273: Navigating Time Anxiety, Reducing Inbox Dread, and Creating Ease Loops with Chris Guillebeau

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Ask yourself did today matter? It's not so much about was it a good day or a bad day, or even a productive day or an unproductive day. It's just like some days we can say, oh, actually, I don't really know what happened today. Like I did sit at my desk for a period of time. Maybe if I think back I can review some of the tasks I completed. But it doesn't really actually add up to much. And that's fine. We all have days like that. But wouldn't it be better to be able to be like, yes, today mattered because I actually made some progress on this thing I'm really excited about and I spent time with people I love and invested in those relationships and I also took some time for myself and this is something that's been really good for me. So yeah, today mattered.

This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host, Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.

Welcome back Free Timers. I am so delighted to be dropping into your feed today with a conversation with one of my longest time friendors in this wild online world that we're in, Chris Gillebeau. Chris, or as I call him, CG, is the New York Times bestselling author of the $100 Startup Side Hustle, the Happiness of Pursuit and a few other books. During a lifetime of self employment that included a four year commitment as a volunteer executive in West Africa, he visited every country in the world, 193in total, before his 35th birthday. You might have even attended the World Domination Summit at one point, which is this very popular event in Portland, Oregon. And you might also have listened to his PODC that he has published every single day since January 1, 2017, the side hustle School podcast that I'll put in the show notes. And today we're talking about his brand new book so related to this show, Time, the Illusion of Urgency and a Better way to live. Cg, welcome to the show.

JB Jenny, Blake, thank you so, so much for having me. I've been so excited for this conversation because we've been connected for years and years and I appreciate that. The drop in episode of the podcast, I know it's, you know, you've gone back and forth on it and I'm sure listeners will be excited to hear this new episode as well, so thank you.

I've taken a page out of your new book even before I read it, which was not doing things perfectly. Like, I really love when I can be super consistent with the podcast. And yet for so many reasons, my capacity changed. So now my criteria is do I leap out of my chair to say yes and get this person scheduled? And you fit that. And having known you since, I think, 2009, we've just been, you know, watching each other from near and far go about making up this unconventional path. So it's really an honor to have you here.

The honor is mine as well.

How do you decide when an idea like time anxiety, when it's time to shape it into a book? Like, when it's big enough, when it's the book that you and only you can write?

For this one in particular, I wanted to write a book that would change me. You know, I think it's important. Like, if we're writing about personal growth, we're not approaching it from like an academic perspective or a research perspective. Like, that's part of it. But for me, that was complementary. I also was just like, I have been struggling for a long time with not knowing what to do next or having this sense of distress or discontent over how I spend my time. And so it was partly like, I need to solve my own problem. And, and then secondly, I think it was as I just talked about the concept with different people, like, people would say, oh, what are you doing? I'm like, oh, I'm exploring this, this idea of time anxiety. And I noticed probably more than anything else I've done, or at least in like the top three, the response was just really strong. And almost everyone was like, oh, I have that. Or I've never heard that phrase before, but tell me more about it. Because so much of my life is governed by my relationship with time. And I feel like the relationship is not very good or not very healthy. And so it's like, if everybody has the problem, or at least a lot of people identify with it, then that to me kind of shows, oh, I might have actually accidentally hit on something here. And then it's kind of worth doing. And then the last thing is, like, I always have this thing about pay attention to the ideas that don't leave you. Like, we all have different ideas from time to time, and not every idea is a good idea, but the ideas that tend to be the ones that stick are the ones that just keep coming up. And you might go away and explore something else, or you might think about something different, but then you keep coming back to this one. And like I said once, if you wake up at night thinking about an idea, then that might be an idea that's kind of worth paying attention to. And you'll be better off if you pay attention to that idea and do something about it than if you don't. So that's kind of how I ended up with this concept of time anxiety and then writing a book about it.

One of the things I love about the book is it's a very gentle approach. And in a way, you're dismantling a lot of the productivity hacks around time management that we're so used to reading in this space. And so there's a very calming feeling of reading the book, which I'm sure is by design. You talk about two main types of time anxiety. Existential time is running out in my life and daily routine. There's not enough time in the day. So I'm curious, did you encounter any time anxiety while working on the book?

Well, it's. Sure, sure. It's nice what you say about the gentle approach. It took me a long time to get to that. I wish that I could have written it all in one draft, or probably not one draft, but like two or three drafts, like a normal approach. I think I probably wrote this book five different times and I actually worked with two different editors on it. And I am very happy with how we ended up. And I kind of switched to this more neurodivergent, accessible writing tone that is kind of like lots of practical stuff interspersed with stories. And I've done that before, but I did it a little bit different in this book, as you mentioned. And did I experience time anxiety? Yeah, well, I always want to do things faster, you know, Like, I always underestimate the amount of time something is going to take. And that's why I actually like to work with publishers as opposed to self publishing, because for me, if I self published, I would never, like, it would never get done. You know, it's like. But to have a publishing partner, it's like, oh, there's other people involved. There are some Deadlines, I don't want to let them down. So that is helpful to me. But as for the, like, the two types, I thought this was especially interesting. Like, as I was talking with people and everybody was responding and saying, I have that, they kind of split into two camps with some overlap. And one of the camps, as you mentioned, is existential, which is kind of, what should I do with my life, or time is running out of my life, or I feel like I'm too late for something, or I have regret and, you know, I wish I'd done things differently when I was younger or whatever that looks like. And then the other type is the, like, I don't know what to do right now. Of all the different options available to me, like, how do I choose what to spend my time on? Or how do I fit in everything? And you know, ultimately these two forms are connected and I've definitely experienced both of them and I still do to some degree, but I think I have a lot more like, self insight and understanding over them. And that's been very helpful.

I always find it interesting when authors like you go through so many major revisions. Not just the usual process of developmental edit, copy, edit, proofread, but actually reshaping the book. In your case, it sounds like five times.

Yes, I would prefer not to. It's not that it's a good thing.

Totally. So what happened with versions one through four where you just weren't happy or your editor wasn't and then how'd you know you'd finally arrived at the main type of manuscript you wanted?

Yeah, well, I think ultimately you just have to kind of like, I probably could have done more, you know, I guess, you know, for the second part, eventually you have to kind of freeze the design. You know, nothing is perfect, but we try to get it to a place of, okay, this is, you know, this. I do feel, feel good about it. Right. I feel. I feel proud of it. What was wrong with the first versions?

There was just. There was more storytelling and less action. I wanted to write gently, as you said, but also kind of viscerally. I wanted to be like, okay, if you are in this situation, if you are feeling really overwhelmed and distressed, how can this book help you? And you shouldn't, you know, it shouldn't be like, you know, I get to chapter eight before I see some light at the end of the tunnel. You know, it should be like, right away. And then there should be a process of like, okay, now that I understand this thing about myself, now that I understand how cognitive distortions affect my worldview and my behavior and my planning. And now that I can kind of give myself some time in some ways, what then does that lead to? How does that help me understand time blindness? How does that help me? And like, like just a whole, like sequencing. So working a lot on the sequencing of it. Um, just the rewriting, going to like much shorter chapters. I think there's like 27 chapters or something as opposed to like, you know, typical like non fiction prescriptive book is like 12 chapters and so.

And citing every academic study under the sun.

Yeah, exactly. Right.

Well, in the marshmallow test, we learned 5 year olds have time anxiety.

Right? Yeah, that's like my least favorite test, by the way. You know, what's wrong with eating two marshmallows? You know, like everything.

And if you're hungry, if you have food shortage at home, you're going to eat every marshmallow you can.

That's right, that's right. Yes. I'm glad we agree on that. So, yeah, it took some time and really grateful to my editor for helping, you know, a ton with that. And then I worked with an illustrator, Emily McDowell, who's done some really great work.

So I didn't realize those were Emily's illustrations. They're so good.

Yeah, she's wonderful. I was really happy and she agreed to work on the book. So yeah, maybe next time it'll be faster, but.

No, no need, no need. I'm just so curious about the process and it's such a heavy lift having to do a major revision. Not just the cosmetic, you know, smaller stuff. And I just want to point out Emily McDowell is a brilliant illustrator and a brilliant writer. Her substack is amazing. She has a podcast that she was the co host of called Quitted. So I think free timers, you'd really love binging those episodes. And I'll put one of the illustrations in the show notes. Coincidentally, I had just finished reading Laziness Does Not Exist, a book by Devin Price, partly because I was going through my own almost catatonic state. Like I just could not bring myself to do even the simplest things like sending a single text message. I was just, I don't know, it was a phase. I'm having a millennial midlife crisis. Who knows? You also highlight that when, when people feel lazy, because it's not just other people saying, oh, you're lazy, you're not effective at managing your time. Sometimes we say it to ourself and you point out early in the book that that could mean lacking Support. It could be underdeveloped executive functioning skills. It could be negative self talk or friction loops, which we'll talk about later. But I would love for you to just debunk this idea that if we're not hyper productive all day, every day, were somehow lazy.

Well, yes, I think you said it very well. And then also it's very easy to get stuck on small things. And small things can seem like big things. So for me, I've often for years and years had a big problem with email communication. And I tend to be either really fast or very slow, you know, and so when people are like, oh, you got back to me right away, it's like, if I didn't, then I wouldn't get back to you for weeks and weeks and weeks or months or not at all. And so what is the problem with that? Is it a problem of time management? I don't think so, because I know this is a problem. Like I'm thinking about it. It's not like I'm, it's not like I've forgotten about all these emails that I haven't responded to. You know, there are things in my life I could do that I could cut out in order to be able to like, you know, be more responsive. Sometimes I will have like open blocks of time and I'm sitting at my computer and I'm like, oh, you know what would be a great thing to do would be to go and respond to these people that took the time to write to me and they're not like sending me AI written pitches. You know, these are like friends or people I care about or colleagues. So why don't I do that? And I realize I have this great resistance to it because of some of those reasons you mentioned, like underdeveloped executive functions or I have this freeze, you know, like, these are the reasons. It's not because I'm lazy. I actually like to work. And working makes me happy. And I'm kind of compulsive about working, working and my habits and such. So I realized there are other answers for why these things are difficult. And maybe for somebody who's listening, their problem is not email communication, it's something else. Some people struggle with cleaning the house or, you know, doing things that other people think are kind of basic, like hygiene, for example, can also be difficult for some neurodivergent people. So once you understand, okay, it's not just that I am lazy, I'm not a bad person. There is some reason, you know, whether a neurological reason or a sociological Reason or like this is some, you know, related to some pattern in childhood or something. Maybe there's some secondary gain that I receive in like beating myself up over not responding to email. Once you start looking for the other answers, then you kind of relieve some of that feeling of shame or that inadequacy or whatever it is, and it might actually lead you to a solution or at least some understanding or some grace.

You also talk about how for some neurodivergent folks, they naturally cycle between periods of hyperfocus and sometimes burnout. But that even prior to burnout, hyper focus means I'm really on when I'm on and I love it. And I'm in the zone and I'm flowing and I'm so productive and on fire. And then it just needs to be followed by a bigger pause than what might look, quote, normal on the outside. And I love how you say rest will come whether you want it or not. Oh, haven't we all experienced that? I'll speak for myself. I might be feeling lazy, but it's actually rest asserting itself. Even if the only thing I'm going through is psychological. It's. It might not even be be that I put in such a grueling eight hour computer day. Might just be the change process.

Well, yeah, I mean, everything has a cost, you know, when you use your energy, it has a cost. And I like to think of this analogy from producing live events. You know, in my very early days of producing WDs, which you were a part of several years, I learned from the production manager, Steve Harper, that we were working with. He was super smart and very, also very patient with people like me because I didn't know anything. And he was planning like a rehearsal day. And I was like, Steve, do we need a whole like an entire day for rehearsal? That's expensive, you know, with the theater and the crew and you know, we're kind of like improvising a lot of stuff and like, everybody's fine, they all know what they're doing and stuff. And he was like, you have a, with any kind of event, there is always a rehearsal. So you can either have the rehearsal on a, you know, separate time or, or the rehearsal happens the day that you actually do it. Like when you do it live, that is the rehearsal, right? So you have a rehearsal whether you want to or not. And it's much better to have it in advance so that way you notice what needs to be fixed or corrected and such. And so rest is like that too. Rest happens. Like you, you. Whether you Want it to come or not? You have to have a time of rest. And so if it comes and you're just fighting it, then that's not gonna be good for your health. You're gonna be very unproductive. Like whatever work you try to like push through, the quality is going to be low. Then you're going to be mad at yourself and you're still not getting the actual rest that you need, which will, then if you take the rest, then you'll actually be able to go back to the period of focus. So for a long time I think I understood, oh, I have this ability to hyperfocus. I just didn't understand that, like, oh, I'm also crash. Like I knew that I crashed, but I was like, I just have to push through and allowing for some greater periods of rest, you know, and then, okay, let's hyper focus some more. That's been super helpful and I think a lot of people don't understand that.

Well, you also mentioned daily rituals by Mason Curry, which is a favorite of mine, and he has daily rituals of women at work. Because in the first edition all these women were just taking care of their creative stuff.

Right? Right.

It was like, oh, and then their wife made meals and got tea and took care of the kids. You say that a common pattern that Mason found is that we really get about three to four solid hours of focus a day. But it's the factory system that. And I'm reading a book, this academic wrote a book called Free Time. So I thought, well, I gotta read that, you know.

Yeah, great title.

Yeah. Doppelganger is very academic and heady. So I don't know if I could recommend it to listeners. It might bore you to tears. Unless you really want to know the history of industrialization and the factory age. But essentially I personally think that the eight hour day works for no one other than the boss. I don't know any human being that would thrive more working, forcing themselves to work eight hours than to try to really make the most of that three to four hour chunk. And then dropping some of the guilt around, not just parking in front of the computer just to hit this arbitrary number. That again, like mostly benefits the owner of the company, not the human beings working in it.

Yeah, for me, one of the things I, that I took from that and some other research Dan Pink has done a lot with this as well is like, we, we can work like a good amount, but we have to do different types of tasks. Like we get those three to four hours a day and then you Know, as you said, nobody should be sitting there for eight hours. But you know, if you, if you have some autonomy and control over your schedule and you know, you want to work, you know, six or seven or whatever the number is, you just have to, you have to be doing some different stuff for that second half of the day. Or for some people, their peak period may be in the second half. So then it's kind of reversed. But yeah, understanding, okay, I have like two to three hours, you know, maybe four, but like, not much more than that, that I can actually like cognitively focus on something. I need to actually really protect that time. And I need to because I am pretty introverted. I don't like to do a lot of like phone calls or meetings. I can do them, but they kind of take some of my energy. So I want to try to like protect, you know, some of my best hours and like understand what those are and then plan for what I'm actually going to do during that time. And when I actually plan and like, oh, I'm going to do these three things, like not my list of 12 things, but these three things, then I can actually do those things. And then anything else is a bonus. You know, if you do more, you're like, oh great, I got more. But deciding what is enough is, you know, something else I wrote about it in the book is like, for most of us, nobody decides like, no, no, like there never is enough. You know, there's always something else that can be done. If you have a job and you're doing some kind of knowledge work, if you work faster, if you work better or more, more productively, then your reward is that you get to do more. And the same is true with you being self employed because there's always like so much more you could do. But if you decide for yourself at the outset of the day of the week for the project, you know, for whatever it is you're doing, this is what enough looks like. Then when you reach that point, you can actually celebrate as opposed to like, okay, let's pull down the next thing or let's expand the scope of this thing and then you're going to feel better.

I love how you share also three reflection questions to that end, that at the end of the day, just a quick check in, no super scientific process. Did I create something? Did I help someone? Did I take some amount of time for myself?

Yeah, you can also just do one question and ask yourself, did today matter? You know, this is something else I learned a few years ago that just you know, did today matter? Every person who asks themselves that question, and you answer the question, you know what your own answer is to it. It's intuitive. And you can look back and say, it's not so much about was it a good day or a bad day or even a productive day or an unproductive day. It's just like some days we can say, oh, actually, I don't really know what happened today. Like, I did sit at my desk for a period of time. Maybe if I think back, I can review some of the tasks I completed, but it doesn't really actually add up to much, you know, in the end. And that's, that's fine. We all have days like that. But wouldn't it be better to be able to be like, yes, today mattered? Because I actually made some progress on this thing I'm really excited about, and I spent time with people I love and invested in those relationships. And I also took some time for myself and I went to the spa fis. Right. And. And you know, like, this is something that's been really good for me. So I did that for me. And so, yeah, today matters.

Even ironically, I remember when I was reading, laziness does not exist. There might have been a day where I was reading for two or three hours that morning. And it's like sometimes the day itself, if you only measure did it matter based on productivity, from the outside, it might not look like much, but then, oh, this thing loops back around later. Or just spending time with yourself or someone you love makes the day matter. Or maybe you had an idea that plants a seed. There's just so many ways to answer that question.

We'll be right back just after this.

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This episode is brought to you by Indeed. You're ready to move your business forward. But first, you need to find the right team. Start your search with Indeed Sponsored Jobs. It can help you reach qualified candidates fast, ensuring your listing is the first one they see. According to Indeed data, sponsored jobs are 90% more likely to report a hire than non sponsored jobs. See the results for yourself. Get a $75 sponsored job credit at Indeed.com podcast terms and conditions Appreciate one of my favorite graphics in the book. Now I'm even more delighted knowing that Emily created them. There's a tombstone and it says I always returned Susan's calls. And that's in a section you talk about the Inbox of Shame. I will link to my substack post Are youe Mad At Me Because I Wrote a two parter? Just saying listen like I'm basically the worst friend in the world. My capacity for interacting with people or responding to messages at all, let alone in a timely matter, is next to none. I'm honestly jealous of people who have the capacity to manage communication in their life. I'm otherwise usually reading a book or taking time with Ryder. So the bottom line is it has been a long time source of guilt and shame for me. You know this inbox of shame when I had a health Crisis Summer of 2024, for the first time in my life, for the first time in having an email inbox, it actually unhooked me from the guilt because for the first time I realized I don't want to go to the ER again. So yeah, going to the spa vis which if you don't know from rolling in doe, it's equinox. I go, I work, I work out. I do a little sauna, steam room, sort of R and R. Sometimes I'll do a work sprint on my laptop before I leave. But that's so essential to me that I've become horrible at answering email. The only difference is I no longer care. Like I was already bad. Now I'm horrible. So you're someone I've always looked to because you were always kind of a little, you know, not a little, a lot farther ahead in your career, farther ahead in your business. Really had big reach. And I feel like email is one of those Sisyphean systems as I talked about with Cal Newport. I'll put that in the show notes where the more you answer, the more you receive and the more successful you are, the more you receive. So as you say, when you're drowning, you can't just swim faster. The logic of email doesn't make sense actually, the more successful you become and sometimes you don't want a big team around you or you don't want a team member pretending to be you. So like, start wherever you want. I would just love to know your journey with the Inbox of Shame, where the inbox is plural, since it's across every frigging platform.

Right, right, exactly. You get direct messages from any different platform or network and notifications and all this stuff. Yeah, the journey of shame. I guess. For years, I would say it's. If I really thought, like, how are things going in my life? I would evaluate it in different spheres and areas and such. But one of those spears would be like, I'm like, oh, what do I feel bad about right now? Or what do I. What is bringing me, like, negative energy? And I would always say, like, I'm so behind on all these messages, and I want nothing more than to catch up. In fact, there's this whole exercise in the book called the 8th Day of the Week, where I ask people to imagine if you have an extra day of the week, not just like, your one single ideal perfect day, but, like, you get. You get one of these days every week, so you get 52 of them in a year. And this is often very helpful because you can do so much when it's a repeating kind of pattern. But I learned I had to put some parameters on this exercise because people would always say, like, oh, I would use it to catch up on my email, you know, or I would catch up on all the things I'm behind. And so you have to, like, take that out. So for me, yeah, I don't. I don't know that I ever really got better at. I guess I tried to study all these, like, productivity things. Like, I was really big into productivity culture. I'm sure you probably talked about this with Cal as well. And I learned all the systems and all the tricks and, like, I bought all the apps and things, and. And I got pretty good at it. And I. I realized I was just ultimately getting good at doing the wrong thing. You know, I was getting. Getting efficient at something that would, as you say, never really solve itself because, you know, you put more out into the world, then more will come back and your reward is. Is more. And so we're all overwhelmed and we're adding to it. So surely, like, more cannot be the answer to too much, right? Like, if there's too much in your life of something, more of it surely can't be the answer. And so I think part of it I had to learn was just acceptance. Like, I'm not going to be great at this. And that's good to know. There's other things hopefully I can do a better job at. There are some tips and tricks and stuff, but ultimately it's not hacks that I'm looking for. Right. I want purpose, not hacks. And so, you know, coming to terms with it and then turning off some of those inboxes so that I don't necessarily get direct messages or responses from 10 different places. Trying to prioritize a few people in response has been helpful, but I think in the future, in the future meaning like now basically this is only going to get worse for everyone just because of AI and how communication can now just be effectively made up by these language models and follow up messages are done by them and such as, well, I think everybody needs to think about what is the kind of world that you want to live in and what does that look like for you in terms of communication. And if you're happy with your current communication, that's great. But if you find it overwhelming, this is probably a time to think about it and maybe do something because it's not going to get easier, it's just going to get harder.

That's so true that these AI tools are going to make it even faster and the quantity even greater.

Like don't you get all these pitches? And then, and now it's still kind of obvious that they're like fake. But I feel like in the future that it will be a lot less.

Obvious, you know, well now they get the AI to say, oh, I listened to your recent episode on X and you talked about Y and it's like no you didn't.

I know.

We both know you didn't. I mean I can tell when it's genuine, but so many of them aren't. You talk about a nuance of this in the book. That is something I think about often and where I feel like a lot of what's written falls short. You know me cg, I am a systems ninja. I love tools, I love software, I love tools. Not just time management, but I love like the whole goal of free time is take small steps today that set your time free far into the future. So with a little system that you implement, you never have to think of it again. Okay, so I have so many filters and automations and email tips and tricks. Like I've got them all.

Okay, that's great.

Now we're left with a pool of let's say 50 or 100 people I genuinely like. I've maybe even known 10 years, 15, and yet my capacity is about 5. So I don't have guilt over the person I don't know emailing. I don't even have it over, you know, acquaintances or Jenny, I'd like you to meet so and so I don't have that guilt. The guilt is people I genuinely like and care about. And I know you Talked in the book about a speaking opportunity for a friend and kind of dropping the ball. So how do you reconcile, not the easy stuff, the tricky things where they are people that you like, but you are. Basically, I feel I'll speak for myself. I am going to fall short of your expectations. I will say it now, even if you're my best friend on earth, I will be slower and less likely to reach out than you will. I can almost guarantee it.

Yeah, I don't know if there's a single magic solution. I believe in the power of doing what you can. And like, you mentioned work sprints. And sometimes it's helpful to do maybe a little sprint of let me try to catch up with, not just like my work emails or whatever, but those people that are really important to me. And there are systems, you know, you can make. And I think of. I always think of you as one of the most organized people that I know, the systems ninja, as you say. And then Laura Vanderkam as well, is really good at all these, like, spreadsheets that track her time. And I'm not, like, skeptical of those things. I know they work very well for her and for others. But I think there is maybe, like, this law of diminishing returns or this point of frustration that you reach in which rather than just like, continuing to optimize, maybe it's better to take a little bit of a step back. And, like, a simple step back would be, this is something everybody can do. Like, right now is just, you know, begin paying attention to how you spend your time. And you don't have to, like, log your time. You can do that if you want. But just kind of noticing, like, every day, okay, what. What are the different decisions that I'm making in terms of where my time goes? And then ask yourself, what do I want more of in my life? And what do I want less of in my life? And by doing that, I think even without making the big strategic plan and setting up the systems, I think you will just logically and intuitively begin guiding yourself, like, towards more of those things that you want more of and away from some of the things that you want less of. So in this situation where you're like, yeah, I have the 50 people, maybe you're going to gravitate towards, oh, I want to actually try to do a better job. Maybe not with all 50 of them all the time, but I want to devote more time, you know, to that. And hopefully there's something on the other side that you're like, I want less time with whatever this thing that's annoying is. And maybe you can essentially make a trade in which you now have two benefits because one is like less time spent on something that you don't like and then more time on something that you find purposeful. But I think you'll never be able to do it 100% well. So I think it's important to accept that because you're never. It's never going to get to that point. Right.

And one of my learnings, and also I would say source of a little bit of grief is just comes with aging, I guess. I mean, I was in my early 20s when I set up Life After College, my first website. It's been almost exactly 20 years now. Publishing online.

Wow.

And 20 years with more. Isn't that crazy? Yeah. And I think I've always said my body has me on a short leash. If I, if I work in ways that are not aligned, whether it's how much I work or on the types of things that are wrong, like, I'll just get physically ill and pretty quickly, I'll get vertigo, I'll get debilitating asthma. I'll. You know, last summer it was Bell's palsy. One day after a work sprint of a few weeks, actually a month and a half, half my face was frozen. And so. And now my life is more complicated. You know, I'm married, we have a dog, we have a mortgage. I love New York City. I've been here 14 years. New York is not the problem, but it's just the level of responsibility and complexity is so much that sometimes I have a little grief, like because of aging. Like, I don't have the capacity I used to. So as is, I barely keep up with paying client emails. I barely keep up with. The house is a disaster. I know you talk about how to Keep House while Drowning, the book by Casey Davis. I mean, so many things are just hovering at the treading water, if not drowning state that, like, I don't know, I guess. Have you gone through that at any point where you just had to reconcile that my capacity today is not what it was 10 years ago?

100%. 100%, I think. And I think aging is a big part of that. And this is something that I, you know, I feel frustrated about because I'm like, oh, I used to be able to like do X more. But I have to remind myself some circumstances are different, hopefully. And the trade off is I have acquired some, some type of wisdom, you know, through, through aging. And so if, you know, I have like Some degree of physical limitations, at least cognitively, can't focus as much as I used to. Hopefully I've gained some like self insight and actualization. You know, I started going to therapy like maybe six or seven years ago and learned so much about myself. Like, I wish I'd started doing that sooner and that was very helpful. And I started getting help for my adhd, which also, you know, I wish I had done sooner. But because like, I've gained tools and insights and so I have to kind of like, okay with the tools and insights I've gained knowing that my cognitive focus or my abilities, you know, are less than they were they once were. Then I have to be even more intentional about the choices that I make. You know, I have to be intentional about the choices and what I choose to work on and such and that. So that's like, that is the ultimate answer is to choose and to choose wisely and then to commit to a choice, you know, as opposed to like, oh, I've got this other thing, or like, really wish I could have done that and this and this. It also can be like pressuring, you know, for people when they're like, oh, I know I have to choose, but what do I choose? Right?

And I guess that's the wisdom of aging too is a lot of people say they stop caring so much about the tombstone being the fastest responder. Or it's like they also have the wisdom to choose not to self flagellate just because responsiveness is not their number one goal in life, which it's not mine. It ever happens.

Right? Right. Well, it's kind of strange. It's like a strange thing to have as your highest value, but I feel like a lot of people do and it's kind of like trying to make money as your highest value. Like, it's very problematic, you know, like, like, what will you do with this money? You're going to die and then it's not going to be there. And like, we all need a certain amount of money, you know, of course. But yeah, the same thing with, with responsiveness. But these things are really ingrained. It's very hard to change these types of like, internal motivations and drive. And for me it was really hard because I, I went through like multiple crises and had to adjust and like really ask myself, okay, what is it all about for me? What is purpose? And I do want to work on things that I care about and I do like to make things. So the other thing is minimalism is not the answer. Just doing less is Also not the answer because as I said, we all want more of some things and less of others. So if you just do less, maybe it can be helpful in terms of a reset in terms of like, okay, like, you know, the Whole30 diet. Like, you eliminate everything, right, and then slowly start adding things back. So that's helpful for like a little season of transition. But ultimately, like, I want to do more of the things that I enjoy and such. So it's partly just it's coming to terms with this process and understanding that we can't do it all and eventually we're all going to die. But you know, until then we have today, we have hopefully tomorrow, but that's not guaranteed. So what can we do today that that matters to us and feels good?

We'll be right back just after this.

Toward the end of the book, you have a really vulnerable interlude that I appreciated and it's called on the Lack of Success in Duplicating the Productivity Patterns of Famous World Leaders. I'll just read a little excerpt. You say this is what it has come to a reckoning of sorts. People always thought you were so productive, but you know many people who are much more productive, you are impressed with them and also a little mad about their productivity. You think about them when you're supposed to be working on something but end up doing anything other than what you should be working on. Instead of time anxiety, you should write the book on status envy. Working title the Art of Looking to Others for Validation and Going Away Feeling Depressed. And then I'm going to skip ahead to one more part I really liked. You did not write a book called Atomic Habits. You do not have X number of Instagram followers. Your special on Netflix will not be debuting next month. Make sure to tell your friends and click the like button. You understand that Barack Obama was able to simplify his decision making process by wearing the same type and color of suit each day. Yet when you try the same approach, simplifying your wardrobe and selecting the next day's outfit before going to bed, it does not yield the same effect that it does for a president. You do not wake up in the Oval Office ready to handle the affairs of a nation. You wonder if this shopworn anecdote about Obama's suit wearing holds up at all. Even if a president knows in advance what he's going to wear, doesn't he still face a multitude of additional, much more complex decisions? No, this life hack will not solve your decision fatigue. Hi, this is Deechan Lackman and I am here to tell you toyotathon is.

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Thank you. That was fun. I remember writing that and was like, I'm not quite sure where this goes in the book, but I'm going to put it in there anyway.

So good.

Haven't you read all those Fast company articles or forbes.com you know, where they're like here's the secret to making decisions and President Obama, you know, wore the same two suits every day, therefore he was able to be President Obama. And you're like that. This is not the shortcut, right? This is not it, right?

It's hard not to compare to other people. Especially Luke Burges just talks about this in wanting Our mimetic desire is often strongest with people who are close to us. I might not look at Beyonce and go, oh, how come I'm not Beyonce with her 24 hours? That trope that I talked about with Tara McMullen. I'll put that episode at the Show Notes. However, there might be people in our industry, like fellow author speaker types, where I look at them basically what feels like running circles around me and feel bad. And then reading that, you sometimes fall into that comparison, which is so natural, like we are status seeking beings. Was it hard for you to include that in the book? And in a way you really can see people who are turboproductive like they might just not have the same limitations.

I don't think it was hard for me to include in the book. Like I'm happy to talk about that openly. I think what is hard is just learning to overcome it because it's not something I like about myself. You see, I don't want to compare myself to others and then go away feeling bad. Like I understand comparison is like the root of misery and all. It just only leads to unhappiness. I understand that. But being able to move on from it is hard. I was actually talking about this with, with Ryan Holiday recently. And it's funny because Ryan is somebody that I would look at and be like, oh, my God, it's. He's. How many books has he written? And he's built this huge business and doing all this stuff and everything. But then he was talking about somebody else that, that he knew, you know, that he kind of felt this way about. So it's always like this. This circle. But what he was saying is, he was saying, like, you try to pick out what is the piece that I can. What. What can I learn, you know, from this person? And how can I, not being that person, not knowing their circumstances and such, there's still something I can probably, like, learn and apply, you know, to enhance what I'm doing. So that was his rule, which I thought was helpful. My. My rule is ask yourself if you would trade your life, you know, everything about your life for everything in this other person's life, like the person that you're feeling envious of or jealous of. And when I started doing that, I realized, like, no, I wouldn't want to do that because you have to trade away everything that you have experienced and all of. All of your life journey and your highs and lows. And sure, maybe you trade away some of the lows, but like, all of the highs as well. And so then I realized, like, oh, you know, it's great that James wrote Atomic Habits. You know, I would like to sell as many copies of my book as James. That would be great. Do I want to be James Clear? Not really, because he's had a different life journey and experience than me. And so that is helpful in that way. Like, would you trade your life for someone else? Someone else's. Knowing that you have to trade everything. And hopefully there are things in your life you can point to that you're pretty happy about or proud of and you don't want to, you know, be rid of those things.

So I'd love to talk about the difference between friction loops versus ease loops, because friction's such a big topic here at Freetime, and the free time framework is how to move from friction to flow. So I love that you address this too. I'd love for you to just share what that looks like.

Yeah, I feel like you have developed much more of the process for it. For me, I just tend to think, like, we get stuck in these loops, whether of being overwhelmed, of being distressed, of lack of responsiveness like we were talking about with email, lack of control, like, lack of initiative, of being able to, like, okay, what is it that I want to do and how can I do more of that? And so these are essentially like friction loops that slow us down. Or they can be internal narratives which we're telling ourselves it's never going to be better, or other people are judging us, or there can be all sorts of things. And so the goal is to kind of flip that process and to say, how can I get into an ease loop where I actually have the flow, to use that word, and I have the momentum and motivation to where I know what the next thing is? And I honestly think that is one of the biggest hangups is not knowing what the next thing is. And so anything we can do to be conducive to solving for that, it's like solving for X, as in what is the next thing? And so, like, you mentioned Casey Davis. Like, her whole thing is if your house is really messy, like, say you've got kids and you've got like seven loads of laundry that need to be done, don't do the seven loads of laundry. Just commit to doing one. Like put one load of laundry in the washer and then hopefully, you know, transfer it from washer to dryer, but just kind of kickstart the process. And the worst case scenario is that you get one load of laundry done, like the urgent laundry, and you still have more to be done, but more likely you're probably going to move on from the first one to the second load and so on. And there's other examples in the book about, like, parents who take their kids to eat at McDonald's. Don't feel terrible about doing that. Hopefully you're not doing that every day, but if once in a while you need to do that, you're not the worst parent. You know, it's like eating is better than not eating, right? So, like, taking steps to like, address the immediate thing, whatever it is. If I if my inbox, if I haven't responded to stuff and like, I've got 70 things to respond to, I'll just tell myself I'm going to respond to five of these things because it's manageable and that creates this loop of ease. And I'll probably end up getting to like 10 or more or something, or maybe 20. But even if I don't, at least I'm going to get to five and I'll feel a little bit better. So I want to create ease wherever possible instead of friction.

I love it. There's so many more gems in this brilliant book. Last question. The usual if you could give small business owners permission to do something differently or drop something altogether, what would it be?

Yeah, this is a wonderful question and thank you again for the conversation. I'm so happy to be able to do this. I would encourage people to drop the belief that they are too late. This is something that kind of came up a lot in the research and writing of this book that people of all ages, interestingly so it's not just like of a certain age, people of all ages tend to believe that they are too late for something or they have missed their chance in life and this belief kind of holds them back because they have this regret either about something specific or sometimes it's just generalized like, oh, I should have been living my life differently up until now. And I love a good reinvention story from wherever you've been until now, tomorrow can be different and you can feel some relief over the distress that you feel and you can change and you can do something different so it's not too late. And so I'd encourage the business owners and anybody else listening to drop the belief that it's too late because there is still time.

Beautifully said, cg. Thank you so much, not just for this conversation, but all your friendship over nearly two decades.

Thank you so much. Thank you. Me too.

If you've listened this far, you get a gold star. Thank you. Word of mouth is the most joyful way we can grow this show, and it helps us land interviews with the luminaries and insightful guests that you would most love to hear from. Please send this episode to a friend who might find it helpful, and for show notes and related links from this episode, visit itsfreetime.com while you're there, make sure you're subscribed to the Time well Spent newsletter. You'll get instant access to my Tech Toolkit, a continually updated list of all the software I use, along with the total monthly spend to run my business where no one works full time, even me. Visit itsfreetime.com join remember, you are running the show. It's time for radical reimagining and everything is up for grabs. Let it be easy, let it be fun, and build with love.

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