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Jake gets a bit vulnerable and talks about Perfection Anxiety, which he’s struggled with since childhood. If you ever feel stuck, or worry your work won’t be good enough, be sure to check out this episode — we share a BUNCH of concrete tactics for overcoming Perfection Anxiety and getting started.
On episode 10 of Jake & JZ, we also talked about:
- How to run two sprints in one week
- Winter in the Pacific Northwest
- Why discipline doesn’t work
- Working at newspapers
- A great podcast episode: Starbucks on Acquired
- A great newsletter: Spyglass by M.G. Siegler
📩 Get an email about every episode at JakeAndJZ.com
💸 Learn more about our seed fund at Character Capital
Creators and Guests
What is Jake & JZ?
Weekly podcast about startups, design, marketing, technology… and anything else we’re thinking about. 🤓
Hosted by Jake Knapp and John Zeratsky, co-founders of Character Capital and bestselling authors of Sprint and Make Time.
JZ (00:00)
So this might be a shorter episode. say might because get us going, you never know. But we have kind of a wild week this week. It's a very full week we're running two sprints this week. We were running a design sprint earlier and then we are yesterday and today running a foundation sprint.
Jake (00:05)
Hahaha
man.
JZ (00:23)
with two different portfolio companies. It's really fun, but it's kind of crazy. We haven't done anything like this in a long time.
Jake (00:29)
I was actually thinking, have we ever done something like this? Maybe, it's been, if so, it's been a while.
JZ (00:35)
Yeah, it would have been probably
back in the Google Ventures days when there was maybe a sprint on the calendar and then some other time-sensitive request from somebody else and we tried to squeeze it in. Do you want to just share briefly how we're arranging it? I think that might be kind of interesting for some people watching. How do you do two sprints in one week?
Jake (00:39)
Yeah.
Yeah. Yeah.
Yeah.
Yeah. So we're doing two different kinds of sprints. It's a design sprint and a foundation sprint. The design sprint. If you're, if you're new to sprints, the design sprint, the big goal is to create and test a prototype in one week, starting from wherever you are, which might be kind of zero. So mapping out the problem on Monday, choosing a target, then Tuesday's sketching solutions, Wednesday deciding on what.
solutions you're going to prototype Thursday, building the prototype Friday, testing it with customers. That was our first sprint this week. so Monday, Tuesday, Wednesday, we did the things I described. We, we mapped, we chose the target. We sketched, we decided along with the team, the startup
on Thursday, we split off to go to the second sprint. You, me, Eli, we split off the team. The founder had a product designer. They're building the prototype. They're running the tests and then we're just kind of checking in with them to sort of see how it's going. They're very capable of building to do a great job on their own. And we've, we've seen that pattern when we're working with startups.
that have these skills and those are the kinds of companies we want to invest in that have the ability to talk to customers, have the ability to build prototypes. Those are important skills that a startup needs to have. So they're going to do a great job on those things, Thursday, Friday. And so knowing that we had these two companies who both really, it was the perfect time for both of them to do it this week. Now, Thursday, Friday, we're doing the foundation sprint with the other team. So with the other company. so for them, this is a different thing. Now we're, okay.
JZ (02:08)
Of course, yeah.
Yep.
Jake (02:33)
very beginning stages foundation sprint defining their core strategy. We'll get more into foundation sprints in some, not too distant future episodes, but that was, that's the week. And, and I mean, it's, there were some times when, you know, it was, I was pretty tired in the afternoons and evenings. I was pretty fried. How about you? do you, well, a of times it hits me after the sprint.
JZ (02:51)
It didn't, you didn't show, you didn't let it show.
Totally.
Jake (03:00)
day, you know, like
I'll be in it, doing it, w w with the team where we're talking, we're getting through solving problems. then after I'm like, wow, I'm just like, like my brain does sort of is like, I need, I need a real, a real disconnect. Yeah.
JZ (03:11)
Yeah.
everything catches up with you.
I found it a lot of fun. I thought I was going to be really tired, but I actually, when we made the switch from the first sprint to the second sprint, I got like a new burst of energy. I don't know why, but I think there was something about just kind of being in that zone, being like the compounding benefits of continued focus in a certain way of working. So.
Jake (03:41)
you
JZ (03:44)
It's been good for me, but as usual, when we run sprints, you do more of the facilitation work. And then I tend to interrupt you occasionally or serve as a sounding board. And definitely I try to contribute my own ideas. So I try to be like a ground level participant in the sprint just because, yeah, I have a different perspective as an investor in these companies we're working with.
Jake (04:00)
Yeah.
Yeah, we found that works well to have one of us doing more of the facilitation, guiding the team, and then to have another one kind of in with the time to think about what the, what the solution maybe should be, what advice this team might need in this moment and, being removed from sort of narrating through and guiding every step. I mean, it's, it's, it's wonderful on both sides. It helps me free up and feel like I can be.
JZ (04:22)
Yeah.
Jake (04:40)
not too worried about that and make sure that the steps are going well, make sure that the team gets it and provide whatever guidance I have. And then I know that I don't have to do all of that on my own. you're watching for what they need. So, good stuff.
JZ (04:55)
That's the idea.
Before we start the episode, I have to make two comments on what I'm seeing through your video camera. The first is that I don't think I've ever actually seen, been able to see out that window behind you. I think it like, it's always too bright. And so I'm guessing, you know, knowing your, your latitude, it's definitely not bright right now. And so that's probably, it's not blown out. And so I can actually see the lovely like green grass behind you. looks super nice. And then.
Jake (05:06)
yeah.
It's not bright.
JZ (05:21)
The other thing is dang, that looks like a very comfy sweater.
Jake (05:25)
This
is a great sweater. are both, both things that you see here are emblematic of it being December as we record. And so there's very little light here in Northern Washington state. That's the, that's why you can see out the window. And that is, it's funny that you can see out the window because for me, it's like, could barely see out the window. It's so dark. But then, yeah, this is a sweater knitted by my mom. So this is a great, cowichan style sweater.
JZ (05:37)
Yeah.
Right.
So cool.
Jake (05:53)
Yeah, I had one of these like when I was a kid and then that she knitted and then when, yeah, when I, you know, became a grownup at some point, I was like, mom, would you make me another one? And she's an excellent knitter. And so, yeah, she, she put this together for me. It is warm though. If you see me wearing this, you know that it's like, it's, it's, it's a different kind of temperature than it usually is because this is not messing around and,
JZ (06:01)
It did fit.
That's so cool.
huh.
Yeah.
Jake (06:21)
It's like too much for most temperatures, but today it's all right.
JZ (06:24)
Right.
Yeah. Well, we promised to start our episode, so we better get to it. What do you think?
Jake (06:30)
to
get to it. Yeah, let's do a podcast.
JZ (06:33)
Let's do it.
Welcome to episode 10 of Jake and Jay Z, the weekly podcast about design, startups, technology, marketing, sweaters, weather, and other topics that we are thinking about and working on. That's Jake over there. I'm Jay Z, John Zyrowski. We are the founders of Character Capital. We're the authors of Sprint and Make Time. This, as you might've guessed, is our podcast. And if you want to get a weekly email when we release...
the new episode and a few other links of other cool stuff we're looking at and thinking about. You can sign up for that at jakenjayze.com. And before we go any further, I have a quick favor, which is that if you are enjoying this, I hope you are, but if you are, please like, comment, subscribe, know, scroll down, whatever you're looking at, scroll down and push as many buttons as you can because that really helps us make sure that other people can find out about the podcast.
Jake (07:51)
It's not just for our egos, although we do appreciate that, but it does really help other folks find it. So, so thanks in advance. Yes, it's a means to an end.
JZ (07:51)
Thank you.
Utilitarian. Yeah.
Jake, I'm excited to ask you about a topic that I don't think I had ever heard you talk about until about two weeks ago. And maybe you did. And I just forgot, you know, at this point, we've had a lot of conversations. I can't promise to remember every single one. But in the last couple of weeks, you you have brought up this sensation, this
phenomenon called perfection anxiety. Am I getting the, is that right? that the, is that what you call it?
Jake (08:32)
That is the term, yes. That is the term. And I don't know if it's a real term or if I made it up. And I think it would be fun to talk about. It's something that is probably, know, veering into armchair psychology. you know, if you really know what you're...
JZ (08:35)
What is it?
Yeah
Okay, yeah.
Jake (08:54)
your, your psychology and you're listening to this, perhaps you'll, you'll find it offensively misguided, but this is my understanding of something that goes on in my head. And it came up. I, I started talking to, I mentioned it to you and, we started talking about it because I was talking to one of our, one of the founders in our portfolio who's at the beginning of, really, really cool.
big ambitious project. That's a theme for us talking to folks at the beginning of big, cool, ambitious projects. And the founder is feeling what I thought as we were talking, we were having this long phone call and I thought, gosh, know, this, this feels to me like something I really relate to. It's a feeling of perfection anxiety. And it's, it's the, the, the stress, the, the fear, the discomfort, the, the really deep discomfort of
Having something that you want to make amazing in seeing something that's that you're excited about. And, yet realizing that you are probably going to screw it up in some way. And, that, know, when it's, when it's in my head and it's just the idea, it's perfect. It's potentially perfect. And any step I take toward actualizing it toward taking it out of my head and into the real world.
JZ (10:03)
You
yeah.
Jake (10:19)
is in some way reducing it, is in some way destroying that perfect vision. And it can be absolutely paralyzing. that's the, yeah, that's my definition of perfection anxiety. I...
JZ (10:36)
Have you found
in yourself or in others specific types of situations where perfection anxiety is more likely to rear its head?
Jake (10:46)
Well, I mean, it kind of for me goes back to all the way being a kid and like even making a drawing, you know, but, and we, and we can talk about that if you want, we can totally psychoanalyze Jake and talk about sort of the roots of where I first struck on this idea. But I, I
I think it comes up in my current adult life anywhere from I've got an email that I need to respond to and I really want to get it right and I'll leave it in my inbox longer than I might otherwise because of perfection anxiety. Or on the more extreme and kind of obvious end, it could be like a book, like writing a book would definitely be vulnerable to perfection anxiety.
start, you know, making the commitment to, to start character could be vulnerable to perfection anxiety. beginning to prepare for a presentation could be vulnerable to perfection anxiety and certainly designing a new product, you know, could be vulnerable to perfection anxiety. So it's on the big things it's, it's almost easier to see, but I think it's something that happens on, on a daily basis.
And I've heard people talk about how procrastination is a symptom of anxiety. And I don't know much about that other than that sort of sounds right to me. And to me, it's all about this fear that I won't make it perfect.
JZ (12:16)
Mm-hmm. sounds like when you were describing those projects, the types of things that give you perfection anxiety, those are all things that you are and should be. And I believe you probably know you are good at those. you didn't say like, I get really bad perfection anxiety when I'm going to like paint a room in my house or like, you know, mow the lawn. I mean, you're probably good at those things too. But like those are all the things you mentioned. Those are like right in your wheelhouse. Those are like Jake Knapp.
Jake (12:41)
Yeah.
JZ (12:46)
like A plus skills. Is there a pattern there? are you more likely to feel this way when it's something you know you should be good at?
Jake (12:49)
Thanks.
Yeah, that's a good insight. I think you're right. think it's harder when I'm thinking about it as this is representative of who I am. This is sort of representative of my existence, the way I create this thing. And also when I feel that the opportunity is large. So if the...
JZ (13:13)
Yeah.
Mm.
Jake (13:22)
a perfect version of this thing would be really great. Like, let give you an example. Suppose you need to ask someone for a favor by email. This is just a very simple thing, but like, and it's important to you. Like whatever the favor is, it's important to you. So maybe it's a person you haven't talked to very often. know, maybe you feel like, that person's like pretty high status. I don't know if they're going to even open my email. But in my mind, when I haven't done it yet,
There is probably, and it might be true that there is a perfect version of that email that has the perfect subject line. It's sent. Yes. Yes. Yes. The highest converting possible email. I've, I've sent it at the perfect moment. It has the perfect subject line. It's, you know, it had been, if I had, it could AB test it for, you know, a millennium, like I would get to, and the body of it is like perfectly written with the right combination of.
JZ (13:56)
The highest converting possible email.
All right.
Jake (14:19)
everything that entices this person to do the favor for me that I want. This is just a very simple example, like, potentially.
JZ (14:26)
Yeah, but it reveals
there's so much complexity in that simple example. So we can imagine then the just exploding complexity of bigger projects.
Jake (14:32)
Yes.
Totally, totally. if I know that there's a perfect version of an email or I'm pretty sure that if it just was done perfectly, the right outcome would happen. Everybody feel great about it. They'd love to do me the favor or whatever. gosh, mean, yeah, you, then you think, well, let's say we're gonna write a book. When it starts out as an idea, well, mean, potentially that idea, if it manifested in the right way,
It could be this, you know, this world changing, you know, James Clear Atomic Habits book. Like what if you got it, you nailed it just right. Like could, you know, could it be that thing that just sort of takes off? And I think the same thing's happening for our founders, right? They have these ideas that they can see what might be possible in the world. And it's true that if they got everything exactly right, well, it's probably not always true, right? There's some things that are, that are out of your control.
JZ (15:17)
Yeah.
Yeah.
Jake (15:34)
But there's this sense that there is a lot in your control. There are a lot of things that you could do to make it better. And as soon as you start making...
JZ (15:41)
Well, that makes it even harder
because we have such, we as humans, think in general, we have such a hard time accepting that there are things out of our control that like we might do everything perfect and it still doesn't work. It makes it even worse. That makes it even harder to like deal with these emotions and to like push through that feeling and actually get started because you know that like not only are you like
Jake (15:52)
Yeah.
JZ (16:08)
working against yourself with this feeling, but then you have this sense that like the world is working against you or not, maybe not against you, but it's at least not necessarily pulling for you in all ways.
Jake (16:22)
Yeah. I mean, to me, the external things that might work against me are comforting in a way. Like the external things take it away from being about my own decision-making and my own navigation of the ship.
JZ (16:31)
interesting.
Yeah.
what if Atomic Habits was the first book about habits? would it have been as successful as it was, you know, coming out when it did when there were, there had already been a bunch of great books about habits. People were sort of primed to like, believe that this was an important topic they needed to master in their, in their daily lives. Like that, yeah, James Clear could have done everything right. He could have written the exact same book. He could have had the right, the exact same
massive audience of newsletter followers and all his great blog posts, but like the world wasn't as ready. Like, that wouldn't have been his fault, right? That wouldn't have been because he was imperfect. would have just, yeah. So it is a bit of comfort to know that it could still go wrong and it's not you.
Jake (17:15)
Right.
Yeah. And in reality, there's a lot of things that are not us that cause things to work or not work. There's a lot of those. There's a lot of those. Absolutely. I mean, even the things that put us into a position to have the idea in the first place or to have the opportunity to do the thing, there's so many of those things that are, that are luck based. And that's, I suppose that's, that's comforting, but anyway, the
JZ (17:32)
Probably mostly, there's probably the balance is more external things than internal things.
Jake (17:51)
The problem with perfection anxiety is it's not, there is certainly a logic to it. As I just sort of laid out, that's my logic. can, can, you can identify the logic thread, but it, it isn't, it doesn't require logic to operate. And it mostly is. It's the most insidious when it's, you know, operating in the shadows, when you don't see it. And it's just like, I'm just not doing that thing. I'm just not pushing the thing forward.
JZ (18:14)
Yeah.
interesting. Yeah.
Jake (18:20)
And I, and I'm not aware of why or I started the thing, but now I just can't quite press on. look back at, so I, I, I'm going to talk a little bit about being a kid because that's the, sort of identification of this comes from when I was a kid and my, dad, yes, that could be one of the sort of the smaller version of this sweater. I, you know, it's not, but it's a, it's a perfect, it's a perfect connection.
JZ (18:35)
back when you had V1 of that sweater.
Is that why you're wearing it?
Jake (18:47)
So yeah, I used to be really into drawing as a little kid. And I mean, I'm still kind of into drawing, so that hasn't stopped. But I remember my dad saying, you you have to be really wary in your life of perfectionism because perfectionism is a trait that many people in his side of the family had. And he said, your grandfather, his father, and...
And his, and my dad's grandfather, so my great grandfather really struggled with it to the point where they often just couldn't do anything. It was sort of just paralyzing to them because they couldn't make the thing perfect. So they just wouldn't, wouldn't do anything. And it's so from the, remember being a kid and hearing that and being like, my God, like, I don't want to, I don't want that to happen to me. And, and yet, you know, when I, when I think back on the way I felt about
projects that I worked on as a kid. when I look back, like sometimes there was this pure joy, but sometimes when the idea was really exciting, it would, I would shut down. And I, I, I look back on like, you know, I have these sketchbooks. I think anybody who's into drawing probably has these as a kid, you have, or as an adult, like I have them too. You have like a sketchbook or some kind of notebook and there's like some cool stuff on like the first two pages and then it stops.
You know, and there's some idea and you kind of run out of steam and some of that is just natural. Like I have this idea, I'm going to make this comic book out of this book. And then you kind of run out of steam on it. And you're like, actually it wasn't as fun as I thought. Some of it's just sort of natural, but some of them I look at and I'm like, too bad you didn't finish that Jake. was perfection anxiety. Like you, you didn't quite bow into it, but it was stopping you from, from finishing. And that is, that's what I like, don't want to do.
JZ (20:10)
Yeah.
Jake (20:39)
And that's when we talk to founders, it's what I don't want them to do. And I think that the design sprint, the foundation sprint, all these like sprint formats that we now do with folks. When I was first putting that stuff together, a lot of those methods, they were just tricks to get me to break through the anxiety, break through the procrastination and just do something, even though it was going to be imperfect.
JZ (20:58)
Yeah.
Jake (21:07)
It would be for, there'd a forcing function because everybody would be together for a week, working together in the same room. I'd have to do some, I'd have to make a decision or we're going to show this to people tomorrow. We did, can't be perfect. You just have to get it done. And that was so powerful. then, you know, the, the idea that you're going to put it in front of people and get another chance to change it.
JZ (21:22)
Right. Yeah.
Mm.
Jake (21:34)
You know, that
JZ (21:34)
Mm-hmm.
Jake (21:35)
was really important. All the little micro steps within a sprint. Now we're going to do this. Now we're going to do this and it's timed and you have to make a decision about who your target customer is right now, because in order to get done with the week, we just, can't linger on this forever. There are all ways to break down perfection anxiety. And I hadn't really thought about that until this conversation I had with the founder, that, we were referencing. And that's why it's been, that's why I've been talking your ear off about it.
JZ (21:56)
Mm. wow.
Now it's super interesting and.
I find it that...
many of the sprint methods that you've created and the techniques you've created and that I've been able to help shape are in some way just like tools for yourself, right? They're just like this set of things that you created to help yourself over perfection anxiety and be able to do the best work possible. I...
You know, certainly it's nice to create things for other people. mean, that's, think what gives us the ongoing motivation to continue. But sometimes just solving a problem for yourself is, is like a really good way to get started. It's a really important way to start because I think it provides a little bit of activation energy that you, that you need. And I guess I sort of knew that about design sprint before, but.
This is a different way of framing it that I hadn't really considered.
Jake (23:07)
It's hard to use as like a motivator that, everybody, we're going to come together and do this thing because we all have anxiety or maybe you don't all, but I do. I bet like one of you does, and it might be slowing everything down. And like, that's not probably going to get everybody like super, super psyched, but yeah, it's, it's totally, it's totally real. And I remember when I was working at Google.
JZ (23:15)
Yeah.
Right, right.
Jake (23:35)
So before you and I worked together, before you and I even met, and I was working with Michael Margolis, who is an excellent researcher. He works at Google ventures to this day. He's, he's just absolutely fantastic. And, and you and I worked with him for a long time and he influenced a lot of things in the design sprint because he was able to come up with all of these methods for running these quick and dirty customer interviews in
going from zero to recruiting to composing the interview to running the interview in one week. And he kind of said like, look, that's not only is that possible to do like once or twice, like you can do that pretty repeatedly, almost anywhere you go. And so that unlocked this notion that we could, we could not just build a prototype in a sprint, but we could test it huge deal. But, but I worked with Michael before on Gmail and actually he was my manager for, some time when I was working at Google.
JZ (24:31)
Mm.
Jake (24:34)
And I remember him saying to me, Hey, Jake, did you ever notice that you seem to get a lot more done when you have some kind of a deadline? And I was like, yeah, but like, isn't, doesn't everybody do that? And he was like, well, like not to that degree. And I think like, it was maybe a compliment, but it was a little bit of like, you know, sometimes nothing's happening. There's no deadline, but he was like, you know, like maybe think about if there's a way you can.
JZ (24:42)
You
Yeah.
Yeah.
Jake (25:04)
You know, create more deadlines. And I was like, huh. You know, okay. How could I do that? And, and that was, that was one of the seeds that got me thinking that a design sprint, although, you know, it was exciting to be in a setting where we're working together and we have to create a prototype and those things happened occasionally at the beginnings of projects, but that sort of sparked this idea in me that, maybe you could create a deadline.
And then when there is a deadline, lot of the, a lot of the anxiety falls away because it just, it just can't, you know, you're either gonna, I'm either going to be in like a huddled ball on the floor, like naughty, or I'm just going to have to do it. And yeah, I know you worked on a newspaper in college and I worked on a school newspaper in high school. And that too was a really powerful, visceral experience of a deadline.
Because how often did the newspaper come out for you? Every day. man. It's got bananas. Yeah.
JZ (26:04)
Every day. Yeah. Yeah. I
was just talking about this with some friends who, they didn't really know like, you know, the story of, this is where Michelle, my wife and I met. We worked at a student newspaper in college in Madison, Wisconsin, at University of Wisconsin. of Wisconsin has two student newspapers.
And I don't know the status if they're still printing, if they're still daily, but they still exist as one of them is the official school paper and the other one is the unofficial one that we worked for. it's called the Badger Herald. It's quite miraculous. A bunch of students just decided to start this in the 60s and just kept going. They sell ads, they put the ads in the paper, they make enough money, they have an office.
Jake (26:42)
What's it called?
JZ (26:56)
You know, it's like pretty amazing, it was a daily newspaper. We printed about 16,000 copies every day. I was my like the main job that I did there. eventually started working on the website. But the main job I did when I first started was like designing the pages and then coordinating with like the other designers and the photographers and everybody to make sure that like the production of the paper was.
was on track, know, like everything looks good, everything's there. We don't have any weird like, corrupted files, you know, when we send it to the printer and all that kind of stuff. and that was like basically the first design job that I ever had. Like I had designed things before I like made websites and other goofy stuff when I was, when I was younger. But the first real design job that I had was that daily newspaper. And yeah, I don't know. Like if I would have
Jake (27:35)
Yeah.
JZ (27:50)
gotten into design or stuck with design if I hadn't done it in that structure of having the forced deadline every day. So yeah, I'm totally with you. It's very powerful to have those deadlines, whether they're created by external forces or created, at least in a convincing way. Internal, your own deadlines, have to be convincing in order to work, but they can be really effective.
Jake (28:16)
It's very hard to make a deadline for me, for myself, for me to say like, I will have this done by this day. Like very challenging. I have done that on occasion, but that's one of those things in the category of like white knuckle. I'm going to use self-control to do this. And it's just, that's just not going to work for me for the long haul. Like.
JZ (28:22)
Yeah. Yeah, yeah.
Right, yeah.
Jake (28:45)
It's, it's a tough, it's a tough way to go. If you can create the deadline with other people, then it's, then the magic happens and the deadline becomes real. I have got, okay, we're all, we're all doing.
JZ (28:56)
Yeah. Yeah. That's one of the big philosophies
in make time, which is that you, you want to spend time on something or get something done or make time for something, you can't just white knuckle your way through it. You can't just say today, I'm going to be better today. I'm going to be more productive, more focused. You really do need to change the, environment that you're operating in, whether that's through deadlines or commitments to other people or
Like we talked about the distraction-free phone last week, you you have to change something that's outside of yourself because, and this isn't just our experience, like there's a bunch of psychology research that shows that self-control just really isn't a sustainable way to make changes. You have to change the environment.
Jake, what was your advice for this founder, this founder you were recently talking to about perfection anxiety? What did you tell him? And was it helpful?
Jake (29:53)
Yeah, well, advice, perhaps.
Well, we'll, we'll see. mean, time will tell. think it, I think it was helpful in the short term and then we'll, we'll have to, we'll have to see. But my advice, perhaps unsurprisingly was to run design sprints. So, you know, this founder was, there's a lot to do when you're starting a company and there, you know, there are people you need to hire or there's conversations with customers you need to have.
JZ (30:01)
Yeah.
yeah.
Jake (30:27)
There's technical investigation that you need to do. And in the very earliest days, like, well, how do you prioritize among those things? And I don't claim to have the perfect answer for every person, but I'm a person with a hammer who sees the world as a nail. But I also know that when it's unclear what to do, taking the action of creating a quick version of the thing and putting it in front of customers is super powerful. And the design sprint.
creates this external deadline because as soon as you start scheduling with customers, now you have to have something ready to show them. And to me, that's one of the most powerful deadlines is like someone is expecting me to show something. even though, even if I arranged for that to happen, once it's in place, it really fights the anxiety pretty powerfully.
JZ (31:02)
Right.
We actually heard that
earlier this week, the design sprint we were running this week. There were a couple of moments where He's like, you know, we got these customers lined up. Like we got to figure out what we're going to do. It's like, all right, like is it working? Like this is why we work in this way.
Jake (31:28)
Yeah.
Yeah.
Yeah, yeah, it's, it's exciting. It takes, it takes me back to making the newspaper and like, we would call it hell night the night before we made the newspapers. We only came out with a newspaper like maybe once a month or something. mean, granted we were high school students. We were not as competent as you guys were, but still the notion of doing it daily and going to college is like, I can't even fathom but that zone that you get into when you're creating it and you know, it has to go to press.
JZ (31:50)
Yeah.
Jake (32:03)
It's like, it's wonderful. It's so liberating because if you are a person, if you like creating things and you can get into the situation, especially if you have perfection anxiety, if you can be freed of it for a while, God, feels great. And, and then if you can make something and see that it's okay, that it's, you know, not perfect, it does, it does make it, I think more possible to get through the next time too.
JZ (32:18)
Yeah.
Jake (32:32)
It doesn't make it go away, at least for me, it's still there. Still there. mean, you could, if you, if this camera could pan around my desk and turn, you know, if I screen shared my email, like it'd be full of things. We'd be like, that perfection anxiety. Yep. We need to deal with that. It's like stop whatever. But the longer you spend outside of your comfort zone, you know, the larger your comfort zone becomes, that's a saying that I've become very fond of. And I do think that when you can get into that.
newsroom zone where it's got to go to press. get into that prototyping zone where the people are showing up tomorrow. It reminds my body, like that's what it feels like to just make something imperfect and be okay with it. And I can come back to that to some extent whenever I can identify that perfection anxiety is what's going on. know, sometimes I can't, I don't see it, but as long as I can see it and then maybe I can say, okay, then it helps.
JZ (33:29)
Yeah, yeah, that seems like a really useful two step little process. One, if you are feeling stuck on a project, like consider whether it's perfection anxiety, consider whether you're not starting because you are you're afraid of what it will be like when it's when it's done, if it will be less than what you imagined being. then to find a way to.
Jake (33:48)
Yeah.
JZ (33:57)
change your environment, find a way to create a deadline to put yourself in the newsroom or put yourself in the design spread. There's something like that kind of bust through it. And yeah, it seems like a really helpful little two-step that people can use.
Jake (34:12)
One of the tricks that I often use, you may not realize this, but you're often my perfection anxiety lifeline. I'll be like, no, like I'm, I'm stuck on this and it's because I can't, bear to make an imperfect decision about the proper action. And I'll like text you or email you and be like, Hey, what, what do you think is a way to, can you, can you think of a way to do this? Or like,
JZ (34:27)
Mm-hmm. Mm-hmm.
Mm. Mm-hmm.
Jake (34:38)
Or if I have an idea, but I just think it's not perfect and I'm afraid to do it, I'll send you like, Hey, I'm thinking about this. And you know, this, might be like, for this, you know, this post we need to send or send an email to a founder or something. And I want to make sure I ask for a phrase that right or whatever, like just to send the draft to you, even if you're just like, yeah, that sounds fine. Or like, I don't think this is a big deal or like, or sometimes you'd be like, you know, you know, maybe.
JZ (34:47)
Yeah.
Yeah.
Jake (35:08)
think about this or whatever, it's like a, it's a way to break the, the hold, the stranglehold that it has on me. And so that's, you know, it doesn't always have to be create a deadline. it can be just like anything that, that makes me see that it's, that it's okay for it to be imperfect.
JZ (35:28)
Yeah.
Jake (35:30)
There's a great quote about it. And I can't remember if it's, I think it's from the book, bird by bird by Anne Lamott, but it might be something else. So I've, if you, if you're the, I doubt the actual author of this, if I know Anne Lamott or the actual author will be listening to this particular episode. But if you were the actual author and I screwed it up, sorry. And if you're Anne Lamott, thanks for listening. the, but the, the metaphor.
JZ (35:40)
Mm-hmm.
You
Hahaha
Jake (36:00)
that this person uses that I just love and so vivid for me is of like having the idea in your head is like a butterfly. And if you want to turn the butterfly into like, you know, you want to capture it and like create it, bring it into the real world. But by capturing it, you're like pinning it down and like ruining it. You know, you're like destroying it as you go.
JZ (36:26)
Yeah, yep, yep.
Jake (36:29)
and
that that process feels that painful to see something beautiful and know that you're destroying it. And I just found a lot of comfort in that metaphor because I was like, yeah, it can feel that painful. It's illogical, but it can feel that painful. And it's a bit freeing to know that someone else felt that way. And I just thought like, okay, I'm not crazy.
when I feel that way, also don't have to be ashamed of feeling that way. I could just try to notice it and use one of, you know, maybe an increasing toolbox of strategies to get past it. and I'm sure it's something I'll always deal with, but, I'll keep, I'll keep trying. I keep, keep trying to come up with, with new tricks to get myself past it.
JZ (37:22)
Jake, do you have any recommendations to share with our listeners?
Jake (37:26)
Well, as it's December here, that's means it's time for Christmas music, holiday music. And my, mean, you know, there's, there are many great Christmas songs. know you're, you're a big fan of, Christmas music yourself, but, one album that I think is. I feel like it's a little off the radar that I think is excellent is the Weezer Christmas EP. And it's okay.
JZ (37:42)
Yeah.
Wow, didn't even know that existed.
Jake (37:56)
If you like Weezer at all, and I'm sure not everyone is a huge Weezer fan, in fact, I'm not such a fan of their later work, but really the earlier work I really do love. And every now and again, we'll have a great song that I love. But the Christmas EP is, I just think it's so delightful. And I listened to it over and over again in December and then as long as I can, as I can into January even. And I actually just converted my son who's 13, who has been like,
JZ (38:20)
haha
Jake (38:26)
not really too into it. And then yesterday he was like, Dad, I got it. I see why you like it so much. They sing Christmas carols. So it's not like new Christmas songs that they've written. like the very traditional religious sort of Christmas carols, a lot of them. But they're done in like fully wholehearted Weezer style. And I just, I love it. They're fun to sing along to.
JZ (38:29)
Yeah.
Yeah.
Jake (38:52)
One thing that my wife and son were pointing out is I really love the, as I think pretty much everyone does the Mariah Carey, all I want for Christmas is you. Right? It's a great Christmas song. Yeah. So good. So good. But, or like the Frank Sinatra Christmas songs. So good. But I can't really sing along to those without feeling like I suck. You know, it's like, but like, and I'm not saying that Rivers Cuomo, know, lead singer of Weezer.
JZ (39:01)
Yeah, there's a reason it's number one every year. Yeah.
Yeah.
Wow, interesting.
Jake (39:20)
I'm not saying he doesn't have a good voice. has an amazing voice, but it's more sing alongable too. Also because there's like loud, like rock music in the background. It's just feels, you just feel more invited to sing along and I don't know. just, it just gives me such good vibes. So I would, even if you're not like really a Christmas person or whatever, just yeah, Chris Weezer Christmas EP. It's short too. It's like 30 minutes, maybe tops. It's good stuff. How about you? You got any recommendations?
JZ (39:25)
Sure, yeah.
Yeah.
Cool.
Two quick ones. first I will admit is probably the third or fourth time we've mentioned the acquired podcast on this podcast. So, know, way to go guys. Big fan of the show.
Jake (39:59)
yeah, yeah.
Hahaha
JZ (40:05)
they put so much work into their episodes, they don't come out all the time. So on the timeline, relatively recent on the calendar, pretty far back. Anyway, there's an episode about Starbucks and so in typical acquired fashion, it's like a three hour episode. It's like incredibly detailed, very well researched, very insightful, but they did something that they rarely do. I don't know if I've ever seen them do this, which is that they had the
Well, not technically the founder of Starbucks, but they Howard Schultz, sort of, all intents and purposes, the founder of the Starbucks that we know today, the longtime CEO, multiple times CEO. He left, he came back, he left, came back. They had him on for the whole thing. It was like a three and a half hour interview with Howard Schultz. I mean, just the stamina, the endurance of it was so impressive. And I love coffee. I love the coffee business.
We invested in Blue Bottle Coffee when we were at Google Ventures. We got to work with that team. I invested outside of character. I invested in a coffee company called Tyka. I have a couple of friends here in Milwaukee who run coffee companies. kind of try to help them out here and there. So anyway, it was absolutely fascinating. The acquired podcast episode about the history of Starbucks, highly recommended.
Jake (41:01)
Yeah.
I started
that one and then I got into the rest is history podcast and I've kind of, need to get back to that Starbucks episode because I found the beginning so fascinating. And one of the things that is really cool about it. Well, one of the things that's really cool about it is I think part of the reason they got Howard Schultz for the whole, the whole show is that those guys are from Seattle, which I really liked because it's, you know, Northwest guy, but this factoid in the beginning where they talk about how
JZ (41:41)
Yeah.
Jake (41:49)
the earliest days of Starbucks rolled out. And this was, was interesting to me because my sister worked at Starbucks before Howard Schultz was involved, like in the really early days. Yeah. Like, I think she said there were two or three locations at that time, maybe just two. And so she would sometimes work in, if you've ever visited the original Starbucks in Seattle down by the Pike Place Market, she would sometimes work there and sometimes work in another location. But the...
JZ (41:58)
Wow, that's incredible.
Amazing.
Jake (42:16)
original owners, the original founders of Starbucks modeled it after Pete's. Pete's coffee was the first to bring the, how do you, what's the kind of beans? The, Rabaka beans, right? Before it was a robust something. Yeah. And they were, they're kind of, you know, like the, what we might think of today as like, I don't know, like instant coffee or diner coffee. That was coffee everywhere. That was first wave coffee. Second wave coffee was Rabaka beans. Pete's was the first.
JZ (42:27)
Eurebica. Robusto, yeah, yeah.
Jake (42:45)
Starbucks guys were super stoked about it and they were like, man, that's great. So they start this coffee company. They're just selling Pete's beans in Seattle. That was like the first thing. You couldn't even get a cup of coffee. Yeah. You could only buy beans. then they, they, you know, are, growing kind of modestly. Then Howard Schultz gets there and he's like, this is really interesting. And then he gets excited about espresso.
JZ (42:53)
Right. You couldn't even get a cup of coffee at Starbucks when it first opened.
Jake (43:12)
He visits Italy and he's like, okay, we need to start doing this. And there are other coffee shops, apparently in Seattle at that time doing espresso, like some that are still there to this day. but his, he wants to do espresso at Starbucks. And then the founders are like, eh, they're kind of lukewarm on it. So he leaves and starts his own coffee company. So then this was what I thought was so fascinating. The owners of the founders of Starbucks get the opportunity to buy.
JZ (43:12)
Yeah. Yeah.
Jake (43:40)
And they love peas. They idolize peas and they're selling peas beans. So they're like, okay, we have to do this. They buy peas and then they get spread too thin and they have to sell Starbucks. So Howard Schultz who's got now this, his own coffee company startup, his own cafe, like two or three cafes buys Starbucks. and so I can't remember what called like Il Giornaio or something. But so Starbucks then corporation.
JZ (44:00)
Yeah.
Yeah, something like that, yeah.
Jake (44:10)
changes its name to Pete's because it now owns Pete's and that's all it owns. And, and Ilgernio changes to be Starbucks. So like under all of the covers, like Pete's is actually Starbucks to this day. And Starbucks is actually Ilgernio. Anyway, I just thought that was like, that was so fun. I just, I haven't, and I've told so many people, you know, in my family or anybody who's drinking coffee, like, you know, and I'm sure everyone's so sick of me talking about that. it's just so, I don't know. It's like, that's so fun.
JZ (44:20)
Right. Yeah.
I enjoyed it because it's a good reminder that the early days of what ultimately become really big successful companies are often not so straightforward. There's often a lot of like weird twists and turns and unexpected things that happen. so if our own path or your own path feels a little bit twisty and convoluted, like hang in there. There's hope. You could be as successful as Starbucks one day.
Jake (44:50)
Yes.
Yeah. man.
JZ (45:09)
second,
my second recommendation is, is a quick one, which is, our, our friend and former colleague, MG Siegler, who's a very, very well-known person. Of course. he started, I think it was earlier this year, he started a new website. He left Google ventures. started a new website called spy glass. It's a great, great blog. I mean, it's sort of almost like a magazine. he writes about a lot of the same stuff that we talk about, like tech and.
different products and business strategy stuff. also writes about sports and entertainment. Interesting. I don't know how he produces as much writing as he does. It's really astonishing. But he recently came out with, I think he calls it the dispatch. It's a daily email. It has become sort of like my one daily read. I subscribe to a bunch of newsletters, but it's kind of the one thing that I prioritize reading because I just
Jake (45:50)
Unbelievable. Yeah.
JZ (46:08)
I just like what he chooses to summarize and I like the way he summarizes it. So if you're interested in those topics and you're looking for a of a daily summary of what matters, spyglass.org, check it out and sign up for MG Siegler's new daily newsletter.
Jake (46:27)
It's really great. And it's, it's really both readable and skimmable. He has a great, you know, sort of narrative take on the news of the day that the tech and sort of product and entertainment news. So you're also not going to get, you're probably not going to get like bummed out reading it, but he is. Also really good about putting in good headlines, links, so forth. So you can, you can spend.
five seconds reading it, or you could spend, you know, 20 minutes reading it. And it's sort of, you choose your own adventure, which is nice. Really prolific. mean, that guy talk about the daily paper. he's, I mean, he's just cranking it out. One man, one man show. amazing. We got to stop recommending other people's stuff though. No one's going to, you know, we, we to start recommending previous episodes of this podcast. Yeah. All right. Cool.
JZ (47:03)
incredible.
Yeah. All right.
Yeah.
Self self recommending.
Well, thanks for listening or watching. This was episode 10, Jake and Jay Z our weekly podcast. If you want to get an email when we release a new episode, go to jakenjayz.com sign up. That's where we will increasingly share interesting stuff that's going on. And if you liked this episode, please scroll down below, hit all the buttons you can like comment, subscribe, please tell a friend. So.
we can help more people find out about this thing. Thanks.
Jake (47:48)
Thanks guys, bye.