Do you ever find yourself stuck overthinking decisions instead of taking action? What if you had a set of simple, proven strategies that didn't just help you start making decisions, but make the whole process faster, easier, and far more effective. Jake Knapp has faced countless tough decisions, and it's clear that he's mastered the art of making brilliant ones. Jake isn't just a best selling author. He's the mastermind behind truly amazing ideas. He's the New York Times best selling author of Sprint and Make Time, the creator of the design sprint that you might have heard of, which is a groundbreaking process for solving complex problems and testing big ideas, and his method has been embraced by some of the world's most influential companies, including Google, Microsoft, Uber, Meta, Lego, and countless others. Now, in his latest book, Click, he aims to help teams pinpoint the right problem to solve and develop solutions in just forty eight hours. And with his wealth of expertise, I was eager to tap into Jake's insights on transforming our decision making processes. In this episode, we explore his approach that ensures you involve your team rather than shut them out of decision making, and how you can structure your meetings to guarantee optimal outcomes. Jake also shares why you should be declining certain commitments if they don't genuinely align with your priorities or passions. Welcome to How I Work, a show about habits, rituals, and strategies for optimizing your day. I'm your host, doctor Amantha Imber. Making a complex decision often means we have to work through a lot of different perspectives and angles. But how do we actually do that? Well, it turns out Jake has some answers.

Do you ever find yourself stuck overthinking decisions instead of taking action? What if you had a set of simple, proven strategies that didn't just help you start making decisions, but make the whole process faster, easier, and far more effective. Jake Knapp has faced countless tough decisions, and it's clear that he's mastered the art of making brilliant ones. Jake isn't just a best selling author. He's the mastermind behind truly amazing ideas. He's the New York Times best selling author of Sprint and Make Time, the creator of the design sprint that you might have heard of, which is a groundbreaking process for solving complex problems and testing big ideas, and his method has been embraced by some of the world's most influential companies, including Google, Microsoft, Uber, Meta, Lego, and countless others. Now, in his latest book, Click, he aims to help teams pinpoint the right problem to solve and develop solutions in just forty eight hours. And with his wealth of expertise, I was eager to tap into Jake's insights on transforming our decision making processes. In this episode, we explore his approach that ensures you involve your team rather than shut them out of decision making, and how you can structure your meetings to guarantee optimal outcomes. Jake also shares why you should be declining certain commitments if they don't genuinely align with your priorities or passions. Welcome to How I Work, a show about habits, rituals, and strategies for optimizing your day. I'm your host, doctor Amantha Imber. Making a complex decision often means we have to work through a lot of different perspectives and angles. But how do we actually do that? Well, it turns out Jake has some answers.

Okay, this is going to come across as a shameless book plug right off of the bat, but the new book is about this new sprint process that we run with the startups we invest in, and a part of the process is making complex decisions. So your startup, you're beginning your company, and you're trying to figure out a lot of things. Who's our customer? What problem are we solving for them? We cover all this stuff in this foundation sprint, which is what the book Click is about. And the second half is sort of Okay, we've established a bunch of these baseline things, what do we think is going to make us stand out in the market. But then there are a lot of different approaches we might take to doing whatever that is, which is the best approach? And so there's a structure that we use to help think through this complex decision where you want to weigh different perspectives, different ways of looking at it, and not fall prey to the biases that we all have about you know, we have limitations in our brain. There's only so much we can keep in our heads at once, so we have recency bias and tend to have a hard time wing the thing that we just heard versus the thing that we heard at the beginning of the meeting, or earlier today or three weeks ago. Anyway, in my day to day life, I also have questions decisions to make that are too complicated to easily weigh. And so one of the experiments I've been doing recently is using the same method we use on our startups on myself. It's charting out these different perspectives, looking at them all at once, and trying to see, okay, which of these perspectives really is the right way to look at it, and perhaps is there a path, does one solution or one answer consistently show up in kind of the top right of these charts, which is sort of the good part.

Okay, this is going to come across as a shameless book plug right off of the bat, but the new book is about this new sprint process that we run with the startups we invest in, and a part of the process is making complex decisions. So your startup, you're beginning your company, and you're trying to figure out a lot of things. Who's our customer? What problem are we solving for them? We cover all this stuff in this foundation sprint, which is what the book Click is about. And the second half is sort of Okay, we've established a bunch of these baseline things, what do we think is going to make us stand out in the market. But then there are a lot of different approaches we might take to doing whatever that is, which is the best approach? And so there's a structure that we use to help think through this complex decision where you want to weigh different perspectives, different ways of looking at it, and not fall prey to the biases that we all have about you know, we have limitations in our brain. There's only so much we can keep in our heads at once, so we have recency bias and tend to have a hard time wing the thing that we just heard versus the thing that we heard at the beginning of the meeting, or earlier today or three weeks ago. Anyway, in my day to day life, I also have questions decisions to make that are too complicated to easily weigh. And so one of the experiments I've been doing recently is using the same method we use on our startups on myself. It's charting out these different perspectives, looking at them all at once, and trying to see, okay, which of these perspectives really is the right way to look at it, and perhaps is there a path, does one solution or one answer consistently show up in kind of the top right of these charts, which is sort of the good part.

Now, are you talking about magic lenses?

Now, are you talking about magic lenses?

I am, yeah, this is magic lenses? Yes, okay.

I am, yeah, this is magic lenses? Yes, okay.

Can we go into more datail that because I would love to hear, like, in your day to day how do you use the magic lenses process? And maybe if we could go into more detail as to what that involves.

Can we go into more datail that because I would love to hear, like, in your day to day how do you use the magic lenses process? And maybe if we could go into more detail as to what that involves.

Yes, well, first I should. I'll preface by saying, in my day to day life, it's only a big decision that warrants using magic lenses, because when you hear me describe magic lenses, you might say, WHOA, that's a lot. I don't want to do that when I'm picking my lunch, you know. So if you're looking at the menu at the sandwich shop, this is not the time. But you know, if you're trying to decide, if your kid is trying to decide what to do after they've graduated from school, or if you're trying to decide if you know what to do with your career, or you know, if you're trying to decide what kind of card to buy, or of this nature where it's like, well, there are a lot of things to weigh. They are real life issues, but they're big. Here's what magic lenses is. It's a simple idea, which is that you make a two y two chart for every perspective that you think is an important perspective for thinking about a question. So, to use the example of the car that I just described, you're trying to decide what kind of car should I get? It can be very overwhelming. There's so many options, you know, So one way of thinking about the decision is cost. What's the cost of purchasing the car? Where do I anticipate the ongoing maintenance or fuel or lack thereof, if it's electric, costs might be And so you can imagine a two y two chart of cost with you know, upfront costs and ongoing costs. And then you might have five or ten different cars you're thinking about. You design each one a color sticky note and you put them on there. And we do a lot of this stuff in Mirro, which is an online whiteboard, but you might do this in real life. Okay, so now I've got one chart, and maybe there's one in the top right, or someone one or two or three up there look pretty good. Well, now we look at something else like maybe reliability, or maybe which one's the most fun to drive. When I'm working with a startup, there are consistently four lenses that are always a good idea for any kind of project they might be working on. And the first one of those is the pragmatic lens. So if you imagine your stereotypical engineer who perhaps is concerned with what's the fastest thing to build? What's the most expensive thing to build? So we want it, we want the cheap to build and you know, fast to build, that would be the top right of the pragmatic lens. And then a startup should think about growth. So where are there the most customers that this solution might reach, and how easy is it for people to adopt this thing? And we could chart all the options there, and then we might think about money. Which of these has the highest long term value and the most potential paying customers. Then we of course should think about the customer, and in fact, this might be the most important lens, which best solves the problem that we believe customers have, and which one of these is the easiest to use and adopt. And so this set of charts. If we plot all of our options in color. On those, we can see like maybe one, maybe the green one is always in the top right, Well, great, maybe we should do that, or maybe it's a mix, but one of those feels the most right. And when we're doing this with a startup, once we've gone through some basic ones, the obvious ones, we start to create some new custom fine tune perspectives. Anyway, it's a lot to hold in your head even be describing it. But the point of this is that I bounce from one thing to another. It's like I'm a pinball machine in my head. And the same thing happens with teams. And when you have a whole team of people, even if you just have two founders or three founders, they're pinballing around between these things. So when we make it plain and we think, if you had a team of advisors who have these different perspectives, what would each one of them say? And then what are the other viewpoints that you think might be interesting, Let's craft a chart for those. It's so helpful. It's like if you're a Harry Potter fan, there's the pen sieve where they take the memories out of their minds, and then you can see you can kind of go into the story.

Yes, well, first I should. I'll preface by saying, in my day to day life, it's only a big decision that warrants using magic lenses, because when you hear me describe magic lenses, you might say, WHOA, that's a lot. I don't want to do that when I'm picking my lunch, you know. So if you're looking at the menu at the sandwich shop, this is not the time. But you know, if you're trying to decide, if your kid is trying to decide what to do after they've graduated from school, or if you're trying to decide if you know what to do with your career, or you know, if you're trying to decide what kind of card to buy, or of this nature where it's like, well, there are a lot of things to weigh. They are real life issues, but they're big. Here's what magic lenses is. It's a simple idea, which is that you make a two y two chart for every perspective that you think is an important perspective for thinking about a question. So, to use the example of the car that I just described, you're trying to decide what kind of car should I get? It can be very overwhelming. There's so many options, you know, So one way of thinking about the decision is cost. What's the cost of purchasing the car? Where do I anticipate the ongoing maintenance or fuel or lack thereof, if it's electric, costs might be And so you can imagine a two y two chart of cost with you know, upfront costs and ongoing costs. And then you might have five or ten different cars you're thinking about. You design each one a color sticky note and you put them on there. And we do a lot of this stuff in Mirro, which is an online whiteboard, but you might do this in real life. Okay, so now I've got one chart, and maybe there's one in the top right, or someone one or two or three up there look pretty good. Well, now we look at something else like maybe reliability, or maybe which one's the most fun to drive. When I'm working with a startup, there are consistently four lenses that are always a good idea for any kind of project they might be working on. And the first one of those is the pragmatic lens. So if you imagine your stereotypical engineer who perhaps is concerned with what's the fastest thing to build? What's the most expensive thing to build? So we want it, we want the cheap to build and you know, fast to build, that would be the top right of the pragmatic lens. And then a startup should think about growth. So where are there the most customers that this solution might reach, and how easy is it for people to adopt this thing? And we could chart all the options there, and then we might think about money. Which of these has the highest long term value and the most potential paying customers. Then we of course should think about the customer, and in fact, this might be the most important lens, which best solves the problem that we believe customers have, and which one of these is the easiest to use and adopt. And so this set of charts. If we plot all of our options in color. On those, we can see like maybe one, maybe the green one is always in the top right, Well, great, maybe we should do that, or maybe it's a mix, but one of those feels the most right. And when we're doing this with a startup, once we've gone through some basic ones, the obvious ones, we start to create some new custom fine tune perspectives. Anyway, it's a lot to hold in your head even be describing it. But the point of this is that I bounce from one thing to another. It's like I'm a pinball machine in my head. And the same thing happens with teams. And when you have a whole team of people, even if you just have two founders or three founders, they're pinballing around between these things. So when we make it plain and we think, if you had a team of advisors who have these different perspectives, what would each one of them say? And then what are the other viewpoints that you think might be interesting, Let's craft a chart for those. It's so helpful. It's like if you're a Harry Potter fan, there's the pen sieve where they take the memories out of their minds, and then you can see you can kind of go into the story.

So how do you know that you've got the right or the best lenses when you're thinking through you know, cost and pragmaticism and growth and anything else with any kind of decision. How do you get to that point where you're like, yes, these will be the themes or the lens or the criteria for these two by.

So how do you know that you've got the right or the best lenses when you're thinking through you know, cost and pragmaticism and growth and anything else with any kind of decision. How do you get to that point where you're like, yes, these will be the themes or the lens or the criteria for these two by.

Twos, those four that I mentioned come from our experience working with a lot of startups, and it just these perspectives would always be useful in every case. So those I feel comfortable if you're talking about a business question, thinking about the customer, thinking about pragmatism, thinking about money, you're running a business, and thinking about growth, you're not going to go wrong thinking about those perspectives. But for the others, and again this is going to get a little nerdy, but what we do is have every possible approach. We list as many as we can, and then we choose the top few. So you know, if we're working with a startup, we have one person who's the decider, the CEO, and they'll they'll choose Okay, we'll vote, everybody votes, and then the CEO will say these are the top, say five approaches I want to consider, and then we'll divide up and we'll say, okay, somebody needs to take a sheet of paper and write a sentence or two about why this is a good idea and maybe draw a doodle of it, you know, right, Okay, for this approach, here's what I think is good about it, and here's just a back of the napkin sketch of what I have in mind how it would look. We all then look at those approaches and we'll take a note underneath with sticky notes what's the criteria this is good at. What does this do well at? Often founders will put on a sticky note this this is exciting to build. I'm excited about building this. And that's often a really important consideration because there's a lot that goes into that. There's a lot of maybe intuition about something, and often after you've gone through the more rational logical progression of the standard ways of looking at it, you find that, well, excitement is really important. Often there's might be something like we can find a partner who will do this with us, you know, a company partner who can help us distribute this, so things that might be particular to the kind of business that a startup is in. But I always trust that the team themselves are going to have good insights into what makes a good lens. And once we've gotten warmed up by doing those classic ones, that's kind of the key. You warm up a bit, then you're kind of in the right mode and it's easy to make one or two or three.

Twos, those four that I mentioned come from our experience working with a lot of startups, and it just these perspectives would always be useful in every case. So those I feel comfortable if you're talking about a business question, thinking about the customer, thinking about pragmatism, thinking about money, you're running a business, and thinking about growth, you're not going to go wrong thinking about those perspectives. But for the others, and again this is going to get a little nerdy, but what we do is have every possible approach. We list as many as we can, and then we choose the top few. So you know, if we're working with a startup, we have one person who's the decider, the CEO, and they'll they'll choose Okay, we'll vote, everybody votes, and then the CEO will say these are the top, say five approaches I want to consider, and then we'll divide up and we'll say, okay, somebody needs to take a sheet of paper and write a sentence or two about why this is a good idea and maybe draw a doodle of it, you know, right, Okay, for this approach, here's what I think is good about it, and here's just a back of the napkin sketch of what I have in mind how it would look. We all then look at those approaches and we'll take a note underneath with sticky notes what's the criteria this is good at. What does this do well at? Often founders will put on a sticky note this this is exciting to build. I'm excited about building this. And that's often a really important consideration because there's a lot that goes into that. There's a lot of maybe intuition about something, and often after you've gone through the more rational logical progression of the standard ways of looking at it, you find that, well, excitement is really important. Often there's might be something like we can find a partner who will do this with us, you know, a company partner who can help us distribute this, so things that might be particular to the kind of business that a startup is in. But I always trust that the team themselves are going to have good insights into what makes a good lens. And once we've gotten warmed up by doing those classic ones, that's kind of the key. You warm up a bit, then you're kind of in the right mode and it's easy to make one or two or three.

More So, once you've got your criteria, let's just take excitement. I like that one. How do you figure out what's your X and Y access? Because I think of excitement, I'm like, well, that's just one access. How then do you tease that apart into the two things that you need to plot your options on.

More So, once you've got your criteria, let's just take excitement. I like that one. How do you figure out what's your X and Y access? Because I think of excitement, I'm like, well, that's just one access. How then do you tease that apart into the two things that you need to plot your options on.

Well, it depends, like I would ask.

Well, it depends, like I would ask.

I turn it around a consultant shake, yeah.

I turn it around a consultant shake, yeah.

Totally right. If we were working together and you were saying, gosh, I'm thinking about doing a new book and I have a few different ideas, and you know, I want to sort of think about excitement, well, I might say, well, okay, what are the components of excitement for you? For founders, it's often this is fun to build or I have conviction, I have a feeling, or like an intuition about this. It's going to kind of vary from first to person often. I think the lens that best captures this is like the conviction lens, and the components are excitement and like matches the mission. That's a really common extra lens for founders.

Totally right. If we were working together and you were saying, gosh, I'm thinking about doing a new book and I have a few different ideas, and you know, I want to sort of think about excitement, well, I might say, well, okay, what are the components of excitement for you? For founders, it's often this is fun to build or I have conviction, I have a feeling, or like an intuition about this. It's going to kind of vary from first to person often. I think the lens that best captures this is like the conviction lens, and the components are excitement and like matches the mission. That's a really common extra lens for founders.

Something else that you I know are very thoughtful about making decisions on meetings. And when we were discussing this podcast strove email, you're talking about how you're trying to reduce the number of meetings that you're going to and you used a term called the medicine in the meeting. Can you talk me through how your rethinking meetings?

Something else that you I know are very thoughtful about making decisions on meetings. And when we were discussing this podcast strove email, you're talking about how you're trying to reduce the number of meetings that you're going to and you used a term called the medicine in the meeting. Can you talk me through how your rethinking meetings?

Well, yeah, so I have a son who has a medical condition. He's got these headaches that have been going on almost NonStop for several years, and we've been trying to find ways to help with it and try all these different migraine treatments and mostly they didn't help that much. And not long ago we had an appointment with a new doctor. He turned twenty one and so he had to go see a neurologist for adults instead of for children. And he found this doctor who is a nurse practitioner and has been seeing migraine patients for decades and is very enthusiastic about the treatment of migraines. And the appointment with her, she said, you're a new patient. I'd like you to come in at the end of the day, and so we said okay, And when we got in there, she said, okay, we're going to be here for at least a couple of hours because I want to know everything about what's going on with you. And this is a person who is just inherently super curious about this top you know, the topic that she treats. She's inherently extremely curious about migraines. She's fascinated with them and doesn't want to take anything for granted about what's been done before. So she wanted the entire backstory everything, and spent a good couple of hours going through all of this, and then before we left, we ended up spending a third hour during which she tried some things. The point of all this is that in this meeting, usually you see the doctor, and we've had a series of excellent doctors for him, but you see them and it's half an hour and you're gone, you know, And that's the usual, And in this meeting, it's a meeting, you know, it's an appointment, but it is a kind of meeting. We're there for three hours and she's trying to uncover everything in the background that might be going on, and then saying, Okay, this gives me an idea of a couple of experiments. Now instead of just telling you about them and having you go off and do them on your own. Some of them you have to, but some of them we can do right now. Let's start doing this. And I left that appointment both encouraged and optimistic that maybe there was some new hope for my son with these other approaches, but also thinking I should apply this to the work that I do, because, like the nurse who helped us, I'm deeply curious. I love my work, and I'm deeply curious about the people who we work with and the problems that they have, and I want to solve them. Why do I meet with them for a half an hour or an hour, It's just the default on the calendar. It doesn't really make sense. It's better if I could meet with them for two hours, you know, or three hours. And in a way I already do that because we work in sprints. Whenever possible, and my general policy is to not have meetings if I can avoid them, except then go all in and be working together for like two days or five days. But I thought there's something in between. Sometimes we can just jump right in and do something, and that's been a new source of experiments to say, can I meet with people for a shorter amount of time or not at all, you know, fifteen minutes or not at all, But then also offer, okay, there's you know when we talk, let's also have these sessions where it's two or three hours and we dive right into it. So that's the medicine, delivering the medicine right in the meeting instead of just talking about what might happen in the future, doing it together.

Well, yeah, so I have a son who has a medical condition. He's got these headaches that have been going on almost NonStop for several years, and we've been trying to find ways to help with it and try all these different migraine treatments and mostly they didn't help that much. And not long ago we had an appointment with a new doctor. He turned twenty one and so he had to go see a neurologist for adults instead of for children. And he found this doctor who is a nurse practitioner and has been seeing migraine patients for decades and is very enthusiastic about the treatment of migraines. And the appointment with her, she said, you're a new patient. I'd like you to come in at the end of the day, and so we said okay, And when we got in there, she said, okay, we're going to be here for at least a couple of hours because I want to know everything about what's going on with you. And this is a person who is just inherently super curious about this top you know, the topic that she treats. She's inherently extremely curious about migraines. She's fascinated with them and doesn't want to take anything for granted about what's been done before. So she wanted the entire backstory everything, and spent a good couple of hours going through all of this, and then before we left, we ended up spending a third hour during which she tried some things. The point of all this is that in this meeting, usually you see the doctor, and we've had a series of excellent doctors for him, but you see them and it's half an hour and you're gone, you know, And that's the usual, And in this meeting, it's a meeting, you know, it's an appointment, but it is a kind of meeting. We're there for three hours and she's trying to uncover everything in the background that might be going on, and then saying, Okay, this gives me an idea of a couple of experiments. Now instead of just telling you about them and having you go off and do them on your own. Some of them you have to, but some of them we can do right now. Let's start doing this. And I left that appointment both encouraged and optimistic that maybe there was some new hope for my son with these other approaches, but also thinking I should apply this to the work that I do, because, like the nurse who helped us, I'm deeply curious. I love my work, and I'm deeply curious about the people who we work with and the problems that they have, and I want to solve them. Why do I meet with them for a half an hour or an hour, It's just the default on the calendar. It doesn't really make sense. It's better if I could meet with them for two hours, you know, or three hours. And in a way I already do that because we work in sprints. Whenever possible, and my general policy is to not have meetings if I can avoid them, except then go all in and be working together for like two days or five days. But I thought there's something in between. Sometimes we can just jump right in and do something, and that's been a new source of experiments to say, can I meet with people for a shorter amount of time or not at all, you know, fifteen minutes or not at all, But then also offer, okay, there's you know when we talk, let's also have these sessions where it's two or three hours and we dive right into it. So that's the medicine, delivering the medicine right in the meeting instead of just talking about what might happen in the future, doing it together.

I love everything that you've just described about how you think about meetings, and my brain is working over time, going, oh my gosh, I think about my diary, and I mean one of the things we talk to our clients about and Inventium is not defaulting to thirty or sixty minute meetings. But I'm now thinking how do I make decisions? And I'm probably thinking more so in the context of sales or business development meetings, which I typically will have for thirty to sixty minutes, depending on how complex I think the brief will be. But also if I'm going out in person, I will generally default to a longer time, but never two hours. But in my mind, I'm like, well, maybe some of those I should be going really deep. So how then do you decide? Where do you maybe curtail things and go fifteen minutes, and where do you go like the whole two hours or longer.

I love everything that you've just described about how you think about meetings, and my brain is working over time, going, oh my gosh, I think about my diary, and I mean one of the things we talk to our clients about and Inventium is not defaulting to thirty or sixty minute meetings. But I'm now thinking how do I make decisions? And I'm probably thinking more so in the context of sales or business development meetings, which I typically will have for thirty to sixty minutes, depending on how complex I think the brief will be. But also if I'm going out in person, I will generally default to a longer time, but never two hours. But in my mind, I'm like, well, maybe some of those I should be going really deep. So how then do you decide? Where do you maybe curtail things and go fifteen minutes, and where do you go like the whole two hours or longer.

I haven't totally figured this out. This is a new idea to me, and what I have been trying to do is think about every time when I'm scheduling a meeting, I try to remember, and it's hard because the default is very strong. The thirty minutes to an hour default is very strong. So I'm meeting someone for the first time, that's maybe actually a good time for the longer meeting, but it's really socially awkward to say, let's meet for two hours, like that's a lot. That's like, wow, it's a lot of Jake, I don't know, I've never met you before. I'm not sure I want to get on board for that two hour call. So what I have been trying to do is have the half hour call or the you know, be maybe like to be ready to offer the two hour call. And the context I'm talking about is meeting a new founder usually, so you know, if I'm meeting someone new, have the first call be sort of like, hey, I'm kind of normal. I won't try to you know, thirty minutes is fine. And then and then as we're talking, like, maybe, oh, there's there's something here I could help you with right away, Like let's find a two hour block to do it. It's a little easier with people who I already know, so founders in whom we have already invested. Then I can say this is a two hour thing. We can solve this on a call rather than doing a whole sprint or rather than me saying here's my advice to you, let's work on it together. And I have found it's very fun. So I just like having it as a tool in the tool belt, like an option to go to. And I haven't figured out a master plan for how it works for everything. I don't have that yet, but I just I just like it, and it feels so good when that meeting happens and it's longer and we work together in the meeting, and an hour is always a rush to get something meaningful done.

I haven't totally figured this out. This is a new idea to me, and what I have been trying to do is think about every time when I'm scheduling a meeting, I try to remember, and it's hard because the default is very strong. The thirty minutes to an hour default is very strong. So I'm meeting someone for the first time, that's maybe actually a good time for the longer meeting, but it's really socially awkward to say, let's meet for two hours, like that's a lot. That's like, wow, it's a lot of Jake, I don't know, I've never met you before. I'm not sure I want to get on board for that two hour call. So what I have been trying to do is have the half hour call or the you know, be maybe like to be ready to offer the two hour call. And the context I'm talking about is meeting a new founder usually, so you know, if I'm meeting someone new, have the first call be sort of like, hey, I'm kind of normal. I won't try to you know, thirty minutes is fine. And then and then as we're talking, like, maybe, oh, there's there's something here I could help you with right away, Like let's find a two hour block to do it. It's a little easier with people who I already know, so founders in whom we have already invested. Then I can say this is a two hour thing. We can solve this on a call rather than doing a whole sprint or rather than me saying here's my advice to you, let's work on it together. And I have found it's very fun. So I just like having it as a tool in the tool belt, like an option to go to. And I haven't figured out a master plan for how it works for everything. I don't have that yet, but I just I just like it, and it feels so good when that meeting happens and it's longer and we work together in the meeting, and an hour is always a rush to get something meaningful done.

So yeah, something else I like about that is particularly and I think because for me, it's just really clear in the sales process of where a two hour deep dive slash you know, consulting while I'm also trying to understand the problem meeting could influence. Is just that escalation of commitment because I'm spending so much time with this new person, and I'm probably doing so because I'm really keen to start a working relationship with their organization. And I think just the gesture of offering two hours of your time is so unique when you know meetings can be just so transactional.

So yeah, something else I like about that is particularly and I think because for me, it's just really clear in the sales process of where a two hour deep dive slash you know, consulting while I'm also trying to understand the problem meeting could influence. Is just that escalation of commitment because I'm spending so much time with this new person, and I'm probably doing so because I'm really keen to start a working relationship with their organization. And I think just the gesture of offering two hours of your time is so unique when you know meetings can be just so transactional.

I think absolutely, I always struggle in the shorter meetings. So I do this investing work. Me and my co author John Zaratski, I think you've spoken to in the past, and another friend of ours named Eli ble Goldman. We run this venture fund called Character Capital. We invest in early stage startups and I won't speak for them, but for me, I do this investing work simply because I love to work with people at the beginning of a big project, when they're just starting out, and it's really fun with startups It's especially fun with startups because they're starting from scratch and they have to figure out a way to make it work. It's a survival thing for their company, and all of that is just a wonderful context for me to get to help them out and to learn about how to make projects work the best, and then hopefully share things like the book Click that have ideas about what I learned. I just love doing it. In a meeting with a prospective company, you know, with a founder in whom we might invest, there is not enough time to get in and really get into that stuff and show this is how it is when we work together and do the part that I love the most. And so it is this kind of sales conversation. You know, they're selling me and I'm selling them on we're a great partner to invest in you, and they're selling me on we're a great company, you should invest in us. And it's too short of a time. Everybody's just pitching each other. And so yeah, it's lovely. It is lovely to get to do that because if I feel like a lot of the pretense falls away and we get to do more of what we genuinely want to be doing. Which is not to just put on a show and show slides, but it's to be together and work together in a more human way that's actually quite We.

I think absolutely, I always struggle in the shorter meetings. So I do this investing work. Me and my co author John Zaratski, I think you've spoken to in the past, and another friend of ours named Eli ble Goldman. We run this venture fund called Character Capital. We invest in early stage startups and I won't speak for them, but for me, I do this investing work simply because I love to work with people at the beginning of a big project, when they're just starting out, and it's really fun with startups It's especially fun with startups because they're starting from scratch and they have to figure out a way to make it work. It's a survival thing for their company, and all of that is just a wonderful context for me to get to help them out and to learn about how to make projects work the best, and then hopefully share things like the book Click that have ideas about what I learned. I just love doing it. In a meeting with a prospective company, you know, with a founder in whom we might invest, there is not enough time to get in and really get into that stuff and show this is how it is when we work together and do the part that I love the most. And so it is this kind of sales conversation. You know, they're selling me and I'm selling them on we're a great partner to invest in you, and they're selling me on we're a great company, you should invest in us. And it's too short of a time. Everybody's just pitching each other. And so yeah, it's lovely. It is lovely to get to do that because if I feel like a lot of the pretense falls away and we get to do more of what we genuinely want to be doing. Which is not to just put on a show and show slides, but it's to be together and work together in a more human way that's actually quite We.

Will be back with Jake soon, and when we return, Jake reveals why saying no to commitments you're not passionate about is crucial for success. Plus, he shares a surprisingly simple decision that can instantly tame your chaotic email inbox and reclaim your productivity. If you're looking for more tips to improve the way you work, can Live. I write a short weekly newsletter that contains tactics I've discovered that have helped me personally. You can sign up for that at Amantha dot com. That's Amantha dot com. I want to talk about another thing that you have been thinking about, which you've termed leave money on the table. I don't want to paraphrase. Can you tell me what you've been thinking about there, and maybe some experiments that you've been doing.

Will be back with Jake soon, and when we return, Jake reveals why saying no to commitments you're not passionate about is crucial for success. Plus, he shares a surprisingly simple decision that can instantly tame your chaotic email inbox and reclaim your productivity. If you're looking for more tips to improve the way you work, can Live. I write a short weekly newsletter that contains tactics I've discovered that have helped me personally. You can sign up for that at Amantha dot com. That's Amantha dot com. I want to talk about another thing that you have been thinking about, which you've termed leave money on the table. I don't want to paraphrase. Can you tell me what you've been thinking about there, and maybe some experiments that you've been doing.

I was just recently hanging out with my friend Jonathan Courtney, and he was talking about how when people say you're leaving money on the table by not doing this thing, to him, that is a message that he does not want to do that thing. He says, there's something about the framing of you're leaving money on the table that is a signal to me that, oh, I'm doing something that may not make sense by conventional evaluation, but I must really not want to do it, and so I'm going to keep doing that behavior. People tell him he's leaving money on the table to try to spur him to do this thing, and he's like, that's a signal to me that I've got it figured out. I don't want to do that thing. And I know that's a bit convoluted, But the thing that I took away from that was there are a lot of conventional wisdom frameworks about how you ought to behave things you ought to do in business because it's making the most of everything. And a simple one for me is being really active on social media, especially on LinkedIn, and it's it's a thing that you know, if you've started to develop followers, or if you're trying to write books, or you're trying to get something out there, an easy way to continue to engage with people is to continue to post on let's say, LinkedIn, and so by continuing to do that, it's going to help you out with all the other stuff. So if I don't do it, I'm leaving money on the table. Right, it doesn't take that long to write a post, it doesn't take that long to respond to people's comments and be active on there. And by not doing it, I've got all these potential connections, these potential people who might see my stuff, and I'm just leaving that money sitting there and I'm walking away from the table. And I do post on LinkedIn occasionally, but I have found that when I'm more active on it just something about the way my brain works. It's very hard for me to do other stuff. It's very hard for me to do big stuff. So if I'm writing a book, posting on LinkedIn is devastating to me. I have to shift gears. It's very slow to like, what makes a good book chapter is not what makes a good LinkedIn post? So now what makes a good LinkedIn post? And you can almost hear the gears s grinding in my head, like, oh LinkedIn, you know, trying to boot up the LinkedIn software. And then once I make the post, then I'm like, well, I want to respond to the people who write comments. And so now I'm like monitoring it and I'm like, stressed out about did people reply? Do they like me? You know? If they don't, then I'm stressed out about that. If they do, then I'm like, well, I have to keep going back and replying to more comments. So that's an example where I think this notion of if I feel that something is unnatural or hurting my main efforts, sometimes that's a signal that I just need to expand my comfort zone. I need to spend more time outside of my comfort zone so that my comfort zone gets bigger. I need to suck it up and go on LinkedIn. Right, that might be the answer, But sometimes the answer is I'm avoiding that thing because of a good reason, and conventional wisdom doesn't help me in this case. That's the whole idea with leaving money on the table is sometimes leaving money on the table is really smart because you're saving your time for what you perceive to be what I might perceive to be a bigger pot of money somewhere else.

I was just recently hanging out with my friend Jonathan Courtney, and he was talking about how when people say you're leaving money on the table by not doing this thing, to him, that is a message that he does not want to do that thing. He says, there's something about the framing of you're leaving money on the table that is a signal to me that, oh, I'm doing something that may not make sense by conventional evaluation, but I must really not want to do it, and so I'm going to keep doing that behavior. People tell him he's leaving money on the table to try to spur him to do this thing, and he's like, that's a signal to me that I've got it figured out. I don't want to do that thing. And I know that's a bit convoluted, But the thing that I took away from that was there are a lot of conventional wisdom frameworks about how you ought to behave things you ought to do in business because it's making the most of everything. And a simple one for me is being really active on social media, especially on LinkedIn, and it's it's a thing that you know, if you've started to develop followers, or if you're trying to write books, or you're trying to get something out there, an easy way to continue to engage with people is to continue to post on let's say, LinkedIn, and so by continuing to do that, it's going to help you out with all the other stuff. So if I don't do it, I'm leaving money on the table. Right, it doesn't take that long to write a post, it doesn't take that long to respond to people's comments and be active on there. And by not doing it, I've got all these potential connections, these potential people who might see my stuff, and I'm just leaving that money sitting there and I'm walking away from the table. And I do post on LinkedIn occasionally, but I have found that when I'm more active on it just something about the way my brain works. It's very hard for me to do other stuff. It's very hard for me to do big stuff. So if I'm writing a book, posting on LinkedIn is devastating to me. I have to shift gears. It's very slow to like, what makes a good book chapter is not what makes a good LinkedIn post? So now what makes a good LinkedIn post? And you can almost hear the gears s grinding in my head, like, oh LinkedIn, you know, trying to boot up the LinkedIn software. And then once I make the post, then I'm like, well, I want to respond to the people who write comments. And so now I'm like monitoring it and I'm like, stressed out about did people reply? Do they like me? You know? If they don't, then I'm stressed out about that. If they do, then I'm like, well, I have to keep going back and replying to more comments. So that's an example where I think this notion of if I feel that something is unnatural or hurting my main efforts, sometimes that's a signal that I just need to expand my comfort zone. I need to spend more time outside of my comfort zone so that my comfort zone gets bigger. I need to suck it up and go on LinkedIn. Right, that might be the answer, But sometimes the answer is I'm avoiding that thing because of a good reason, and conventional wisdom doesn't help me in this case. That's the whole idea with leaving money on the table is sometimes leaving money on the table is really smart because you're saving your time for what you perceive to be what I might perceive to be a bigger pot of money somewhere else.

I love that thinking. I mean, because it sounds to me that that's almost become a trip wire for you in terms of deciding where to put your time, Like, how does that play out in the day to day like, you know, I love the LinkedIn example. How else like and where else have you caught yourself going oh, I'm leaving money on the table, and then that then triggers you to go down this decision making path.

I love that thinking. I mean, because it sounds to me that that's almost become a trip wire for you in terms of deciding where to put your time, Like, how does that play out in the day to day like, you know, I love the LinkedIn example. How else like and where else have you caught yourself going oh, I'm leaving money on the table, and then that then triggers you to go down this decision making path.

Almost I'm on the lookout for commitments that either came from me or from outside folks, it doesn't matter. But a commitment that I've signed up for with the expectation that it's going to return something, I want to reevaluate those. My co author John and I started a podcast recently and we said, hey, you know, let's do this podcast, and we should do it every week because that's kind of how you continue having people you know show up and listen to your podcast. You probably know this. And we recorded a few episodes. It was really fun, and then I had this leaving money on the table sort of trigger of like, well, if we don't keep doing it every week, we're leaving money on the table. And then I realized, but wait a second, I'm starting to feel like it's a better idea if we do this in seasons, because I don't have the continual well of new ideas to do it every week, and we're not going to put in the effort at least right now, to like find a guest every week. You know, that's a hassle. Like you every time you got to find a guest and you got to deal with their schedule, you got to deal with their everything, got to prepare for it. It's a lot. I mean, it's a full time job. So I've realized, like, Okay, I'm going to have to leave money on the table by not making it a weekly thing. We're going to have to take breaks from it. And I know that's not the optimal way to do it, but if it's going to happen, it has to be that way. If that means the podcast doesn't work at all for me, that's going to be okay. Because again, for my brain, which takes a lot of gear shifting to get into a different mode, even recording a podcast in the morning might make it harder for me to do other things the rest of the day. And so I really value doing these big things like spending a week with a company and a sprint or writing a book, and those big things take more intense focus that is easily fractured, and it means giving up on some things that I'd like to do. Another thing that i'd like to do that I give up on. That's sort of leaving money on the table. Is being really responsive on email. I'd like to be a lot more responsive than I am, but it comes at a cost, and so I have to leave the money, so to speak, on the table, of being someone who people think of as being really responsive, which people like, and I value it in other people when they're responsive to me. I have to give that up, and it's a bit painful, but I think it's the right trade off because there's like a bigger, hopefully treasure chest that comes from the uninterrupted work.

Almost I'm on the lookout for commitments that either came from me or from outside folks, it doesn't matter. But a commitment that I've signed up for with the expectation that it's going to return something, I want to reevaluate those. My co author John and I started a podcast recently and we said, hey, you know, let's do this podcast, and we should do it every week because that's kind of how you continue having people you know show up and listen to your podcast. You probably know this. And we recorded a few episodes. It was really fun, and then I had this leaving money on the table sort of trigger of like, well, if we don't keep doing it every week, we're leaving money on the table. And then I realized, but wait a second, I'm starting to feel like it's a better idea if we do this in seasons, because I don't have the continual well of new ideas to do it every week, and we're not going to put in the effort at least right now, to like find a guest every week. You know, that's a hassle. Like you every time you got to find a guest and you got to deal with their schedule, you got to deal with their everything, got to prepare for it. It's a lot. I mean, it's a full time job. So I've realized, like, Okay, I'm going to have to leave money on the table by not making it a weekly thing. We're going to have to take breaks from it. And I know that's not the optimal way to do it, but if it's going to happen, it has to be that way. If that means the podcast doesn't work at all for me, that's going to be okay. Because again, for my brain, which takes a lot of gear shifting to get into a different mode, even recording a podcast in the morning might make it harder for me to do other things the rest of the day. And so I really value doing these big things like spending a week with a company and a sprint or writing a book, and those big things take more intense focus that is easily fractured, and it means giving up on some things that I'd like to do. Another thing that i'd like to do that I give up on. That's sort of leaving money on the table. Is being really responsive on email. I'd like to be a lot more responsive than I am, but it comes at a cost, and so I have to leave the money, so to speak, on the table, of being someone who people think of as being really responsive, which people like, and I value it in other people when they're responsive to me. I have to give that up, and it's a bit painful, but I think it's the right trade off because there's like a bigger, hopefully treasure chest that comes from the uninterrupted work.

Because on the topic of email, actually, I've heard you talk about trying to slow your inbox, and I love that. I am a superhuman user. I am not sure if you are also a yeah, superhuman. So there we go, the fastest email software in the world, but you're trying to slow it down. How are you doing that, Jake?

Because on the topic of email, actually, I've heard you talk about trying to slow your inbox, and I love that. I am a superhuman user. I am not sure if you are also a yeah, superhuman. So there we go, the fastest email software in the world, but you're trying to slow it down. How are you doing that, Jake?

I slow down my inbox by trying to be comfortable with the discomfort of having emails sit in my inbox, and it is it is a discomfort. It feels good to go through and empty it out and respond to everyone. But the more I respond, the faster than people will right back. And so it is there's a feedback loop there where the more time I spend an email, the more time I'll spend an email. I can never really get on top of it. And when whever you're doing something that's important to you, the constant feedback loop of email or slack or whatever messaging it might be, it has a cost. The slowing down the email thing is largely a practice of looking in the inbox when I do. You know, one thing is not looking at it and trying to sprint on a focus thing throughout the day. Another thing is looking in the inbox, picking out the one or two things that I need to respond to you right away, and then leaving everything else sitting in there for a week. You know, it might be two weeks. Sometimes it's embarrassing, but eventually when I get back saying I'm so sorry but or you know, thank you for your patience. But here's finally your response.

I slow down my inbox by trying to be comfortable with the discomfort of having emails sit in my inbox, and it is it is a discomfort. It feels good to go through and empty it out and respond to everyone. But the more I respond, the faster than people will right back. And so it is there's a feedback loop there where the more time I spend an email, the more time I'll spend an email. I can never really get on top of it. And when whever you're doing something that's important to you, the constant feedback loop of email or slack or whatever messaging it might be, it has a cost. The slowing down the email thing is largely a practice of looking in the inbox when I do. You know, one thing is not looking at it and trying to sprint on a focus thing throughout the day. Another thing is looking in the inbox, picking out the one or two things that I need to respond to you right away, and then leaving everything else sitting in there for a week. You know, it might be two weeks. Sometimes it's embarrassing, but eventually when I get back saying I'm so sorry but or you know, thank you for your patience. But here's finally your response.

Something I want to ask you about finally, Jake, is because of who you are, who you talk to, the companies that you invest in, and that you meet with her for two hours or well, I would love to know, like what a two or three pieces of software or tools or tech that but are really exciting you that you think me and maybe listeners should absolutely try out.

Something I want to ask you about finally, Jake, is because of who you are, who you talk to, the companies that you invest in, and that you meet with her for two hours or well, I would love to know, like what a two or three pieces of software or tools or tech that but are really exciting you that you think me and maybe listeners should absolutely try out.

There are three things that I'm the most interested in or have found the most useful lately. One of them is I'll admit this is a plug for a company that we've invested in, but it's really useful. It's a tool called Fathom, and it's a note taker for your Zoom calls or your Google Meet calls or whatever. And it's one of these, you know, one of these note taking bots that sort of sits in your call. But I just found it to be incredibly useful to have those text notes that I can link to afterwards and go right to the spot and replay the spot. I don't do that for calls i've had myself, but when our team on our team, when one person's been in a call and they say, hey, here's what happened. Can you give me your opinion, and I can go back and look and see what the conversation was, it's just a huge time saver. I really like that. So that's an interesting one because it does the note taking for you, and there's a pro and con to having notes taken for you. It's nice and I have to take notes, but if I don't take the notes myself, they don't really stick in my brain. So the other thing is a remarkable tablet, and I've had one for a long time. I just got the newest one. I'm not sure if I think the newest one is better than the older one. It's got like a backlit screen, and it's kind of heavier, it's bigger, it's nicer, certainly in some ways. But the old one is also great. And anyway, I have the old one at my desk and I have the new one kind of you know, and my bedside table. And I like taking notes on a device that I can't check email on, that I can't get distracted on. I just can write notes. There's always paper, you know, and I can easily print copies or email copies or whatever. But it's a very simple device that I love. And the third thing, which I'm still kind of developing how to use. I'm using right now, is we're on this call as a teleprompter. Teleprompter is you know, the it's a screen with a reflective mirror. You probably do have one, Amantha.

There are three things that I'm the most interested in or have found the most useful lately. One of them is I'll admit this is a plug for a company that we've invested in, but it's really useful. It's a tool called Fathom, and it's a note taker for your Zoom calls or your Google Meet calls or whatever. And it's one of these, you know, one of these note taking bots that sort of sits in your call. But I just found it to be incredibly useful to have those text notes that I can link to afterwards and go right to the spot and replay the spot. I don't do that for calls i've had myself, but when our team on our team, when one person's been in a call and they say, hey, here's what happened. Can you give me your opinion, and I can go back and look and see what the conversation was, it's just a huge time saver. I really like that. So that's an interesting one because it does the note taking for you, and there's a pro and con to having notes taken for you. It's nice and I have to take notes, but if I don't take the notes myself, they don't really stick in my brain. So the other thing is a remarkable tablet, and I've had one for a long time. I just got the newest one. I'm not sure if I think the newest one is better than the older one. It's got like a backlit screen, and it's kind of heavier, it's bigger, it's nicer, certainly in some ways. But the old one is also great. And anyway, I have the old one at my desk and I have the new one kind of you know, and my bedside table. And I like taking notes on a device that I can't check email on, that I can't get distracted on. I just can write notes. There's always paper, you know, and I can easily print copies or email copies or whatever. But it's a very simple device that I love. And the third thing, which I'm still kind of developing how to use. I'm using right now, is we're on this call as a teleprompter. Teleprompter is you know, the it's a screen with a reflective mirror. You probably do have one, Amantha.

I am looking at you through a teleprompter making great eye contact.

I am looking at you through a teleprompter making great eye contact.

Now, I don't really have the camera dialed in, so if people are watching on YouTube and I look like I'm in a grainy webcam, you can blame the teleprompter. I did have a better camera before. We'll get a better one. I'll look like Amantha in the future at some point in terms of resolution, Christmas and everything. But the thing that I found is so great about this that surprised me. I did it because, look, I selfishly, I just wanted to look better on camera. I wanted to be making eye contact, and I wanted people to watch and think, what a great guy, you know. But what I found about it that's surprising is how much more comfortable it is to have a conversation over video with a teleprompter. I didn't queue into this before, but normally when I'm on a video call, I'm constantly thinking about I should be making eye contact, and I'll make the effort to look at the webcam, but then I'm not looking at the person, and I feel like my brain is kind of straining to do that. Or I'm looking at the person and they're not quite making eye contact with me. I'm just not sure where to look and it's fatiguing. And I didn't really notice how fatiguing it was. I knew all zoom calls are fatiguing, but sin switching to the teleprompter for calls, I'm like, it's great. I feel so much more like I'm actually in the room with the person because where I'm looking is where they are. And it's been nice. So that's I'm in early days with this. But that's the third item.

Now, I don't really have the camera dialed in, so if people are watching on YouTube and I look like I'm in a grainy webcam, you can blame the teleprompter. I did have a better camera before. We'll get a better one. I'll look like Amantha in the future at some point in terms of resolution, Christmas and everything. But the thing that I found is so great about this that surprised me. I did it because, look, I selfishly, I just wanted to look better on camera. I wanted to be making eye contact, and I wanted people to watch and think, what a great guy, you know. But what I found about it that's surprising is how much more comfortable it is to have a conversation over video with a teleprompter. I didn't queue into this before, but normally when I'm on a video call, I'm constantly thinking about I should be making eye contact, and I'll make the effort to look at the webcam, but then I'm not looking at the person, and I feel like my brain is kind of straining to do that. Or I'm looking at the person and they're not quite making eye contact with me. I'm just not sure where to look and it's fatiguing. And I didn't really notice how fatiguing it was. I knew all zoom calls are fatiguing, but sin switching to the teleprompter for calls, I'm like, it's great. I feel so much more like I'm actually in the room with the person because where I'm looking is where they are. And it's been nice. So that's I'm in early days with this. But that's the third item.

It's the best. I mean, it is quite novel, but also I think so important to be able to look someone in the eyes in a virtual meeting. I used to think, oh, well, I need this kind of setup because I do a lot of virtual keynotes and the podcast. But I think for everyone that is able to afford even a basic setup, it makes so much difference with just connecting with the other human on the end of your virtual call.

It's the best. I mean, it is quite novel, but also I think so important to be able to look someone in the eyes in a virtual meeting. I used to think, oh, well, I need this kind of setup because I do a lot of virtual keynotes and the podcast. But I think for everyone that is able to afford even a basic setup, it makes so much difference with just connecting with the other human on the end of your virtual call.

It's wild.

It's wild.

Oh, Jake, I just I love chatting to you. Always just got such unique ways of thinking about things. I feel like I've made some notes through hacking. I must experiment with that. I must experiment with that. So I just want to say a massive thank you for coming back on how I work. I'm sure this might be the last time. But thank you. I've just thoroughly loved this chat.

Oh, Jake, I just I love chatting to you. Always just got such unique ways of thinking about things. I feel like I've made some notes through hacking. I must experiment with that. I must experiment with that. So I just want to say a massive thank you for coming back on how I work. I'm sure this might be the last time. But thank you. I've just thoroughly loved this chat.

Thanks so much for having me about that.

Thanks so much for having me about that.

I hope you loved this chat with Jake as much as I did. I know that I'm very curious to see if his strategy for meetings can actually work. And if you want to learn more about Jake, I highly recommend checking out his latest book click and there are links to that in the show notes. If you like today's show, make sure you hit follow on your podcast app to be alerted when new episodes drop. How I Work was recorded on the traditional land of the Warrangery People, part of the Cooler Nation

I hope you loved this chat with Jake as much as I did. I know that I'm very curious to see if his strategy for meetings can actually work. And if you want to learn more about Jake, I highly recommend checking out his latest book click and there are links to that in the show notes. If you like today's show, make sure you hit follow on your podcast app to be alerted when new episodes drop. How I Work was recorded on the traditional land of the Warrangery People, part of the Cooler Nation