Deep Questions with Cal Newport - Ep. 157: JENNY BLAKE: Help Me Do Less!

Episode Date: December 20, 2021

In this episode, author Jenny Blake joins me for a conversation about her new book, FREE TIME: Lose the Busywork, Love Your Business  (https://itsfreetime.com/book), which helps entrepreneurs engineer the stress out of their work. I ask her to use myself as a case study and apply her principles to helping me reduce stress in my working life.Though FREE TIME doesn’t come out until March, if you pre-order a copy now (at https://itsfreetime.com/book) you’ll get immediate access to a pair of free copies of the audiobook: one for you and one for a friend.Thanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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I'm Cal Newport, and this is Deep Questions. episode 157. For the first time in a little while, we have an interview episode. So as longtime listeners know, we've more or less had a hold on interviews as we're preparing the Deep Work HQ to actually have in studio guests. We're figuring out our whole strategy for how we want to invite guests and who we want to invite. But every once in a while, someone I know will mention, hey, we should chat.

And I say, yeah, why not? and this is one of those instances. So the interview that's going to be featured in today's episode is with my longtime friend Ginny Blake, who has this great new book coming out in the spring that is called Free Time, Lose the Busy Work, Love Your Business. Now, I read an early version of this book and I gave the following blurb. Stress is a systems problem. This was one of the most arresting statements I've read in a business book in a long time.

an important vision of entrepreneurship freed from overload. In other words, I really like this book because what it's about is how do you, if you're an entrepreneur, build a professional life that's not overwhelming and stressful. Ginny has done this with her own business and she gets into the details of how to do it with your business. These are things like automation, building systems, being careful about growth. So I thought this was a cool idea. And I heard from Ginny that she was doing a pre-order giveaway right now in December in which if you pre-order the book, you immediately get access to the audiobook. So yes, the hardcover does not come out until March, but if you pre-order it, you immediately get the audio version.

And not only do you get the audio version, you get an extra copy of the audio version to give to a friend. So I like this book, and when she mentioned she was doing this promotion, which I believe will be open until the book comes out in March. I said, yeah, come on the podcast. Let's talk about your strategies for building a business without being overwhelmed. And what I basically did, as you will hear, is I hijacked a conversation and said, let's apply all of your advice to me. And that's basically where we go in this conversation is, how do I make the business aspects of my own life less stressful? And we stress test her advice on my own life. So, yes, I made it all about me.

One quick note, I recorded this at a moment of peak stress. So professors in the audience know this. There's a point at about the four-fifths way through a semester where everything peaks and everything is due and all these things are going on and you feel like you have no time. It's always very stressful. And then the semester ends and you feel a lot better. Well, I was at that peak point when I did this interview, so I sound pretty stressed in this interview. I will say, actually, for the most part, I have things at a pretty good balance. The issue about, and this is a quick aside, but the issue about academic life is you don't necessarily want to optimize for that peak stress.

If you optimize to keep that moment of peak stress low, then you're probably not getting enough of the right stuff done during the normal moments. You just have to put up with the fact there'll be twice a year where you feel overwhelmed for a few weeks. And that's the way I run things with my academic life too. So I'm not probably actually as overwhelmed as I sound in this episode, but it makes for a very good stress test of Ginny's ideas. So we hear her ideas. We hear about what's going on in my life. If you want to find out more about this book, if you want to do the pre-order, the website is it's freetime.com slash book. So ITS free time.com slash book.

Without further ado, here is my interview with Ginny Blake. We've known each other for a long time, and I've done your various podcast over the years, but I'm excited about this one because you have a new book that I loved and I need, and I'm going to get you to essentially coach me and improve my own, my own. own overworked busy life right now. You are going to be the guru for Cal. So I've been really looking forward to this conversation. I'm honored. This is a high compliment and high bar. And I've told you this before, but for listeners, when my husband and I first met in New York City, my husband looked at my bookshelves and he saw deep work by Cal Newport. And that's when he knew that we were simpatico.

So we have a connection to Cal through my bookshelf, which is a really funny story. So I never let Cal forget it. And yeah, it's been an honor, Calder, just run into you throughout the years. And I'm excited to talk about free time and the friction that ails you. Because I know you're so good at this stuff too. Well, I'll tell you, for every one story I hear like that, I hear two where it said, you saved me. I was getting serious with this person I was dating. And then they said, hey, you have Cal Newport.

He's my favorite. And I knew it's time to break up. It goes both ways. I was going to spend my life hounded hearing about deep work and time blocking. I thought you were going to say the deal breaker was they had never heard of you. And then they knew. Yes, that should be the case. This should be the test. This should be the test everyone does. Exactly. So right off the bat, actually, I want to do a quick tangent just based on what you just mentioned. A very common call I get on this show is how can I run a startup of any type, especially one that is internet based without social media. So I try to answer this, but, you know, everyone knows I'm weird and not use social media. My business is kind of weird. But you're on actual normal. person, internet-based businesses. Give us what we're looking for here, Jenny. Tell us about how you can do

this without social media. I get this question a lot too. People are almost aghast. How can you possibly have a functioning business if you're not on social media? And I call it sailing the sea of shiny sheds. There are so many shoulds in business. And even if you don't run your own business full time, there are so many shoulds around building your personal brand and your platform. With social media, just like you, Cal, I felt years ago that this was not going in a good direction. I felt worse every time I signed off. Moreover, I was not actually getting that many clients as a direct result of my brilliant tweets, for example. Once I started posting on social media and I was too overwhelmed to read the replies, I didn't want to read the comments, I didn't want to read the main feed. I realized it would be kind of hypocritical of me to continue.

And not just that. Now more than ever, I think there's growing awareness. and conversation around surveillance capitalism. And the question that I ask myself and I encourage everyone to ask is who is profiting off the pressure that you feel? So there's pressure to be on social media. Who's profiting from that? Well, who else? The social media companies, if you look at your business and how you get leads and how you get clients and where your favorite community members come from, if social media is joyful for you and it's a great source of connecting with new community members, great, there's no need to ditch it. In my experience, I found that not only can I function without social media, and it's not like I'm somehow hobbled by it, I have so much more focus and

concentrated attention and ability to do deep work because I'm not experiencing that death by a thousand cuts of fractured attention all day. So I'm able to produce what I think is better work, deeper research, more curation, that then that deeper IP is, what attracts clients, community members, podcast listeners, and so on. So what was the nature of your business, which has shifted a couple of times? What was the nature of it at that moment when you were using Twitter and then you decided, this sounds scary, but I'm going to stop? Our audience probably wants to know, like, what were the types of services, what type of tweets

were you doing that you thought might be helpful at that time? I was, so I worked at Google for five and a half years. I left in 2011, so about a decade ago at the time of this recording. And I had had a blog, just like you with the study hacks, I had life after college that I set up in 2005. So always my side hustle involved blogging, tweeting, some Facebooking. And by the time I left Google, I was on my own and I realized there's no paycheck that I'm getting every two weeks. Like the way that I spend my time is crucial and it's not going to be automatic that that time is correlated. with earnings, especially if it's fractured across, again, social media and things like that. So I was coaching. I was teaching courses. I was doing a lot of keynote speaking in the before times. And now I've shifted toward more scalable models. I license pivot the IP to companies like Google and Chanel. I trained a team of pivot coaches. I've trained pivot facilitators. None of those corporate contracts come from social. They come from the books. So I realized that

the books, and I would say my podcasts, I've had people at Fortune 500 companies bring me in to speak for a keynote. And then only once I'm in the room delivering, they go, we all listen to your podcast and on our morning commute. We're so happy you're here. And I found that the podcast, just like this, because it's so much more intimate, that when I was getting on sales calls, people were already, they were the ones excited to talk to me. So it was this interesting shift where instead of me feeling like I had to kind of pitch myself for things like speaking events. Now people could get to know me so much better, which wasn't really happening as much on social. I think as long as you pick one or two key channels, which I know you say too, Cal, for what I call public original thinking,

like, yes, you should put your best crack at original thinking out there on a regular basis. But there's nothing saying that means you have to keep up with infinite scroll attention hacking, but nightmare. that is endless notifications. And just for the extra clarification for the audience, so pivot goes back to the, I guess that was the first book you wrote after you left Google, after life after college.

Yes. It was a book about pivoting in your career and the business you built up around it, as you just mentioned, just so the listeners know, is you were speaking and was doing corporate consulting for companies on this topic. And then you said,

as we'll get into, that eventually morphed into more of you licensing the content. So this is client-facing and content-based work where people would traditionally think about social media. But I like the way you're talking about because it makes sense to me that you were putting out high-quality IP, which is really the only type of thing that would make me think, I want to invest a lot of money in this person. I mean, how could you possibly replicate that with, you know, I really love Jenny's tweets. So let's fly her out here or let's have her train. So what's the terminology here that the social media is like low quality or shallow IP?

Might as well produce the stuff that's really high quality. That's the only thing that can move the needle. I mean, I'm assuming that's what you were thinking more or less when the time came. Yeah, and there are some people who are great at Twitter threads and building Twitter momentum or whatever platform. A lot of people in our industry are on LinkedIn right now. And it would be the obvious connection. I do a lot of work with companies or companies could license Pivot and other materials. So I should be on LinkedIn.

And I remember even a year or two ago, the hot new thing was creating a LinkedIn newsletter. And I just thought, you got to be kidding me. To me, it's like renting versus owning. I can own my land, my digital land, my platform, my newsletter, my podcast. What I'm not going to do is just jump. Every time a new platform says jump, oh, now the hot new thing is let's create LinkedIn newsletters. And I see friends doing it.

And I see friends building million person followerships on LinkedIn. and I don't care because, as you said, I think some people can do it well. And if you can do a platform well and it's joyful for you, great. That's amazing. But what I refuse to do is fraction my attention across 10 just because a new social platform gets going. Like TikTok, whatever it's going to be, who knows after this comes out, no, I'm not just going to jump. And then all of a sudden, you know, I don't have to tell you, like the exponential refraction that's going to happen with each new platform. it just gets ridiculous.

So for you, you have people hear your podcast, people read the book, and then word of mouth. Are those the big three when it comes to new business? Those are the big three. And then everything in the last 10 years of my business has been creating greater scale through smarter systems. So I will, from time to time, I'll do things like create a LinkedIn learning course that allows me, instead of running around into everyone's homes, teaching them pivot one-on-one, I can create these courses and then companies can access.

and, you know, hundreds and thousands of people can view courses. So I try to stay focused on one to many. For example, I don't have one-on-one coaching clients anymore. And now, instead of me discussing with someone one-on-one privately on a phone call, I like to answer out loud. So now if I get a question in an email or from a friend or wherever, I try to answer in a public way that does also contribute to that growing body of work, as you described. This sounds familiar. Yeah. Yeah, the whole premise of your podcast, right? Yeah, exactly. All right, well, okay, so now let's go back to the, where I want to build up to and where I'm going to start soliciting your help is I want to hear the, I want to pull apart the backstory of how, you know, Jenny post-Google building this company becomes overwhelming and the genesis of free time and rethinking, how do we build a business in a way that supports your life and makes it better and doesn't completely overwhelm you?

that's the advice we all want to get to. But let's build up to how you got there. So maybe you could tell us a little bit about as you started building up your first independent business after you left Google, how things began to get busy to an extent, to get overwhelming to an extent. What was that trajectory for you? What led you to thinking about free time, the book and everything goes around it as a topic? One of the things that working in corporate and being self-employed have in common is that if you don't create constraints and boundaries, again, it's so aligned with your work. But I realize very early on that if I don't draw the line, no one else is going to drop for me. So within the context of Google, it's no one person's intention to like crush employees with burnout. But what ends up happening is just

the system itself can become crushing and the pressure can mount. And I found when I was then moved into self-employment, I just needed to be more targeted with my energy. So even when I was in college, I used to try to cram all my classes Tuesday, Wednesday, Thursday, ideally just Tuesdays and Thursdays. And because I was in the liberal arts, I was able to do that. I started setting a lot of parameters for myself because I realized I'm not doing anyone any good. If I try to have a coaching call, this is in the early days at 4 p.m. as one of my clients says, I don't even know my own name at that time a day, I just started to notice that given my energy, like you, I really, I really value deep work, deep connection, deep conversation, and sort of deep cognitive engagement. And that is not 24-7 for me.

So part of the impetus around free time is that I think it's harder to work less. I think a 40-hour week when you're self-employed is too much, honestly. I've been a 40-hour week. that for me, I like to sit at my computer work five highly focused hours, three or four days a week, and have that be the baseline. And so I just became obsessed with how do I design my time? And how do I reject certain ways of working that are so ingrained in our culture? I tell people now, whenever they're leaving corporate, don't assume that you need to work Mondays through Friday. Who does that work for? If we all designed our working life, starting from scratch without considering the factory model, without considering corporate best practices.

Would entrepreneurs starting from scratch design a Monday through Friday 9 to 5 workday? I don't think so. So I just get really passionate about getting creative and not assuming that if I work less time, I'm going to get less done or be less successful in my business or earn less abundantly. I like to combine these questions and say, as I'm sure you read in the book, how can I earn twice as much in half the time with joy and ease? And then later I added this bit about for the highest good of all involved. Now, did you come straight into entrepreneurship with this goal?

This is why I'm going into entrepreneurship is so I can have more control. I'm not happy with what corporate life was like. Or did you go into entrepreneurship for other reasons and then discover through experience, oh, wait a second, I need to start taking more seriously what my working life is like. Well, before there was a book called The World Without Email, I was... We called it The Dark Times. Yes, the Dark Times. I was totally burning out.

Part of it was that not only was I working at a very fast-paced company like Google, and I had a side hustle, and I was writing and launching a book on the side. I was just kind of bonkers in my mid-20s. Was Pivot Your Book on the Side at Google? No, Life After College. Life After College was. That's right. Okay. Yeah.

Life After College came out in 2011, and I took a sabbatical from Google to launch that book. And that's when I realized I cannot do both any longer. It would not be fair to Google and my teammates there. I was launching a global dropping coaching program called Career Guru. I just couldn't do all that and launch my book. And I felt that while I loved my role at Google, I was a career development program manager. It was my ideal role on paper. However, I was in so many back-to-back meetings,

crushed by so much email that I felt that I was only in my zone of genius, as Gay Hendricks calls it, about 20% of the time. And I had this hunch that if I go out on my own, I honestly did not identify as an entrepreneur at that time. I thought, I don't know that I can hack it. I don't know that I'm willing to take enough risk to do that, but I also knew that I couldn't do both. So I figured I don't have kids. I'm not married. If I'm going to take a risk, now's the time. And so part of it to answer your question was reducing this feeling of burnout that I kept experiencing. I mean, my body, I like to say now, it has me on a short leash. Like as soon as I get off track and I start overworking, it yanks me back so fast.

As we record this, I'm getting over a bout of bronchitis. And that was my body saying, hey, listen, you, you know, whatever your perceived capacity, my actual capacity is just less. And so I think entrepreneurship also the freedom of it really appeals to me, the freedom of my schedule, but also the freedom of what to work on, and not to have to work on assignments that didn't mean anything to me. So I could work on really big, meaty projects. People are afraid of that shift. So I'm just curious, what was on the docket when you, that first day you walked away from Google? I mean, did you have some things lined up? What was the plan? What was the answer to the How Will I Make In's Meek question at that early stage? I had six months of what I call pivot runway. I had six months in the bank that I said, if I spend every penny of this and I don't earn a dime, that's okay. And it was the first time in my working life that I felt comfortable spending that entire

six months of runway of living expenses. And I figured if I don't earn any money or if I don't earn enough money, I'll go get another job. Maybe I'll go crawling back to Google and say, well, you take me back. And I started earning within the first month. I started just through coaching. That was kind of my bridge income. The book had just come out.

So I did a book tour. I think I saw you at WDS that year, if not South by Southwest. And then I started launching online courses before that was the big thing that everyone was doing. So I was just experimenting. At one point, I had 12 different streams of income, just testing to see what can work. And I always had financial ups and downs. But even now, 10 years later, first of all, Google is still one of my clients. So I think a lot of people would be surprised at how creative you can get with a current employer working on the other side just as a partner, consultant, contractor.

But people will ask me, do you regret leaving Google? And they especially ask that in the beginning because there is so much fear. And I always said no. You know, there's no matter how low things got financially, no matter how much of a crisis of confidence I was having, and I have many. around what to do next, what's next in my business, no matter what, I never regretted it. For one second of one day, I always appreciated this bigger container of freedom, even though it comes with that cognitive load of uncertainty and the financial pressure too, because I'm the earner for our household. So I realized that because of all that added sort of complexity and uncertainty,

working less is important to me just so that I can have time with my family, time for my health, time for myself, time for deep reading, which is really important to me. So that's why I'm so passionate about designing the time within the workday

to be more creative than I think what so many of us are used to. And by the way, there's another just a tangent because we have so much in common, these tanges are inevitable. I love a good tangent. So, yeah,

we met at this conference, WDS, back, maybe it was like 2011 or 2012 or something like that. I mentioned it in Yorker piece. I was talking about some conferences I used to do. And I don't do that. That part of my life went away. And I don't know if it's because I started writing different types of books or if that was just a moment in time when you could have these giant conferences in terms of lots of people would be there.

But it was all internet related people. And you look back at it. Like look at World WDS 2012. And think about everyone who was hanging out there. I mean, you were there, I was there, we're hanging out with The Minimalist were there, Bray Brown was there, Jonathan Fields. Jonathan Fields was there. Like all these people that went on to, you know, have these big splashes,

everyone was just kind of hanging out. And because I wrote about it, God, I can't even remember what, there was an article that came out recently, but I mentioned doing another one of these things, and it was at Lincoln Center. And it was like online, I think it was like, like the 99 U conference or something. And again, it was like, I was hanging out with Bray Brown backstage, and it was a thousand-person

stadium or theater. And the teamsters that were there, all I remember is how baffled they were. Like, what are all of these like young guys and complicated glasses and flannel shirts? Like, why are they all here? I don't, like, it was baffling to them. I don't understand. So anyways, does that still happen and I just became more businessy? Or was there a weird moment of time, this sort of 2010 to 2015?

where a thousand people would just gather. I know. A thousand people would just gather and it would be awesome. So is that nostalgia or is that still going on? I'm just not involved. It's so funny you ask this because it was such a special time. And I think what that time represents to me, because it was so crazy when people's little two-inch avatar,

whether it's from a blog avatar photo or a Twitter bio photo, you just see these little squares pop to life at these conferences. And what strikes me about them was these were all people who early on kind of stuck their neck out and were creating things and creating things in public. Once social media platforms, I mean, the one thing they did do was sort of democratize public pontificating, if you will. Because in the early days when you and I were meeting up at all these conferences, you had to have some tech savvy and some willingness to fumble around and bigger things out a little bit the hard way in order to put your ideas out there onto a blog. And now I do think that that's shifted. What I do think is that anybody who is creating meaningful content, I call it Serendipity Popcorn.

And I think what those conferences represent to me is that, Cal, because you and I just showed up and posted on our blogs once or twice a week, you create all these little popcorn seeds that lead to invitations to conferences or connecting. I remember at South by, I was walking down the street and someone passed me in the intersection. And they go, Jenny Blake? And I said, yeah, and you know how it is. This never happens. I always say, I just want to be known among nerds.

Like, it's never going to happen on the regular streets of New York, but at South by. And I said, yeah, that's me. And next thing I know, I did a 180 turned around and we walked and had coffee somewhere down the street. And that is, I think, the gifts of doing the deep work that you talk about is that gift of serendipity. Because by doing deep work, by putting it out there publicly on a regular basis, I love that it opens the door, whether at those big events,

or now through more virtual channels. I still do feel nostalgic for those. And I don't know, excited to see if they can happen in the future. But we're in such a new world now. Yeah. Who knows? Well, okay, so here's my snap theory then, based on what you just said, because I love to theorize. All right.

So what to find that moment, I'm restating what you said, is blogging balance two things. It was democratized. So anyone could do it. So now it wasn't, here's six magazines. And if you're not writing for one of these, you can't be seen. but there was friction because you have a blog it's hard to set up

and zero people will read it. So there's actually quite a bit of friction involved in building up a readership of any type and that friction sort of was pretty good at doing a democratized filtering.

So it's democratized. You got an interesting people like James Clear was there too. You get an interesting people thinking about interesting things but there was enough friction that they were filtered up to and they had interesting things

to say about and it kind of honed it where if you then move to a social media reality today, that piece of the friction is gone, that distributed curation that's induced by the difficulty of actually getting someone to subscribe to your blog and come back to it again and again. So in some sense, the crowd is,

it's too big and too undifferentiated to be able to say, here's 20 people to base the conference around. Or, yeah, so that's my new theory. Also, it's more fractious, fratious, conflict-inducing, just the nature of social media interaction And you don't come away from that saying, here's 60, you know, Jenny Blake nerds that love what Jenny Blake does and they really like each other.

It's all so antagonistic. And so you don't really want to get together. You don't come on with YouTube comments, be like, man, I can only get all these people together in one room. Like, I'd love to just hang out with them. Instead, you're like, my God, I hope my real name's not on here. Right. I mean, I think the way you just summarized it is perfect.

And to add on to that, the algorithm changed so much because with blogs, as with podcasts, You need to manually add that podcast. Whoever's listening to deep questions or free time, you have to add it. There's some intentionality. And I do find that podcasts tend to be a little more nuanced because they are more intimate. They're harder to create. They're harder to produce. And there's no algorithm.

I mean, now Spotify and Amazon may enter the race. But what the algorithm does is it just twists us around six ways from Sunday. So I think with blogs and podcasts, you get that, yes, intentional subscribers who are sticking around for a little bit of a more intellectual engagement approach, whereas these other platforms that are algorithm-based, the algorithm, capital T, capital A, is just there to keep you hooked. And so the content becomes so polarized. I don't have to tell anybody listening this. We all experience it. But I think the algorithm gets in the way of that beautiful utopia that we used to have, you know, before it was all about clicks and dollars and eyeballs

and keeping us addicted. Yeah, those were the times. So that's why I love podcasts. That's why we're here. Because this medium still works, still fulfills, I think, the values that you and I stand for, which is that more thoughtful, reasonable engagement. Like, it's very hard to troll a podcast. You know, you have to sit and listen to a long spiel.

You can't just troll us. You know, there's no comments to, like, put crazy comments into. It's hard to do. Yeah, it's hard to troll. You have to, like, call in. Not easy to do. All right, good. I love that.

Thanks for going down that tangent with me. I can geek out about that with you. Okay, so I want to get back to your story then. So you leave Google because, in part, the corporate life was burning you out. You're going to have more control when you're running your own business. And at first you're doing coaching and you had a book out and you're doing some speaking, but the business evolved. Were you pretty successful right away at keeping the business in the right place in your life, or was there a learning curve there where things got out of control and you had to

pull it back? What does the trajectory look like from those early days to where you are now, where you really have your act together on how the business runs? My commitment to all this started early, and I will tell you that I had a hyperthyroid disorder. It's called Graves disease that I took a daily pill and monthly blood test the entire duration of the time I was working at Google. I think it might have developed when I worked at the start up prior to that. From the day I quit and moved to New York City three months later, it was vanished. Yes, partly because of the medicine I was taking, but also I never needed to refill that prescription. I had had chronic lifelong asthma. I did not need to order a new inhaler

for the last 10 years. I only had to in the last month because of who knows what. I'm examining this as we speak. There were things that cleared up so immediately by shifting into a more humane schedule and giving myself these permissions early on. So yeah, from the beginning, I was pretty strict about no calls on nights, no calls on weekends. I would rather not take on a client than talk at times that would interfere with my ability to rest and recover and recoup and have my morning rituals. So I just became so clear that no amount of money was worth it to me. And that's something I talk about in this new book that we know the term high net world. earth. But I'm really talking about high net freedom. And that is the value that is most important

to me. And I will, I remember I had a chance to put in an RFP to work at a very big fortune, I'll say 10, so I don't give it away, tech company. And the RFP alone was so drawn out. It was 20 pages and I just knew it was going to be a bureaucratic nightmare. And I thought, I don't care this company's brand, their name, how much they pay me. I don't want to do it. So I guess there just becomes a point in life where you become allergic to bureaucracy and the BS. And again, no one can claim your time but you and nobody's watching. I don't know. I just think there's so much more permission we can give ourselves to do things differently. So yeah, I'd say this theme has been present for a while now. And it's the way that I stay healthy. If you're doing creative work, if you're a knowledge worker, but especially somebody creating ideas and synthesizing, your body is your business. You have to be in top condition to do your best thinking and synthesizing and problem solving. So I also think it's not like frou-frou to be talking about this. It's crucial to keep my instrument in top condition.

Right. If you're an athlete, your coach is going to have something to say if you're smoking or something. You have to take care of your body. Exactly. Your body affects your mind. We all know that. We all know that when you're sleep deprived. Like, I can't remember words.

I trip over what I'm saying. It's so clear to me what happens with my mind when I'm not sort of taking. taking care of myself. And I think one thing I've had to give myself permission over the years is that, wow, maybe I just need a lot more free time than other people in order to function well. You know, maybe I just need to give myself more space and be more forgiving and not get as much done, but get really meaningful things done. I think this is one of the big unanswered questions of basically the entire office work sector. Why don't we actually care about the underlying brain cognitive psychological aspects of doing this type of work.

We just ignore it. We say we don't want to know about it. We don't want to know about what state is going to be better for producing this work than others. What's going to produce the best, you know, report or code here versus bad reporter code here? Like, we don't want to think about it. We just want to say, do your work. Here's the tech tools. If we want to be more productive, we need tech tools that gives us more information faster.

But there's just no conversation about exactly what you're talking about. the physiological component, the productivity, beyond like maybe some discussion on sleep. Okay, that's the one discussion that we'll sort of half-heartedly had. We should maybe sleep more. But no one thinks about, well, wait a second, if I have 55 things on my plate and 150 emails I have to answer every day. And my calendar now is public so that anyone can grab, see when I'm free and grab time to put on my calendar at any point. This has got to be terrible physiologically, which means I can't be working very well. but we don't talk about physiology.

And it sounds like you were thinking about it from the beginning. And maybe the graves help put you in that mindset. But you were starting. If I'm saying this correctly, you were starting from this component of I care about how I feel, how my body is, my mental state, my stress, my psychological state. That has to be one of the things I'm optimizing. Yes. And that that is going to lead to my best work. And exactly as you said, as we would treat any pro athlete, we would say,

They don't smoke. We would do things to stay in shape and their body is their vehicle to do what they do and to do it well. And I think that this is what can differentiate us. So exactly as you described, I know you've given the example of Bill McKibben. And you said a word in your New Yorker article about him, time affluence. What I find is that we are all so time crunched most of the time that I realized I grew up with an energetic blueprint of busyness because my mom and dad.

Dad worked full time. So I was basically sent off to go do back-to-back activities every afternoon after school. And I realized that no wonder I was cramming my schedule chock full as an adult. That is what I was used to since I was in elementary school, was just go here, then aerobics, then gymnastics, then ballet, then piano, then come home, then do your homework. And it was very hard for me to unwind that energetic time blueprint as an adult and as an entrepreneur. And being an entrepreneur is the first time I had full-time autonomy over how I set things up. So now what I strive to create is abundant margin. Because I think what you're saying about physiology, it's not just, oh, shoot, I'm crashing.

I better take some rest now. I like to call it deep rest in an ode to you in deep work. It's not just resting when we're already burned out and crashing. It's for me, it's like every week, week after week, creating a lot of time margin that I can go with my energy on any given day of what types of projects and things that I want to work on. And that's also how I keep my mental organ. I don't know, how I keep my mind sharp. I mean, I crave time affluence like someone who is anemic would crave iron. You know, I need red meat. I need to eat something with iron in it. A few things old. I mean, I was, that's what my talk in 2000, whatever, in WDS. I was talking

about Bill McKibbin and his time affluence and how attractive that was to me. and I felt the exact same way talking to them a month ago. You know, that's got to be something. So you were craving that. I crave that. You've been more successful at getting it. So you're about to help me here. So beware.

I don't know about you, but I also find that as life gets more complex, I just came to this realization recently. You have kids where the number of programs running daily on my CPU has grown in complexity. It's not just me anymore. I'm thinking about how am I doing? How's my husband doing?

How's our dog doing? How's our relationship doing? How's the house doing? And these programs are running as a baseline. And that creates a lot more cognitive load and complexity too. So I don't know about you, but as is, I don't get that coveted, quiet, solo time that I used to back in my days when I was living alone. It's easy then to create that solitude and time affluence. But it's so much harder when you have a family. And it's not like, I think there's so much joy that comes from having a family, but it creates a lot of added complexity too, and especially for people like you and me that love and crave deep quiet, it can be challenging. Yeah. Well, so before we get to the principles of it, I guess the big picture question a lot of people have is what's the right way to think about money in this

context? Because it's an easy metric to say more money is better than less, right? So that's a metric that makes sense and it has payoffs in the sense that literally you can have more stuff. But obviously that metric leads to overload because every activity has the potential to make more money. So what's the right way just to get started? When you were starting with your startup and you're thinking about money, what's the right way to think about that aspect of building this type of life with margin? As an entrepreneur, the first thing is decouple money from time. They don't have a linear correlation. It's not like if I work more time, I earn more money.

It just doesn't work like that when you're self-employed. In fact, the smarter you can work and the better systems, the more. more you can pull yourself out of the time for money trade and the more you can earn. So I think for some reason around these conversations around time, I think hovering somewhere in the background is this assumption, well, then I'll have to earn less, or then I'm going to just be living paycheck to paycheck. That's where my abundance question of how can I earn twice as much in half the time, it's almost rhetorical. It's not an, these aren't exact figures, but it's not buying into the assumption that if I work half the time, I'm going to earn half as much. It's actually the

constant continual question is how can I earn twice as much in half the time? And I do believe that if we are creatively sitting with this as an inquiry, you will find ways. But you won't find them if you're just assuming that it's a direct linear correlation. Right. So it's just something like the amount of money, roughly speaking, but the amount of money that you can bring in, the metaphorical price you get is pegged to the thing you do. best, the best thing you've produced. And so if that simple model is true, then it would speak to the most profitable thing you could do is actually do less and spend more time on the things you do best and do it better because net net, that's going to have the highest return for you.

And what can you create that is at that sweet spot of revenue, ease, and joy? So for example, with licensing, I made a mistake. My first two licensing clients, I worked with them in this really bespoke manner. Consulting calls with them week after week. We collaborated on all the materials. And then I realized I looked ahead to getting licensing client number three. And I go, oh, no, it's going to be as much work every time. And even though these were big six-figure contracts, I realized I was not creating any freedom for myself. I was just creating a really high-pressure job every time I would land that next client. So what I did was I spent a year getting all the materials ready to be off the shelf. So now the licensing materials are basically one-click order ready.

And it is still a six-figure contract, but it is not a bespoke process to deliver it. So the product now exists. It's off the shelf. It's beautiful. It's branded. It's ready to go. And I used to be self-conscious that, oh, maybe companies would not like that, that I'm not as involved.

But now I realize they're happy. It means it's ready. It's tested. It's successful content that they can easily roll out and scale to hundreds of thousands of people without me, Jenny, being the bottleneck for that delivery. So that's an example of just using systems thinking and scale at that intersection of abundant earning as well to say, how can I start to pull myself out of this and create things that actually are not only more scalable and can have greater impact, but even easier to deliver

than the original. So let's talk systems thinking because I need this. So here's the setup for why I need your help. There's different things that have emerged. I have my writing I do. And then there's the podcast and the things to go around that. you know that, the things that go around that. And they're speaking.

And then there's the whole Georgetown stuff is its own. That's like your Google. There's only so much you can control. You have so much. You have Georgetown, New Yorker. Yeah. Your blog. Yeah.

Your podcast. Yeah. Speaking. Yeah. Books. Right. Writing books. On courses.

Being a family man. Yeah. Courses. And by the way, we put Georgetown as one of these eight, but that itself has eight subparts, I'm sure. Yeah, don't get me started on that. Yeah. So this is a ton. I honestly don't know how you're doing all that you do. Well, you're going to help me. You're going to help me. Because I was doing the math the other day, putting Georgetown aside, there was something, I think it got the nine, maybe nine or ten different people, one way or the other I pay money to on a regular basis.

So there's like, whether I think of it like a company or not, there's now a non-trivial number of people out there in the world that I give money to. They take some of the money I make. that need to be organized. They're doing things for me. This kind of feels like a company. So why don't I think about this like a company that I want to make like jenny's, right? So this is what I'm thinking. So where do I get started?

Do I get started with, I love the systems thinking piece of your book. Because I talk about this a lot, but you do it better. Where do I get started? Is there, do I need this, is there a stepping back phase first before we get our hands dirty with the teeny teams trademark and the great-nit-old? gritty details you have. Where do I begin reclaiming things here, Jenny? Such a good question. I'm excited to talk this through. So the free time framework has three parts, align, design, assign. And the primary central diagnostic is similar to when you've shared on

your podcast. Where are you in friction and where are you in flow? Just two poles to simplify. Where are you in friction? Where are you in flow? So, Cal, first I would ask you, if we look at this align piece and we can align your strengths, your energy, just kind of where you're trying to go with everything. Where are you experiencing friction? So with these many, many hats that you're wearing, like, not only do you have eight or nine job roles, but you have eight or nine people that you're paying on a regular basis. So at this moment, where are you experiencing the greatest friction? I mean, everywhere is that an answer? Everywhere that's not, so where I'm feeling the flow is anytime I'm creating.

So if I'm when I'm writing or ideating, solving a proof, writing an article, working on a book idea, talking into the microphone for the podcast, I feel like I'm at my fighting weight. I feel like the craft is there, feel great about it. So almost everything else in the, and again, I'm putting Georgetown aside here, but just talking in the writing world of my life. Everything else kind of seems like friction. Anytime I'm jumping, quote unquote, jumping on a call, email. You know, I have huge amounts of things I put in place around the email, but it's a, you always have to keep refactoring and refiguring. So, and just having to deal with email being used in the right way. I mean, these are quick questions that should be answered asynchronously that I have the answer to.

That's actually a good use for email. I talk about that my book. But if you have too many of them, because you have too many things going on, that becomes a whole context shifting morass where just this to this to this to that is too many things. I can't get my mind around it. projects, overhead. I don't know. Talking to people, I don't know if that sounds antisocial. The same way.

I totally get it. Honestly, anything that's not, anything that's kind of in the way of craft, of production. I think the thing I've always had a natural skill for is idea formation. I can kind of pull together an idea, see what's going on in an area,

pull out a thread that's interesting that captures something. And then through hard work, I've built up over time. enough craft to actually express these ideas, you know, reasonably well. And it's like, okay, that's my jump shot.

And so how do I spend more time doing jump shots for a contender? And, you know, less time, I'm just really stretching a metaphor here, talking to shoe executives for advertising. All right. So there's my setup.

It's just a lot. It's like the back and forth, the conversations, the overhead, the logistics, the, well, what about we need this?

And can you sign this? And what about this? And also, I'm just ranting now, so thanks for this. This is a therapy session. Every once in a while, I'll come home to my wife and say, here is my impression of every person in the world. We need your time. So there's a constant influx of people coming in. Like, we need this, we need that.

Can you just answer this question? And, you know, like, everything's reasonable in isolation. It's just nothing, I went through a period a few years ago where just everything stopped scaling. I had this all locked down good. I would write. I did my book writing and computer science was great and was all locked in. And then it, you know, it got out of control because the books did better. And then I got tenure.

So in Georgetown, once you get tenure in academia, other obligations come in. So they kind of protect you from it pre-tenure so you can focus on your research. So it's a different type of job. And then after 10-year, it's can you help with university initiatives? And then deep work hit a nerve and so good they can ignore you. retrospectively hit a nerve and and that just then things kind of blew up in a way that book writing didn't, wasn't what it used to be, which is I just kind of work on these things. And when I'm done, it goes out in the world. And there's a couple weeks where I do a little bit of publicity and that's it.

Now suddenly there's everyone in the world needed my time. And so that's where I am now. There's just things don't scale anymore. So lots of people need my time for lots of things. lots of hats are spinning and the spinning is preventing me from putting on the best one. So what I'm trying to do here is do as many weird mixed metaphors as possible. I really appreciate you saying this out loud because I can relate and I'm sure many people can. This is one of the paradoxes of success is that success itself brings added stress and stresses your systems in this case, almost beyond the breaking point a little bit because the earlier systems hit their capacity. and it's this weird, I think nobody ever wants to sound ungrateful for success. Like you haven't, you're on Netflix now in the box special and things explained.

And you have a New Yorker column. These are these are crowning achievements of a career. And that success, you kind of get punished for it. I hate to say it. Again, not to be ungrateful, but the punishment is great. We're going to like crush your inbox even more. Now there's even more opportunities to vet and consider. So I just appreciate.

you calling that out. What I'm hearing is that when you're most in flow, it's when you are thinking, problem solving, and then the craft of communicating around that, writing, speaking, teaching, podcasting. Does that capture the flow state? Yeah, I think that sounds about right. And the friction is coming from not just the admin, one of my favorite words, administravia. just probably life and work admin. Admin that comes with tenure, a little bit of pressure. I think, you know, I'm hearing also just a sense of sort of pressure. How is it with your team members? You know, some people have the model where they have one chief of staff that manages all team members and points of communication.

I like how you describe what you do. So let us let the audience in on your setup. Well, I don't currently have a chief of staff because I try to get. every single person on my team working less, just like me. I don't believe in me having free time and then burning everyone out on my team. So I say nobody works full time, even me. Right now, just like you, I hire a lot of outside specialists. Some are project-based like creating a new brand for the free time book and podcast. That has a start and an end. Then I know you recently started working with Jesse as a podcast producer. Then there are people that are sort of part of the

core team on a recurring basis and there's no specific end date insight. So I don't currently have a chief of staff, but I know that, you know, once you get to about five plus people, even if they're all part time, there can be friction and communication where, as I call it, it's like death by a thousand question cuts. All of a sudden, when I started expanding my team, I became the bottleneck for everybody's questions. And although I was grateful to have a team, I also felt like, oh, I just don't want to be managing people and in meetings and answering questions all the time. So one of the things that helps me is my team knows that I don't like email, that I'm slow at it. I don't like instant notifications either on platforms like Slack. So I tell them, make decisions and take action.

Don't wait for my approval. I just constantly tell them, do not let me be the bottleneck. Make decisions, make recommendations. Tell me the deadline that if I disagree or don't want something to happen when I need to respond by, but if you don't hear from me, keep moving. So I'm constantly giving people ways to do what they do, even if I'm radio silent. And part of that involves a really good documentation too, that every time someone asks a question, it gets captured so that if there's team turnover, I'm not just recreating the wheel, training every new person. How big is your team right now?

It's about five part-time, super part-time. And when I say part time, I mean five to ten hours a week. No one really even spends 10 hours a week. It's like usually five hours a week. It's hard to spend 10 hours a week on anything. It's kind of a reality. Yeah. I don't know.

I've heard business owners say, oh, they really got to hire people full time. But for me, my mindset, as soon as someone, myself included, is full time, becomes about filling the time. Yes. I would rather have less time. People do less work, make things more efficient. Well, it seems like the people we know maybe in common who have a full-time person, it's usually because of that person. It was someone they were working with that was just so good that over time they evolved into that role to become like a right-hand person.

But it's not something you can go out and hire for. You can't put out an ad on LinkedIn jobs. I want to hire it. It's someone that you've known for a long time and they're just great and they've become involved in your business. And it's almost like a, that's what I don't know what you've seen. that's what I've seen. And usually I have one person like that. And then that's it. Like, I've never actually met someone in our space that had multiple full-time people. Yeah, it's interesting, depending on the business model. I want to come back to you for a second. One thing

you said recently was the archetypes underlying. It was a recent podcast of should I move to a cabin in the country? That was the listener question. This podcast is sponsored by four sigmatics. a wellness company that is well known for its delicious mushroom coffee. For Sigmaics mushroom coffee is real organic fair trade, single origin, Arabica coffee with Lyons Main Mushroom for Productivity and Shaga Mushroom for Immune Support. I like to drink this mushroom coffee right before each of my deep work sessions. The mushrooms give it a unique physiological,

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tone. You can use the Grammarly Goals feature, and they will make suggestions to help you match that tone. End of your feedback report, it can help you do a formal tone. Writing out a holiday card, it can help you write in a friendly tone. Let's say you already wrote something and you want to know if it's coming across correctly, it's built-in tone detector will tell you, hey, this is the tone of what you just wrote. I'm telling you, the things that Grammarly can do these days really is amazing. It really is like having that grammar nerd friend looking over your shoulder, making sure that you are communicating what you really mean to say.

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Like, if you put your Bill McKibben hat on or your Cabin in the Woods hat on, what shift would create more freedom for you? It's less roles. I mean, so it's too many roles. And it's a lot of the thinking I'm doing now is figuring out how to reduce roles. Now, Bill brought it down to extreme simplicity. So him and his wife Sue Halper, and who's a staff writer

at the New Yorker now, and is a Rhodes Scholar and smarter than all of us. So they were both very good at writing. They got it down to nothing, right? Like, it was, we will do freelance, freelance article writing. That's it.

And we're going to live so cheap that it doesn't really, we feel no pressure to do much of it. Like, that was their whole plan. You know, Bill was living in the sublet on Bleaker Street in Manhattan and was just, and it was expensive.

It was like a little space. He didn't own anything. He said at some point, a burglar's broke into their apartment. I think he was living with David Edelstein, the one on to become the famous film critic. And the only thing of Bill's they stole from the apartment was a cardboard box that Bill used to put his clothes in. And they used that to put in all of David's like beta max players and video players.

So they went extreme, you know, they went extreme simplicity. And that, the extreme simplicity does sort of appeal. But I think what he would say or what, you know, I did, I think who I'm interviewing is probably telling, right? I'm talking to you. I talked to Bill. Before that, I talked to Tim Ferriss. It's all people who, like, really advocate for designing, like, being very intentional about your lifestyle. But I think they would all say, you've got to reduce the roles. It's too many roles, which I agree with. That's what I'm trying to, at the big picture, so it's big picture, small picture. Big picture. I'm trying to figure out how to, what's the right

roles to reduce down to. I need to just the things that I do, I need to reduce. And then the little picture, which I think your book gets out really great as well in your principles is getting at, okay, but even for the things you choose to do, how do you set up the systems and structure that so that your time's going in the right place? Because you can take one, you know that, you can take one thing. One thing. All I'm going to do is a podcast. That, how many people have we met that their entire life is 12 hours a day somehow supporting their podcast? It's all these different people and this and that, whatever you choose.

So that aspect is important to you. So I'm thinking about both those things right now. I have some moves in mind for the big picture, just reducing roles that bloated kind of experimentally. And now I have to pull it back in again using what I learned. But even after I do, I know I have to be very careful about what remains should be tamed because the littlest things, I'm assuming you would agree with that, that the littlest focus is I'm just doing this can take up all your time.

Everything can grow. If you had to stack rank your top three of within all the activities you described, what are your top three? Well, I like being a professor. So I do like university. Oh, yeah. Let's say Georgetown aside. I'm assuming that Georgetown states. That seems like really core.

Though I need to rethink how I have that set up. I love being a professor and teaching my classes and doing research. I'm doing a lot of service right now, which is normal, but I'm not, my situation's not normal. normal because, you know, most people, it's like, now you're going to add this extra service onto your plate, which is reasonable for professors to spend time doing, but they also don't have the other things. And I got to tell you, it's a real source of confusion. I don't talk a lot about this part of my life in the academic part of my life. Now the cat's out of the bag, the prominence is too high. But even up until pretty recently, I kept those two parts of my

life pretty well isolated. And I think there was a lot of people had no idea what I was up to. And that caused a lot of dissidents. And I've talked about that before in the podcast, but just I remember having to tell a chair at some point, they're like, we need you to do this service role. And like, I can't because, you know, I'm going on an international book tour. And I'm just not understanding. They're like, yeah, you have this like student productivity stuff you do. Like those tips are good. But like, this is the important stuff.

You need to, you know, take this administrative role. And I'm thinking, I don't think you understand. Like, I'm touring the country. I'm going on all the major TV shows. Like there's teams of people involved in that. And so there was this like real disconnect. And so again, I'm going off on a, and that's better now because the cat's kind of out of the back. So there's work I have to do at Georgetown.

Let's just assume I can do that work and figure out how to make that role reasonable. I don't know. That's a good question. I mean, book writing has always been my thing. Podcasting is new, but somehow it seems valuable. It seems like just the way that blogging seemed valuable to me 15 years ago, like I think I should be doing this. I should be in touch with my audience. It feels like podcasting is a new blogging.

So that seems important to me too. And the other stuff, I don't know. I don't know. It's just kind of accreted over time. Where does something like the New Yorker fit in? Because don't you write twice a month? Yeah, that's temper. Yeah, that is true.

But that's for a limited duration. So not to get too much into the weeds on it. But that was never meant as a permanent thing. I wanted to do it this fall because it felt timely. The topic was very timely to what was going on this fall. Everyone's rethinking work as the pandemic is in this later stage. It just felt like a really good time to be writing about that. Absolutely.

But yeah, that was pretty clear. I wasn't going to be able to write a twice-month column in the perpetuity because that's basically a full-time job. Right. I know. I was thinking even recently, it's so funny you bring this up because I was thinking truly, truly, how is he doing all of this? And I think what happens is that you had this real energetic pull, like a magnet to podcasting. And I'm glad you did. I've been listening since the day you launched. And knowing you and

knowing your values, which is still part of this align stage, is that it does align with your values. You're connecting with your community. They're asking really interesting questions. You get to just riff on the mic. It's something you're good at and produce twice a week. And you even kudos to you brought someone on to help you as a producer. And you created a studio. Like I love hearing your journey of just creating a studio so ritualizing the space. And I think you created a writing shed too. did you not? Or your aspiration is a writing shed. I'm an aspiration for a writing set. The offices I have now, the HQ has a studio and a writing room. And like, it has various offices. Some of this is just pandemic boredom, which we should, we should say. Well, I just love the physical manifestation of your values and the work that you most enjoy. And having known you for over 10 years, I do think we can unquestionably say all of us here on behalf of your listeners, your books are brilliant. And this is.

is a huge part of how you contribute to the world. So your books aren't going anywhere. Your podcast has that zing of energy to it. I just hear it in your voice. Like, I don't know what this is, but I like it. And there's momentum and you've created space for it. And the New Yorker is a time-bound thing that's high status. It's just freaking epic that you are writing for the New Yorker. It seems like then you'll get these one-off opportunities like the Netflix special, which is really cool to be part of and that you'll know when you're sort of jumping out of your chair. And I would imagine that everything that goes beyond these are sort of legacy holdovers. So for one thing, I would just start to question.

For example, I don't think people realize it's just a podcast is so much work. It's so joyful. But if you launched your podcast without, let's say, ramping down how often you post on your blog, there's going to inevitably come a decision point where you go something's got to give. Yeah. It sounds like probably one of the biggest drains is this. as we all experience, why you wrote a world without email is email, decisions, and meetings. Yeah.

Would you say that's the biggest friction bucket? Yeah. Yeah. Switch a context, answer a question, do a meeting. Yeah. I'm getting curious about the context switching, because I know you talk about that a lot. Do you feel that if you reduced that, let's say, to one day a week, would it still be too much? Like, if you were to address the context switching aspect of it,

would you be okay with the volume that requires you to weigh in? So you're talking about in this hypothetical all the various things that come into my inbox, putting that aside to like one day a week, basically. Yeah, if you checked email once a week, would anything fall apart? If you got back to your team members, one or two days a week, would anything fall apart? All right. Well, let's see. Let's do it.

I'm going to load this up. Let's look at what's in here. Okay, I can't wait. Let's do an experiment here. There's multiple addresses, multiple inboxes, so it takes me a second. Okay, so in this one, this is all things from the last 24 hours. So there's something from one of my speaking agents, something from my mom, something from an admin in the department, something from a New Yorker editor, something from someone else in my department. Barber needs me to confirm I'm coming for a haircut, a couple things from you, something from, oh, there's a documentary film product I'm involved in.

So let's just add that to the list of something from the director of that. All right, different inbox, something for my agent, a podcaster inviting me on. This inbox, someone who heard one of my talks and wants to go on a call, someone who, oh, this is cool. Someone heard on a recent podcast we were talking about designing a, what I learned, a kindergarten poster, but for Cal Newport advice, and she made one sent it to me. All right, moving over to another one. final exam.

There's a lot of Georgetown stuff. I won't get too much. There's a bunch of Georgetown stuff. It's not, the details aren't interesting, but obviously Professor Life generates a lot of email. So those are full of things. We'll skip those.

And then that's it. Okay. So I'm thinking about what I just said to you. I don't, I mean, honestly, I basically already just do this twice a week. Because I just don't have time.

I mean, I'll just, I block my time and I'm writing or I'm recording. And so like a day or two will go by and then I'll get back to people. and people get upset about it, but that's kind of the reality of my life. So maybe I'm already kind of close to that. Let's talk about the second stage design is ideal outcomes.

So describe to me your ideal work. If I was able to wave a magic wand and as a result of this conversation, you had a breakthrough. What does your ideal week look like? Oh, man. Autonomy, autonomy, autonomy, right? This is why book writing is well suited for me. give me a big project that's intellectually demanding and say, I'll see you in a year and a half. That's like my ideal.

Tons of autonomy. Your time is free, but you want to make progress on a small number of very important projects, and it's just kind of up to you to make progress. And you can kind of, there's not much on that calendar. Not seeing much on a calendar is a secret joy of mine. There's just not that many appointments. There's not that many calls. I just like autonomy.

Hey, if I'm having a bad day, I don't have to do much today, no big deal. Maybe tomorrow I'll do more. To me, that's ideal. I love it. I can just hear the smile in your voice when you say like, oh, an open calendar. It's just a secret source of joy. Yeah.

I mean, come on. There's nothing better. Blank day in Google Calendar. I mean, come on. Yes. So what I wonder is that if as you've grown more successful, which is awesome, like as a result of your hard work, it's almost like the calendar, it's just these little fractures,

these little things started to impede on this like pristine, beautiful, quiet calendar. So it sounds like what your ideal is, as you said, autonomy, autonomy, autonomy, bigger, but fewer projects where you can really dive deeply and where people know what to expect from you. You say, I'm not coming out for a year and a half. Just like you, I can relate where when I'm working on a book, it's almost the perfect excuse and people understand. It's like I'm working on a book, see you in a few months.

So it sounds like you're also quite happy. happy when you're in that mode. Yeah. Yeah. Is there anything else that would have you feel total time affluence? Fewer projects, simplifying, deep, meaty projects, sounds good. Yeah, fewer projects.

Yeah, this sounds good, though. Fewer projects, bigger, but executed more on your pace and minimizing more of the sort of smaller incertices, the things that sort of this and that a little bit, why not do this, line us do that, the opportunities, etc. Yeah, maybe it's not so hard. sounds about right. I mean, I'll tell you, here's where I put your advice. Your book helped me is podcasting. So I agree. It feels like there's an energy to it. It feels important. I love to just democratize. You control the medium. So I did it myself, learned a medium, did it during the

pandemic when, you know, you were kind of on your own anyways. And now what I'm doing based on the systems thinking from your book is working with Jesse now. The goal that Jesse and I are going for is called the 90-minute goal. And we're getting closer to it. And the 90-minute goal is I walk into my studio, I sit down, 90 minutes later I can walk out, and there's the two podcast episodes will appear that next week. I love this. We're getting closer. We're working on it.

It's not, but we're getting closer. You know, Jesse pulls the questions for me now. We bought a printer. He prints them out for me. They're waiting for me. He runs the computer. He runs the recording software. We're doing videos of all the questions as part of the plan.

But when I say, we, I mean, Jesse is. So the camera's turned on. And then that gets worked on later. He can, here's the ad read you need to do, gets the files to the mastering person posted. And we've been working on it week by week. They get more of the stuff into it. We're seeing where the time is being wasted. Where am I spending too much time?

When am I taking too much time on questions? And we're getting there. But it's a very Jenny Blake free time type idea is like, okay, figure out the system here that just says the 80, 20 of it, most of your time is in talking to a microphone. And almost none of the time is sending easy. emails to a sound engineer or adding transition, dragging transition effects in an audio editing software. So that's great. I'm like, this would be great. If there's like a

half day each week, that's the vision. And I'm at the studio and doing podcasting and thinking through that part of the business. And that's where that happens. That feels controlled to me. Yeah. I love this. Yes. And just to highlight what you did. So align, the podcast is aligned. It fits your values.

So I think that's really important to the first check is not how to optimize everything a person is doing because you shouldn't optimize something you shouldn't be doing in the first place. And I think we change and evolve. And it's so important to drop things that are no longer aligned. And one of my favorite quotes, John Maxwell, you have to say no to the good so you can say yes to the best. It's kind of cheesy, but sometimes you have to drop good projects, good requests, good speaking gigs. You have to drop some good stuff, especially the more successful you get. So the podcast is aligned. You and Jesse designed this 90-minute sniper operation. I friggin' love it. And then a sign you've given Jesse more and more

responsibility to get to this goal of this 90-minute power session. So Jesse now vets the questions. Jesse prints them out. Jesse's the one doing the engineering and editing. I mean, that's just incredible to see how you followed that process, even if you didn't call it that. But we can see how that has created some freedom for you that now the podcast is in a happy place. You know, you have your studio, you have Jesse, you've delegated a lot of it so that closer and closer to that vision where you show up and do what you do best, which is riving. I love it. All right. So we can review for the listener.

So the align came first and then assign came third. Say again what the second one was. Design. Right. Okay, good. And that's where you're featured in the book. Yes. Because it's about designing the ideal outcomes of the project, the ideal impact, let's say, of the podcast, and designing the process before you assign it to someone.

Because what happens is sometimes people just jump to assign things, but they haven't really thought through. What is my ideal outcome here? What is the ideal impact of this project or business area? And what is the ideal process that we're going to follow? So what you and Jesse did so well is come up with this 90-minute process. And you designed it before you'd, because you could have just brought Jesse on and said, hey, could you read all the questions and we record on Tuesdays? Or like make a podcast work. Go. Right. And in that case, you're both fumbling in the dark. And so what you've done now is set this really aspirational design on the process. So align, should I be doing this at all? Does it fit my values? How? What kind of podcast aligns with your values? and your energy and your strengths. Then once it's aligned, then you design ideal outcomes impact process.

Then you can assign who, when. So then you say, okay, Jesse, on these days, we record and the episodes go live twice a week, right, on schedule. And a podcast is a complex thing. So it's a great example showing that that can still happen. I mean, every episode of a podcast is a little mini project unto itself. Yeah, it's not trivial, folks. But I thought about your design because I'd read the early version of the book. So that was in my head.

You read the very embarrassing version and still blurbed it. So I'm very grateful. In PDF format. But that was definitely in my head of, okay, wait, figure this out. And that's who do I, I need someone to do this and that. You have to send it out here. And how does garage band work? And how does the microphones work?

And yeah, and then you assign. I like that. So align design, assign. The hard thing, I guess, is, What's the hardest for people? Is it a line because that's where you say no? And that's where you say this could be an opportunity or money or whatever the thing is, but I'm going to not do that. And some people might be upset, but I am going to do that. Is that where the rubber hits the road when you're trying to. I think you just hit on something that yes, I think sometimes why is it that we're overwhelmed by email? It's exactly what you say in your book. We have this primal need to please people, at least I do, to make people happy to not disappoint them. to not let them down. And what I find so fascinating about email as a medium is that you and I, Cal, like we have no control over what comes into our inbox on some level. Like anyone who can find

one of our email addresses can send an email. And yet I experience the impact of once they all arrive, I'm overwhelmed or I feel guilty or I get anxiety. So it's like on the one hand, we have no control over what comes in. I mean, again, we can. can set up filters and apps and tools and different aliases and you do so well of setting expectations of for interesting ad. I don't usually reply to these. But the bottom line is that once you start getting inbound emails from things like the documentary you're working on or, you know, they start to be things that are not obvious to say no to, that's where I feel like the pressure grows and it's not going to go down. So I do think that the align piece is about yes, it is being willing

to say no, being willing to say no to increasingly good things, being willing to disappoint people, as you and I are being willing to be curmudges about social media, being willing to be slow at replying to email, being willing to be slow to reply to your own team. You know, I think that I like to run experiments that question my own expectations about how quickly I need to respond to things. Yeah. So even like with your speaking agent, for example, maybe you ask her, and maybe you already do this, but send me all requests in one weekly email and I'll review it one day a week, but I'm not going to review them one by one unless it's truly urgent and the event is for the UN and it's on Tuesday. By the way, I've literally had a request, that request. Well, there you go. And I didn't. And I said no. I said no.

You mentioned Tim Ferriss. He talks about the Peter Drucker quote, don't make 100 decisions when one will do. So I've loved watching him say, I will not read any new book in 2021 or 2022. I like thinking about, you know, credit to Tim and Peter Drucker, but I like thinking about what one decision can I make that cuts out all the rest. So the day I decided not to participate in online summits anymore was a happy day. My team, not only did I not need to make the decision, neither to my team. What else have you, in doing a line in your own work, what are some other examples of things that you took off the plate? Well, definitely around calendar. I don't meet after certain times.

So what I think is helpful with the spacious calendar and like, see, Cal, this is what I think would be so interesting for you is what if the, like, so I block off Mondays and Fridays on recurring. There's just a block that no one can schedule. And then I block off the fourth week of every month. month, and that's recurring. I'm so curious, like, what would happen, not the Georgetown stuff, but what would happen if people could only meet with you one week a month? What would happen? Like, would things break? I would just be so curious how that experiment would go. Definitely telling my team anywhere that they can proceed without approval. I just, I basically want everyone to always, I call it making ourselves replaceable every day. And also, I'm just constantly saying,

don't let me be the bottleneck. I might try to wiggle my way into this and don't let me, you know? So I kind of get people involved at a meta level. So speaking change for you, right? Because your shift towards licensing IP versus more consultant style engagement. That was probably a big one. Recently a big one around speaking was I stopped negotiating my prices. I used to send out custom proposals, even for licensing. I used to send out custom proposals and just go, oh, well, a proposal is just a starting point. Whatever, whatever the organization, whatever their budget, I'll work with them and we'll figure something out. And this created a lot

of friction around creating a proposal from scratch for every client and then negotiating with them and feeling bad if they negotiated me down and I accepted at too low of a rate. And this is just something I've found challenging over the years. And recently it felt really good. I put out my rate, they told me their available budget was about half that. And I said no. I just said we have pivot facilitators. And it felt so good not to have the cognitive load of, well, should I do it for less? Should I negotiate? Now, it is a privilege. There have been times in my life and business

where I'll say yes, no matter what. Like any paycheck is going to be critical. But where I'm at now with my time and my energy, that rule of not negotiating is very freeing. And then on the proposal front, instead of doing custom proposals, my friend Lindsay taught me this, and she learned from Alan Weiss, she just has three standard options,

good, better, best. They're not negotiable and they don't change and they're not different for any next client. And so I think these kinds of standardizations are really helpful. and just reducing the, again, this bespoke customization of things, that creates a lot of friction. Right. Yes.

You're offering a product as well defined. You're not offering access to you as someone to hang out with and talk to. Yeah, and everything's not up for negotiation anymore. And it's not, you know, I think who teaches this really well is John Worrello in his book Built to Sell. And he says, instead of offering. this huge menu of services, pick one thing and create the systems and process and documentation around it and do it well. And that is going to be a bigger service to people than doing 10 things

customized for every different client. That's 10x the level of complexity. And that's really hard to maintain and more mistakes happen. And so at the end, everybody's actually happier. And this kind of ties into your question, Cal, because the whole point is that if you say, simplify, you can focus. And I know you had a chat with Greg McCown of essentialism. My favorite diagram in his book is that he shows focus that when we work on too many projects, our focus are these short rays out of, let's say, an image of a sunshine. And we have like 10 short spokes radiating outward. But when we focus, we have one. We have one ray that is big and tall and it's so powerful. And so I wonder, like for you, it's like you have book and podcasts, and I just wonder how ruthless you can be about cutting out some of the rest.

I'll tell you what, I've got some plans in store that are pretty ruthless. And inspired in part by your book because it makes concrete this intuition, I think a lot of people have of the way I'm working is not working. There should be ways to simplify this, but not just, as you talk about, it's not just about, that's a lifestyle business. where I want to just barely work and just make enough to live by the beach or whatever. No, like a really good, impactful doing your best work, being well compensated for it, but also without being in seven Zoom calls a day. Those two things are possible. Those two things.

Your book, I think, does a great job. And I'm holding back a lot of details now for privacy. There is some ruthlessness queued. And you probably would see that. It's pretty cyclical sometimes, right? So you go through a period. Like for me, the pandemic was a period of exploration, right? As part of my response to it is I want to rethink my business and what I do and let me put my, I'm going to put some irons and some different fires and try to see what's going on.

And now as we get past that acute stage, like now it's time to take in all that information and get back to principle one, stage one, step one, align. All right, now we got to redo that again. And sometimes we have those moments, I suppose, where let me let me get back, try some different things and experience. with this and that and what's working and what's not and what's becoming overwhelming and integrating that data back into your decisions. And that's where I am again. But free time, the book, I would say, has been a great guide, which is why I'm glad you wrote it. Thank you so much. I'm so thrilled to hear that. And it was really exciting to have you go on the cover, front and center, because that's really what free time is about. It is freeing

our time, yes, to enjoy leisure when we have it, be truly present. with our families, with ourselves, our coveted solo time, but also freeing up our time to do more deep work. And I just resonate so much with your work, Cal. And I think I can speak for all of us when I say, like, we would celebrate you going into Hermit mode to write your next book because it's exciting. Like the next books, that's where the real, you create such transformation for people. And transformation in the conversation, you are so able, the fact that your books are getting picked up more by the mainstream. It's not surprising. And it's so cool to see that. And so I guess my parting thing would be permission to question all the assumptions to around who needs what by when

that it's like the permission that that we are able to give when we say, oh, I'm working on a book. Sorry, I'm going to be a total recluse. It's a great one. Yeah. It's like, oh, it's the best excuse. And I write books about every five years. And I have to say, I was the happiest writing free time because I was out in the woods. I was in the cabin in the woods. And of course that shifts, like when we go into marketing mode and doing a podcast tour and these things. So of course, it's not like we do that necessarily constantly. But I love how you've already got your eye toward designing that next beautiful pocket for yourself. So I'm just really thrilled to hear that free time was helpful. Well, and inspired by your openness in that book, I will be

talking about or writing about my retreat to Hermit mode as it happened. So it's It's fun. So the whole world can see. That's what makes it interesting. It's like, look, okay, things got, I had things locked in. Things got out of control. Now I'm going to lock them back in again. And everyone can have a front row seat to, you know, me being yelled at.

I get yelled at all the time. I'm going to use to it. Well, I think it's also refreshing that, because I get a lot of imposter syndrome around. Shoot, I wrote a book called Free Time, but like I've been sick twice in the last month. So I'm clearly doing something wrong. And oh, no. I was having all these fears that the book is coming out and I'm overwhelmed. I'm overwhelmed by family life and house admin and house repairs. And sometimes it can feel like so much pressure,

even as those of us who write these books, to like live it all perfectly all the time. And that's really not how it goes. As you've said, too, we write to figure things out. And I think the fact that you have been so open and vulnerable sharing in this conversation and that you will do that in your next book is such a gift because I think it gives the rest of us permission that, okay, if even Cal doesn't necessarily have this solved all the time, or that as you become more successful, you have to deal with like the next level of the video game around these principles. That is very comforting.

And so I hereby second and affirm your direction of just sharing your process as you go. That would be a real gift. I love it. And I'm going to blame you every time I say no. I'll say no. Yeah, perfect. Jenny told me. So, right.

Everyone, remember, the book is called Free Time. It comes out in March, but right now, if you do the pre-order, you get access to the audio book early, and you get a version you can gift to someone else. Jenny, where do we go to take advantage of this pre-order campaign? You can go to It's Freetime.com slash book. So that's ITS. It's Freetime.com slash book. If you want the direct URL, it's just fun to say, it's freetime.com slash bogogo. Buy one, get one, give one.

And check out free time wherever you listen to podcasts. And I would just recommend don't email Jenny and try to negotiate a different pre-order offer. She doesn't do that anymore. Oh, my goodness. Or if you email me, just know that I put the snail back into email and it will be a while. But I'm going to believe that on you, Cal. We'll trade permissions. When I say no to speaking engagements, I'll blame.

you. And when you email back real slowly, you'll blame me. And that'll all work out well. And then listeners, you can blame both of us and you can say, sorry, I'm working in a new way now so I can do my best work and take care of my instrument. Yeah. So it's great. It's a whole circular blame game that gets us all a little bit more free time. Which is the title of the book. Yeah, creating new work of the world. All right. Well, Jenny Blake, thank you. Thank you for coming on the podcast. And everyone, check out the book. All right. Well, thank you to Jenny Blake. for joining me for today's episode. We'll be back on Thursday with a listener calls episode.

And until then, as always, stay deep.