big as a book, to do the best job that I can. It doesn't even make sense to me on a podcast to say, please share this episode with a friend. Like, if it's good enough, someone can't help but share it with a friend. So I'm always trying to create from that intention. Like, I don't want any favors here.

Like, don't share it with a friend because I ask you because I wanna grow my stats. No, the episode should be so good that I don't even have to ask. You're so moved that you can't help but send it to 3, fellow business owners that you know. That's the, that's the energy that I create things with. And that's what I think is almost the meritocracy of any results that I get from my work, that my book should be good enough that when you put it down, you tell a friend or two. And then the viral coefficient, even if it's slow, is positive over time.

So word of mouth is always my favorite marketing mode. And, and that viral organic growth is really important to me. One of my favorite lines from you is that you don't have launch energy, you have long game energy. And I always try to do the best I can with the launch, especially try to have fun with it and make the most of it. But ultimately, no amount of launch energy creates longevity for something like a book or a podcast. You cannot, you cannot brute force getting people to like your work.

And if you're, you can sell, you can like brute force sell 100,000 copies of a book. but it will still be dead on arrival. Like if, if nobody, then they put it down and nobody tells a friend, it's not gonna have a long life. And so sure, you could maybe like make some lists, but I'm interested in creating an experience. Like you said, free time. The whole goal was delight.

And by the way, I did not give myself permission to talk about business building publicly for 10 years. I did it behind the scenes. I always loved doing it. I loved tinkering with systems and efficiency. And automation. But I never thought, because I had never earned 7 figures no matter how hard I tried in a year, I never thought I would— I was qualified, really.

And finally, when the pandemic hit and so much of my corporate work went away, I just said, eff it, like, I'm going in this direction. This is where my heart is. And so with free time, I had the most fun writing it. To your mantra of what work makes you come alive, I felt so so alive. And going the hybrid publishing route, I felt like for the first time in my life, I got to see my creative vision fully realized. And just like leaving Google, this was something that I wanted to know once in my life that I went all in.

I even sold a property that I owned back in California in Google's backyard to fund the project. So like, I never thought I would be one of those people sharing some dramatic story about like selling a house to, you know, to create a book, but I did do I did that and I don't regret it. I'm still in the journey of trying to see what the free time startup part of my business wants to become. But it, we're in this wild moment where I keep having like corporate doors, I'm not gonna say slam in my face, but basically I'm trying to kind of read the room. Like, what is this? It's so weird.

There's so much friction for that side where for so long, just like the comfy days of having a full-time job, I had comfy days of corporate funding a lot of my business activities where if I was getting 1 or 2 paid speeches a month, I could tinker whatever the heck I wanted on the creative side. And now I'm in this moment of a Pathless Path where I have to figure out like, how serious am I about going all in on that creative side? And so I'm still in it, you know what I mean? Just like everybody else. And the last thing I'll say, sometimes books are scary because they're inevitably just, they're a fossil the minute they hit the press. Like, it's a one moment in time and it's always an evolution.

So I think sometimes it's easy to read a book and think, oh, that person has it all figured out. And you were really clear in yours. And I try to always be in mine. I'm still learning. This is what I figured out so far. Try what works for you, ditch the rest.

But I do believe that we can build a better way together.

[36:06] Paul: Now that you're in this moment, you've shared you've lost a couple corporate clients and you're sort of in this transition, final space. Do you have a practice you come back to? Do you have any mantras that are like, okay, this is what I wake up and do this week, here's how I spend time or don't spend time?

[36:24] Jenny Blake: Well, I— again, I know, I know you talk about this a lot too. One of the things you say is that people start to write, and I'm noticing I'm having a lot of creative, authentic writing when things don't go what feels like a positive way. I'm a big fan of the Zen parable, "We'll see." So one of my mantras is, "We'll see." Like, "Oh, this feels like the sky is falling and it's the end of the world. We'll see." 12 years in, I've always followed my intuition and I'm not somebody that's gonna go chase old forms of my life or work. So I really try, I call it like when the financial tides recede, I don't go run toward the ocean trying to catch a wave that has disappeared. I try to be patient and wait and see what washes up on shore.

There's new gifts that arrive. And so if I can remind myself, don't panic, you stay calm, be patient, get curious, and all the meanwhile, there's a real sense of aliveness when there's so much. And I do support multiple family members. So when there's a sense of fear and pressure, there's also a lot of aliveness. And I start to write and think. And so I'm finding that the writing is providing a lot of catharsis because this— I have a secret project that I might launch soon that I want to be able to talk about this side of running a business.

And I think that a lot of people don't because it's kind of a smart business not to talk about things going badly because none of us wanna become a self-fulfilling prophecy, you know, or create a doom loop. Like if you start, I have a fear, oh, if I talk about losing business, people will lose confidence even subconsciously, and then even more business will be repelled in an anti-mimetic way, saying like, oh, well, let me not bet on her or hire her or join her, like she's on the downswing. And therefore, there's so many fewer people who write and speak about this part because nobody wants to like manifest even less work. But that for me now, it makes me spot an opportunity. I actually put into Spotify what to do when you lose your biggest client to see if there was any podcast episodes that come up. And there wasn't a single one, not even close.

And I just thought, great, maybe I'll record a podcast that'll be kind of a tongue-in-cheek title because I'm not, I don't know what to do. I'm not gonna tell you to just like go prospect and call your next 20 potential clients. That's not my style. It's like, what can I learn from it? And what does my business want to become? And that's what I get more, more interested in listening for and following.

[39:03] Paul: We, this reminds me of at the beginning of 2020, I was working with this company, this College Board, and they wanted me to do a training of this corporate training consulting skills stuff. And I had it all set with them and we were gonna do it virtually. And then they just come back and they're like, all right, we paid you this upfront payment. It wasn't a major amount, but they were like, you know what? Virtual training is not going to work. This is January 2020.

We're like, sorry, we can't do this project. Me and my wife were about to like travel for a couple of years and I was sort of like thinking this was going to help me. Pandemic happens. I end up getting like sick after a tooth extracted and not working for a few months. And I like basically didn't— wasn't able to do anything for several months. But in that time, like stuff started to emerge organically, basically because of the pandemic and people working from home.

It's kind of crazy when that happens. But at that point, I had sort of been cultivating a practice of not being attached to outcomes or success. And I think once you're comfortable with that, a lot of interesting things can emerge because you're sort of open instead of closed. When you're in scarcity mode, you're like, I need to make money, I need to focus on this, and you sort of miss all the clues that the universe gives you. Have you had experiences of that, of sort of clues emerging and giving you, like, pulling you in new directions? And how do you tap into that?

[40:38] Jenny Blake: I'm smiling because I treat everything as a clue. Everything, everything, everything. And of course, losing one client or one prospective client, or let's say a speaking gig doesn't come through, that's not as interesting. But the patterns are fascinating to me. And I run my business entirely off of intuition. Some people are all about the data and the goals and the projections and they're— and I'm not at all.

Like all those numbers I share in Free Time was the first time I was crunching any of it just out of my own curiosity. Whereas like my brother is really data-driven and it's all about the data and he's in real estate and real estate investing and he's a numbers guy and he's utterly shocked and, you know, borderline appalled with how I run my business. But it's the only way I know how. Which is that I just genuinely believe that, I don't know, like there, it's no one moment that's a clue or an aha. It's like, it's all clues. It's all interesting.

And right now it's so fascinating when I think when the reality stops matching up with like the good on paper, you know, perfect on paper. So that's the moment I'm in now where it's like, wait a second, this was perfect on paper, but was I enjoying it? That part of the business, if I'm being truly honest, I had started losing steam for serving clients and like the rigmarole and getting paid 4 months late. And there was a lot that was starting to annoy me. And I also had a big corporate contract with a big, well-known American retailer that they were supposed to sign at the end of January and pay me upfront for 2 years. It was almost a 6-figure contract.

They dragged out signing it and they over-negotiated. Like, I gave away too much. I always do that. And basically they were like, okay, we have legal approval now, we're gonna sign. And it was March 6th. And at the 11th hour it fell through because the world started to fall apart.

And in a minute it was like this 6-figure contract vanished. But I just couldn't help but think, but I had given away way too much. Like it was, it had already stretched beyond what felt good to me. And I had already felt this really bad energy of having— feeling like someone was extracting from me and like doubling what they wanted to get from the price that I said. And long story short, I was kind of glad that it fell through. I wasn't glad about losing that income, including every speaking gig I had booked for the next 3 years.

But it was this wake-up call of like, wait a second, you weren't— I wasn't happy with that contract either. And that's what I'm always trying to look at. Like one of my friends, Penny Pierce, she says that when it comes to relationships ending, it's both souls that are ready to move on. So even if somebody dumps you and it feels like you got broken up with, most likely your soul was ready for the next thing as well. And I'm trying to think about that in business, that even something that seems bad on paper, is it possible Aka yes, that in my soul, for my highest growth and expansion and even impact, like maybe I do need to put my full focus in a different place than I had been. And the places that I had been were because it was comfortable and profitable.

But it's not because I had so much like, I mean, I really love keynotes. I do. I really love them. But client work in general, it's like not the most soul-stirring thing. And I know it sounds very privileged to say that 'cause any work at all is good. But that's kind of what I'm thinking about now.

[44:17] Paul: Yeah, it sort of goes back to what you were saying before is I have called this self-gaslighting. It's like I shouldn't complain because I, because I have high-paying job. And I always find that interesting, especially when people are in jobs. It's like, well, if you're experiencing like this is a really bad experience, like you should just be honest about that. Like you can give your job to somebody else if you, really, like, it doesn't quite make sense. Um, and but trusting your intuition in a positive direction is really hard.

I, I have gotten a lot of wisdom from like poetry and people like David Whyte that sort of can put these experiences into words that can transcend the rational. And I mean, early on in my path I did freelancing, but then 9 months in, I decided, well, I'll just stop freelancing because I feel good headed towards this writing and other stuff. And I wouldn't have created anything I've done to this past couple of years if I hadn't taken that bet on myself. But it's so hard to explain to other people. It's like there's this energy in the future I'm aiming at, and I I can't prove to anyone, I can't tell anyone, but it like feels right. Like, how do you think about this?

[45:43] Jenny Blake: Well, just like you, when I'm not aligned with my path or even a Pathless Path, my body kicks in immediately. I'll get vertigo, I'll get sick, I'll get incredibly painful ear infections. This year it was asthma, like really intense. Woke me up several times a night where I couldn't breathe for 3 months. That was post my first COVID bout. But long story short, I really, I joke that the universe has me on a short leash because the second that I'm veering too far off, I just get yanked physically back into place.

And so not only is it, you know, not a great energy match if I go the wrong way, I kind of can't do it. Like my system shuts down. I think I'm just too sensitive. Something about it. It's just how I'm wired. And then the flip side, I've always appreciated something from Susan David, wrote a book called Emotional Agility.

And she makes this point in there that when things are going well, we're not very observant. We're just kind of coasting. Like, life is good, it's easy, and our brains, the wiring of our brains, pick up less information when things are good. So it's not that we wouldn't wanna enjoy the good times and be present for those, But what I find when I'm on my Pathless Path and things are uncertain, that's also an edge of creativity because my brain is so observant. And I did go through a grieving process where I felt like I got punched in the gut and I couldn't sleep at night. But certainly when I was walking through New York City the next days, I felt very raw and very observant.

And I had so many thoughts about the experience, and that's why it kind of fuels the writing. And so I think for those of us who do feel compelled, I've always felt like I'm a messenger. Like, I really try to channel what wants to come through me, what's in service of the broader collective, tapping into kind of collective consciousness. And because of my sensitivity, I often feel like I'm a little bit early to things. 'cause things I just can't tolerate, certain ways of being or working a little earlier than maybe the research will start to show or society catches up with. And so I think when you're in that role of being a messenger, it's like, that's what the— to answer your question the long way, of that magnet pulling me forward, I really try to follow that aliveness.

And if I can solve things for myself, that's the satisfaction I was saying of sharing it. Usually my intuition, it's like, I don't know, I'm just thinking to myself that it's, it's not even failure. Like when we need to make these shifts or pivots in our business, in our income streams, in the types of clients that we're serving, usually it's just a natural conclusion. Like we've outgrown the previous path, you know, like a snake shedding their skin or these animals that have to go find a bigger shell for themselves. That's That's really how I see it too. And I loved all the quotes you included in your book about faith along this way.

Like, I really love Outrageous Openness by Tosha Silver, but sometimes there is no answer and I just have to surrender and say like, show me the next step. And that's where I just become open to what's one clue that can move me forward.

[49:08] Paul: Yeah, talk to me about the relationship with your parents and their reaction to your path. I think this is something interesting we've shared. I think my mom said to me a couple of years ago, like, have you thought about like getting a government job? They have good health care. And I was like, what? I'm making more than I make— I would make in a government job.

I'm like, oh, geez. But what, what are some of the, like, conversations you have with them and like that? Because this is a really big thing for people on unconventional paths is they often trigger the fears and uncertainties of people around them in surprising ways.

[49:51] Jenny Blake: I have a mix of both because my dad was self-employed for 3 decades before he retired. He was an architect, and then now he's really engaged in writing, reading, guitar playing, singing, painting. He's like a complete Renaissance man. Every room of his house is dedicated to art making. And my parents got divorced when I was very young, when I was 5. My mom has had the same job for 25 years.

And so I kind of have one on each shoulder. My mom, of course, is more about security and practicality. And so even recently, as I told you offline, when this big contract fell through, one of her first reactions was, well, could you go work for them as a job? And I know she meant well by it, but there's a small part of me that I go, is it as if I haven't been doing anything the last 12 years? Like, are you not seeing like what I've built? Like I would just throw it away.

And I think maybe people think, oh, you could just put your business on hold and go get a job for a year or two. But it just feels like, it just almost just flabbergasting. Although of course there were times where I thought, do I need to go get a job? Like, I'd be crazy not to at least ask the question because I have a lot more responsibility now. And then on my dad's side, he's really, he's all about the creativity and the arts and stuff. So I think that, I don't know, I noticed that I just don't love worry energy.

And I think that friends and family, naturally worry. But one of my least favorite things to hear is, "I'm worried about you." And like, I never wanna prevent people from giving me honest feedback. Like, "You're spiraling downward. I'm worried about you. You need help or you need to make a change." I wouldn't wanna prevent that. But I also think like, I don't know, I have faith in myself and my process.

I appreciate when people can have faith alongside me. And that actually boosts me more than their worry or concern, which again, always comes from a good place. I do appreciate it. One of the things Tosha Silver writes is worrying is praying for what you don't want. And so I've learned to be not cagey about things that happen, but even with certain friends, sometimes the impulse is just to tell me what to do or how they would solve the problem, which doesn't align with my way of working. So it kind of, I, I have to be more, intentional about who I'm going to for advice or input or even just a listening ear, because it is a vulnerable place to be in, of being like in the thick of mid-pivot, the liminal space, the goo state, and not on either side of it.

[52:43] Paul: Yeah, these paths are incredibly vulnerable and I feel insecure a lot. I think similarly, I do not react well to worrying. I close off. I want to run away from those people. And I get so much more excited when I'm around people that are dreaming big. They're thinking of possibilities.

They're brainstorming ideas. Like when you tell me you lost your corporate clients, my thought was like, oh, this is great. Like, Jenny's going to have room to explore. Like, she'll probably do some really cool stuff. Like, and this is why it's so important to surround yourself by people that complement what you need. And I think being really clear about what you need.

I think I realized early on I needed people that were optimistic and appreciated what I was doing. But it's hard because oftentimes those people may not have been the people you grew up with or the people you used to be surrounded by on previous paths. So it, it can be hard on these paths. Have you had any really strong mentors or models on this path that are like your biggest fans that you go to when you know you need somebody to root for you?

[54:01] Jenny Blake: Well, I feel very grateful to have many. I have so many people who were decades ahead of me going this path. I have so many friendtors. I often, like even in Pivot, I said—

[54:14] Paul: Friendtors, I love that phrase.

[54:16] Jenny Blake: Yeah, like let's drop the obsession with trying to find one holy grail mentor. I feel like that's another piece of very common advice. You don't need it. Actually, if you have peers like you, me, Kay, Al, we alone can help each other navigate these moments. And obviously sometimes you— it is helpful if someone's 5 years ahead, 10 years ahead, or they just have a new solution that has emerged at this moment in time with technology and the apps that are out and the creative opportunities like, but it can come from any direction. And so I have often had, and I'm very lucky, we started, I started with a couple friends 2 different actually Marco Polo groups.

I do a lot of asynchronous chit-chatting with business-owning friends on Voxer, Marco Polo. I love good asynchronous anything. I do even a 3-month Voxer coaching pop-up because I don't want things on my calendar and I like to be outside and I like to be with my dog playing in the grass. But with asynchronous, it's so easy to just leave a voice memo or I'm debating this, what do you think? And getting input that way. So more than any one mentor, I really love trading ideas asynchronously with peers.

And that way it helped me stop obsessing, like, am I meeting the right people? Am I networking hard enough? It's okay. Like, just having friends goes a really long way. Friends who are at a similar stage. It doesn't— oh, you don't always have to befriend the smartest person on the planet.

To learn how to have peak performance at the thing you're trying to do. It's okay. Like a lot of those people have podcasts or they go on podcasts, so you can learn plenty from them without ever having to bother them to pick their brain for a cup of coffee. Like you don't have to be that person picking brains. You can reach out to your friends doing similar things and like help each other in a really mutually beneficial, supportive, energizing way. And I would just say find people that have good energy.

Because it's— life's too short. Life's too short to have it be just—

[56:21] Paul: I love this word. I love this word, friend tour. I'm going to steal it. I want to close with some shorter questions. Do you have any PATH role models?

[56:35] Jenny Blake: Oh, gosh. So many. See, it's hard for me to pick one. I'm too indecisive. No, I'll just say like every, like so many other in this arena, I read 4-Hour Workweek long ago and was super inspired. And I don't know, I really love podcasts.

They do so much for me in my life. So I love looking, I love listening to all kinds of shows. I listen to a really a range. I love, I just love seeing what people are doing in this space. And podcasts are like my best friends, you know, they just reassure me even whether I've met the people in real life or not. And it's also the way I make friends.

But I'm sorry, I'm not giving you specific names because there's too many. It's like my brain just started overflowing.

[57:13] Paul: No, I think it's an interesting point. I sort of do this too. I, I absorb so much from so many sources. It's like I'll see people like Seth Godin and they'll— I don't want to take everyone's aspect of all their lives, but like Seth Godin to me is like, oh, older man still energized with life. I'm going to take a piece of that. I might look at somebody else and it's like, oh, they're able to like launch and ship stuff very easily and that inspires me.

Or this person's able to take extended breaks off and be comfortable with it and that inspires me. So it's sort of like a jigsaw puzzle of different people. Yeah, I love that answer. Are there any podcasts that stand out that you listen to over time? Like, are there ones you go back to? I listen to one with On Being, Krista Tippett and David White.

I've probably listened to it 20 times. Any favorite all-time podcasts you've listened to?

[58:12] Jenny Blake: There's some really good ones with Oprah and Byron Katie. That one stands out. Byron Katie, the work helped me so much to turn my thoughts around. And I just love how she says any stressful thought is an alarm clock waking you up. Saying that something could be more true. And so especially in business, finding those stressful thoughts and turning them around through Byron Katie's work has been enormously helpful at work, even in my personal relationships.

And I subscribe to a lot of podcasts. My Overcast stopped working because I was subscribed to too many podcasts, hundreds. And so I go in waves of which actual shows that I listen to, but I tend to listen to business podcasts in the morning and then I, I am so crazy about my reality TV that I'll even listen to like episode debriefs of Love Island as I go to sleep or Joe Rogan, something before I go to bed. Like the podcast even put me to sleep.

[59:11] Paul: That's awesome. I, yeah, sports is like my guilty pleasure for just like listening to fun stuff that's not related to the work I'm doing. Well, This was an absolute delight. I will link up to your book Free Time, which is here in the video if you're watching. It's a beautiful book. It's got this like—

[59:35] Jenny Blake: thank you, Paul—

[59:37] Paul: marker. I forget what these things are called, but yeah, it's really cool. There's a lot of inspiration for just thinking about business in a new way. And I think you're always early to these trends. And I love that you're sort of codifying a different approach for Actually just orienting a business not around profit and more in growth, but orienting it around your life. So definitely recommend the book.

Your podcasts are awesome. They've inspired me to do some solo episodes. But where else do you want to send people? They can't find you on social media or you'll respond slowly, but where, where can they find you?

[01:00:17] Jenny Blake: You can search for Free Time with Jenny Blake or Pivot with Jenny Blake, wherever you're listening to this. And then there's the Free Time Toolkit that's free and a quiz. If you visit itsfreetime.com/toolkit, there's a lot of templates. That's my joy. I've shared 'em since the days I started blogging in '07 of like, I give away as many templates as I can. So all those related to some of these topics are at itsfreetime.com/toolkit.

And thank you so much, Paul, for modeling the book. You're great. I appreciate your product placement. It's just a delight to be here and talk with you and be on this path together. And I know your listeners are on this Pathless Path too, so it just means so much for you to have me here and for everyone who's here listening.

[01:01:01] Paul: Amazing. Thank you so much, Jenny.

[01:01:03] Jenny Blake: Thanks, Paul.