Focused - 120: Caveday with Jake Kahana

Episode Date: March 2, 2021

Jake Kahana from Caveday joins to talk about his journey and how Cavedays can help you get your focus mojo back.

Welcome to Focus, a productivity podcast about more than just cranking widgets. I'm David Sparks, and joined by my co-host, Mr. Mike Schmitz. Hello, Mr. Schmitz. How are you today? I'm doing great. How are you, David? I am excellent. I am always happy to sit down and talk about getting focused with you. Got a great email recently from somebody who said that when she first started listening to us, she was rolling her eyes at the name of our show, but now she's come to be a believer and she's really interested in getting focused and that's why we're doing this. So that made me feel kind of good. Makes

me want to jump on the microphone and make another show. Awesome. Yeah, exactly. We are focused evangelists. There you go. Joined with us today is another evangelist. Welcome to the show, Jake Kahana. Yeah, thanks, David. Thanks, Mike. So, Jake, tell us just a little bit about yourself as we get started. Sure. I'm sure I'll go back into my personal history, but right now I'm the co-founder of a company called Cave Day. You may have heard of us, caveday.org. We run focused work sessions every day of the week. I'm also a US faculty member with the school of life. I teach emotional intelligence workshops to companies all over the world. And I do my own art and design work. So kind of a lot going on, but seems to all focus around

helping people show up better at work. Well, one of the things I like about you, Jake, is that you're, you know, you're in addition to writing and thinking about this stuff, you're also, you know, carrying a gig and you're facing the problems that we all face. Thanks. Yeah. I think one of the challenges that I see a lot is, you know, it's more or less easy to write a book or to, you know, write a blog about how to do things. And I think with Cave Day, what we see every day, and I'm sure we'll explain what Cave Day is,

but with Cave Day, you know, we're showing up every day. We've got seven, eight, nine sessions some days a week where we're trying to help people meet them where they are and help them overcome some of the challenges that they face when it comes to focusing at work. Well, actually, why don't we start there? Let's talk about Cave Day. What is it? So Cave Day is a company that tries to help people improve their relationship to work. And what we do is we run focus sessions every day. So we meet on Zoom with our community of hundreds of people from all over the world in what we call a cave. It's sort of this metaphor for shutting out the world and doing our best work in this facilitated environment.

shutting out the world and doing our best work in this facilitated environment. So the same way that you would, you know, go to the gym to join a class to, you know, have someone sort of push you like a trainer and be surrounded by a group of people, you know, pushing themselves. And as a result, you do your better, your best work, same thing in the cave. So we've got a facilitator, we have a community of people that show up together and we do deep work together in spr cave. So we've got a facilitator, we have a community of people that show up together, and we do deep work together in sprints. And it's all based on the science of how long our brain can focus and how should we take breaks and how do we expand our attention spans and those kinds of things. I mean, this is such an important point, I think, for people to learn is the idea that a focus as a muscle, you know, that it's something

that if you want to start trying to be more focused and work like in, as you call deep work, you can't just sit down and do that for two hours the first time you try, just like you can't bench press 400 pounds, you know? Yeah. I think that's a great analogy that it analogy that your focus is a muscle. And what's funny is like when we're not working, a lot of us don't realize how we're training that muscle to react. And so, you know, Microsoft, I think it was Microsoft did a study that showed that the average focus time at work is eight seconds. And I think this is even pre pandemic. There's another sort of parallel

study that shows that during the pandemic, we most of us check our phones on average of 150 times a day. It's like every three to four minutes, we're like unlocking our phones. And so what we're doing is we're training our brain. And we're training that focus muscle to look for distractions every eight seconds, every three to four minutes, you know, there's something in there. And so, yeah, if we want to expand our attention span, if we want to do deep work and it requires some focus. And what I like to say to our community and when I lead workshops is, you know, think of the most important thing you want to get accomplished in your career, right? You want to write a book or a screenplay, you want to

record an album or launch a new product or start a company like all of those things take deep work and long periods of focus. You can't, you know, write a book eight seconds at a time. Yeah, definitely. I like that analogy of the trainer and the muscle aspect of focus going to the gym. If I could tweak that a little bit as a runner, I kind of view focus more as like the aerobic base because running is the kind of thing just like focus where you think in your head, oh yeah, I can do that. And then once you start doing it, you realize that you really can't do it very long. Whereas if I go to the gym, I'm not a real big guy and I have no doubt in my mind there is no way I can bench press 400 pounds. I probably never will be able

to bench press 400 pounds. But having gone through the process and became a runner myself, I feel like that's something that anybody can do, just like developing your focus muscle is something that anybody can do. Is that that fair? Yeah, there's something interesting that's connected with those two, which is endurance. It's like, you know, how much can you put up with over a long period of time? Can you get get over the boredom? Can you get over the need for dopamine and distraction? I think both of those apply to running and to focus. So, yeah. I also like the idea of having a trainer. I think the aspect of a coach is often overlooked. Maybe you think, like, I can figure this out on my own. But you really can't put a price

tag on someone who can shortcut that process for you and show you the right way to do things so you don't have to make all the mistakes and possibly hurt yourself in the process. Yeah, completely. And what's interesting about that is there's sort of this self-selecting group that joins the community, right? Like there are only, there are certain kinds of people that are open to being taught by a trainer or led by a coach or we call our facilitators cave guides, like guided by a cave guide because like you're saying,

you know, I can focus. I'm just gonna, I work every day. I've worked for the last 20, 30, 40 years. I know what I'm doing. I don't need to do this. And the kind of people that are open to, one, acknowledging that I'm having a really tough time focusing and to being open to being taught by someone or sort of putting that on display publicly that I'm going to join this group.

I'm going to, you know, go to the cave every morning at 930. That's my session. And, you know, get help working. Like that creates this like in-group of people that subscribe to our values and philosophies. I feel like every time I meet someone who's productivity curious, you know, somebody who's like getting into this, ultimately they stumble into the Pomodoro technique. And it always seems to be like that's the thing. I mean, and if you're listening, you've never heard of it.

It's based on a tomato-shaped oven timer. But, you know, you set a timer for a certain amount of time and you just plan to work for that amount of time and then you get a break afterwards. And, you know, there's all different sorts of theories about how long that is and whatnot. But people are just amazed by how powerful it is. And it feels to me like cave days are like an extension of that in a lot of ways. Yeah, I think that there's a lot of value in Pomodoro.

And, you know, early, early on, that was a lot of our research, you know, how do we design this methodology? And the, I think there's two challenges, or I'm not going to call them problems. But there are two challenges with the Pomodoro method. One is ourselves, like, you know, you set a timer for 15 minutes, you work great, I'm going to set a timer for a five minute break. Let me just make it 10 minutes, or I'm in the middle of something, I'm making a sandwich, and it's taking a little, you know, we get in our own way. And so there's our own fault that, you know, we don't always stick to the timer. And the second is, I believe, we believe at Cave Day that social interaction energizes our work that, you know, you can't just sit in front of a computer by yourself and work that. So we try to structure, you know, our breaks

and we do a check in and a check out, you know, our breaks and our, we do a check-in and a check out, you know, what are you working on in the beginning? And at the end, share your wins. What did you, what did you get done in the last hour or three hours? Because we need that dopamine and studies have shown that we used to do them in person, that even a high five or a hug or a fist bump, those things can get a hit of dopamine and similarly, you know, sharing accomplishments. So, you know, in our, in our early research, Pomodoro method was, comes up all the time. And I'll say one other little piece, which is that our brain can focus a little bit longer than the Pomodoro method actually is designed for. So I

think Pomodoro is like 25 minutes of work, five minutes off, 25, five, 25, and then a 15 minute break. But the studies have shown that your brain can focus at its peak for up to about 52 minutes. So if you're cutting yourself off at 25, you're sort of just getting into that state of flow and immersion in your work. This episode of the Focus podcast is brought to you by Squarespace. Go to squarespace.com slash focused and make your next move. Enter offer code focus to check out to get 10% off your first purchase. You should make your next move with Squarespace.

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squarespace.com slash focused and code focus to get that 10 off your first purchase we thank squarespace for their support of the focus podcast and all of relay fm squarespace make your next move make your next website talk us through a cave day. I mean, what, how does it work? Sure. So you become a, you become a member. You, we have a schedule, right? Exactly. You, you book a slot, you know, book a cave, like you would like a fitness, fitness class. We've got our schedule. And when you show up, we give, you know, we'd send you a zoom link, you show up and, you know, we'd say we've got some music playing that sort of sets the tone. We've got a facilitator welcome you in. A lot of our work is sort of trying to see you as a person, calling you out by name. Welcome, David. Welcome, Mike. Nice to see you again. Welcome, Mike. Nice to see you again. And essentially, I don't mind giving this away because it's the brand itself. It's the community we built that is our brand. But essentially,

like I mentioned, there's a check-in, there's a work session, and a checkout. So the check-in, we put you in breakout rooms, and we're going to share what are you working on today and something that makes you human. We call it a micro-vulnerability, as in what are you working on today? And something that like makes you human, we call it like a micro vulnerability, as in, what are you leaving out of the cave today? Or what'd you do this weekend? Or what are you? What are you? What are you going to say to yourself if you get stuck? Some of those things that sort of connect us in our humanity when it comes to work. And then we do our work. We do 45 to 52 minutes of work in these sprints. And then the guide will lead a break in between.

So she'd say, she'd ding a bell and say, all right, everyone, let's do a quick stretch. We'll stretch our shoulders. We'll stretch our neck. Maybe you stand up and do five jumping jacks. In this way, we're sort of energized and guided through how do we bring energy into our work so we're not just staring at a computer for eight hours or 10 hours or 16 hours, depending on your workday these days. And like I mentioned at the end, you know,

we check out, you know, it's either in breakout rooms or in the chat, you know, what's something you accomplished today? How do you feel about your work? And actually recognize the accomplishment that you have from being in the cave. And this structure scales. And we have a one-hour session. We have a three-hour session. And I'm not really here to promote Cave Day as this, like, you know, come sign up for Cave Day. to promote cave day as this like, you know, come sign up for cave day. But I think like the Pomodoro method, like creating some structure and having a guide, a facilitator, you know,

walk you through this to push yourself to create some sort of boundary that, oh, I'm on a break, I need to come back now, is helpful for all of our work in training that focus muscle. Yeah, I mean, just the idea of accountability, I would imagine really helps people get through that and work on those muscles. Totally, it's designed exactly for that. And I will add that you don't have to be shy about promoting Cave Day because this was totally our doing. We were on a panel with you for the Big Ready, and that was actually the first time

that I had come across your work. And so after that, I went and looked at your website and this whole concept of Cave Day and these focus sessions. And I had heard about these before, and there's a service, which I can't remember the name of it right now, Focus Mate maybe, where I've heard of like you book these one-on-one sessions when you really need to focus on something. And Cave Day just seemed like a much more polished implementation of that on a regular basis. And I was like, yes, this is more useful. So this topic is fascinating to me. And I think that this is something, correct me if I'm wrong, but anybody

can implement this, right? When you were talking about the people who come and join this, unlike a fitness class, you don't have to be at a certain level of endurance in order to benefit from signing up for a session in the cave. You don't have to have been developing this muscle and be able to go a certain distance before you can put this to work for yourself. Right. It's people of all levels, people of all, you know, there are people that have come every day for the last four years and people that are signing up today. So it's really for anyone. And yeah, I don't have any more than that. Yeah. I also like the idea you mentioned a whole list of things when you were just describing how these caves work. But one of the things that jumped out to me was the description of the things that you are not going to bring into the cave. I think that there's a lot of value in just naming a distraction before it would interrupt your workflow.

And probably that causes a lot of those to just not even happen. Do you have any examples that you'd be willing to share of that kind of stuff? Of the things that we shouldn't bring into the cave? Yeah, yeah. I mean, really, that's a personal thing. I'll share some of the things that come up regularly. I think, so when we did these in person, one of the requirements of coming through the door was that you had to leave your phone in the box. We had like a little lockbox. And we were written up by Fast Company, and they called us productivity nannies was sort of like, it's just a funny way to think about, you know, oh, we're going to take your distractions away from you. You're not allowed to have that. But I do think that there's a lot that gets in the way for all of us. And I know that for me, like, I still get stuck with email and sort of the trap of like, I don't know, I have a couple minutes,

or I'm in between tasks, or I'm not sure what to do next. So let me just check my email. So I might commit out loud. And David, to your point about accountability, just to say out loud, like, I'm working on my newsletter, I'm not going to check my email for the next hour, for the next three hours, or I think email is a big one, social media is a big one. What's coming up that's really interesting are like mental blockers that aren't actual things, they're not social media, They're not the internet. It's not my phone. But instead people are saying, you know,

I'm working on my novel and I'm not gonna bring in doubt. I'm not gonna bring in fear of not finishing. I'm not gonna bring in perfectionism because those things are the things that can get in the way too of, you know, just getting something out on paper or the idea of writer's block and all of

these creative blocks are not real things. If you acknowledge that, like, it's actually a fear of something or it's a not willingness to be wrong or, or, you know, and so that's become a really interesting component beyond the tech things that we want to leave out of the cave. I mean, in a lot of ways, it's just like kind of the trick of acknowledging the enemy and then making them less powerful, you know.

Right, giving it a name. Yeah, and I really love, though, the idea of saying, you know, I'm going to consider and specifically address that before I start this. I mean, that's so much more than just setting a Pomodoro timer, but it really resonates. I'm sure you've got some great stories from people who've used that technique. Yeah. And I think that that's the root of improving your relationship to work. When I mentioned that's what Cave Day is, because I think it's easy to think about us as a productivity company, as someone who's like, hey, we're going to help

you cross more to-do lists off and we're going to help you hustle harder and all of that ethos that comes with productivity. And maybe you feel that there's this world of productivity that you're in and I'm in that is like sort of selling you an unrealistic and ideal and sort of unhealthy lifestyle when it comes to productivity. And so this idea of improving your relationship to work is, is acknowledging like it's a relationship, like some days, some weeks are going to be awesome. And I feel really energized by it. And I'm, I'm excited by this relationship. It's working for me. And there are other weeks where I'm like, okay, you know, I got my butt kicked this week. Like

my work is just like taking over. That's not a good relationship. And so acknowledging that like, hey, there are some emotional things that get in the way, right? Perfectionism and doubt. And there are technical things that get in the way of that, the internet and checking my phone and, you know, all these other distractions. And What's getting in the way? What are you stuck on? You know, Cave Day is sort of this place where I can do the work and also acknowledge some of the problems and work through them. That's really cool. Why don't you explain how, because you shared with me when we did our discovery call, you've got a pretty cool story on how you came to question your relationship with

work and some of the insights that you got from this. So do you mind kind of telling us how you got here and maybe how that led to the development of Cave Day? So I started as an artist, I, I always sort of was a drawer and painter and, and, you know, in, in high school or so I was like, I'm going to make this a real thing. I'm not going to be like the starving artist. I'm going to find a way to like, be serious about this. And there's a whole, you know, if you want to be my therapist, there's a whole background for where that came from, but okay. So I want to take art and make it serious. And so, uh, I went to art school thinking I'm going to go be an animator. Like when I was in high school, you know, Finding Nemo and Monsters, Inc. came out and I was like, that's what I want to do. So I went to, I grew up in Chicago, outside Chicago, went to school in LA. It was like,

I'm going to go to film school and art school. And I pretty much got there and decided, oh, I don't like animation. I don't want to be an animator. It's really tedious. I like the creativity and the story and the design, but I don't like that. So it was actually this blessing in disguise because I spent most of my college career exploring. I took songwriting classes and acting classes and science class, you know, just all over the place, just trying to explore. And it allowed me to find different internships and different jobs. And I ended up in advertising. So I was an art director in LA for about 10 years. And, you know, making commercials, making making ad campaigns for companies like PlayStation and Google and Samsung.

And I was working a lot. You know, the culture of advertising, the culture of entertainment is sort of like, you got to love what you do. We're all creatives and the work is never done until it's shipped. So we're always editing and tweaking. And so the culture of the agency that I was at, you know, was one of the top agencies. I was working on one of our biggest clients. I was working on some of our biggest projects.

And the culture was essentially, you know, it's expected to be working 80 to 100 hours a week. It's just sort of the nature, you know. And there's like a Parkinson's. I'll come back to the Parkinson's law of that. So what happened is, I was an art director, I was paired with a copywriter. And so the two of us, you know, we had a lot of fun together, we were working late nights, we were working most weekends. And one, one week, our creative director, our boss, went out of town. And we said, you know what? Let's go to the coffee shop near our house and just sort of hang out there all day and work.

We know what we have to do. We have a deadline on Friday. Let's just hang out there. I'll meet you there at 9.30 on Monday. And what was amazing is every day that week, we were done at like 2.30, 3 o'clock, 4 o'clock at the latest. And we'd get a beer and we'd be like, what's going on? This is weird. Because if we were at the agency, just down the block, we'd be here till 9. There's something going on here and and that's where i started to realize one there's a parkinson's law that it relates to to work so parkinson's law is work fills the time that you give it we all know that experience of if you have a week to do a deadline you know you work until the last night and if you have a month to do the same project you're filling the month and still

the last the night before you're staying up and getting it done. And so when you know that you're going to work 12 hours, 14 hours, and I know I'm going to be eating dinner at the office, I'm going to stretch the work. I'm going to hang out with my friends and I'm going to take a long lunch and I'm going to hang out a little bit more. And when we sat down to really focus, we knew what we were doing. We were clear on what we each had to do. We got it done and we were done. We didn't think about filling the time. We just allowed the work to fill the time that it needed, which isn't 12 hours or 14 hours. working differently. And that was back in 2013. I spent a couple years traveling and freelancing and doing a bunch of other things. I come to New York. So this is the 2013. I'm in the coffee shop with my partner. And I moved to New York in January of 2015. So a year and a half later, I'm in New York. And I'm thinking a lot about time, thinking about how do we how are we using our time both for work and socially. And so I come

to New York and I started a club. I started a club called You're Better Than Brunch. And You're Better Than Brunch was this idea that, you know, I have all these friends, I want to meet new people in New York, and everyone just wants to meet for brunch on the weekends. And brunch in New York is like this whole thing, you meet at, you know, noon or whatever, and you wait for a table and you spend $16 on eggs and you get a mimosa and you're sort of half drunk and you go home and you take a nap. And like, I just moved to New York City, I don't want to like, you know, waste a Saturday, waste my whole weekend waiting in line and overpaying for egg. Like, let's get our bagels and coffee to go and let's go explore the city.

And so Your Better Than Brunch became this monthly weekend adventure club. I would plan an adventure and we would go. And it was awesome. I did this for a little over two years and sort of this is going somewhere, I promise. And to wrap this up, to wrap up You're Better Than Brunch, I decided to do a retreat. I was wrapping it up because I was getting married and I had met a good number of friends. I felt like I had a group of friends and community here.

And I decided to do a retreat, which is how Mike and David, you and I, all of us met talking about retreats. And so I did this retreat that was just thinking about how do we spend our time intentionally? How do we, you know, be clear on how we want to spend our time? And I put out applications and I had 15 people come to this weekend retreat that I designed. And two of them happened to be my co-founders, Jeremy Redleaf and Molly Sonstang. And we spent this whole weekend talking about how do we spend our time? And we all have these side projects we're working on. And, you know, this was October of 2016. We started meeting more regularly and,

and, you know, we've all got side projects we want to work on. How do we spend our time more intentionally? And basically out of that, we said, let's create a cave day. Jeremy came up with the name after he sort of blurted out to his therapist. He was like, you know, I've got this deadline for a screenplay I'm writing. I just need a cave day. Like, I need a day in the cave. He didn't know what that was. And we were meeting the next day, and we talked about what could this be?

And Molly's background was in event production. My background was in branding and marketing. And January of 2017, a few months later, we ran our first event. So sort of a long story to go from advertising to realize we're working in the wrong way. We're not working smart, thinking about time and then into starting Cave Day. One of the things that you said regarding advertising is that it's implied that everybody loves what they do. And that's kind of the excuse slash enabler for the mindset of working the 80 hour weeks. What was that process like for you? Because I'm sure you probably identified with that as well,

or you wouldn't have put up with that for as long as you did. How did you go from, I love what I do and I want to work on it all the time, to this is unhealthy, I need a break. And then eventually, how did you land on cave day? Like, this is the message that I got to get out. So I'm going to abandon what I was doing and co found this with my co founders. There's a there's another specific story that comes up for me. So I missed the process. I'll admit it right now. I miss coming up with ideas, spending a whole day or a couple days being in a room, you know, whiteboarding and post-it noting all over the room, coming up with

ideas and then going out and making it like, right. Working with a director, a film crew, like a client is spending money on my idea and we get to go make it. And that is exciting and gratifying. And I miss that. And I find it here and there in other ways. But what happened was, so I was working on this project. It was for Google. And Google was this dream client of mine. I'd always wanted to work on Google. And the one problem with Google that I didn't expect is that Google has a very flat structure.

I mean, like within the marketing team, meaning that everyone has a relatively equal voice. And the other problem is that Google has basically an unlimited budget. So while I thought, you know, as a young creative, that's exciting, we can make whatever we want. The problem with that is that they don't mind starting over. They've got six people in the room reflecting on the work that I'm presenting. And three of them love it, two of it, two of them hate it, and one of them thinks it should change. Why don't we just start over? Let's, let's just keep going. And so a couple things started to happen. One is, I felt like I could, there was no incentive to care anymore. Why should I work all night, work all weekend, you know, put all this love into this work

knowing we're going to start over on Monday, which was a rare process. You know, every other client has deadlines and, you know, specific metrics they need to hit. And so I stopped caring. And the second is I had to cancel a lot of plans. So I was in a relationship at the time and we had planned two separate vacations that we had to cancel so that I could work on the weekend to edit this project that ended up getting killed the next week. And that was just, that just like was so demoralizing to the process. And there was a lot of things going on. I don't blame anyone. And I still talk to my old creative director. It was just like a difficult time. And it made me realize like, I'm missing out on like this relationship. I'm missing out on living in

LA in the summer. And my brother had just moved to LA and I'm not spending time with him. And so I just felt like work was taking over without giving me the rewards that I was looking for, the finished piece, the awards, the recognition in that way. And I just had a conversation recently with a young lawyer who she just got out of law school and she got the big job from the big firm. And she was telling me the amount of hours they want her to bill. And it took every bit of self-restraint not to tell her, you know, you're walking into a meat grinder.

It's like, how do you, people have to experience it. You can't really tell them about it. Yeah. And, and yeah, it's, it's, it's so common. It's so common that you're expected to work long hours. And a lot of it is rooted in this idea. I could go for a long time. It's rooted in this idea of meaningful work. It comes from like the 70s and 80s where that was the way to motivate your team was like, you know, you got to find meaning in your work.

And if you don't love what you do, you know, love what you do, and you'll never work a day in your life. And so if you don't love what you do, suddenly, there's something wrong with you, or suddenly, you're not the right cultural fit or something. And there's this sort of groupthink around, you know, you got to love what you do, which means you got to work long hours, which means you got to sacrifice a lot of the other elements of your life. And, you know, to a 23 year old, it's a lot different than a 33 year old. Yeah. Well, well, not that implied in that is the cultural belief that you have to work 12 hours days in order to make good work, which I think the more we study this, the more we realize is

just the opposite. Right. There's diminishing returns that, uh, I mean, if I, I wasn't this way, but I know a lot of my friends are like, if you pull an all nighter, there's sort of that point where you're just like, the work is not getting better. I'm actually creating more work for myself. I have to write an essay overnight. You know, it's like, I'm writing bad things that now the next day I have to like go back and edit instead of like, you know, getting sleep and waking up fresh and coming in with good ideas the next day. I think kind of an ancillary point to that is kind of what you're talking about, Jake, where you have to love what you do, but you can love what you do without working 14-hour days every day for the rest of your life, I would argue.

So for me, that's where the sticking point comes in. How do you define what it means to love what you do? How do you bring passion and purpose to the things that you're going to be doing and recognizing that you have other things in your life that are also important and balancing all of that? That's the eternal struggle. Yeah, exactly. I mean, this idea of the relationship to work

comes back to mind, and it's rooted in David White's book, The Three Marriages, that we have a relationship to our work, to other people and to ourselves. And that if one is a dysfunctional relationship, like you can't really do the others. If my relationship with work is dysfunctional and I'm, you know, working 100 hours a week and not able to do anything else, right? I'm not showing up as a good parent or friend or partner. And I really can't take care of myself. It's hard to sleep. It's hard to, you know, eat properly. I'm sort of getting fast food meals and eating at my desk, and I'm not exercising. And all of those things are interrelated that get in the way. And all of those things are interrelated that get in the way. You may not know this, but by default, Netflix hides thousands of shows and movies based on your location.

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access to a fraction of their content. Get your money's worth at expressvpn.com slash focused. Don't forget to use that link so you can get three extra free months. That's expressvpn.com slash focused, F-O-C-U-S-E-D, express.com slash focused to learn more. Our thanks to ExpressVPN for their support of the Focus podcast and all of RelayFM. So let's unpack that idea of the future of work. You've alluded to this a little bit.

You shared your story about how you founded Cave Day. You saw the light and recognized that it was not sustainable to continue to work all those long hours. I guess the question I have in my head is, number one, you are working in advertising. So you were creative and you had this epiphany that I was able to get done in four hours what I was previously doing in 16. Do you think that applies to other industries? And then number Number two, can anybody benefit from this Cave Day session? Or is there a pocket of the world of work that, you know, you just have to put in the hours? There's a lot there.

So I think with regard to your first question, I think largely what we're talking about is knowledge work, meaning, you know, probably not, you know, being on the assembly line or manual labor. Although some of the principles in terms of like monotasking, which we harp on over and over in Cave Day, one thing at a time, put all of your focus into that until you're done or until, you know, it's time to take a break moving on. Like, I think that can apply to anyone with regard to, you know, quadrupling your output or efficiency. I don't know that that applies to everyone, but I do think we all have inefficiencies in our work and you know, whether you're a salesperson or a designer or a coder or a teacher, you know, with focus and monotasking and some structure, we do tend to expand the work given the time we have.

So there are ways that we can make that more efficient. The second question is cave day for everyone. Yeah, we've gotten some funny stories of, you know, obviously people are a lot of writers, a lot of designers, coders, freelancers, but we've had people come to prepare dinner, cook a chicken and, you know, you've got your screen on and all you have to do is,

you know, you need the accountability. You need the time to just put aside to chop the vegetables and stuff the chicken, like go for it. You need the time to just put aside to chop the vegetables and stuff the chicken, like go for it. You need to plan your wedding. We've had people plan a wedding and write all of their thank you notes in half a day. There's something to that that, you know, otherwise you're dragging things on for weeks and months or maybe for some listeners, like a year, you're like writing your last thank you notes at your anniversary. So, you know, anything that requires focus, sure. Well, that's an interesting point that, you know, focus is not something that you just use to do the thing you, you know,

you work on between nine to five to earn money to buy shoes, you know. And so the muscle, you know, to go back to the tortured analogy, can be used also for anything in your life. And it doesn't necessarily have to be just for work. Yeah. I mean, that's that point of checking our phones 150 times a day. Like, you want to learn how to play piano? Cool. Just start by putting your phone away and committing a block of time and stick with it, you know, monotask. This section, we're titling the future of work. And I feel like this is kind of changing, especially now a year into the pandemic, where I've never really liked the idea

or the concept of work-life balance. It's just really all your life and you got to figure out how to make it all all work but especially when you don't have an office to go to and you don't have a commute and everything happens at home which it does now for a lot of people the lines are a lot blurrier and so i think it's really cool to think about that in terms of using something like Cave Day and Focus specifically as a tool to get the things done that you need to get done, even if prior to March 2020, you maybe wouldn't have defined it as a work type task. It does impact your work, though. Yeah, I mean, it seems like I know that both of your lives have changed a lot given the pandemic. But, you know, we're all dealing with these messy boundaries. I know

that all three of us are parents and that that can get in the way sometimes of, you know, knowing when are you working, when are you on a call and when are you like making lunch for everyone or, you know, whatever all of our responsibilities are. And so what might be an interesting shift is thinking instead of work life balance, but a little closer, like work life integration, right? Like work and life are fitting together. And those three relationships are sort of coming back here where you've got your relationship to your family and friends, you've got your relationship to yourself and you've got your relationship to your work. And as long as you're thinking about, you know, do I have some time for myself? Am I, am I eating or exercising or sleeping? Right. Am I spending time with my family? Am I making

sure that I'm spending time with work? All of those things are, you know, it's an ongoing balance. These relationships are going to go up and down. And just to borrow an idea from Jason Freed, who maybe you know of him or from Basecamp. But he had this idea that, you know, oftentimes work is borrowing from life. That like, oh, you know, I got to work late tonight. That time is borrowed from your life where you'd spend it with your, you know, if we think about work life as separate. And in the future of work, we should also think about life borrowing from work. But like, if work is going to borrow, you know, time from your weekend or from your evening, like your daytime should allow you to borrow time from work to, you know, run an errand, go to the doctor, you know, take a nap, like,

you know, take care of yourself, all those things. So that, you know, work can't just keep taking and taking and taking. This integration is something that we need to work on. I have seen that happen, though. I mean, I know some people, and I probably fall into this first camp where, because I'm working from home all of the time now, I do have more flexibility in my day to go run the errands. My kids are at home too. We homeschool. So when I take a break, go play a quick game of foosball or something. But I also know people who they're working from home. And what that means is that they are in Zoom meetings all day, every day, and they're expected to get all their normal workload done even though they have no time to do it anymore.

So I feel like there's a learning curve here, but also I feel like if you find yourself in an organization like that, you're going to have to go through some growing pains maybe. Any tips for somebody in that second camp? It's a little harder as sort of like a mid or junior level, you know, individual contributor. I think what I like to say is,

if you're a manager, this is much easier to implement. And if you're sort of an individual contributor, you can suggest this, but we often talk about this idea of the first day of kindergarten meeting, you know, get your team together and have a first day of kindergarten meeting, which is sort of a funny idea. But if you think about the first day of kindergarten, it's the first time that kids are like socialized together, right? You've been in preschool, you've been at home and kindergarten, you know, the teacher sits around, sits the class in a

circle and says, what are the rules of the playground? And we share our toys and we clean up after ourselves and we don't hit. And those rules get written down on a big sheet of paper and those go on the front of the board and we follow them. And as a company, as a team, we rarely, if ever, sit down and share what are the expectations? What are the agreements we're all coming to about how do we communicate? How should we run meetings? How should we think about our schedules a little differently? And, you know, gathering people. And I'm not saying that, you know, you need to

totally change your work culture. Like if you are a meeting work culture, I don't know that I want to work there. But, you know, that's the way that some people's work needs to happen. And so part of this meeting is to say, look, rather than the default meeting time of 60 minutes, what if we said every meeting was 50 minutes? You know, Parkinson's law says we can still get through our stuff and have 10 minutes to have people, you know, change the laundry, go to the bathroom, grab a snack, even rather than 60 minutes. What if we said our meeting time is 25 minutes? Could we still get through stuff? Or if we said, you know, Friday afternoons are focus Fridays and we're going to have no meetings, or we just agree that Monday we don't have client presentations because

that means people are working over the weekend. We move our client meetings, you know. So all of these little things can help just be clear on, do I need to respond to a Slack message within five minutes? Do I need to respond to an email immediately? Or can I wait two hours? And even those kinds of little cultural shifts can, and it comes top down, you know, if you're the manager, if you're the boss, and you're sending weekend emails,

and you're sending, you know, ideas and work at 10 at night, one in the morning, you know, that culture feels like everyone else has to do the same. And so there's an amazing tool called Schedule Send on almost every email and messaging platform. And so I know that's a long tip, but this idea of the first day of kindergarten, gathering people together and just being clear on what's expected of you, just in terms of like meeting and communication. Yeah, you know, I can't help but feel another part of this is just technology in general. You know, you were talking earlier about, you know, the three roles that you have and all the stuff going on. But what you have to realize is also you've got a digital jerk tapping you on the shoulder every couple of minutes if you're not careful.

And so you've got to really be intentional about that as well. I mean, I think that the reason why focus is so hard for people is because it's under assault right now. And, you know, every day there's a new app that wants to tell you about something. And it's just so easy to get caught up in that stuff. And then you bring it into a work culture and it gets even worse because then it has these implications that you're not doing your job right. If you're not letting someone interrupt you every time you sit down for more than 90 seconds. So I totally agree, David. But and what when you say you have to be intentional about about that, what does that mean?

What does that mean? What does that look like? Yeah, I mean, that's the question, isn't it? I mean, for instance, I have a day job, too. And the understanding with my clients is I don't read email but two times a day. And if you send me an email, don't expect that you're going to get an immediate response. And I train people for that. You know, it's like they'll call me and say, did you read my email? I'm like, no, I didn't because I'm working, you know.

And very quickly, you can kind of reset expectations. I think in a work environment, you can do that as well. And you are not going to get work done if you let, you know, I guess I look at technology kind of like this horse, right? You can hook up the horse to the wagon and it can pull the wagon. It can do a lot of work for you. Or you can just let a horse in your kitchen and let it run wild and see what happens. And it's up to you. I mean, you have to take control of this horse or you got a wild horse in your life and that doesn't help. That's a great analogy. Yeah. I think you're bringing up a really

interesting insight that I want to like unpack a little bit, which is email is not our work. Like if I thought that about that for a little bit longer, like almost every job I can think of has a work component where you need focus and you need to do the work. And email is just sort of like I can communicate about my work. I can prove that I've done it by sharing it with my team and asking for feedback or I can reach out to people. But email is not your work. Email is not your work. And to confuse being in your inbox all day with working is really detrimental to feeling accomplished at the end of the day because you're not working. You're just sort of communicating about the work that you're not doing because you're

emailing. It's even more deadly than that because there's a part of your brain that feels like you're being productive when you're doing email. Right. When what you're getting paid for is to make Google ads, you know. And at the end of the day, you don't have any Google ads, but you answered 400 email. And then it's like the trap is sprung and you realize, oh, wait a second, I didn't do anything today. And then tomorrow you wake up and you jump right into the same trap. I think the problem, I completely agree. I think the problem with what you're saying is like,

I don't think people have that realization. And I'll put myself in that category. There are days where I'm like, inbox zero, awesome, cleared out my inbox. And I'll show up the next day and be like, oh, I got 30 new emails overnight. You know, and I didn't, I don't think I didn't get anything done yesterday, because it feels good. So I'm going to do it again today, without realizing, oh, I'm just on this hamster wheel. I'm doing the same thing over and not really going anywhere. Yeah. And you know, the problem is like, we do stuff that's public facing all three of us. So if you answer 150 emails, you get like 100 replies.

So you actually just added to the work. It's not that you don't want to talk with everybody that sends you an email. A lot of the people that email me are way smarter than me. And they're people I'd like to have time to talk with. But if I just engaged in that, I would never make another podcast. I'd never release another field guide. I'd probably get kicked out of my house. You know, that's the trajectory when you go down that road. Yeah. I think email is, like you said, Jake, a placebo for, and it feels good. It feels like you've accomplished something when you talk about it.

And I can't help but think of people who I have met when you use that definition of talking about your work, who they're completely satisfied with just talking about the idea that they have. Like, I am going to write this book someday and I've got it already mapped out in my head. They haven't done anything, transferred it in any way, shape, or form to anything physical or digital.

It's all in their head. But it's almost like, as long as they don't do something with it, they have the ability to say, well, yeah, I can do that someday. And on some level, I think sometimes the thing that can hold people back is the fear of, well, if I try to do this, I might fail at it. And so I kind of view email as like a form of hiding and not putting your work out there, which is scary, but also like that's where the magic happens. I think that that's so insightful that like email is a form of

hiding. And there are people that are great at it. Don't get me wrong. Like you can, there are people that I know that can sell an amazing idea even though they haven't done any of the work. I think that's a really insightful point. It's not just email. You know, there's a whole bunch of digital distractions out there for you. And maybe that's part of the problem is you need to stop and think through, you know, what are your placebos? Yep.

Another thing you said, Jake, which I thought was really good was about having the conversation. David, you mentioned that like people, when they email you, you have the right to say, cause you've already had the conversation. I'm not going to get back to you within a day. And I feel like myself also, I've kind of, when people email me for the first time, sometimes they're kind of shocked that it takes me a while to get back to them. Some people I don't get back to. Sometimes it takes me a week. And I'm completely okay with that. I guess I kind of define it as like, I'm great at being bad at email, but that's intentional. And I think that when you work in a company or organization, and you're not

the person on the top of the totem pole, it can be scary to have those conversations about how you communicate. And you also said, Jake, something about the boss. If you are sending the emails on the weekends or even sharing the ideas outside of the established, even if they're written down like these are the company guidelines, it doesn't matter when you see the boss breaking them. There's implicit pressure to do the same. Right. And I think that that level of modeling expands to work and not work. Like I want, I want to, if I'm in that environment, I want to see my boss, my manager, you know, spend some time with her family, take a vacation, even though none of us are taking vacations right now or taking time, you know, take time off, take a day and like, let me know that it's okay for that. And parental leave, you know, that's a whole other topic. having a kid and coming back to work in three weeks, it's like, Oh,

if I want to take three months now, I feel guilty even though my family needs me. And there's that whole other issue of responsibilities and modeling something that modeling a culture that is healthy for your workers. So when people sign up for cave day, do you ever get them coming in with, you know, wanting to spend their time on email or something where the back of your mind, you're thinking, this isn't really what you're supposed to be doing here? Yeah, it's hard. It's hard these days. I think when we were doing work in person and meeting,

you know, we had a little bit more time and we had a lot smaller of a community, you know. And so one of the tenants that we introduce, you know, we have a whole like email drip for how to work in the cave, things you should be doing. And one of our tenants is start with the hard thing first. You should always be, while you have the most mental energy, you know, start with the challenging task. Don't, don't like build momentum with some emails and the quick to-do list because, you know, now you're putting things off and now it's three o'clock in the afternoon and you still have to do that big thing. So we, we often tell people to start with the hard thing first, but at this point, you know, we're growing and there's, you know, last week we crossed a milestone of having over a hundred people in a

cave. You know, I'm not going to be looking over your shoulder. If you want to spend your time working on email, that's great. It's our job to continue to facilitate and instruct and let you know like, Hey, our core tenants and our core way of working is still monotasking. It's still working on the hard thing first. It's still asking for help if you need it. Those kinds of things are based in the science and research and methodology that we design. Now, conversely, I'm sure most people get through your caves doing exactly that, you know, working on something that has been a block for them. And it must feel great at the end when people start talking through the things that they felt like they could never get done. And all it took was for them to sit down with a little bit of accountability and the progress they make.

Yeah, I think that's the most gratifying part. I think, you know, regularly we see that in the cave that people are making progress on, you know, their novel, their book, their screenplay, their company, whatever it is. I think where that gets even more attention is, you know, I'll often do workshops where, you know, in 90 minutes, I'll basically explain Cave Day in 10 or 15 minutes, and then we'll do 45 minutes of work. Like half of my time in this workshop is on mute. Let's just work together.

I'm going to ask you to commit to something. And then at the end, I give them some tips and we check out and share our wins. But in those sessions where you just sort of expected to be in a workshop for 90 minutes and learn something and take some notes, the amount of, oh my God, like I've, I've published that blog I've been putting off for a year, or I finally organized all of my photos from, you know, the last decade or whatever, you know, put everything into folders or, um, I finally shipped shipped my whatever it is.

That's where it feels great because you didn't expect it. And that's when exactly like you're saying, David, like you just needed to sit down. You needed some accountability to use someone to say, put away your phone and do that one thing. And you get a lot done that way. It's amazing what you can get done in 90 minutes of focused work. Yeah.

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It's just like we've lost sight of that. I mean, going back 20 years before there was an iPhone and before there was like instant messaging, we all really didn't have a choice but to work in a focused way. You'd sit in an office. I mean, even my career, professional career started in 1993. And the biggest interruption you'd get is somebody would send you a fax, you know? And so we had focused just by the nature of the existing technology. And for people growing up in this world of instant communication, they don't have that experience so you know it's very difficult i think for them to put all that stuff down and really just do the work and i think that's i mean that's the reason this show exists i'm gonna add two things to that david one is i i while i agree with you about the generational thing i also see that anyone who's being introduced to technology now is running into these problems, right? When we go back to that metaphor of the muscle, like, you know, my parents actually just signed up for cave day. They're in their late sixties and they're coming to caves a

couple of times a week because, you know, they got introduced to cell phones and smartphones in their late fifties, right? 10 or 15 years ago, where now they're checking their phones just as much as a kid. So I think there's that component. And related is all of these, you know, the more that we learn about our brain, the more that does, you know, companies and technology is designed to take advantage of that. So social media companies, apps, hardware itself, like everything is designed for you to capture and keep and hold your attention as long as possible. Yeah, I mean, when I first I, you know, I had a Zen teacher and the thing she kept explaining is how important it is to be mindful. And she gave me all these cues during the day

that I still follow. Like one of them is the grocery store, you know, or anytime you're at a checkout line, just be in the checkout line. And so I do that. I don't pull out my phone when I'm waiting to pay for groceries, but I do observe the people around me and everybody is on their phone. I mean, they just can't sit there for two minutes and wait for their turn to check out. It's just, it really is a problem. And I think just people, it's just, it's happened without a lot of people realizing it.

And then when you think about that, you don't have enough, you don't have the ability to sit with your own thoughts long enough to buy groceries. How on earth are you going to focus on work? I mean, how are you going to be able to do that when you ability to sit with your own thoughts long enough to buy groceries. How on earth are you going to focus on work? I mean, how are you going to be able to do that when you need to sit down? Yeah. The siren song of the endless feed. I'm curious, Jake, do you have anything specific that pulls you back in? I mean, you're listening to this, shared a lot of great stuff.

You co-founded this company called Cave Day, where you just go work in the focus cave. But do you struggle with this too? And if so, where? Totally. I think it's easy for me to like, like we said in the beginning, you know, it's easy to write a book and sort of put out in the world and not do the work yourself or help people with the work. And so for me, I think I've, I've, I've sort of tamed the wild horse, if you will, going back to that now, tame the wild horse of my phone. I've deleted social media from my app, from my, from my phone. I plug it in usually an hour or two before bed. I put it across the room when I'm working. I've managed my phone.

I think email is where I really struggle. I think, like we've talked about several times here, like it feels good to answer a couple emails. It feels good to get new email and say, oh, wow, I got an email from an old friend or a business lead or, I don't know, any update. That literally is a hit of dopamine. It feels good. And if I'm being totally honest and I'd like to be here, you know, I checked my email while we were talking quickly, you know, in the last hour. And I don't,

I'm not proud of that. I want to acknowledge that, like, this is a struggle that I'm working with. And, you know, I'd love different technology that made it harder to check email, or at least like, turn it into a game in my advantage in terms of like, if it counted every time I went to my email or timed how long I was in my inbox, maybe I would check it less. And I'm down to about, I'll call it five or six times a day of like actually checking email. But yeah,

I feel like that's, that's my default when things, when my brain has more than 10 seconds to just sort of wander and I'm in front of my computer, that's what happens. And I struggle with it, but I'm working on it. And I think that you do need to check your email. I guess the point we're not trying to say is that you become a monk and you never contact the outside world but but you find containers for it and the you know the the thing we need to work on more than checking email is is finding time to to do the work that you know when they put us in the

ground we're going to be proud of and i just think a lot of people are losing track of that. Totally. I think about that a lot. Yeah, I'm not going to go depressing here. We're living in a time where we're a little bit more aware than ever of our mortality. And maybe a different way to think about that, like you're saying, David, is thinking about our legacy. Yeah, I think yeah i think any legacy work requires any legacy work in our work requires focus the non-work legacy is is about showing up for the other relationships in our lives is is um you know consistency and character and actions and anyway that's a whole other podcast episode i'm sure sure in in running cave day i'm sure you've talked to a lot of people that have kind of gone through this process. What are some of the hurdles people have to overcome

before they get started on something like this? And how do they overcome them? I'm not sure I understand. So in starting Cave Day or in like joining the cave and working on their own work? In the idea of like sitting down for focus work and joining a cave, I mean, I'm sure you see folks that struggle with that process. How do people tame the wild horse? There we go. Oh, he's speaking in analogies. I get it now. Part of it is scheduling. Some people just don't have—just their wild horse is their schedule.

I don't know how to block off an hour to do deep work, let alone three hours. Uh, so there's that as committing, committing the time. Um, I think there's, uh, again, like there's a willingness to want to be around other people and to integrate some level of social connection, human contact as part of my work. I know my dad has a tough time with that. My dad has been an entrepreneur for 30 plus years and, you know, he's taught himself if he needs to learn something, he jumps on YouTube, he does something. So the idea of like, I'm going to come and have this person tell me to put my phone away and to not check the internet and to not check my email and to tell me when to take breaks. Like I'm not into that. Um, and so there's, there needs to

be a willingness of like essentially surrender to, to my time and, um, to having someone guide me through that work. I think those are the two big ones. And then, you know, if, if you're a Steven Pressfield fan, you know, resistance shows up when you're, when you sit down to do important work. So, you know, whether that's doubt or perfectionism or suddenly your, your keyboard needs to be wiped and your screen needs to be cleaned. Like that, you know, those are forms of resistance that like, it feels good. It feels productive to get those things done, but you're not really pushing the rock up the hill. If, It feels productive to get those things done, but you're not really pushing the rock up the hill, if you would use another analogy.

Why not? Let's use them all. But I do think one of the things I heard you say earlier is that you have a one-hour session. And I think that's really good because I get emails from people all the time who say, look, I read your blog or heard you on Focus. And what you're doing is great, but you don't understand. My boss is a jerk and I don't have any freedom and I don't get to choose anything. And I always want to say, well, take what you can. I mean, do you have one hour a day that's under your control? You know, and one hour, starting somewhere is all it takes.

I mean, I kind of had that experience. I worked in a law firm for a long time where we didn't have a lot of control and a lot of meetings were set for us. And I just started slowly taking control in little bits at a time. And as I was getting results, people started to get out of my way. But you just got to start somewhere. And I think that, to me, is if you're listening to my way but you just got to start somewhere and i think that to me is if you're listening to this thinking that you just can't make this work find 30 minutes you

know just find some way to to get started with something like this and i think you'll be surprised at the results and i yeah i think that we i often talk about 30 minutes being like, I think everyone can block off 30 minutes a day to do important work in a deep flow state. And by that, I mean, if I'm going to be a little bit more prescriptive, like spend 30 minutes, put it in your calendar. So you're committed to the time. Nothing's going to take that time. And then do two things. Put your phone in another room and turn off all notifications if you can turn off wi-fi and you know no emergency uh is so severe that within 30 minutes or an hour

you couldn't get to it and if it is they'll find a way to get to you yeah but if it didn't also when i hear the term flow state i always feel like it's got some magical incantation attached to it you know like it's going to just magically happen or not happen but i feel like you know choosing the focus is frankly how you get there and it's just just you got to put in the reps you know because i want to go back to the 400 pounds thing because we're going to hit them all like twice today i like that advice though to start small control what you can control uh especially if you work in an organization and you've got meetings all day every day you're not gonna be able to carve out four hours to do deep focused work. And that can be frustrating.

But that doesn't mean that you can't start moving in that direction. We've already talked about some of the things you can do to have that conversation, whatever. But if all you can find is 30 minutes, start with the 30 minutes. And if you're focused for those 30 minutes, you'll be amazed at what you can get done. Yeah. I think there's also an argument around doing that for your side work, side project. You know, if your work is back to back and, you know, you want to write a book or you want to paint or you want to, you know, whatever, like a lot can be accomplished in 30 minutes a day of focused work. And you're talking about two and a half hours a week. You're talking about, you know, 10 hours a month. You know, there's a lot of great artists

make work in small focus periods of time, you know, small being half hour, hour, here and there. You know, artists and writers are not all spending eight hours a day in front of their work doing the work. It comes with focused attention and small spurts. But if you get that muscle built up and you get to a point where you can spend four hours a day of focused work, the universe is yours to take. It really is that simple. All right, Jake, if someone's listening and they want to check out Cave Day, where should they go?

Sure. Caveday.org slash focused will give people, will give your listeners a one month free trial for Cave Day. We're generously offering that to anyone listening here. Caveday.org slash focused. And you can find me at jakekahana.com. I think it's a great idea again, and especially the idea of having other people, fellow travelers, I think may be what you need if you're having trouble getting started with this. So go check out caveday.org slash focused. And Jake, thanks for sharing some time with us today. Yeah, thanks, David. Thanks, Mike.

It was a great conversation. Appreciate your time and for having me here. We're going to talk in deep focus today for subscribers about what the three of us do when we have our deep focus time. But we are The Focus Podcast. You can find us over at relay.fm. I want to thank our sponsors today. And that's our friends over

at Squarespace, ExpressVPN, and Indeed, and we'll see you in a couple weeks.