053: Facilitated Focus with Caveday's Jake Kahana

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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.

Hello.

Hello everybody. Welcome back to Freetime. I am so excited to be chatting with Jake Kahana today. He is a designer and entrepreneur who teaches creative leaders the tools and skills to build thriving creative teams. He's a co founder of Cave Day, a company that facilitates deep focus sessions and deep work training. I found out about Jake and his team through Monica McCarthy shout out Manvan and I loved Cave Day so much. I even feature them in free time. So, Jake, without further ado, welcome to the show.

Hi Jenny. So great to be here. Thanks for having me.

Cave Day was the OG pre Covid. You guys were doing something so innovative that I know at least here in New York City now you've gone global. You were organizing caves where people could go and basically focus together. I almost think of it as like perfect for introverts. It reminds me of the silent book clubs that were happening in New York. Caves were this place where and I never got to go in person, but I know Monica did. I would love for you to just tell us about the origins of Cave Day, how it started and of course then we'll get into all the many pivots you've made post pandemic. But just tell us about the beginnings.

Sure. So we started five years ago, almost to the month. Our first event was January of 2017. Me and my two co founders, Molly Sonstein and Jeremy Redleaf. We were friends. We met over the summer of 2016 and we started, you know, having coffees and conversations around, getting stuff done. We all had side projects, we had friends with side projects. We were all, you know, doing work on the weekends and we said, you know, we could come together and create something that feels a little more magical than just working, like just sitting at the library, going to a Starbucks or being in a co working space. And so Molly's background is in event production and Jeremy has a lot of entrepreneurship experience and my background in marketing and branding all came together and we created Cave Day, which was just supposed to be this one off event where we did all this research on how our brains work and how we need to focus and how we should take breaks. You know, those kinds of fundamentals of how to work that nobody ever taught us. And we created the first ever event. It was called Cave Day because it was like, you're going to spend the day in the cave, you're going to shut out the world and going to feel like a different kind of place. And it was just at a co working space in Tribeca in Manhattan. Yeah, basically what happened was it was an eight hour day. We got it catered and sold tickets and then sold out. It was sort of this thing where like people at the end were like, oh my God, if I were working at a library for eight hours, I would want to go home and take a nap. I'd be exhausted. And now I have so much energy. Let's all go to a. Let's go to a bar down the street and just keep talking. People were just so energized by the combination of deep intense work and deep social connection that was happening during the breaks and during the lunch break. We had to do it again. So we planned the next one a month later and we got some press. We were written up in fast company as like, you know, the next big thing. And we sort of were like, okay, I guess, I guess we're a real company now and it's had a lot of iterations since then. We've pivoted a few times and now we run entirely remotely. Yeah, it's been a fun journey these last five years. Helping people learn how to focus and get stuff done and do it with social connection and energy along the way.

You mentioned the aspect of deep work, deep focus, deep social connection being in the same place. I think a layer that Cave Day also adds is facilitation. So you and your team are very purposeful whether the session used to be in person, whether it's virtual. You even have a self guided sprint. I think part of your special sauce is that it's a facilitated focus session. How did you start to design the experience? Whether it's an eight hour cave or a three hour virtual cave. How did you and your team over the years iterate to the facilitation layer that you put on top of it? Because it's not just showing up and working and then hanging up there's. You bring in, you weave in purposeful elements to facilitate this deep focus.

Yeah, I mean that's, I think that you're right on to say that that's part of the special sauce. Like we've done a lot of research on is rituals, which are repeated actions that create more meaning. And how do we use rituals in our work to get us in the right mindset to create a space that feels special and that leads us to the other piece. Well, I think there's three pieces. One is ritual. Two is the idea of transformational spaces, feeling that the rules here are different than the rules out in the world. And the third is the research behind what we do. So everything is very intentional from how long are each sprints, how long are each breaks, what are we doing for each break? Again, the idea of weaving social connection in as a place to sort of balance out intense individual work that we're doing. You know, there was, there was a time two or three years ago we were talking to some VCs and just investors in general, we're a bootstrap company and we ended up not taking any investment. But you know, a couple of them were asking, you know, would you ever turn this into an app? Could you just create the Cave Day app? And we actually were pretty adamant. All three of us were on the very aligned on the idea that no, the cave experience is designed around human connection, real people. And that's such an important part of not only community building and feeling connected to the people around you, but also just the way that that changes our motivation and helps us focus. It's sort of the difference between getting a workout in by watching a 15 minute YouTube video or doing 15 minutes with a trainer by your side sort of pushing you in that way.

And it strikes me that even in the using the personal trainer analogy, there's a personal trainer, but there's also the motivation of just going to a gym and seeing other people around you working out. Or is the difference between taking a yoga class, let's say doing a self practice, taking a class on a mirror, which I used to have in my office here, going to a yoga class or then having a private yoga class and it's like each and every one is a different experience. And it sounds like one of your values around this is that human connection and is showing up in a room in person or virtual, knowing why you're there. I wrote the little featurette on Cave Day in a cave. It was a self guided cave which was so creative how you built that oh, and I also did another cave. The day that I compiled the book proposal, I did a three hour virtual cave. So I did connect with some other people. And I'm super introverted. I don't always to myself, I don't say to myself, I need to be around people. But there is something very intentional about paying, signing up for a cave, paying for the cave, showing up, telling a pod of people in a breakout room what I'm going to work on, and then having the facilitator guide you through and then at the end of the cave saying, how'd you do that? Is very, very powerful. As opposed to sitting and easily getting distracted without all of those extra little almost like bumpers at a bowling alley saying, hey, stay, stay on, stay on task, stay on, project again.

A lot of this is based on research that we've done around habit building and really trying to create an experience that is applying the things that a lot of us have read about in books. Some of us have read books like Deep Work by Cal Newport or Atomic Habits by James Clear, Tiny Habits, BJ Fogg Wen by Daniel Pink and Better than before by Gretchen Rubin, who talks about habit building and the four tendencies. And in general, it's like you can read about it. And then there's not a lot of places or companies structured around, okay, let's put this into practice. And all of those things that we've learned from all of these people that we look up to is applied directly in cave day. So accountability methods like paying for things like signing up and having this thing in your calendar that you have to show up to and having human people that are there waiting for you, that you feel connected to, that you feel accountable to. And you have a, we call them cave guides, but a facilitator that is pushing you the whole time and making and reminding you, put your phone away, or this is why we take breaks. And all of those things are really important to the experience.

Let's talk about monotasking. I know that's a big area of your research and something that you feel very passionately about. This podcast, the audience is mostly business owners, I think, and you could relate, Jake, because of you've been building Cave Day for the last many years. You have two young kids at home that even sometimes with our best intention, our mind is distracted. Like, as you mentioned, I think many of our listeners have read a lot of the books that you've talked about. We know the principles of productivity. We might intellectually know that multitasking is not a great thing. And yet it is still sometimes so elusive to get to that really deep work that you and I both share, a love of Cal Newport and this value of deep work. And for me, that's what free time is. It's like enjoying the time that you have off, but it's also freeing up more time for deep work, which is such a big emphasis of cave day two. So tell us about monotasking. Like, give us the 201 class. I'm sure we've all had the 101. We know we should monotask, but. But what is truly getting in the way, especially for business owners? And what have you tried that has worked?

Part of it is our brains want to avoid extra energy. You know, they want to. It wants to conserve energy. It looks for pleasure. And it's sort of this really fundamental organ that guides all of our experience. And by fundamental, I mean sort of primal. Like, it just wants to keep you safe and seek pleasure and avoid pain and extra work. And so part of that is the technology that we have around us knows that and is designed for that experience. In other words, your phone, specifically your phone, is the worst one, is designed to capture and keep your attention. And it captures it with these notifications that are designed very intentionally to tap into that part of our brain that keeps us alive that wants to look for survival. And so the way that the notifications pop up or vibrate, the sounds that are composed are composed at the same pitch of a baby crying, which taps into something. It's so messed up, like, so biologically primal that, like, we have to pay attention to it because our bodies and our brains are, like, trained to listen to that pitch. Things like red circles are things that our brain pays extra attention to because it can mean danger out in nature, right out in the jungle. And so what ends up happening is we get attracted to that thing. It captures our attention, and then it keeps our attention by reducing what we know as friction. Friction is just sort of like any barriers to stopping. And so things like autoplay, right? YouTube and Netflix and whatever streaming service has just plays one after another. And there's no friction that says, oh, I've been. I've been watching this for a long time, or the swipe down to refresh, or the infinite feed of just scrolling and scrolling and scrolling. And those things are designed to keep our attention. And so part of what we've been doing our whole lives, really, you know, you can talk about the last 14, 15 years since the iPhone came out or smartphones, really, is that we've been trained to seek pleasure in our phone. It feels good to get a notification and say, oh, it's not life or death, or to refresh our newsfeed, or to check our email and say, oh, we've got a message, or we've got new information. That feels good. And so what ends up happening is that our brain is used to getting pleasure. Very often we're not good at delaying gratification. And so Microsoft did a study a few years ago that showed that the average focus time in the office is about eight seconds at a time before we're jumping to something else, which is mind blowing. I usually say in some of the workshops that I give that just for context, like a goldfish has been clocked at having a nine second attention span. So what this ends up doing is leading us towards shallow work where it's not just like, oh, there's so many notifications. I'm just bouncing around from one thing to another. It's that our own brain is seeking out pleasure and avoiding anything challenging. So I sit down to write a really important email and I get a couple sentences in and I'm like, ah, this is really hard. I'm going to jump to something else. Let me open up that Google Doc that I was working on and I start writing the notes that I had in that. And then my brain says, oh, you know What? Today's the 15th of the month. I got to go check my bank account and make sure there's enough money. If I have enough money, I'm going to go buy that new book by Jenny Blake on Amazon. And now I'm on Amazon and I'm, you know, might as well buy my grocery and toilet paper stuff. And, you know, I was just sitting down to write an email and it feels good, but it ends up being really shallow. The important things that we want to get done in our lives, in our careers, you know, you want to write a book, you want to go forward an album or start a podcast or launch a business or grow your team or whatever it is. All of that requires deep work. The people who think that they're the best at multitasking actually are shown that they're not. That they're the ones that are the most distracted and can't focus on two things at the same time. And the way that I like to put it is, you know, even if you think you're good at multitasking, your brain is not. And what multitasking ends up looking like is continuous partial attention.

We'll be right back.

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Everybody listening can probably relate that monotasking is a muscle. It does take reinforcement and I notice like this is why I still subscribe to a paper newspaper that gets my hands full of black ink and then everything I touch. Because even reading in a digital app, of course it's a nice experience and there's often enhancements to it by design. But if I'm reading an article and it's full of links, I'm going to go click on the links. It's something so simple. Or the next article I read is going to be what the algorithm recommends that I read at the bottom rather than me following my own pace and linear process reading the inky version of the paper. And I do think that a lot of what you're talking about and this idea of monotasking, it's so, it can be so elusive and it's really is a muscle. And as you said, everything surrounding us is like by design. This is what's driving me nuts about the way things are going with big tech. I'm not trying to be a Luddite and I love tech and I love what apps have done for it's like so funny what you said about the VCs that told you, could you make this into an app? I love apps. They allow me to run my business from my phone and I'm more and more awed by what I could do from my phone for my business with every passing week. But at the same time I have noticed that the willpower that it takes to carve out the time for deep work and mono focus is becoming herculean. And both because of how the apps around us are designed, because of how technology is grabbing our attention and then even something like being part of a household. I mean, everyone's been working from home. The last and not everyone, the people who actually can work from home, which itself is a privilege. Now you're not just juggling all the apps and algorithms in the computer and in our phone, but the attention and the guilt, the micro guilt of like, if I look at my dog and he's bored as hell and I'm like, I'm sorry, I'm working. It's like even that is going to pull attention away. It's challenging.

And to me it goes back to like, yeah, we have real humans in the cave that are guiding you, that are surrounding you. Because I think in an increasingly technological world where everything is sort of relying on AI and algorithms and tech to guide your behavior, it's like we're missing a lot of analog and human components that actually make our lives better and more meaningful, even though it takes more work. And that goes back to like what I would call like your lifestyle design of getting the paper. It's called the paper. And I'm thinking like, you know, the.

Paper paper, right, that old analog device called paper.

The newspaper, yes. For anyone interested in self improvement, it's sort of like apps and technology are amazing. And there's also like this major component that is. Is ignored.

Let me ask you two questions about hesitations I've had for thinking about things like Cave Cave day or joining a cave. One is, can someone join a cave and be just as distracted? So that's part one. Then part two is what about people who go, oh, I don't need the cave. I mean, I know you know, because it's your business and you guys have, you have done an incredible job. And I, I do see so many companies following suit now that we're in post Covid world. But you've been facilitating these virtual coworking sessions for a long time. What would you say to the person who goes, like, I don't really think I need that.

If you're already sold, I'm not going to convince you. I think there are. Cave Day is not for everyone. There's a lot of people who it just won't work for because they're so convinced that I don't really need, I don't need to pay someone for that. I could do that on My own. And I guess my real answer would be like, but do you. You don't have to pay someone to do that. I could do that on your own, but I don't know that everyone does. I doubt, like, Cal Newport pays someone for the accountability. He's built up this lifestyle design that is surrounding deep work. And I think that that's such a rare thing. And so, look, I just don't. I don't think Cave day is for everyone, but I do think that it's for people that have accepted that, hey, look, I get distracted. I've accepted the fact that I need some help and accountability and support in building better habits and getting my stuff done. Because I know that if I did deep work for three or four hours in the day, that the rest of the day is sort of bonus time. Right. It's free time. Exactly. The way that you're putting it, it's like, if you can monotask, if you can do your deep work in a focused way, then you're getting all your best work done, and then the rest of the day is your time. Yes, you might be just as distracted. In the cave, I see people. You know, I was in a cave this morning, and sure, I see people on the phone and, you know, my wife called in the middle of the second sprint and I have to pick it up. It's like, I usually put my phone away, but I have her on, like, a special. You know, her phone calls and texts come through. You know, if that's the case, like, we're still ultimately building better habits. We're still saying, we know that your phone gets in the way. We're reminding you every time, put that away. Close the tabs and apps you don't need, and then, yeah, it's really up to you to do the work. Nobody is going to do your work of focusing. We're just here to hold you accountable to building it yourself.

Two behind the business questions before we wrap up, is it challenging having two co owners in a business? Because I would imagine that introduces a little bit of friction in terms of decision making and planning. How has that been for you?

I mean, definitely ups and downs. You know, early on, there's a lot of figuring out politics and personalities and ego. And, yeah, it's not easy, but I'm so grateful for my two partners. And I've said to them multiple times, I feel like I'm a better person in my life because of my partnerships with them. Like, I understand my marriage better. I understand how to be a better parent. I Understand, you know, collaboration broadly in a much bigger way than I did before. You know, we're dealing with a lot of. A lot of issues, financially, logistically, values, that conflict. That's more of like, my personal answer. I think one of the. One of the things that we've done that is sort of a game changer in how we navigate difficult things is that we. So there's three of us, and we often say that there's a fourth chair in the room, and the fourth chair is Cave Day. You know, oh, I think we should hire this person. Molly says, I don't think we should hire this person. And Jeremy says, what if we rethought the whole thing? Do we even need to hire someone? And then Cave Day, we have this metaphor of the fourth chair. It's like when we can't get along, when we can't agree, it's like, well, what's best for the company, what's best for the community? And that often allows us to remove our egos and talk through things a little bit more rationally.

You mentioned bootstrapping, not taking outside funding. Was that a tough decision? And I'm curious to know how, even maybe, as it relates to having that fourth chair for Cave Day business, how did you decide that ultimately you didn't want to take outside funding?

I mean, the true peek behind the curtain is we're lucky that we didn't have to make the decision. Like, nobody offered us money up to this point. We've had people that are interested, we have talked to VC people, but nobody was like, here's a million dollars. Do you want it? And we had to turn them down. The true story is, as I mentioned, we started as this little, hey, we're going to run an event. We made 200 bucks. That was cool, let's keep doing it. And it's just sort of evolved into like, oh, now we offer membership. Now we're going to do it remotely. Now we can cut costs by automating this thing or that thing. And so we've built the business sort of naturally bootstrapped, and we haven't had the problem or fortune of having any VC. Funny story is back in January of 2020, right before the pandemic, we had a deck prepared and sent it out to a few people. We were planning to open up a flagship studio in New York City. We were trying to raise money to have rent for a studio in New York City that would sort of run like Soul Cycle or something. You go to the studio, there's a locker room, you Check your phone. You put your, you know, distractions away and then you go into this studio where there's desks and lighting and sort of this whole system of getting to work. And obviously the pandemic hit a month later and a month and a half later and we that didn't ever amount to anything. But it's on our mind. And it's not to say that we won't ever take money, but I think what's important to us is keeping some of our values around community and sort of that human component we talked about before about keeping the research at the center. I think it's really easy to try to solve everyone's problem and try to cater to the majority of our clients or customers who are asking, can you do it at this time? What if we had 20 minute sprints? What if we had 24 hour coverage? And our mission is around improving the quality of your work so that it improves the quality of your life. And so the idea of 24 hour working is not in our ethos. The idea of going against the research so that people are happier, it's easier to join a cave is not ultimately going to serve people.

It's also that grace of timing that you hadn't just signed a lease. And then the pandemic hits. Could you imagine there were things like mindful, no vowels. Of course. Because any startup, why have vowels that were popping up all over New York that was like you would go in for meditation. And I remember some of the critique was, come on, we're going to pay $25 to go sit in the studio. But you know, pre pandemic, that was a thing that busy New Yorkers, maybe it was nice that they could pay and go in. And I think cave day, a cave day space would have been pretty epic. For sure. This is why people pay membership.

Yeah.

Even places like we work, I was shocked. Now they offer this thing where you can pay. See. But then you would have been competing with WeWork. Alexa. A giant like we work pivots and they go, oh yeah, it's $29 a day to drop in anytime. And they have their huge infrastructure. But I think you guys would stand out no matter what, even if you did this. And it's kind of like the unanswered prayers are a good thing when a pandemic is going to hit a month later.

Totally. The idea of competing with WeWork is real and not real. And I don't even know how, if.

Anything they'd bring you in. There are two different things. Yeah. And they offer the space and space some sense of community. But what you're doing is so different.

Yeah.

If you could give listeners permission to do or drop something, what would it be?

It goes back to what I was saying before about accepting the fact we need some help. I think it's, it's really easy to say, look, I'm really good at picking up habits. I'm really good at focusing. I don't need cave day. I don't need help. I don't, I don't need someone to, to do that. And all of the science and psychology research is around. Almost all of us do better in social environments when there's some level of support and friendly competition and when we can accept that, hey, we just, we need some help in focusing, in staying accountable and in building habits. That goes a long way.

Know you're gonna be doing some habit related stuff in January, so tell us about that and where listeners can find you. You and Cave Day both.

We're doing a January habit challenge, which in short is you sign up and we're gonna host daily 30 minute Zoom meetings, sort of like caves to just show up and be held accountable to do to build a habit. Learn about it@caveday.org and then, yeah, you can learn more about Cave Day in general. At caveday.org, sign up to be a member. We also do corporate workshops and private caves. If you're a manager or lead a company or a team that wants some structured deep work on an ongoing basis, we do that.

Awesome. Thank you so much, Jake. I'm gonna put all these links in the show notes as well as Jake's newsletter. The email refrigerator. Not a newsletter, it's the email fridge. And we are brainstorming about how to do some kind of cave day slash freetime event leading up to the free time book launch in March.

So stay tuned, we'll do something for sure.

Yeah, can't wait. Jake, thank you so much for being here and for doing this incredible work in the world.

Thanks, Jenny. Yeah, you too. Excited to read your book.

Yay. Thank you. And thanks everybody for being here. Listening.

If you've listened this far, you get a gold star.

Thank you.

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