In a world flooded with information, how do you think clearly enough to create something that matters?
In this episode, I talk with Nick Milo, former Hollywood editor turned creator and founder of Linking Your Thinking. We explore the shift from traditional creative work to modern creator workflows, and how to navigate the overwhelm of ideas in an AI-driven world. Nick shares how to build systems that help you connect the dots, think more deeply, and turn your knowledge into a true creative superpower.
Nick Milo has spent the last 15 years using digital notes to create and grow a fitness boxing into an international company, produce two independent feature films, and become a TV and film editor. Most importantly, as he shares in his website, his use of digital notes helps him calm his thoughts and make better sense of the world.
He has tested and stretched the limits of linked notes in the real world from the fitness industry to the film industry, the football field to civil engineering, strength training to the boxing ring, public speaking to content creation and learned that being effective at managing knowledge is a superpower—and linking your thinking supercharges it.
Today, he teaches through his educational site, Linking Your Thinking, the frameworks to unlock your ability to work with ideas in a way that is fast, flexible, and future-proof.
Zack Arnold: Nick, my friend, it is wonderful to have you back once again. You and I are having this conversation today to talk all about the world as both of us see it, in multiple Venn diagrams. And today is going to be about the Venn diagram of: here we have the creatives, here we have the creators. And one of the main themes of this entire five-day Summit is, how do we find the overlap of these two areas? Because I believe the future of entertainment lies somewhere in that overlap. And I really believe that rather than seeing ourselves as separate ecosystems, where the Hollywood creatives are over here and the YouTube creators are over here, there's tremendous value in that intersection. You live directly at the epicenter of the intersection of those Venn diagrams. So I just wanted to thank you once again for having the willingness to do round two, given that you and I also did a podcast a little over a year ago.
Nick Milo: Yeah, thanks, Zack. I mean, without hesitation, I'm happy to be here, and I'm happy to share any wisdom and just kind of bandy around ideas because I think it's a very exciting time. It's very terrifying too, though, especially for creatives, figuring out what "creator" means to me and all that. And there are ways to navigate it that it can feel internally very good and like you are aligned with who you already are. So I definitely want to approach some of this world from that angle.
Zack Arnold: Yeah, and I can tell you, and I'm sure that you can maybe not relate to it, but I think you can understand it, having lived in the Hollywood creative space for many years, that for a lot of people in the creative space, when you say the words "content" and "creator," it's like saying a four-letter word out loud. And I want throughout the course of today's conversation for you to help dispel some of those myths because I really believe that there's just so much value in these two groups helping each other. And frankly, I'm not sure we have a lot of choice.
I do not have all, and frankly, I don't have any of the answers about where we're going next, but damn it, I'm going to work pretty hard to talk to the people that I think can help us find those answers. And I just think your journey is both an inspiring one and also one that can help provide us with the tools to navigate all this massive amounts of information and uncertainty.
So just to set the table a little bit, I want to talk a little bit about your jack-of-all-trades journey. You and I originally connected, I think you were one of my "COVID Kids," or around there, where you'd come into my community at the time where I was helping creatives figure out how to navigate career pivots and find more meaning and purpose in their work. And you had come to me really trying to figure out how to transition into that editing chair. But even before you were in the Hollywood creative space, you did a bunch of other stuff. So let's just start to connect some of these, quote, "random dots" that kind of define Nick as a jack-of-all-trades that are going to eventually lead us to you becoming the creator of Linking Your Thinking.
Nick Milo: Yeah, absolutely. I'll be quick in such a way that we can touch back to them as we need to. But grew up in Montana, I played college football at a small college. We won three national championships. And as that was winding down, I decided to do something I never did before, and that was to audition for a theater play at the college. So this willingness to go into something I wasn't good at was something that was always there.
After college, two paths kind of happened at the same time. One, I had an undergrad in civil engineering, just because I happened to be decent enough at math. I did that for about a year. But there was something else that was going on with one of my friends, a fitness boxing business. Just actually teaching mostly women how to box. My friend and founder, I was the co-founder, but his mom, and then eventually my mom and a bunch of women would get together and box. And they said, "What do you want to call yourself?" And they said, "Pink Gloves Boxing." We wrapped that into a business that we could sell to health clubs, and it worked best with universities.
Also during that same time, I produced and acted in two indie feature films in Montana. So outside of the industry, had no clue about how to navigate it. Went to New York, trying to make Pink Gloves Boxing bigger, and then three years there, and then came over to Los Angeles. The boxing business had kind of plateaued. So then I thought, with my partner coming here to teach at UCLA, "Okay, here's a great time to finally fulfill a dream and enter the entertainment industry." Instead of having all the answers with all these entrepreneurial efforts, I started at the bottom as a post-production assistant. I was getting people coffee, I was driving around Santa Monica Boulevard with soggy cheeseburgers that had tomatoes on them, so I had to go back all the way across town—just really humbling myself.
After some time, I was working my way up. I had gotten to an assistant editor. That's when I found you. I was like, "I want to get to the editor chair." Nine months later, I got my first editing credit. Around that same time, COVID was starting, and I just started sharing something else that I was always passionate about: taking and making notes. And that led to Linking Your Thinking, which is a way to make sense of all the information that we have by making notes and linking ideas together.
Zack Arnold: There's so much good stuff in there. The part that I want to talk about first is the very small portion where I actually got to work with you directly. Anybody that works in the industry, to hear that you went from "I'm an assistant editor, and I want to get in the editor's chair," and you did it in a year, just doesn't happen. To watch you do this so quickly was astounding to me. Something tells me that in your process of learning and consuming information and taking action on it and organizing it, my guess is that that served you, not only in the transition from assistant editing to editing, but also from football to civil engineering, from civil engineering to entrepreneurship. My guess is one of the connective threads is your ability to synthesize and organize information.
Nick Milo: Well, I think you nailed it. I feel like it's the missing step. My favorite time was when I was a post-production coordinator on a Netflix show, and because they were behind shooting, I had all the time in the world to sit in with the assistant editor and the editors and just see what they were up to. I would ask questions, I was very forward, and I would take notes. That wasn't enough. Then, after hours, I'd go back to my own computer and I would just start synthesizing. I would type it all out, and I'd say, "Oh, this connects to what Walter Murch said in In the Blink of an Eye." And I would literally make a connection to Walter's notes. This is a way to make better sense of the world and rapidly improve how quickly we understand something. So this really accelerated my journey with editing, from a confidence angle, from a capability angle. I was putting myself in a position that when opportunities came, I'd be ready for them.
Zack Arnold: I always appreciate people that will create their own luck. You could have said, "Oh, production's behind, I'm just going to chill out," as opposed to, "Here's an opportunity, here's me really using this time to my fullest."
Nick Milo: Just one point on that. I don't want to make it sound like, "Oh, I had to work so hard and grind," because it wasn't that. It was actually, I had made it really fun. It was a fun game. It was all a game, just to be like, "Okay, what did Skip Macdonald say, and how does that relate to what Walter Murch said?" And then it's like, "Okay, what do I think about that?" So it was a fun thing to do. It was reclaiming what's been hijacked from us, which is our agency, to not just consume and collect more, but to actually have fun engaging with these ideas that we love.
Zack Arnold: I'm so glad that you brought that up. I see here a seed that's now been planted, and you feel like you're being pulled to something. It was something that you enjoyed doing, but then you started to see the utility in this skill. So even before you were Linking Your Thinking, you were linking your thinking. So I want to zoom a little bit forwards to when you had to make what was probably one of the most difficult career decisions, which is, "I've made it, I'm here, and I'm not sure I actually want the job." I want to break down how you were able to make that decision because I think understanding how you came to that decision is so important.
Nick Milo: Okay, I'll do a brief version. Joey Reinisch, who's an also an editor on Better Call Saul, he was going to edit a few episodes for season six, and he needed an assistant. Because I had worked with them both, they were familiar with me. And I was like, "Yes," so positive through the phone call. And then I got off the phone, and I thought, "Why am I hesitating? All my dreams are coming true." And it was because for the past year and a half, the pandemic had happened, and this other thing that I was naturally enthusiastic about, notes, was having a moment online. I shared some stuff to a nerdy group that I was a part of, and they said, "Tell me more." And then I started to share more, and they were asking, "How do you not lose your notes? How do you find them and make sense of them?" And I was giving answers, and then it just kind of became this feedback loop.
So when I got that call, I was like, "Yeah, I'll totally get back to you," but really, I was also running it past myself. I knew I couldn't say no, but I was just checking in with this strange hesitation, and that just let me know, "I'm totally doing the show, but after this one, I might be done." And that's exactly what happened. I had the greatest experience. I mean, it was really the pinnacle of my short-lived career, but I knew this other world was for me.
Zack Arnold: Along the lines of those nerds that are saying, "Tell me more," I definitely want you to tell all of us more because those are really important details for the sake of this conversation in making the transition from creative to creator. So let's get into the details here.
Nick Milo: When the pandemic happened, my forward-thinking boss, Gina Scheer, before she even got approval from Sony, was like, "Put all the data on hard drives so we can work from home." And that's what happened. We were locked down, which meant that when I didn't have work to do, I had a little bit more flexibility. Something else happened at exactly that time is this developer couple, just two people, came out with an application called Obsidian. It was the first time that we had an easy way to take a note and just immediately link it to another note. For anyone who's an idea person, this is like amazing, a kid in a candy store times ten. Any ideas I have, I can now connect it to other ideas.
In those early years, they had a Discord, a forum for discussions to happen, and I was very active in there because I was helping with the development of the app itself. There was kind of this predominant way that was considered the best way to do something, one is to have many small, "atomic" notes. And I had resistance to that, and I shared that resistance. I shared a counter-opinion, and that was, "It's great to have the small notes, but we can get lost in a forest of our notes that way." I proposed that we have a "map of the content" below that can give us a bird's-eye view. When I did that for myself, what I found was in this new tool, it was so fast that I could actually use this bird's-eye view as the place to do my best thinking.
I started to just share those ideas. I was like, "Try this thing. I'm calling it currently a 'map of content.'" There was resistance to someone opening their mouth and sharing a counter-opinion, but there were also people that supported it and said it's working for me.
Zack Arnold: You're always going to have haters, and you know that you must be doing something right if there's going to be a lot of people that are pushing back. What I find really interesting and valuable about this is that you didn't say, "You know what, I need to generate some supplemental income, so I'm going to put together a thing and start asking people for money." Instead, you saw a problem. You said, "People are struggling with this. I think I can be valuable, and I can bring them a solution." And you just started helping them. That, to me, is often where this starts.
This is so eerily familiar with my experience with Trello, where I discovered Trello, I think, 2013, and I was starting to use it to build all of my workflows. I would have people looking over my shoulder saying, "What's this?" There was no training for Trello at all, and I thought, "Oh, well, maybe I can teach some Trello training." And then by de facto, I became the Trello guy on LinkedIn Learning. It was just me saying, "I love Trello." And like you, to this day, I still get comments where people say, "I've never seen anybody have so much fun teaching a piece of software."
Yes, it helped me generate some supplemental income, but that's where the seed was planted where I found my voice. It was, "Here's something that's really complex. I'm really good at simplifying things. Here's a useful digital tool that people are not integrating into their workflows." And I think there might be something here. It took a few years for those Venn diagrams to really intersect, but that's where I started to realize, "I think there might be a future for me, not just as a Hollywood creative, but as a content creator," which was not a term that anybody used back then. I'm curious if you had a similar experience where it wasn't just, "Ooh, here's a place to monetize this," but it seems like you really found yourself in this community.
Nick Milo: 100%. A couple of points. It wasn't a top-down, strategic sort of thing. It was, "I have this actual problem. I personally deal with information overwhelm. How am I going to solve for this?" And then just naturally, you watch a good show, you want to talk to other people about it. It's the same thing.
For some of us, we might think everyone knows this thing because I know it so well, and that's one of those major fallacies. You have dedicated experience that is valuable; you just might not know it. But when you start talking out loud, your tribe will start to find you, or you'll get some sort of feedback, and then from there, you can kind of figure out what that special thing is that you provide because it might not always be obvious.
I recognize a lot of what I do, yes, I help people organize their ideas, but it's also giving people permission that they can spend time lost in ideas without feeling like the toxic productivity police are going to tell me I need to get the next ten tasks done. It starts with joy.
And then circling to the identity, Zack, and this was funny, you just said that you're coming to terms with being a content creator. Last year in Anaheim, they have VidCon, a YouTube conference, and so I finally went. My first YouTube video was in 2020. Four years into being on YouTube, I came back and finally wrote a newsletter, and the title was, "I'm a YouTuber, I'm a YouTuber, I'm a YouTuber." It was my attempt to finally own this identity that I was feeling so resistant to. It's really funny, these identities that take so long to shed, and that can hold us back. The negative connotations, if you're coming from the Hollywood world, that's only getting you in trouble. So it's like, how can we observe ourselves authentically and kind of get on with it?
Zack Arnold: Well, now you've really piqued my curiosity because never in a million years would I have thought that you, of all people, would still be struggling to accept the identity of content creator. Since you started this, you built a very successful YouTube channel. You're literally the guy if somebody says, anywhere in the world, "I want to learn Obsidian." And now because of you—and I don't say this lightly—because of you, my entire life and my entire brain is now in Obsidian. And you now have a publishing deal for a book to talk about Linking Your Thinking. Why in the world are you still struggling to accept the identity of being a content creator?
Nick Milo: Yeah, it's tough. I think it's because when I look online and I see the YouTube shorts or the certain type of YouTube that's for a younger audience, I'm like, "That's not me." And I get in my own way because I'm like, "That's dumb, the stupid thumbnails and this and that." But those are things I need to get over because it's only getting in my way. You're right. So "YouTuber," I'm trying to own. "Content creator." I think one that's a little bit easier is just "educator." That takes me back to Dr. Seuss: "You are you, that is truer than true. There's no one alive that is youer than you." So you have experience that no one else has, and that's what needs to be shared. No one else can share your unique experience in your unique voice.
Zack Arnold: I'm so glad that you shared that. That's exactly the way that I feel. I will own "educator" until the end of time. When somebody asks what I do, I say, "I run an online education business." Boom, done. That's who I am. I happen to create content as a podcaster, but I, too, very much struggle with the idea of "content creator" for a lot of the reasons that you brought up.
And if you think you feel old looking at the stuff on YouTube, imagine how I feel. What you're never going to see from me is, "Make sure to like and smash that subscribe button." Like, that's not me. Every three frames, adding Metal Gear sound effects and graphics. Watching a lot of the videos that are super popular now, to me, it feels like throwing razor blades into a blender.
I think there's tremendous value in this intersection because in Hollywood, we have the best storytellers in the world. We understand how to tell great stories. We suck as entrepreneurs. We do not know how to sell ourselves. We solve so many problems, and we don't even have the ability to look at the problems we solve and say, "Hey, this might be valuable to others." With high levels of creativity comes very messy, unorganized minds, high levels of being sensitive, and with that sensitivity, high levels of imposter syndrome.
On the creative side, we have the best storytellers in the world that are too afraid to put themselves out there and monetize their value. On the creator side, amazing entrepreneurs, amazing business people. They know how to game the algorithms. By and large, I can confidently say they suck at storytelling. Most of the stuff that's out there, it's just not stories.
My fear is that when my son has kids, he's going to show them Back to the Future and Raiders of the Lost Ark because he's not going to show them Mr. Beast videos. It's just all very disposable content. So my fear is that there's this gap. And if we have the YouTube creator economy that is just destroying Hollywood, but they've yet to crack the code on telling great, timeless stories, that's where I think the convergence of these two areas is so important, and that's where I think you could potentially be beneficial in helping all of us link our thinking.
Nick Milo: Absolutely. Well, that is interesting because, man, that can go in so many directions. YouTube is probably the best one to look at. It's no longer really a social media platform; it's an entertainment platform, a media platform. And yes, it is just outpacing everything. And I'm so happy it's YouTube as opposed to Twitter or Facebook.
Yes, the storytelling is going to be even more important because they just introduced "series." Now we're going to have something that looks like a Netflix-type of series. So instead of having all these one-off videos, you'll be able to actually tell cohesive stories with some arcs. Here's something else that's really important: connected TVs are the fastest growing platform on YouTube. So no matter how we think about content, just think of YouTube as Netflix or Apple. That's where people are consuming content. If it is on a big TV, guess what comes back? The desire for those stories. That's very natural.
There will be so many nice and fun creative opportunities to not so much worry about just getting one viral video, but you can think creatively about how to string videos together. The opportunities are endless, and it's scary too, but the water is warm, and YouTube wants you to succeed. They provide many, many tools. The algorithm is people, more or less. So YouTube wants people to stay on the platform. If you have a video, they're not looking at your channel to decide, "Are we going to recommend the channel?" They're looking at a very specific video with a title and a thumbnail and a generalized concept that someone can grok at a glance and say, "Should I click on this?" If you say, "1950s Costume Designer Ultimate Guide," you are going to be in a category of one, and you'll get that attention. Those people will find you. It doesn't matter if they're 18 or 88. That's incredibly empowering.
Zack Arnold: Yeah, I love the way that you put all that. I wasn't even aware of the "series" feature in YouTube, but to me, that's a complete game-changer. It doesn't surprise me at all because we always come back to story, not in Hollywood, but as humans. We make sense of our realities in this shared collective experience through storytelling. I had no idea, but it doesn't surprise me that there's this new series feature, which tells me that all of those that are doing really well on YouTube, they're going to look at that and say, "There's the next opportunity. We have no idea how to tell a good story. Anybody out there available that can help us do that?" That, to me, is the exact spot that we need to focus our attention.
This is not a bug that I'm being repetitive; this is a feature. I've talked over and over that I believe we're going back to the four-network system. When this worked the best was in the broadcast days where you had ABC, CBS, NBC, and Fox. When you do that, you know where the eyeballs are. And I really believe we're going to go back to that, but instead of those four networks, it's going to be Apple, Netflix, Amazon, and YouTube.
The thing that I realized where it really was game over as far as "maybe this is a blip" was one statistic: more people watch YouTube on their TVs than their phones. And when I saw that, I said, "It's over. The legacy world of Hollywood is gone."
Nick Milo: May I share a few things? So I just talked to a former YouTube employee who worked at YouTube for nine years. A few things is, yes, YouTube is the largest media company in the world. One billion hours are consumed daily. And for everyone here talking about storytelling, they're providing features. Some of them are AI. And we don't have to go, "Oh, that's, we can never use AI." We can explore it with our values intact because they have Veo, which are six-second clips that you can add to any YouTube short video right now. Why not experiment? Keep it private, but just play around with these features. They're introducing Flow, which is going to be huge for both Hollywood and for the individual. It's going to be an AI filmmaking tool.
Do I want to watch a film made by AI? Hell no. But if I have my own creative idea and I'm thinking about it, but I can't hire a whole VFX team, wouldn't it be nice to just have something that can show that? So whether you like it or not, there are changes coming, and if we can bring our values to it and have an open mind, these are all really fun and creative ways that we can get our ideas across.
Zack Arnold: Yeah, I'm really very glad that you brought that up. And it's so both coincidental and ironic that you're literally reading it from your notes and once again, linking your thinking. I've had a lot of people that have been asking me my thoughts on AI, and I was coming at it from a place of maybe this is something to explore. I've gotten a lot of hate.
I do not believe that AI should unethically be scraping past films, past artwork, and allow us to regurgitate them by stealing other people's ideas. Management is replacing you with AI; the AI is not displacing you. Where I really see the opportunity is in the things that it allows us to do as individuals that we couldn't do otherwise. It's not a matter of, "If I decided that I wanted to make a two-minute short about giraffes in outer space, well, I'm displacing a crew that I would have paid for." Like, I'm never going to have the means to make that. This gives me the ability to generate new creative ideas and experiment.
For me, full disclosure, I use ChatGPT on a daily basis, but I never will hit the export button and say, "Here's my newsletter today, courtesy of ChatGPT." For me, it's more about helping me synthesize and brainstorm ideas. It's allowing me to link my thinking. And I want to know how to get much better at getting Obsidian to talk to ChatGPT because it's kind of messy.
Nick Milo: I can talk about something crazy that just happened.
Zack Arnold: I would love to hear more about that in a second. But my biggest fear as an individual is, when I think about smartphones, I don't remember phone numbers anymore. I need Google Maps to get around. My greatest fear is that with ChatGPT and other AI platforms, we're going to lose that critical thinking ability. And I know this is something you have a lot to say about.
Nick Milo: Yeah, absolutely. It's fascinating. The story goes that there was a party, and an ancient Greek dude went out to get some fresh air, and then the building collapsed under an earthquake. He remembered where everyone was and could identify the bodies just by his memory. Cicero is known famously for memorizing two- to three-hour speeches. They were worried about the written word, and sure enough, we can't memorize two- to three-hour speeches. It wouldn't make sense for us to.
Now we're in an age where the ways that we had to remember something is changing on us again. The pace of information will continue to unsettle the majority of the population, meaning that they will lose a sense of agency and just consume more. I think there are ways that we can reclaim agency. An obvious one is just to step away from the device, go for a walk, or get into a mindfulness meditation practice. I have spent the last five years working on a very practical one that doesn't turn away from the screen but figures out a way that when you look at the screen, you can still feel fully in charge of your thoughts.
When I say, "How do we go from the consuming to the creating, the collecting to the connecting?" Well, what if we had a space that no one ever taught us how to make in the digital world? Because in the physical world, we have a home. We don't have a home in the digital world, and the mind needs a home. On these platforms like Obsidian, I call it the "ideaverse," but we need to give ourselves our own home for our mind. This is a place that's basically turned off from the outside world and gives us something that nothing else can: a sense of calm, grounding, foundation, a sense of security. If you think about Maslow's hierarchy, we don't even have the bottom need met mentally throughout most of the day.
Zack Arnold: Yeah, I want to go a little bit deeper into this idea of Maslow's hierarchy of needs. You mentioned that we don't have this digital space that's meeting our basic need of food, water, and shelter. I would argue that where so many people are emotionally right now is the fear that they're even going to lose that. A few years ago, the mere thought of somebody that's working at your level or my level having to go work for Trader Joe's or deliver DoorDash to pay the bills would sound absurd. Even though anybody watching this probably isn't physically homeless, we feel like there's so much uncertainty, and we've lost those basic needs.
The reason that I wanted to bring you on is your ability to help people see patterns where there aren't patterns. You talk to any great, successful entrepreneurs, they almost all have the same origin story: "There was this thing that was just bugging me, and I couldn't find a solution for it, so I figured I would just putz around and find the solution myself." And I think the problem that you're helping us solve is going to be one of the most universal, important problems: there's so much information. And I think our ability to know how to synthesize it and, most importantly, figure out where we can be valuable and provide solutions, that, to me, is the way out of this giant mess. I feel like that's where you are in the exact right place at the right time with the right solution.
Nick Milo: Yeah, totally. Right before going into that, I just wanted to double-click on one point, which is even if it feels so intimidating to go from creative to creator, what you can do is find a community. Find the communities of the things that you're interested in, whether it's gardening or whatever, because of "wandertivity." It's based on Tolkien's famous quote, "Not all those who wander are lost." I've recognized in all these pursuits that they weren't meaningless hobbies; they were fueling the next thing and giving me a unique perspective for whatever field I went into. That's invaluable.
I really encourage everyone to not have shame or feel like it's incorrect to explore their interests and find their communities online and then learn from those individuals and be like, "What are you doing? What's working?" That's going to open up all sorts of doors because with community, there's just natural energy you can feed off of. If you're just alone in your room, it gets lonely fast.
Zack Arnold: I actually have one of the world's experts on reaching out and building communities, Selena Soo, in day three. But I want to get back to Linking Your Thinking.
Never in a million years did I think I was going to build an academy for creatives where one of my specializations was going to be teaching introverts how to write cold outreach. But I've now become the de facto person to go to when you say, "How do I reach out cold? How do I provide value?" And what I found is that everybody kept coming to me with the same questions. And that's where my intuition said, "Maybe there's something here." Maybe, like you, you were just doing this thing with notes, and you figured everybody was doing this thing, but you had a very highly specialized skill and a unique perspective. It was, "Here's a problem. I feel like I can solve it," but not just, "Here's a way to monetize my skills," but "Here's a way that I can genuinely be valuable to other people."
And that's where I think Linking Your Thinking and all the frameworks that you provide is absolutely essential for people right now that have all these random dots that are their skills, their experience, their unique knowledge, and passions. Creative people are fascinating people. So I want to make sure that I leave people today with something that they can take action on. So help us start to use at least some of the basic ideas that you teach so we can just start to figure out how to put the pieces together for ourselves.
Nick Milo: Yeah, well, thanks for that. I would say it starts with this: we hear so many of other people's thoughts, we can no longer hear our own. That's a problem. So how do we go from this collecting habit to a connecting habit? I believe we can get there with one word: "because." Whenever something sparks, you simply say, "because." The show Andor is interesting to me because… What you say initially is going to suck half the time, but if you externalize it, you get it out of your head and onto the page. Now we get to iterate it, and it's fun.
And then we say "and," and Andor connects to Tony Gilroy, and you make a note on Tony Gilroy. And then you start to just make this web of understanding. It's not for an outcome of being a creator tomorrow; it's just, "This thing's interesting to me so much, I would like to get it out of my head and onto the page to honor it."
That would be what I call the "spark method." When you feel the spark, make a remark. The last part of the spark method is to relate. So, spark, remark, relate. What does this relate to? What does this remind me of? I was watching the Tom Cruise movie, and I was like, "Tom Cruise reminds me of that time at the Cinedome 4 when my mom and brother were on a soccer trip, and my dad and I went to watch Mission: Impossible for a dollar." I made a note from Tom Cruise to the Cinedome 4 and that memory. And I called my brother, and he filled in more details. This whole thing is just this amazingly meaningful, cathartic sort of thing because my dad's no longer with us. When you do that, it's going to lead you in places you wouldn't expect, and you're increasing the surface area of luck, of insight.
Zack Arnold: Yeah, I think that's a great place to start. One of the days that we have for this summit is all about this idea of a career transition in crisis, where I don't think we're giving ourselves permission to wander. I've had so many students that have been navigating career pivots, and they feel like they have to have it figured out. There's no emergence of, "Oh, I enjoyed gardening growing up," or "I really enjoy rock climbing." What if I taught this thing or did that thing? We just feel like we have to have it figured out. And when we don't, the fear of not having it figured out leads to the anxiety of, "Well, I'm just going to scroll instead." We're not giving ourselves that space to both be bored, but I feel like so many people don't give themselves permission to not have it figured out. And that's what I love so much about your system.
Nick Milo: Yeah. I think generally, we're just button-mashing at this point. I think we're so tied into being an architect, thinking, "How can I structure everything?" That's very important; that's half of how we think. But the other half is the gardener who allows for the chaos and the creativity. So if we can figure out how to have good gardener energy, that's less chaos and more creative within a space that we own. And that's what I help people create, a system of linked notes called the "ideaverse." Then all of a sudden, the world opens up, and someone says, "You know what, I'm going to do a career transition," or "I totally now have the space to see I was looking at this the wrong way."
Zack Arnold: It's funny that you brought up the gardening versus the architect analogy because that was what drew me into your new world in the first place. When I started to search for what tool I want to use for my second brain, I found one of your videos where you introduced the idea of being the gardener versus the architect. And as soon as I saw that, I'm like, "Huh, I've always been an architect. I've never allowed myself to be a gardener," because to me, gardening is messy. So you planted a seed for me, which is, "There's a different way to do this." You are the solution. And that's where you come in with all of your diverse areas of interest, just sharing this one idea. That stuck with me years later.
Nick Milo: Amazingly well said. And so it's a scary time, but it can be a hopeful time too.
Zack Arnold: I want to go into the nerdy portion of this program where you're like, "Oh, if I told you the stuff I'm doing with AI." What are some of the things that you're experimenting with, not so much the tech and the tools, but more like, how can I maintain my humanness but really collaborate with AI without losing my critical thinking skills?
Nick Milo: Yes. So one, I'll start with the crazy thing I did. With a friend, Dan Shipper, he is the founder of Every. It's really great if you want to stay on top of AI news. I was curious how to incorporate AI into something like Obsidian in a way that felt wholesome. I'm not talking about B2B; I'm talking about how this can be used for the "inner guide" archetype.
So since he knows how to code and I don't, we downloaded the Claude code, and it took five minutes for us to be able to point all 11,000 of my notes and have Claude look at that. And then here's the key, though: what questions do you ask? And the question was something along the lines of, "You are a clinical psychologist. Based on all of the notes that you see in here, what are three blind spots that I'm completely oblivious to in my life?"
The first one was, "You're not entirely altruistic. The reason that you care to share so much is because you suffer abandonment trauma from being lost in the Mall of America when you were five years old." I was like, "Whoa."
Zack Arnold: Whoa. I just got goosebumps. That's nuts.
Nick Milo: Yeah. And I was like, "That is true. I was lost. I want to help other people get found, too, just in a different way." So that's just one very fast example of how you can use AI in a wholesome way. Now, that made me realize something else. A very important word that starts with 'I' is "integration." Whatever interaction you have with AI, you then need to integrate with humans again. So that's a really important point. I wouldn't advise AI to be your only therapist, but if you're using that in concert with conversations with family and friends or an actual therapist, then yes, you're integrating it.
There are still shortcomings. It's wrong on that one. It's over-indexing a very specific note and thinking that that then applies to who I am. So what it says doesn't mean it's true. We have to bring ourselves to it.
Zack Arnold: Your intuition knew that there was something true about it, which was one of the blind spots. Another 'I' word: intuition. So lastly, are there any rules or guidelines that you give yourself so that you're not outsourcing your critical thinking skills to AI and atrophying those skills?
Nick Milo: Yes, another word that I think is important is "discernment." With whatever comes at you, you're being discerning about what you see and bringing all of your own experience to it. When it comes to content, why do I feel disgusted when someone's writing something that uses AI to such a degree? I think it's if I don't think that the human on the other side of an article had any sort of cathartic release, even if it's a small one, in creating a piece, I don't want to touch it. And part of that release is another 'R': risk. What risk was there in the person making that? So these are things that I'm now turning an eye to when I think about how something was created because I want the content that I consume to be very human. And yes, I know we'll all be fooled by AI content a million times over, but when we are, and if we find out about it, trust is just shattered, and you can't get that back.
Zack Arnold: I think that the best place to leave us then is for those that are watching today, I'm going to link your thinking because what you just said is exactly what another member of this summit said in completely different words. In my conversation with Jay Clouse, he said that content creation is nothing more than the transfer of emotion. And what you just pinpointed is that if there wasn't some form of emotion behind the content that was created, ultimately, it's the transfer of emotion from the creatives that are telling those stories and putting it out into the world.
Nick Milo: And you said this, I just want to be clear from my own understanding, the transfer of emotion doesn't just start from an AI-assisted piece to the reader, but it has to be from the creator into what is being assisted by AI. That's the transfer from human to human.
Zack Arnold: Exactly. Using AI to help synthesize some of those ideas, do the research, whatever it might be, but ultimately, I believe it has to originate from a place of emotion and feeling. Everybody's doing that, and it's becoming so much easier to identify it. "Yep, that's AI, that's AI… Oh, this one's interesting." And the reason is, I feel something because you can tell that person is bringing themselves into the piece. So if it's about synthesizing and sharing more information, I think that's a dead-end road. AI is just going to eat all of those kinds of content creators alive. It's those that can bring true emotion and true storytelling.
That's why I wanted to organize this summit, and that's why I wanted to have you in this summit because I have learned so much from this conversation, and again, barely feel like we got started. But before we leave, where can I send people to find you so we can help them link their thinking?
Nick Milo: Yeah, I would just keep it easy. Go to linkingyourthinking.com, look around, or go to YouTube and type "Linking Your Thinking." Go down the rabbit hole and kind of see what's up.
Zack Arnold: Awesome. And is there anything else that you can bring to the audience, as far as any kind of a guide that they might be interested in downloading?
Nick Milo: Totally. So the best free guide, the most downloaded set of notes in the entire world of all time, is called "Ideaverse for Light." So it's a free version of Ideaverse. If you're curious about using the note app Obsidian, you just download this folder, and it's got a bunch of files in it. You open it up using Obsidian, and suddenly you have this interconnected web of ideas. So you can just learn, explore, treat it like a kid would a play box or a sandbox, and just see what happens.
Zack Arnold: Well, for anybody that's unfamiliar with Obsidian, it is now literally my external brain. There wouldn't be a summit without Obsidian. I would not have a year-long mastermind program without Obsidian. I would not have a Substack newsletter without Obsidian because it's helped me take all of the messy shit that's up here and put them in a place where I say, "Huh, that's interesting. What if I explore that?" Even with what I know so far, Obsidian for me has been a game-changer, and I'm excited to both share Obsidian, but more importantly, Linking Your Thinking with all of them. So Nick, one more time, thank you so much for taking the time to share your knowledge and expertise with us today.
Nick Milo: Thank you, Zack. Pleasure to be here.
Edited by: Curtis Fritsch
Produced by: Debby Germino
Published by: Vim Pangantihon
Music by: Thomas Cepeda
Scott and I make the case that creativity is a way of being—one that thrives when we let go of the fear of judgment and embrace the parts of ourselves we’ve been told don’t fit the mold.
