Our guest is Jay Acunzo, an award-winning podcaster, energetic keynote speaker, captivating storyteller and a guy bothered by conventional thinking.
We LOVE this already!
Jay is host of the amazing, Unthinkable Podcast, where he weaves intriguing—better-than-NPR—stories that inspire imagination and motivation to do more… to think more and to unleash your creativity into work that matters.
Jay’s MISSION is to help you hone and trust your intuition to do more exceptional work.
Devani and I have been listening to Jay’s podcast for over a year. We also enjoy his YouTube channel of presentations and keynote speeches.
Jay is one of our favorite inspiring millennials. So much self-awareness and wisdom, freely shared through his podcast and emails.
We could’ve spent all day with Jay. He’s sharp, personable, brilliant and self-aware and definitely an influencer to follow.
“I believe in creativity.
I reject shortcut culture.
I defend craft-driven creators.
I make things to help makers.”
~Jay Acunzo, Unthinkable Media
Links & Resources Mentioned:
- Never Let Me Go, by Kazuo Ishiguro – [our Amazon affiliate link]
- Kitchen Confidential, by Anthoney Bourdain – [our Amazon affiliate link]
- A Beautiful Constraint, by Adam Morgan & Mark Barden – [our Amazon affiliate link]
- Calvin and Hobbs, by Bill Watterson – [our Amazon affiliate link]
- Unthinkable.fm – Jay’s Podcast – [no affiliation]
- SorryForMarketing.com – Jay’s Website – [no affiliation]
- 90 Day Goals Journal – [our very own creation]
- 90 Day Creator’s Challenge & Mastermind – [our very own program]
Full Episode Transcription:
[00:00:01] LeAura: This is the I create daily podcast. I’m LeAura.
[00:00:07] And I’m Devani and we’re here with Jay Acunzo. Welcome Jay.
[00:00:11] Jay: Thanks for having me guys. I’m excited to chat.
[00:00:14] LeAura: We are. We have a pre intro pre podcast intro already so we’re not going to get into introducing ourselves but we’re going to introduce this amazing guest. So Jay Acunzo is an award winning podcaster, energetic keynote speaker, and a guy bothered by conventional thinking. Host of an amazing, better than NPR podcast my opinion. Unthinkable. Jay’s mission is to help you trust your intuition so you can realize the full potential work your full potential more quickly. So to start we have with I create daily a little bit of mantra invocation. We start. We sustain and we succeed. And so for the podcast we’re going to start with a little brief another little brief excerpt on you and then ask you questions.
[00:01:01] Jay: Sure.
[00:01:02] LeAura: So on your website sorry for marketing dot com. Jay says I believe in creativity. I reject shortcut culture ideas and craft driven creators and I make things to help makers. So this is amazing. As I said to you right before we started recording we could talk with you all day and into your podcast. We feel like we’ve already had so many conversations I’m sure you get that. But you speak to our heart and you inspire our souls is very much the work that we’re doing. I mean look Unthinkable, we’re having this podcast out in the woods right. This is like this is not normal but this is who we are and what we do. So tell us more about what you do and how you got started.
[00:01:46] Jay: Yeah. Thank you so much. There’s my favorite comedians is named Mike Birbiglia and he has this quote about there’s a lot of people that are good. There’s a lot of people that are great but very few people basically speak to your soul when they perform. And so that complement meant the world to me. So thank you. So right now I do three different things. I travel the country and a little bit the world and I speak so I’m a professional keynote speaker. That’s the bulk of my business. And behind that I have this podcast that you mentioned unthinkable where it’s kind of like this public lab where we lob out ideas and go investigating and largely through narrative story and you know it’s evolved over the years. But right now what we built it as what we promote it as is stories about conventional thinking in our work and the people who dare to question it. And so often people who do work that we deem crazy whether that’s crazy good. And I wish I could do that or insane and that’ll never work. Usually they know something we don’t about their own context. And so when you talk to these people and tell their stories it’s not they took some giant leap. It’s not that they had some giant ideal or montra or all these things that we hear about in our culture today and they certainly didn’t rely on some list article from an expert. They just knew their context better than you because it’s their context. And so you hear them talk about their story like it’s smart or logical or certainly meaningful.
[00:03:08] And so we call it unthinkable not because what they did was actually unthinkable but that’s the perception from the outside. And the reason I’m doing this is because I want to tell more meaningful stories about work. And that’s kind of my whole thing. I like to make people feel with the work I create and the work I create centers on the working worlds coming out of start ups and you know B2B companies mostly. And so I mentioned there’s a third thing I do which is I help other organizations try to spark movements bigger than themselves in the B2B space primarily through the creation of original shows about work. And so those That’s the kind of three I guess legs of the stool of my career right now. But my background has been writing and marketing and working for tech companies even a venture capital firm and I’ve just kind of moved around a lot and it always came back of this one idea of like drawing a lot of meaning from the work that we do and I just don’t think that that work is covered by the media or even brands that talk about work quite the same way that we all like to talk about it.
[00:04:04] And so I wanted to change that.
[00:04:07] LeAura: yeah, that makes sense and I’m going to go off script a little bit here so Dave and I do this all the time we have our questions just so that guests can have a sense of what we might ask. And yet we get into conversation it’s like we also want to follow that. And sure I want to go a little deeper into the. Story. So that’s like.
[00:04:24] How you kind of got to be what you’re doing what you’re doing. But how do you begin. What was the precipitating factor factors that began to inculcate in you this concept and intuition and essentially you like unconventional and the confidence to pursue that because that’s the other missing thing like you sad about you know people you know like they got there but they also have to have that confidence right.
[00:04:50] Jay: Right. Right. I feel like it’s always an amalgam of everything you experience that leads you to that moment right. So it’s hard to pinpoint one thing but I’ll try to put a couple of dots on the map if I can look backwards at it. So I think one of those things was I had a job at Google. Those My first job out of college and I liked everything about the job the brand that people actually met my wife at this job so I have a great return on investment from my first job ever. And I liked everything around the job itself. But when it was time to put my head down and do the job I hated it and I felt kind of guilty about that because here I am at this company especially in ’08 ’09 and beyond where startups weren’t as exciting and tech companies weren’t as ubiquitous. I was at Mecca. I should have been so grateful I should have been so happy. And it was all because I think I think we’re sold this kind of like lie about career which is a great career is built on one foundation. The most important thing and that is expertise and expertise comes with prescription and all set of instructions and a career ladder. And we always get these feelings especially as creators. That something’s not sitting right. It’s like we can do better than that. I can do better than that. I want more from my work than that.
[00:06:00] And we’re never told like how to view our work or how to view the pursuit of great work differently than just get better and better at the craft. And today. That like how to stuff is so commodified. It’s everywhere like you can watch a show like this or listen to a show like this in a world where you know all this information exists. Expertises Now table stakes knowing how to do something. Table stakes. So I think rather than building a career on expertise you have to build a career on self awareness which nobody has taught us how to do. Nobody has advised us that that’s actually the most important thing and everything else including the expertise you want to acquire follow suit from that. So the foundation isn’t how to. The foundation is like why or why me or why are my customers you know insight about yourself and others that you’re trying to serve. So Google I had no insight about myself or others I was trying to serve yet. And so I was just riving. I was just super unhappy and I quit and I joined a bunch of startups and I started to feel better and I started to get a lot more self-awareness because I was allowed to experiment and try and fail more which let me get more data points into my brain that said OK I’m I’m about this I’m not about that. And then it just kind of narrowly got into one more direction that looks like the one I described because I was trying so much different stuff and learning about myself learning about the audience that I wanted to serve.
[00:07:17] So so if there’s one moment to me that paints a picture of that it was my decision to quit Google because that was my moment to say this is the prescription This is what I’m supposed to be doing to do good work and have a great career. And I’m realizing now it’s not for me. I don’t know what it is for me but I’m going to try to figure it out. That’s the thing that started me on this journey of like self-awareness and a shorthand for all of this stuff to me is intuition is intuition is really I think just knowledge from within.
[00:07:44] We’re asking the right questions to pull out that knowledge from within and that is your contacts about you and your audience.
[00:07:50] Devani: Um, you say on your Web site but I think this ties in really well to the point you’re making about I just following that gut feeling. This isn’t necessarily what I want to do. Even though everyone says you work at Google you work at one of the best companies ever. Why do you like the happiest person alive. But you talk about you on your site you said it’s your aspiration to create the world’s most powerful business stories. Yeah. And I know on your unthinkable podcast you definitely find some great stories we listen to the Grato the ear company’s story had some company story the other week and it was amazing. And can you elaborate on on what you mean by that as well like just what you’re doing with that beyond just the podcasts.
[00:08:37] Jay: So yeah I mean it very simply boils down to this like my whole thing. I mentioned briefly was I want to make them feel. So whether you’re consuming my work in the form of a podcast a written article or a speech I want to make someone else feel and the whole gamut of feeling from laughing and just enjoying yourself, to kind of introspection or crying like that you know like not crying per se but feeling the emotions associated with tears or you’re kind of like really moved because like that to me. Is when you get to realize your full potential like as a person like you’ve you’ve you’ve kind of like. Been told again that this working world is about like expertise in you know a stock ticker at the bottom of your screen and you know like how to tips and tricks articles and those are really hollow things. And a lot of us draw significant meaning from our work. And so why can’t there be the daily show of tech. Why can’t there be a sports center of marketing or the this American Life of sales or on and on and on whatever you do. I feel like it needs to be portrayed it deserves to be portrayed in a way that matches how you actually experience it. So this is kind of like outside of unthinkable outside of my speeches. This is just like my personal kind of driver. It’s like I really want to be someone who contributes to people doing their best work. And I think part of that is they see themselves reflected in the media they create or rather consume about work.
[00:10:01] And so if I can create some of that media and I can inspire some people to be like I’m going to unleash my full self I get it now it’s about me and my own self-awareness not about some expert guru great right. But if I totally fail in serving others in that way and I hope I don’t at least I get to create some really cool stuff.
[00:10:19] Devani: You know I can’t see you failing at doing that.
[00:10:24] Jay: Well it’s it’s early. Thank you.
[00:10:25] Devani: You do a good job of highlighting the stories and I think something that’s also important as you said and you said I hope people get to create the media they want to see. And I think that’s really important right now in our community. We have several people who are several artists who talk about how you know there’s this bombardment of media that they don’t necessarily want to hear and they don’t and it impacts their own art because it’s like how do I process all this information in the world. I can’t do anything with. And so creating media that you want to see out there and creating And you also said helping people feel. And I think that’s what creatives do. Whether you’re an entrepreneurial creative or an artist creative or a mix of all of that it’s helping people feel up full range of emotion that’s really important I think that’s why all of us get into doing this because we do the job route and that’s fun and that’s cool and that’s great experience and then or like there’s something more and you have to scratch that itch of something more.
[00:11:29] Jay: And by the way if you are working for a larger organization and love it or if you just want a job that pays the bills so you can go home at five and draw meaning. You know outside of work great as long as you know that about yourself if that’s what you’re about and you get it. Awesome. I would look back at people at Google that stayed longer than I did and maybe even some that are still there and I’m like how could you be doing that. Like I felt so crushed at that job that I wanted to prescribe that others leave or. Join a startup. And I did it first and then I realized you know what. Hold on a sec. This whole life is just about this this continual journey to become more and more self-aware. And and as I became more self-aware and obviously we’re all continuing that. But but in the moments I’ve had since leaving Google I’m able to look back now and say OK as long as you’re happy they’re great. And so I’m not trying to get on a stage or in front of a microphone to be prescriptive about how you can find happiness. I’m trying to encourage people to pursue that in whatever context you have whatever that means to you. Right I can hand you the seven tips and tricks of the one simple secret. I can’t teach you to be rich and all that other stuff. I happen to play on the same channels using the same mediums as people who profess to have secrets. I have no secrets. What I want to do is have you leave with a list of questions like the right questions to ask of yourself and your situation and then you will pull out your own unique answers understand your context better. And I think do more exceptional work right.
[00:12:52] Devani: Yeah. Have you found the more that you. Dove into your own self-awareness you almost naturally become more aware about others. I’ve always wondered just because for me it seems like the more self-aware I am the less worried I am about that person doesn’t seem happy. So I should go tell them do this thing and launch into this thing. But have you ever noticed like the more into your own internal awareness you get the less you really like.
[00:13:23] You just kind of release that need of like I have to tell everybody.
[00:13:30] Jay: It’s I mean it’s so tempting to do that right because if you’ve found a way that work you want to feel good about that way and sort of bragging to others but be and hopefully more importantly you want it to feel that sense of belonging like humans are wired to want to be in the middle of the group because we’re safest. Right. And so you want others to do it your way so you feel like you’re part of something. But yeah I think to answer your question I have stopped trying to be prescriptive. But it is hard. It’s not like I’m just like oh I don’t feel any urge to tell you a good example as people ask me how to podcast. And I used to try to prescribe but there’s a million ways to do a podcast and do it well. And so now what I do is I try to start asking them questions because if I can learn a little bit more about their context instead of being like an expert who leads them. Maybe I can be a mentor who just kind of points out possibilities. It’s like hey I would never take this path and I would never prescribe it because that’s not me. But it seems like given X Y and Z that you just told me that I just learned you might actually want to go down that road. Right it’s sort of like a lesson from my show. So yeah in general don’t do that but you’re not operating in a generality.
[00:14:34] We’re all operating in a specific context or in general that’s crazy until you understand something about their reality instead of yours. So but it’s really hard. You know we all do things we want and the things we do to matter and therefore we want the things the way we’re doing things to be the right way. And you know I I kid with some people in the startup world that I come from that if there was one documentary we should all create being from the startup world. I think we should call that documentary Infinite Roads. Right. I think that’s true of any work like there’s not one way to do something. So who are you to say you have to do it this way. And we live in this culture unfortunately that there’s a lot of how-to’s was a lot of you should’s and there’s a lot of you have to’s and the only thing you have to do I think is think for yourself.
[00:15:19] LeAura: Yeah the only thing you have to do is think for yourself.
[00:15:25] Yeah for sure for sure. I want to go back to Google for just a minute because I’m short about being miserable there. And it seems like maybe there you were working on your what but not your why. It’s just like you had the outer shell but your purpose you know essentially the soul of who you are was not able to to come out and do its work. Would that be somewhat of an accurate description.
[00:15:48] Jay: Yeah I wish someone told me that the point of early work is you know especially in your 20s is to try stuff and figure out what you do and don’t want to do or who you are who you aren’t. Instead of find the one thing that will carry you for years and years. Yeah. That that’s kind of how I was frustrated because I was like This isn’t the job or these stops for me. And that was the wrong mental approach.
[00:16:07] LeAura: Yeah. So where you are and then when you left Google I mean you were up against a couple of things one is sort of stepping outside of the culture being from you were stepping outside of the middle because hey you had the coolest job and the coolest company in the world and you’re leaving and I said Now you’re going to be on the outside. So that was one like bold move. And you didn’t know for sure what you were stepping into. So many people in our audience that would be growing and becoming ever more so are those who are in that place of where they are they’re looking to make art their full time. They’re looking to do work that matters to them as a way to also earn revenue earn income make a living. So there is that chasm for you. And you talk about that in the end show six which I’ll mention again later. But there’s that chasm. What did you do in that chasm How did you build that bridge to the other side. And what was that.
[00:17:03] Jay: Yeah I think that’s I mean that’s the bulk of. We did this like mini arc within the show to try to make sense of intuition and the application of it to make it practical not lofty. And this idea of a chasm. The word you used is bolts too. Like it was a bold move for me to leave Google. And again I come back to the principal of the show. Yes. From the outside looking in. Or yes. From their perspective. Outside of you. Right. But if you knew me if I you know and if so if i knew me better I maybe would have left earlier or not viewed it as this leap I would have to take. You know and so what got me over that leap is I think through frustration and pain and time all things that you can get rid of if you’re more self-aware. Right. But through all that stuff I finally realized like look I want to build something from scratch because that’s where I draw meaning in my work. I’m not the guy who wants to tinker on the machine incrementally. I’m the one who has a bunch of parts laid out in front of them. Or wants to figure out what the parts should be and build it early OK version of that machine. That’s what I love. And I you know the sooner I realize that the easier I got to make that move. So from the outside maybe it looks like a bold move to leave a great company cushy job reputable brand.
[00:18:12] But if you knew that about me or if I knew that about me which again now I do. It’s not a leap at all. Right. And so what we talk about in the show is when we want to do exceptional work you know we talk about that gut feeling that’s telling us we can do more. That gut feeling that has an idea or that sense of frustration there’s some kind of like inert just thing and I can’t put my finger on it all the time but it’s like it’s moving me forward it’s moved me towards like this mountain peak and I don’t know how to get there. And so often it looks like a leap looks like a massive journey. It looks like a bold adventure or whatever but if you know the right questions to ask of your own situation you can start to like be an investigator in your context about yourself be an investigator about your audience or the people you think you want to serve be an investigator about your resources which so often we think we need more of which I think is the great lie of creativity. Creativity doesn’t mean big. But anyway is asking the right questions kind of builds this bridge.
[00:19:09] LeAura: I don’t want to forget what you said. Sure sure. Creative creativity doesn’t mean big.
[00:19:15] Jay: No no not when you get hey are so creative creativity doesn’t mean big. Perfect example. If you’re a writer I get this a lot of speeches like J that was great but my boss but my time but my team or industry and it’s sort of like when you unpack what they’re trying to do when I ask them questions and I hope then they leave and ask these questions of themselves. We can actually distill it to like the first principle insight the truth underlying all the anger and angst and desire to do something big and what they’re saying is I’d like to write better things for the company blog great in their mind because they’re motivated and creative and aspirational in their work they want to write. Long form essays about amazing people. Great. Keep that in the back of your mind. Keep that mountain peak in view. Right. But what are the first few steps they get there like they’re saying that they can’t do that because their boss doesn’t get why that’s important. OK. So you’re going to write a blog post this week right. Yup. Does your boss control the first few sentences you use in every single article. No. OK. Can you just make those better. Like why not start each post with an anecdote which is like a flavor of what you’re trying to do an echo or a small piece right.
[00:20:28] And then what you start to do is collect little true believers people that respond in a big way to what you’re doing doesn’t have to be a lot of people can be a few number of people but like a small number of people but you can show your boss hey you know I started with the story and people started adding their own look out look at the comments section or look at the the the tweets we got their original thoughts not just a like or retweet. And you can hold that up and say I’d like to expand from this tiny little box to the slightly larger box not the full field but the wide open creative freedom which actually we should talk about creative freedom because I dislike that term too but it’s all about trying to paint creativity as a work ethic instead of this kind of big lofty ideal this wide open field this bigness. I don’t know where that comes from. Maybe because the people that inspire us do things that are so different than us or they’re so fine and all that we haven’t considered the journey they went through to actually do that. Right. I don’t get it. What do you have any thoughts on that.
[00:21:27] Devani: For me on my dream Well after reading so I was an avid reader when I was younger. I was home school for the most part. And so I got a lot of enjoyment and my own creativity from reading Harry Potter Lord of the Rings all those fantastical to me as a natural as a naturally creative person who wants to explore the arts in all sorts of forms. It was this romantic image.
[00:21:53] Oh I bet they spend their time thinking about these amazing things and I want to do that so sort of like how you’re coming up how you were talking about perspective from the outside without knowing the context. To me it was like these highly educated incredibly intelligent academic people sitting in this amazing setting writing these epic fantastical books. So that was my sort of perception of something and I didn’t know anything about it. And I would sit in front of the computer screen and type out a couple sentences and be like I’m just sitting here in my house and this everyday to me environment doing this thing that doesn’t feel fantastical. And so it sort of those gaps for a creator. I think that it’s like closing the gap between the romanticized vision and perception you have of something versus the daily grind of actually doing it. And so I think for me when you close that gap and you like OK well if you want to get to this what romantic version of whatever it is you’re doing you need to realize that every single day you have to do those small things right. What might that might feel like work which is a funny thing for creatives and like I don’t want it to feel like work because it starts you know like work it’s not art any more. And I think that’s a myth too.
[00:23:15] Jay: It does get me so fired up right now. So if it is just work not OK. So just as the wrong word. All it is is the work. Right. If you’re not in love with the process of doing the thing of painting of writing of podcasting if you’re not in love with the journey you’re just obsessed with the end results you’re going to get worse and results. There’s actually a psychological term for this approach which is Telic. It’s T E L I C. Telic. it largely comes from game theory. Basically what it means is done to a definite and or done for the end result alone. So it’s a chore. Right. So let’s take like to two quick examples sweeping your floor versus eating ice cream. I love ice cream. It’s my Achilles heel. So do you eat ice cream for the process of getting to the end faster quicker or more cheaply. No. You enjoy the process right. The object is not to have a dirty bowl or so you don’t outsource it to a friend to eat the ice cream. You go try to like find cheaper ice cream or try to like spend less time eating ice cream right. So when you enjoy it’s intrinsic right when you do when you have an intrinsically motivating task at hand you want to spend more time with it. You want to improve it. Right. So what do we do with ice cream. We we put more topics. Right. We try to make it better.
[00:24:30] We have more flavors we eat it in extra large cups or we’re like extra large cones where we all compare it right by the way do not do not even bring up kiddie sizes. I think kiddie sizes are for quitters. So but the point is if it’s an intrinsically motivating task you focus on the process and what happens as a byproduct is you get better results. And this to me is what it means to be craft driven. It’s not that you’re trying to be an expert in theory it’s that you’re so in love with the process itself with the context you’re in with the motion forward day to day every single day the grit and the grime like that’s all there really is there isn’t some finish line. And if all you’re focused on is the finish line again you’re going to look for the cheap the hack the quickest way there that’ll dilute the work. And also you’ll borrow from people telling you go this way. And that’s their way maybe not yours. Right. Or that’s the average. And so you end up doing commodity things in your work. So when I hear creative whether you’re in business or just an artist trying to sell a painting once in a while or you have a side project whatever it is you’re doing in hobby or in in work if you’re like well I don’t want to make it feel like work. I understand. I agree. The perception of work that we have in the world. Sure. But if you say you don’t want to make it about the process that’s all this is and it actually gets you where you’re trying to go better.
[00:25:54] Devani: Absolutely.
[00:25:55] LeAura: Life is the journey not the destination especially our life. So really it’s a good correlation.
[00:26:01] Devani: And you hear the quote. And when you don’t stop to think about it like oh that’s just a cheesy quote but the one you really like try to digest. It’s like. Right. OK. Every day is the process which is when we played it I create daily because right daily process it is that tomorrow you wake up and it’s not tomorrow you wake up an hour earlier it’s OK so you have five minutes today to try and perfect the beginning of that blog post or make it more interesting even if your boss says you can’t write the full length thing that you want to create. So you have that five 10 minutes do that now.
[00:26:38] Jay: Right. Again power of power of questions. Do you want to be doing this for a long time. Yes. What does a lot of time look like to you. Years. Decades. OK great. What you’re frustrated by right now is you can’t do that awesome thing right now. I understand. I’m with you. What could you do now and how do you measure your constant improvement not over days not over weeks but over months or years. Right. Because like I always butcher this phrase but like we we overestimate what we can get done in a day and underestimate what we can get done in a year or whatever it is like you know it’s about aligning how you view the work it’s again self-perception self-awareness if you’re measuring your improvement every single day. It’s really frustrating because some days you have a bad day I do this all the time. Yesterday I was in a bad mood at the end of the day because I didn’t get done what I thought I would and my wife who is in psychology reminded me she’s like you want to be doing this forever the reason you’re in this job and on your own doing it is because you’re looking at the five ten. Twenty five year arc of time. So you should measure your progress at least week to week but probably further out than that. Right the macro level. ARC versus the micro level arc. So it’s sort of like measure your progress on the macro and then engineer behavior on the micro. Right.
[00:27:52] It’s not like I’m going install this new behavior five minutes a morning and did it work in a week. No. Right. Did it work in seven months eight months 12 months. Because again I asked you that question of the beginning do you want to be doing this for a long time. Yep. OK. Act like it.
[00:28:05] LeAura: Yeah definitely. That’s brilliant. So one of the things we’re doing with I a brand is we’re running a 100 day creator’s challenge lies where we’re in day 16 as valid right. Sorry 18 is out right now and I’m not behind. We’re in 18 of that right now. And you know that’s one of the things there’s so many lessons in that experience and we’re going to be doing that on a regular basis at least maybe two a year or so will probably start when again January 5th this one and September that’s what we’re advising people is if your work doesn’t compel you to get out of bed in the morning then either. You might ask yourself Is this the work you really want to be doing. Or it could just be that you haven’t go into that river yet fully you’re not into that flow because you’re thinking about it outside of yourself. It’s not something you’re doing from the inside out. Yeah. Yeah. Well and as entrepreneurs you know we what we recognize is one of the reasons we’re working all the time is because. Part of what we’re creating is our life that’s who we are. It isn’t that we are working that our work is to us. Right.
[00:29:18] And so it’s sort of like if you know where many artists who might be working in a job and I say artists we’re thinking create as speakers authors entrepreneurs engineers coders anyone who’s creating anything in the process of literally creating something that didn’t exist before. Inventors that’s creating so. Creators and entrepreneurs are before they get going and that if they’re working at a nine to five job in the meantime concept of work is nine to five. And so then there’s thinking they will replace what they’re doing in their art with that 9 to 5 concept. What happens when you get into the flow as an entrepreneur. It isn’t about a clock in clock off.
[00:30:00] And once you dive into that deep sea of creativity you don’t want to get out you know the water is great an idea will deliberate.
[00:30:09] Jay: Well you know it’s interesting there’s two there’s two quick stories I can from the show that illustrates two of the different things you just said so one is I’ll tell you quickly about Alec Brownstein and quickly about Chase Jarvis. So let’s start with Alec Brownstein. He is now. I’m going to butcher his title the executive creative director I think ad dollar shave club which was acquired for a billion dollars I think last year or something. But his claim to fame early on in his career was he did something called the Google Job Experiment where he really wanted to work for these large premium level agencies in New York and he wanted to know the creative director and get hired by them at all at these five target agencies. And you know it’s really hard to meet these people and everybody wants a job from them and everybody has. Again the table stakes stuff. I know how to do the work. Because that’s the commodity now. I have a portfolio because the advice is saying Have a great portfolio. That’s the commodity now. So how do you stand out. How do you reach these people if everybody is sort of like already here and what he did was he realized like these people are high powered individuals and probably more so than the average person or at least just like the average person they probably Google their names once in a while.
[00:31:14] And so he ran Google ad words against their names and said Hey so-and-so Googling yourself is fun. You know what else is fun hiring me. And any link to a quick video he created for them with his portfolio behind it. And then he got four out of the five. Interviewed him two out of the four gave him a job offer and then he went to work for Y & R in New York and it blew up that you know the firm promoter of this project he got. I think that the video he created or the page he created got over like a billion views. It was on like all these TV shows and all these you know media companies picked up the story and it exploded. And it really was a slingshot for his career propelled him. Now what he talks about to your point of like and I’m sorry what was that phrase again about the work and us that you said before.
[00:31:59] I see the work. Oh can’t.
[00:32:01] It’s like the work we are at the work the work is us. Yeah do that. Yeah. So yes. Except you can’t prescribe who you are to the work because who you are is this person that wants to do that great kind of work but the work you’re capable of is only right here right. And so if that’s how it is in reality then if you’re like I am my work my work is me we are equal then your person becomes work that’s unfulfilled or work that’s still a work in progress. So Alec talks about you know he’s a serial side project creator which got him the skills to do what he did. And he’s like I just think of it as. It’s not who I am it’s what I’m doing right now and when it’s what I’m doing right now instead of who you are even if you get meaning from it now it’s about constant improvement instead of I got to launch the thing that will forever define me which is yes sometimes you want to get to that point but to get to that point you’ve got to launch stuff along the way.
[00:33:00] I’m not sure that’s the Alec Brownstein story.
[00:33:02] Devani: and for like messy Creative’s or Creative’s you want to do many different things. That’s almost more. And it’s easier to relate to the person who is doing. I’m doing this thing now. And it’s constant improvement and that’s easier to relate to than forever. My new title will be that soon you know. And look I know that that was a frustration for me for while it was like well am I this forever now versus now. You’ll get to improve you’ve got to do something else. And right now you’re doing this writing or Right now you’re running this company or whatever.
[00:33:40] Jay: Yeah yeah. I was an athlete so I I view creativity as as a sport or as as an exercise. I think there’s muscles were working out just by virtue of doing the job. And if you know do you guys know what the weird thing about Rafael Nadal the tennis player or the weird thing about his arms. I mean I heard of this. So he’s a lefty. So when he practices and when he plays he uses his left arm quite a bit and his right arm less. And so if you look at a picture of him his left arm is significantly larger right. Like we should never ever be that way unless we have this one thing we want to do forever. Like Rafael Nadal is like I am a tennis player. That’s what I am. I know that to be a tennis player you’re going to have a strong arm and or a weak arm it doesn’t matter for him. But for us as creators like if we use this muscle over and over every day we can get into a rut and everything else can start to atrophy. You can use side projects where you can use the next version of the project you just created to tweak or improve something tiny. But there’s another way you can look at it too which is the Chase Jarvis approach. So he is the CEO of Creative Live just a live streaming education company that teaches creatives how to build their companies and their careers and that. Kind of social media influencer guy.
[00:34:51] He’s been around the block a while in photography in particular and he became known for that first and the company. So he has this saying We talked to him on the show. I think the title of the episode was the muse is an excuse.
[00:35:04] Devani: And I loved that title.
[00:35:06] Jay: Thank you. That was that was one of my favorite episodes. And and because he comes on he talks about the work ethic he talks about all the stuff you know and he talks about not externalizing your own inspiration but you know owning it and owning your creative power and you have to actually execute yourself it’s not going to just hit you from some random source. So but anyway he talks about his secret like people are like how do you get to do such cool where Chase or you know why are you able to be creatively fulfilled or so many of us are writhing and struggling and he says his secret to the extent that there are such things is he doesn’t try to make art as the work he does. He tries to do work that allows him to make art. In other words. It it’s not the same the job and the art he’s going to select projects that give him the financial or schedule freedom to make great art. Right. So in my case I love giving keynote speeches. I really really do. And you’re great my real art. Thank you. But my great art the art I love to make the art I want to improve is narrative storytelling. And right now that happens to be a podcast. Yeah. And so I get to speak and that’s a privilege and I love it but I use that to allow me to make my podcast which directly leads to $0 in my life.
[00:36:24] You write it but the schedule of travel being on a plane for all these hours getting to meet all these interesting people and hear their stories or getting to tell these stories in front of audiences and see what resonates all of that allows me to earn a living and have a schedule that allows me to make my art. And so sometimes you can view it like that too. It doesn’t always have to be or together.
[00:36:45] LeAura: Absolutely. You know it’s it’s the old cliche of a means to an end. You know so it’s. And you know that the other thing that’s important is inspiring people to follow their their intuition and do the work that matters to them. And you certainly are able to do that as a keynote speaker as well you know. And and you’re able to do the narrative storytelling because you’ve done a lot of your stories from your podcast and the guests that you interview you know in your keynote speeches which leads us into on YouTube a number of them are free on YouTube. And I know you do a great job with that. So I think it could be both. And so part of that too is like some of that some of the things that we advise people does and I’ve done this with the kids as well and that is that you may not always do what you love to do but you can always find a way to do put love into the doing you know essentially because we’re still who we are. And while it may not be my favorite saying you know if I’m you know clocking in to 9-5 and I’m you know pushing pencils or somebody out. But there’s always some creative way to look at that job. You know even in what it is we’re doing and so.
[00:37:57] So that’s it’s like you know if we have within us a fulfillment in a sense of fulfillment a sense of love a sense of being more fully who we are in the world in our own time and we can bring that into the work that we do even if it’s not our favorite thing. Amen. Hear hear. Yeah.
[00:38:16] LeAura: And you mentioned earlier sorry. It’s your turn to take. You mentioned that it would be good to get into this other topic I think it’s something to do with constraints creative freedom creative freedom. Did our debt our connection break up.
[00:38:32] Are you there. OK sorry. Know I know I have you yet. OK. So yeah you mentioned creative freedom and I know that we learned about the creative constraints author but I forget right now a beautiful constraint I think something that we learned about from is not not in your podcast.
[00:38:47] I don’t you think a thing goes from somebody else.
[00:38:49] OK. Well if you haven’t read it you haven’t read the book the beautiful constraint you will not to go ahead with your creative constraint concept.
[00:38:56] Jay: Well it’s not it’s not my concept so much as I’m trying to like investigate the truth and deliver it right and so I’m using lots of other sources but constraints actually help your creativity through your strengths instead of what they usually turn out to be which is sources of complaints. So there’s some there’s some rhyme in there that we could create say constraints are first drafts not complaints I don’t know. But anyways so before we get on Dr. Seuss. Yeah. The idea of creative freedom to me is a myth. And what I mean by that is if we had total creative freedom to build whatever we wanted Let’s say you wanted to write an article you picture that blank screen with a blinking cursor. What do we automatically do in our minds or subconsciously we install our own constraints. What do I want to write about what am I excited about. Do I have an anecdote for my life. How long is it it’s going to be where am I going to publish it. You start to install your own constraint. You literally cannot operate in total creative freedom. And luckily if you look at all the studies and research being done around like idea generation and execution constraints help you yield more ideas. So quantity and more effective ideas quality together at the same time. When you have constraints because you have direction you have purpose you have an understanding what you’re trying to do. So when we complain we don’t have the freedom to create. I think what we’re actually saying is. We don’t agree to the box that we’re in.
[00:40:16] But it doesn’t mean we should try to get out of boxes in general. Right so like a good boss report relationship or a good team mate relationship or good client you know freelance or relationship you agree on the box together you’re like these are our constraints these are our resources you know and maybe you’re thinking this way and I’m thinking that way but look this is the reality. It’s a statement of fact. These are constraints. We have this time constraint is budget constraint etc. and we have this many people all that. And the key if you’re a leader listening is once you establish the box for your team for your client or freelancer stay out of the box. Let the people that do the creative stuff innovate inside that box. When people get mad when they’re like I need creative freedom. It’s that they feel like someone is watching them or jumping into the box and crowding them. But again there is no such thing as creative freedom so there’s one of two problems. You don’t agree to the boxer in where somebody is in this box bugging you after you’ve agreed to one so you don’t need to fight constraints. You need to embrace them because it actually yields more creativity. It’s just the nuance with which you discuss these constraints that needs to change.
[00:41:23] LeAura: And that certainly applies to our life in general. We all have constraints within our life. So we do what we can within that and we push the boundaries of that constraint. Right. They grow to be more back to the physical fitness metaphor. The only way to grow our physical activity our muscles is to write and to push and pull against constraints.
[00:41:45] Devani: And you know in the early enough if you hadn’t had the feeling of the Google constraint in your earlier career if you had had the job that allowed you to pursue narrative storytelling within somebody else’s box it might have taken you a lot longer to realize hey I want to break out on my own and do this and explore these other different stories. So it’s also like sometimes being in a certain constrained to box will help you leap into a next one where you’re like oh this is the one I belong and this is the one I can do something more with. And this one is just a stepping stone to the next.
[00:42:25] Jay: I give a great example of that exact process so there’s an amazing blog called The First Round Review published by First Round Capital it’s an investment firm in the startup space and they have a prestigious brand and the woman behind that blog her name is Camille Ricketts. And when she was hired there was like literally hundreds of blogs covering the startup space and probably about 100 to 120 of those were by VCs that First Round competes with. So the stakes were high because this brand she was hired by Were is incredibly public and prestigious. And the competition was fierce. And so what she did and again they basically created like the Harvard Business Review for startups. But the way she got there is what we can learn from the constraints. So she had 30 days to launch a blog. It had to be a brand new blog for startup CEOs with zero writers on staff. Zero budgets and basically like zero proof that this is going to work. There is just so many constraints. And instead of looking for the creative freedom for freedom or open field she put herself in that box and she’s like, alright what can I do with that. And so she started going to local startup events in San Francisco. Look for the most passionate responses to these speeches that were being told in these rooms and transcribed the best speeches onto the blog. And then what she did because she didn’t want that to be the whole goal. Right. She had this vision of I want this big publication. She had that aspiration.
[00:43:46] She said OK this is a case study. And went to her bosses and said look at the emotional response to these transcriptions we’re not getting the big numbers yet. But I think we’re on the right path because look at the visceral reactions we’re getting to the small experiment. And then she got permission to hire a writer and they started doing long form essays and she used that as a case study to build out community groups to get more resources to build community. And then she used that as a case study to get more resources to create original research reports and now they even build out like technology to help their audience grow and learn. And today. Everybody loves this publication in tech it’s subscribed to by hundreds of thousands of people read by hundreds of thousands more. But the moral here is it wasn’t like she had permission to do this at the beginning. You know it’s like there’s probably a lot of doubt that she should. And by embracing her constraints by moving from box to box like little by little she did something big now and so that is the power I think of the willingness to embrace your constraints innovate and succeed within that and move on to the next set of constraints.
[00:44:47] I think that that kind of power on display.
[00:44:50] LeAura: Excellence in every creative has their medium of constraint or device. So you mentioned Harvard Business Review and how is it that your work has been used at Harvard Business School. How did that happen.
[00:45:04] Jay: So I worked for a venture capital firm after working for three different tech companies Google another one that went public called HubSpot and then a very small startup so I kind of saw very big right in the middle very small and then it went to work for a venture capital firm. And one of the things that was missing I thought in a lot of publications run by venture capital firms First Round Review maybe the exception here but it was this focus on like navel gazey you know thought leadership stuff from the partners because they are smart accomplished guys that people want to hear opinions from all is missing was like a focus on what the entrepreneurs going through and how you as the. The VC can solve it cause ostensively thats why you want an investment from that firm eventually right so the content should mimic what the product does. And so I built out this series of board deck and pitched deck templates. We got like really really specific and had a couple of people that we treated it like a product really and then released it to the world and it got picked up by Harvard Business School as part of their curriculum for their kind of entrepreneurship focus classes. So I didn’t set out for that to happen. But that was a really nice byproduct and I think if there was something I learned there its just the power of involving the people you’re eventually going to ship this to in the process before you ship it. And I think that’s what good tech product managers do especially in software.
[00:46:27] I think as an artist or a creator you can learn from that too because it improves the odds that whatever you’re producing is actually going to be effective and beloved by the other people.
[00:46:36] LeAura: Yeah. We’re already going over and I’m happy with you because we had we haven’t even gotten nearly through our list but it’s just there’s so many things that we could talk with you about like we said all day. But. We’re moving on because we probably should honor your time and keep it to the closer to the 45 minute time frame for those you’re creating daily. So that includes you and me. Let me just mention a quick snippet in your podcast like I’m one of the things that lets you know but I want to take your time being telling me now is how you create your podcast. It’s so well. I mean literally like it’s so well put together so that in itself could be you know that’s artistry but it’s a whole artistry. But what is your daily creative structure that you know allows you to create daily.
[00:47:27] Jay: I don’t have one. And I struggle with this question for a long time. And I thought I needed one and I read the articles about how you need one and I don’t have them. Again self-awareness. I think if I’m going to do anything that helps my structure or rather helps me produce and be prolific. It’s its constant focus on. The first principles of why I do what I do right. Like finding the fun is very important to me, if it feels like a chore. If it feels like instead of intrinsic. I don’t do it or I struggle to do it. And so I don’t have a structure I’m really really good at organizing my thoughts and my to do’s and largely using technology like Evernote and Trello to do that. But daily I have no recurring routine. I just know I’ve got to do this today and I come in and I’m excited about it and I have to make myself excited to the point where sometimes you catch me on youtube watching a cheesy sports montage or you know like a rock group report performing to some giant arena to get the energy flowing and inspiring myself right there’s different ways. You know I sometimes go to a coffee shop. I’m not feeling it in the office but I just I try to focus on. The North Star and where I’m trying to get to and use that hunger and inspiration I feel because I’m so focused on. I want more. And then focus me back on. I now have to create something today as one step in that direction. So that works for me.
[00:48:49] LeAura: Only makes perfect I mean it’s so good to hear in a way that you know all of a struggle with that day to day thing and have to look for what works for us to keep us motivated and keep us going. Sure you’re so human. That’s good to know.
[00:49:01] Jay: Right. Right. And I think largely we we try to obsess over creative structure because we want to be more prolific in our own lives and try out a bunch of stuff make it a bunch of experiments right. Like it’s finding the groove that works for you. But then also if you get into a groove I think you’d become dulled to potential inspiration and you and so they need to break those patterns too. So if you’re going to walk the same coffee shop because that works for your structure cross to the other side of the road. Go around to the other side of the block like become sensitive over and over again to the world around you. And that’s what travel is so good for it’s automatically knocking you out of your routine so you find inspiration easily. You can do that in the routine. So I’d say it’s about finding patterns that work and then finding subtle ways to break those patterns.
[00:49:45] If it starts to get dull.
[00:49:47] Devani: So here’s one like how many times you’ve watched ice age to inspire you. I was so happy to hear that. Another adult who loves it as much as I do.
[00:50:02] Jay: I’m on lot of plans and so my welcome email for subscriber’s mentions the movie Ice Age and the terrible coffee I have to drink on all these plants. So I buy my wife to watch some new hit movie if we’re flying together and I’ll watch anything animated and I say it just happens to be on those planes a lot. You know I watch I watch far fewer of those things to inspire me. That’s like kind of how I like scrub my brain of like rigorous thought like I’m going to unhook. I play sports and I watch. Well basically children’s movies I guess.
[00:50:34] Devani: I was so thrilled to hear that because I was like crazy that I’m full grown and I love these Pixar animated films.
[00:50:42] Devani: I’ll give you one more. Calvin and Hobbes comics. Yes so good. If there’s one type of book I give as gifts the most it’s collections of Calvin and Hobbes comics that does it for me.
[00:50:53] Devani: That was one of those in Florida I had like the complete complete collection Book of it and it was just so good for the soul.
[00:51:01] LeAura: Amazing I said speaking of that to bring it to closure. You’re so Calvin and Hobbs is one of your inspiration. What other book or books. You say have been most inspiring to and for your creative life.
[00:51:16] Jay: Yeah. That’s interesting I’ve lost the time to read books. I mean I’ve just been I’ve been creating more than I’m consuming so the things I consume they really have to be short which is not something I’m thrilled about like I really want to read more. I really like the book in college called Never Let Me Go by an author named cuz it get a bunch of this name Kazuo Ishiguro I think is his name. I’m a sucker for big cheesy endings and things that make you feel and maybe even don’t sit well with you. And that was one of those books in college I loved it. Kitchen Confidential by Anthony Bourdain and everything Anthony Bourdain really does and his storytelling is so. Inspirational for me and informative. I like to sit with things I admire and try to extract the underlying framework for how they can build that thing. So I do that a lot with his show or different people shows. You know so I think those are the two big ones that I would mention.
[00:52:08] LeAura: OK. And just so one of the things I want to mention to close with because it’s so pivotal and critical to you and I think an important message and that is the back to the self awareness thing. Yeah. Gary Vaynerchuk whom we follow and tune into from time to time is that we need a boost of motivation and not he talks about that he basically specializes in self-awareness. Burchard another thought leader you know speaks about self-awareness. You know we’re big on that. And so it’s like it’s beginning to come out there as an indication. And yet it’s like like you said it’s not in school you know so how and what you just mentioned about the meaning that you try to extract from things all of that is about self-awareness.
[00:52:55] You know you are building and growing yourself and you’re thinking about the world by virtue of kind of investigating those kinds of things and thought. So any parting comments about you know just about self-awareness topics in general or or its role how people develop it such or whatever you would want to say.
[00:53:12] Jay: Yeah I feel like a fundamental shift here is stop obsessing over everybody else’s answers and start asking yourself the right questions. Like you’re going to switch from wanting to be the expert so wanting to be a constant investigator because what is self-awareness if not just an understanding of your own context and your context involves in my mind three things yourself like you cannot remove yourself from your context and just by you existing the work the company everything you’re doing is going to be different than everyone else because everyone else doesn’t have you in that scenario. So it’s your self and I think that’s the most foundational part to ask questions of. The second is your audience the people you’re trying to serve. And that could be in this moment in time a boss or trying to convince to let you do something. It could be an entire group of people you’re trying to serve with a product or piece of art and then your resources. Right. The reality is we we all have constraints. And so you can ask the right questions about those three. I think you’re well on your way to mastering your own self-awareness and in the show we try to document stories and then rip out what do we think the questions were that we can ask where we can think more like those people not do what they do not copy them not be commodity. But have the self-awareness that they have. And so that’s that’s the purpose of my show and my speaking is to handover those questions to people and watch people fly.
[00:54:27] LeAura: I love that love that we’re going to leave at the rest of the questions for another day. Thank you so much. Sorry to keep you over but think you.
[00:54:34] Jay: This is so much fun. Thank you for having me. Great. You enjoyed it too.
[00:54:38] Devani: Oh yes. Your website and best way for people to connect with you. We’ll put it on the show now.
[00:54:43] Jay: Oh I appreciate that. Unthinkable.FM that’s the source of the show and my weekly newsletter which is a lot more intimate and a lot more behind the scenes. And I do do a lot of like one on one video calls and interactions over e-mail and the newsletters is the starting point for that and having everything turned out.
[00:55:00] Devani: Definitely listened to his podcast you will love it.
[00:55:03] Closing: Absolutely amazing. Thank you. Thank you. Thank you guys.