Episode 18: Billy Oppenheimer
Making Your Creative Process a Lifestyle with Billy Oppenheimer
Episode 18: Show Notes
Writing and researching to produce content is a full-time job that demands hours and hours of dedication. Today’s guest is the wonderful Billy Oppenheimer, writer and research assistant for Ryan Holiday, and he is here to share his creative process with us. Tuning in, you will hear all about what it’s been like to see his audience grow, his research process, his notecard system and how he measures them, the time he spends reading, the idea of honing your filter, and why he likes making physical notes instead of digital ones. We then delve into his incredible newsletter and how it has evolved before Billy tells us about how he aims to achieve his ultimate goal; to write books. Finally, we discuss Billy’s definition of ‘creative health’ and why he is basically always working. To hear all this and more, press play now!
Key Points From This Episode:
• An introduction to today’s guest, Billy Oppenheimer.
• How Billy has grown his audience and what it’s been like to watch it grow.
• Why Billy relies on his research to create content and he shares his notecard system.
• How often he spends reading and how he knows when to give up on a book.
• What honing your filter means and how Billy does that.
• Billy walks us through his entire process when reading and making notes on a book.
• The pros and cons of physical notes as opposed to digital ones and why he prefers physical.
• Billy’s newsletter, the process, its evolution, and how it helps him consume information.
• Why Billy considers social media after he’s written his newsletter.
• He tells us about his ultimate goal to write books.
• What his mentor, Ryan Holiday has taught him about writing.
• How Billy divides his time between working on his newsletter and working for Ryan.
• The (very small) role ChatGPT plays in Billy’s work.
• Why Billy measures the number of notecards he makes every single day.
• Billy’s definition of ‘creative health’.
Quotes:
“Everything I put out comes from something I’ve read at some point in time.” — @bpoppenheimer [0:05:43]
“I feel like a big part of creative work is finding this sort of overlap between what I find interesting and what other people find interesting and filtering out all the stuff that is not in that sort of Venn diagram.” — @bpoppenheimer [0:10:51]
“I do think [that] the creative process is largely just connecting dots.” — @bpoppenheimer [0:42:42]
Links Mentioned in Today’s Episode:
Billy Oppenheimer on Instagram
EPISODE 18 [TRANSCRIPT]
“BO: I don’t do notecards as I’m on the first read. I read it, I’m dog-earing pages. Another thing I do is I write questions in the margins and I find that like, for some reason, the question jogs my memory faster than if I were to just write some sort of note because I used to just write notes in the margin and I found out when I would go back to the book, I would think, “What was I trying to note here?” I always forget what I was trying to point out.”
[0:00:54.5] JU: All right. Welcome to The Paint & Pipette Podcast. Nice to see everybody here. If you’re joining, drop a note in the comments, let us know where you’re joining from. Billy and I like to hear from people. I am delighted to introduce a real-life Internet hero of mine, Billy Oppenheimer, welcome to the show.
[0:01:14.2] BO: Thanks for having me, Jeremy. Excited to chat.
[0:01:16.4] JU: Yeah, likewise. I have been an admirer of your work from afar for a long time, so, I was really delighted when you agreed to come on the show. For folks who don’t know your work. First of all, I think you’re a big deal – Hey Parker from Nashville, good to see you. I think you’re a big deal. Do you feel like you’re a big deal? Do you feel like you're getting like, steam and momentum from your audience?
[0:01:38.6] BO: Yes and no. I mean, I definitely can sense that the audience is picking up but I do not feel like a big deal. I listen to your podcast, I’ve seen who you’ve had on the show before, and I just felt like I am probably the least qualified and experienced person you’ve had on.
[0:01:54.1] JU: No way, no way.
[0:01:55.0] BO: So, I’m a little nervous to do it but it has been cool to see the audience pick up a little bit and I’ve kind of been behind the scenes for four or five years there with Ryan Holiday and some others. So, it’s been cool to come out behind the curtain a little bit and –
[0:02:10.0] JU: We were just talking before we went live about watch our hero, John Mayer kind of rise through the ranks and Billy is saying, he’s wearing a John Mayer shirt right now, he just saw him in Austin. I saw John in Austin like 20 years ago. By the way, it’s weird to be in an age where you can say you saw somebody 20 years ago, that’s like a really weird thing.
Tell us about these last four or five years for you as you’ve kind of – as you're building an audience, what’s it like to kind of be – if you think like, almost from like a surfing analogy, what’s it been like to watch the wave kind of grow and how have you thought about building your following and audience over the last four or five years.
[0:02:44.8] BO: I was in a good spot in terms of – I mentioned Ryan, who I’ve been working with for five years now and I initially just reached out to him as a fan of his work and sort of offered to help out in any way on the research side, primarily was my interest. I sort of told him, I would read his books and I’d get to the bibliography and then pick up a few books that he mentioned and was just kind of like, trying to reverse engineer his process as I was starting to write a little bit and just, “How is this guy who is writing I really love, how is he doing it?”
So, I was kind of already doing what I imagine his research process looked like, so I just reached out. Like, “Hey, I’m doing all this reading, if it be helpful, I’d love to have that kind of be focused by projects you're working on” and that was kind of my initial foot in the door with him and I’ve seen his audience grow. I think at that point in 2018 and he had a hundred thousand followers on Twitter, 50,000 email subscribers.
He hadn’t yet launched a podcast or YouTube channel or anything like that and watched his audience grow from my vantage point of just kind of helping him along the way and it was really instrumental I guess, in terms of when I set out to start doing it myself. I already kind of knew some of the tactics that would allow me to do that and he’s also just been a huge supporter of mine and he’s probably been one of the most influential in helping my audience grow with just him, sharing stuff and mentioning it on podcast and whatnot.
But I think the main thing I learned from him was like, just focusing on quality content. Like Ryan doesn’t even have the login information for Convert Kit, which is what we use to send out the daily stoke email every day. He has a vague sense of how many people are bringing each morning but he’s not checking in every day to see how many followers there are, how much it’s grown today.
His kind of sole focus is the quality of what he’s putting out and just kind of trusting that in time, those things like the audience size and these sort of external metrics will take care of themselves and that’s really been my – what I’ve tried to focus on as putting out good stuff and setting out with the expectation that I want to do this for a long time. So, I’m not in any rush to grow on any platform and if people are showing up, that’s awesome.
But I still hope to be doing it in 10 years, so if I just remain focused on putting out stuff that people are enjoying and just kind of trusting that those other things will take care of themselves.
[0:05:16.3] JU: When you talk about people enjoying and that the kind of healthy disassociation from audience or things like that, is your own kind of taste and interest your primary guide? I mean, setting aside kind of Ryan and his practice, just for you if I think about your practice, what causes something to hit your radar so to speak? What causes you to go, “Oh, there’s something there.”
[0:05:38.5] BO: It’s like, I’m super reliant on the research side of things. Everything I put out comes from something I’ve read at some point in time and I have adopted Ryan’s notecard system. So, I have two boxes right beside me right now full of notecards that as I’m coming across stuff, whether it’s in a book or I hear it on a podcast or if I’m watching a documentary, I’ve always got notecards on me.
I’ve always got a pen near me and I’m just – something strikes me as interesting, I just try to get it onto a notecard, and then I sort of filed those away, loosely separate it into categories, and then by the time I write about something that comes from a notecard, it might have been in the box for weeks or even sometimes a year, two years. So I’m kind of slow to see how the notecards connect to each other.
But yeah, it’s just an initial kind of spark of interest that I’m looking for and I would say that’s the dopamine hit for me is when I read a story in a biography or something and I connected to something else that I read before like that is one of the most exciting moments for me more so than when a tweet gets retweeted or I get an email from somebody that’s read the newsletter and maybe they liked it like, that’s nice.
But I love that kind of search for interesting stories that are connected to something I’ve come across before like that’s the moment for me. I’m looking out for that feeling.
[0:07:06.4] JU: Yeah, I can relate, definitely. It relates that kind of spark of delight of, “Oh, that reminds me of you know, what somebody else did or said.” I think people can imagine, you know, research, reading, being somebody’s life as – I don't know about others but I would say, for me, it’s a dream. How do you create the space to do it practically?
Because I would say, for me, a lot of times, my own – just in my own practice, I can find that the space for research so to speak, kind of gets crowded out. How do you protect it? How do you make sure, you know, if you think almost about like compartmentalizing, I don't know if that’s the right word but how do you structure your days or weeks, so that you create space for the kind of input side of the equation?
[0:07:51.4] BO: Well so, it’s the first thing I do every day. For the first two hours every morning I read for at least two hours, first thing I wake up, pour a cup of coffee and just sit down and read and I always have like two or three books that are going at any one point in time, and then that’s really the only like protected kind of nonnegotiable slot of time every day, and then I just try to find pockets throughout the day.
So, some days, it’s more than others just depending on the work day or what I’ve got going on but – and I can pretty consistently carve out an hour or two in the afternoon where I go for a run and that’s kind of other block of consumption for me, whether it’s a podcast or another thing I like to do is like if I’m reading, I’d prefer physical books but because I also like to try to read on while I’m exercising.
So, I’ll also get the audiobook for a book that I’m reading and I’ll listen to parts of it while I’m running and then when I get back to the physical book, I’ll just pick up from where I left off in the audio. Yeah, it’s just like any pocket of the day where I can get a few minutes, I try to take advantage of it, and then again in the evenings, like after dinner, my girlfriend and I would just kind of plop on the couch to watch something on TV and I’ll just read while she’s doing that.
[0:09:07.0] JU: You said in one of your newsletters recently, I resonated with this line, you said I don’t remember the exact phrasing but something like, spending 16 hours reading a book not knowing whether you’re going to get anything from it. I can so relate to, it’s like, you know, you pull some anecdote out and somebody’s like, “Whoa.” All of a sudden like, for them, you know, for somebody’s listening to you, it’s like, you pull that out and then now they have it forever.
But it took you, you know, 12 hours of reading to get to a point of like, “That’s interesting” and I really resonated with that because sometimes it’s painful, right? You’re like, you're reading and reading and it’s like, nothing, nothing, nothing, nothing. How do you know when to shift between books, when to give up on a book? You know, stuff like that. Do you think about that at all?
[0:09:46.2] BO: It’s hard, it’s really hard. I do think about it and that line specifically, what I had in mind was we’ve – I have seen this be something people struggle with, like as we’ve – with Ryan, we try to bring on other researchers over the years and it’s probably the number one thing I see them struggle with is we’ll ask them to read this, you know, thick, dense, biography to see if there’s anything there.
And he’ll come back and like, I can sense just the – they’re defeated and they feel like they just wasted all this time and they struggle with that frustration of spending a lot of time that seems wasted. As you do it more like you become aware that that time actually wasn’t wasted. Like, there’s times where on the first read, I’ll think there is nothing, and then a year and a half later, I’m reading some other book and it reminds me of something I read in that last book that – so it’s like, you actually don’t know if that much wasted it. It might prove to be valuable and it’s also just like honing your filter, I think.
[0:10:46.7] JU: What do you mean? Say more about that, honing your filter.
[0:10:50.0] BO: So, I feel like a big part of creative work is finding this sort of overlap between what I find interesting and what other people find interesting and filtering out all the stuff that is not in that sort of Venn diagram, and I can look at notecards that I made three years ago, I can tell that they were made before I’ve started putting workout because I’ve been doing it longer. I would not have made that notecard because I know that wouldn’t be interesting to other people but it’s just –
[0:11:16.6] JU: Can you give – is there – just to make it practical, is there something that you would say you’ve noted in your practice that you look back and you go, “That’s not interesting to others” like what hits your circle but not other circles?
[0:11:27.7] BO: And the other thing that happens a lot is I’ll – as I’m reading it, I’m earmarking pages. I then set the book aside for a week or two and I’ll go back through with a stack of blank notecards and I might have folded like 50 pages and only make two or three notecards.
[0:11:46.5] JU: Oh wow, so not everything that you note while reading then gets transcribed onto a notecard, you mean?
[0:11:50.7] BO: Right, and I find that there’s like, a sort of novelty on the first read that you’re drawn to but then when you come back to it and it’s now – it’s no longer novel, it tends to not hold up as interesting but there’s something about like first seeing it on the first read that you’re drawn to that. So, and it’s similar with just like the more books you read, the more kind of context you have for what is and isn’t interesting to you.
[0:12:15.6] JU: It’s like Seinfeld’s question, “Is this anything?” You know, it’s almost –
[0:12:19.2] BO: Yeah, exactly.
[0:12:20.2] JU: You’re asking yourself as you’re flipping through the dog ears, “Is this anything? Is this anything?”
[0:12:24.2] BO: Right, exactly, and the other thing I think about like speaking of comedians, Mitch Hedberg had this joke about how he would keep his pen on the other side of the room and if he thought of something funny, if he couldn’t sort of muster up the energy to go get his pen, he would just convince himself that the joke wasn’t that funny.
I always think of that with notecards because if I can’t kind of muster the energy to write down, to transfer it from the book to the notecard, then I just – it must not be that good. So, it’s kind of another filtering mechanism of like, “Do I want to take the time and put the energy into making this?” If it’s really good, then I can muster up the energy.
[0:13:01.3] JU: Let’s dive into that process a little bit. Is it – you start with – and maybe this just walk me through like a typical, you read the book, you dog-ear pages. Do you do notecards while you’re reading on the first pass or do you wait until after and then what happens with the notecards once they – just like, walk me through the whole journey?
[0:13:18.4] BO: Yeah. So, it’s – I don’t do notecards as I’m on the first read. I read it, I’m dog-earing pages, another thing I do is I write questions in the margins and I find that like, for some reason, the question jogs my memory faster than if I were to just write some sort of note because I used to just write notes in the margin and I found that when I would go back to the book, I would be like, “What was I trying to note here?”
I always forget what I was trying to point out. For some reason, asking a question that corresponds to the information or the story in the book itself, when I come back to it two or three weeks later, I immediately remember, “Oh yeah, that’s what that was about.” So, I’m doing that as I go and I put the book aside for a week or two just because again, like the time as a filter kind of thing.
Like letting that novelty wear off and then going back and putting everything to that test of like, “Is this still interesting?” And then the thing to hold up, I put on a notecard and I try to put it in my own words so I’m not copying it directly from the thing. I want it to be as if I’m going to use it in a future piece of writing. So, I might add some context leading into the quote from the book or whatever it may be.
I wanted others to kind of take that notecard and slot it directly into the newsletter or a Twitter post or whatever it might be. So, I try to do that work on the front end, and then I file them, these boxes right here.
[0:14:38.6] JU: Yeah, let’s see a box.
[0:14:39.7] BO: I’ve got like six or seven of this kind of shoebox things and then they’re separated by – these are just kind of like categories, and then what I’ve realized the most important part is like the active reviewing the notecards consistently.
[0:14:54.1] JU: Yeah, I was going to say, what happens once a notecard in there? Do you rifle through that random, do you systematically go through it? How does that work?
[0:15:01.2] BO: Random and sometimes – so, the newsletter’s been really helpful in this way because I do it once a week. So, I have to – I’m going through all of my notes at least once a week in the process of putting the newsletter together.
[0:15:13.3] JU: All?
[0:15:13.9] BO: Yeah, all of them, and often, I’ll find notecards in a section that’s like, “It actually works better over here.” And just as you get more and more notecards, like the connections can shift. So, I usually have a sense of what the newsletter is going to be like I pick a theme, and then I just want to kind of make sure there’s nothing in a different section that actually belongs in the theme I’m currently writing about. So, I like to rifle through all of them.
[0:15:40.0] JU: And so, okay, so you rifle through, do you just do it once a week whenever you’re preparing the newsletter or do you spend time with the notecards at other times as like, whenever you read the book, you dog ear the pages, you make the notecards, then you’re putting them in a box. Are you looking at stuff around that area?
[0:15:56.7] BO: Yeah, as I’m –
[0:15:58.2] JU: In the box as well?
[0:15:59.6] BO: Yeah, as I’m like, looking for – so, if I make a notecard from a book and I’m like, “Do I already have a section where this card belongs?” So, I’m kind of reviewing each section as I go to see where do I put this new notecard or it can also happen where I’m just like, “I know exactly where this one goes.” Another thing I’ll do in the margin of books is I do like a less than sign, equal sign, greater than sign.
That to me is like related to, is kind of what that means and I’ll sometimes put I’ll know I have a notecard section related to this. So, I do that a lot, so I know there are times where I know exactly where those notecard needs to go but then there’s times when like, even if I know that, I forget which box that section is. I have to look through everything.
[0:16:43.7] JU: Just if you find where it goes?
[0:16:44.9] BO: Yeah, exactly but I like that because it’s also like – I forget what writer said this. He had this line about like, the things you discover when you weren’t looking for them and I find that to be true. Like, I don’t know what I’m looking for and I stumble on stuff in the box of notecards.
[0:17:00.0] JU: I see a question here. Parker just asked, “Do you ever crave the ability to search notecards” and I would love to hear what you think about that, Billy. I think about it, there are tradeoffs between digital and physical. I’d love to hear you talk more, maybe more broadly about tradeoffs between why physical, what do you lack in the physical, what do you gain?
[0:17:19.2] BO: The searchability is definitely a lack. There’s no way to search physical notecards but what I’ve seen with other people who have like, their Notion setup or Evernote or whatever it may be is it gets unwieldy. I think if I were to do a digital system, I would be tempted to copy and paste. The thing I was mentioning about the pain or like the effort to write the thing as a filtering system, I think you lose that with the digital because you’re just grabbing stuff on the go, and then before you know it, you just have this huge database of stuff you copy and pasted and it’s just out of hand and –
[0:17:56.2] JU: One thing I’m hearing is the inefficiency is kind of the point.
[0:18:00.5] BO: Yes, yeah, a hundred percent. I also think about like – so, Ryan uses this system and the writer he came up kind of apprenticing under Robert Green uses physical notecards and they are some of the most prolific/like high-quality writers kind of working today. I’ve not heard of someone producing at their level who is using a digital system. So, to me, it’s like, I want to work backward from like, who is putting out their kind of work I respect. What is their process?
If I were to come across someone that’s doing that caliber of work with the digital system, I would want to ask that person a lot of questions and find out how they’re doing it but I just have not seen someone writing books at that level using digital and there’s something about being able to move things around physically. Like I said, there’s a lot of times when I put one thing in one section and later find out it belongs in another section and I just enjoy the physicalness of that, of being able to take it out and to hold like these are all of my notes on this topic, I enjoy that, so.
[0:19:03.5] JU: Well you know, I mean, in the D.school, that’s one thing we’re really big on, you know, physical sticky notes, things like that. I’m in the middle of a class right now, like a class on AI, like a business strategy class on AI, and they’ve got all of these kinds of digital templates and I find myself just behind this poster board here.
I’ve got another poster board of I’ve recreated the thing that they made in digital physically because there’s some value to moving stuff physically that you just – when you're using your kind of cursor, you just don’t get the same impact as the kind of the physical movement. I wanted to mention this idea to you, this – I don't know if you know, Charles Duhigg. I don’t even know how it happened, I don’t know if it’s the podcast or what but sometimes, publishers send me books. So, this is his new book.
[0:19:49.3] BO: Super Communicators?
[0:19:50.8] JU: Yeah, and the publisher just sent it to me. I’m not bragging but I don’t even know why. Maybe I’ll get to talk to Charles, which would be cool but seeing this book on my desk, speaking of like physical triggers, seeing this book on my desk reminded me, he wrote about – I can’t even remember where or maybe talked about it with Jordan Harbinger, now that I think about it but he talks about information disfluency.
I don't know if you’re familiar with that term. Basically, and he sights this study, you’ll love this, you’ll totally resonate with it. He cites this study where I can’t remember it exactly but I’ve got a blog post about it, so I can go ahead, I can jog my memory later but basically, students are you know, given information, some are allowed to use computers to take notes and others were only allowed, you know, notebook paper.
At the end of the semester, the students with computers took much more, almost verbatim notes than the students with notebooks, and then like three months later or something, the students were tested on the material, and the students who wrote in notebooks vastly outperform students who took verbatim notes in their computers, and the notion or the thing that Duhigg mentions is this idea of what he calls, disfluency that when you’re writing with your hand, it’s impossible to be verbatim.
And so the processing that occurs, like you are encoding information by writing it in your own words in a way that it doesn’t get encoded when you’re almost like an empty vessel, just kind of transcribing.
[0:21:15.2] BO: Yes, yeah, that makes a lot of sense to me. I can’t remember if I wrote about this or not but there’s an interview with David McCullough, the biographer, and I talk about another guy that was just incredibly prolific and doing high-quality work, and he wrote on a typewriter. He said whenever people would come see his setup, they’d be like, “Why don’t you get a computer? You know you could work a lot faster on a computer”
And he was like, “I don’t want to work faster if anything, I need to work slower because my mind works slower.” I always thought that was interesting of like, working at the speed at which your mind works, and I feel like writing on a notecard is much more in sync with the speed at which my brain works than on a computer.
[0:21:53.3] JU: You know, and what’s funny is actually, I was talking about the woman who's a business executive in the sports world, let’s just leave it at that and she was telling me yesterday how listening to my episodes, she loved it but she’s like, “I needed to listen to it 2x.” She goes, “You guys just talk so slow.” And I said, “Respectfully” I mean, she’s like giving me a hard time but I said, “Respectfully, we’re thinking while we’re talking. When you’re listening, you don’t have to think” you know?
[0:22:17.7] BO: Right.
[0:22:18.2] JU: And it’s just this weird thing. It’s like, but I find that with myself that when I’m in consumption mode, I’m trying to like, 2x, I wanted to go faster, you know, come on, come on, come on, come on but when I’m in processing mode, I don’t need to be at 2x. Sometimes I actually need to slow it down, you know?
[0:22:32.3] BO: Yeah.
[0:22:32.8] JU: And analog is a great way for all the benefits of efficiency, et cetera. There’s some stuff that actually being inefficient actually is probably better.
[0:22:42.2] BO: Yeah, I think so.
[SPONSOR MESSAGE]
[0:22:46.1] JU: How much time and effort does it take to test an idea? When I ask individuals and organizations this question, they typically overestimate both the time, effort, and expense required. Tests need to be quick, fast, and cheap. You need lots of tests. So, when I work with organizations, I help them take ideas out of the “waiting for testing” pile and move them into the “tested” pile. That’s where lessons are learned and impact is created.
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[INTERVIEW CONTINUED]
[0:23:30.7] JU: It reminds me like – have you heard of the Seinfeld line by the way? Like I think HBR interviewed him about could McKenzie help him with jokes, you know?
[0:23:38.1] BO: Yes. Yeah, yeah, yeah.
[0:23:38.6] JU: He’s like, “If you’re doing it efficient, you’re doing it wrong.”
[0:23:41.2] BO: Yeah, I love Seinfeld. You know, when you get in someone’s car and like their Bluetooth connects and what they had been listening to like picks up, I thought I have – when I get into friend’s car and he’d be listening to a podcast on like 2.5 and starts pulling like, “Dude, how are you? How are you hearing any of this?” It doesn’t make any sense to me.
[0:23:58.7] JU: Let’s go back to your process for a second. You are saying you know, here’s what I’ve got so far and I’ve love for you to fill in the gaps of especially as it comes to sharing. So, there’s the reading, there’s the dogearing, there’s the going back through with no cards, and then you have this weekly outlet. I’ve made the joke before, I don’t know if you resonate with this, just like nature abhors a vacuum, a newsletter abhors a lack of –
I don’t know what the end of the statement is but it’s like having a newsletter, having that kind of almost pull function means you’ve got to keep feeding grits for the mill, right? And so can you talk about the role that the newsletter plays and then also just your – by the way, I love your newsletter. I can’t wait to get it every Sunday and it is one of the few newsletters that I save it about by the way.
Talk a little bit of your process for how do you think about pulling it together. We are going through no cards but then also what role does the newsletter play for you in your own synthesis process and understanding process?
[0:24:55.4] BO: That’s been huge, what you’re describing is like it being a forcing function for the consumption process. I am constantly as I’m reading stuff, I’m just constantly like could this be part of a future newsletter and it’s really been helpful in that way and it also is – it motivates me because I know I have to put out a newsletter once a week. I wrote a couple of weeks ago about lead metrics, sort of the actions or behaviors that are predictive of the results you want.
So, for me the newsletter is a lagging metric and the research process, the consumption, the new card-making process is a lead metric. I’m motivated to keep reading and researching because it has this result that I am trying to hit once a week. It’s been really helpful in terms of – and the way in which the newsletter has evolved has been helpful. So, at first like –
[0:25:49.2] JU: Say more about that, how do you mean?
[0:25:50.4] BO: When I first started the newsletter, I was trying to think what are the things I’m currently doing that lend itself to a weekly newsletter and the answer was the new cards. So, my first idea for the newsletter was just to scan six notecards each week and I did that. I scanned six notecards, I upload it to my computer, I just didn’t like the way it looked and my handwriting is kind of sloppy and it just didn’t look great.
So, then I was like, “Well, I’ll just transcribe the notecards.” So, the first year or so of the newsletter was just six random notecards each week.
[0:26:26.4] JU: Are there are archives of this by the way? I’d love to see it.
[0:26:29.5] BO: Oh yeah, yeah, yeah, they’re all on my site. So, the first 20 or so are just six completely random stories and concepts that have nothing to do with each other, and then at one point, I don’t know how it happened but I just was like, “I’m going to do on this one theme” and then that’s become what I do every week is like the first one's kind of an introduction to an idea and then the next five are stories that are kind of circling that theme.
I could have like conceived of that format setting up but that’s what become and I really love that. I love putting it together and I love seeing a broad concept and being like I love that concept, now, let me go find five stories that illustrate that concept and I love that hunt for those stories, so –
[0:27:18.5] JU: Yeah, that is such a great phrase, I love the hunt for the story. So, that brings me to the next thing is like what comes first, the story or the theme? You know, maybe even play through it, it’s like Sunday. You’ve got another newsletter coming up, like are you already right now you go, “I know what the theme is, now, I’m kind of back of mind processing” how does it work?
[0:27:36.3] BO: I usually decide the theme on Saturdays. I go to the gym and I sit in the sauna until I think of it.
[0:27:41.2] JU: In the sauna.
[0:27:42.0] BO: Yeah, and it’s usually like I just try to let my mind like drift and see what it goes towards and what it returns to. So, I’ll be like I’ll just be sitting there and I’ll of something I read about that week and I’d be, “Oh, that’s interesting that that’s what my mind drifted towards” and then I’ll go back, and just look through all my notes to see if I’ve got enough to support that, that concept.
[0:28:09.5] JU: Is the answer always yes or sometimes you find yourself going, “Oh, no.”
[0:28:14.0] BO: Usually the answer is yes.
[0:28:16.1] JU: There is not enough material here for a newsletter on letting your mind drift or whatever.
[0:28:19.3] BO: Yeah, usually the answer is I have enough at hand after I decide like on the theme and then I started thinking like, “Well, do I have stories related to this?” and then I started thinking about the stories. I’m like, “Okay, that’s one, two, three, yep, I’ve got them” and then I go home and put it together but –
[0:28:35.5] JU: That’s after the sauna.
[0:28:36.6] BO: It’s after the sauna, yep. There’s other times when it’s like I’ll be on the run like I go for a run every afternoon and there’s times when it will hit me on the run what I want to write about that weekend but I love that sauna session to think through it. That tends to be how you go about it. So, like right now I don’t know what I’m going to write about on Sunday.
[0:28:56.5] JU: You’re okay waiting until Saturday and if something comes to you, do you have like a parking lot of potential ideas or do you actually refuse to even entertain it until Saturday?
[0:29:06.1] BO: No, I have a parking lot. I call it the waiting room. I’ve got a section at the front of my notecard box, it’s called the waiting room. Those are ideas and concepts that I think I’ll be able to write about but I don’t have enough material on hand for those.
[0:29:19.7] JU: It’s a theme where you’ve got kind of five stories and it’s kind of waiting for it’s – for the Acai berry, the free radicals, you have them and be like, “Boom.”
[0:29:27.5] BO: Yeah, exactly, yep.
[0:29:30.2] JU: Oh, that’s hilarious. I’m really curious to know how does social media factor into the equation because – meaning do you test material? I know authors who say, “Social media is where I test to see if people like material” or how does or is it and I’ve never like – I’m sure if I actually went in and kind of look, I might be able to discern patterns. Is social something that happens after the newsletter? Is this something that happens before or is this something that’s totally separate from the content of the newsletter?
[0:30:01.3] BO: So, most of my social media content comes from the newsletter. So, I write the newsletter on Saturday and Sunday and then usually, I’ll adopt some of that content into a Twitter post. So, the kind of style that I’ve gravitated towards on Twitter is I tell a story and then there’s usually two takeaways and you’ll notice that the story is what I wrote about in that week’s newsletter and the takeaways are two of the concepts also in the newsletter.
I’m always thinking newsletter content first and then once I put the newsletter together, I’m thinking, “How can I adapt this content here into the Twitter format?” I’m not coming across a story and thinking, “This would do great on Twitter.” I’m always thinking newsletter first.
[0:30:48.0] JU: And then same for LinkedIn as well, that just gets that same kind of that gets repurposed, yeah, yeah, yeah. Why start with a newsletter?
[0:30:55.9] BO: Because my goal is to write books and what I learned from Ryan was to start, you know, building the audience or the readership of people who are familiar with your work so that when the time comes, when I do have a book, I already have a lot of people who are familiar with my writing style, the things I’m interested in and I can go straight to those people and say, “Here’s a book that’s coming” like that.
[0:31:20.2] JU: Yeah, that makes sense. That makes sense. Is your expectation that the book will flow from all of this material? Because there is different ways of thinking about books, right? One is kind of, “What do I already know?” and then another is almost the book project is cover for learning in a particular direction. I don’t know if that’s – one way I think about it. I think broadly about books kind of at least in those two buckets. How do you think when you say your goal is to write books?
[0:31:44.6] BO: I think it will be a combination of those two things, like I’ll have – I’m sure there is material that I’ve already published that will find its way into a book at some point and then I would look forward to having an idea for a book that like I already know I’ve got some stuff about. I would be looking forward to researching and reading and learning more to kind of round out the book.
[0:32:06.2] JU: I had an experience, which was really illuminating to me at Stanford a couple of years ago. I was in the middle of the kind of research project for the book that my coauthor, Perry, and I wrote. That came out last year and you know, we’ve been teaching together for 12-plus years. We got a lot of material but then when you start thinking about how do you want to shape that material, what framework that doesn’t belong, and what stories kind of support those frames, you realize you need more material, right?
It’s like, you don’t know everything about a subject, you actually need to be learning more and so I found myself – I had never written a book before and I didn’t have somebody like Ryan Holiday who was able to tell me how to do it. So, I’m kind of winging it, you know? And but I found I need to be reading on the weekends and I started reading different biographies and different – a lot of history and stuff that I actually love that I can’t believe is like it’s kind of my job, although it is mostly on off hours that I am doing it.
But I have permission to do it because like I got to write a book, right? But then I start realizing stuff starts kind of jeling in different ways and I’ve been randomly invited to guest lecture in this product management class at Stanford. So, like a random class, one of my students who was a TA of the class asked the professor if I could come in and give a talk and so I just kind of came in and I just drew a little bit on the board.
It’s irrelevant but the subject of the talk – but basically I just kind of, it was kind of like a brain dump of stuff that I had been learning and the moment that was surprising to me was at some point, there was like a Q&A with the class. You know, it was like 100, 200 students in the class and someone asked a question that part of my response was, “I mean, I didn’t know 80% of this stuff a year ago” and when I said that, people in the classroom are like, “The thought.”
And what I realized was people think that there are some kind, you know, professor or author, whoever it is, there’s some kind of person who already knows all these, everything they ever need to know. It was shocking to the students to learn the professor is still learning and I think that’s where there’s kind of a mistaken belief around like there’s almost like these wrong buckets.
Either you know it all or there’s no way you’ll ever learn it rather than like the third way, which is actually like you’re learning and sharing while you learn, right? But I feel that’s – very few people appreciate that every one of us is capable of learning and capable of sharing what we learn and synthesizing that. How did you discover this input/output kind of equilibrium yourself because you haven’t always been a writer, right?
I mean, you said you started working with Ryan five years ago. How did you discover that kind of equation for yourself?
[0:34:41.6] BO: Really from Ryan. What I do is largely adopted from his system but adapted in some ways like it’s Ryan notecards for instance are more – if you pick up one of his, you wouldn’t know what he is writing down. They’re very shorthand and things that only makes sense to him, whereas mine, you could pick it up and it would read like a paragraph in a piece. So, there’s thing I do a little bit differently but it’s largely been a result of watching him go about his work and how he does what he does.
And that’s really what I was – when I reached out to him like that was what I was hoping to do is like I had this vague sense that I wanted to write books and I had no conception of how one goes about doing that. So, working for him was really like, I just want to see like how does he actually go about writing a book and it’s very much this notecard process and just constantly collecting material to then weave together in the books. So, it’s been through watching him do it that I’ve picked it up.
[0:35:44.3] JU: One of the things that I’m just curious about with your time. You know, you mentioned Ryan doesn’t touch the convert kit, right? I assume you and the team and folks handle that. How do you think about your time? You know, like what is work to you? What is play to you? What are you kind of on the clock for your day job? Because your newsletter is not your day job, right? And how do you think about even just portioning your time and setting expectations with your team and things like that?
[0:36:14.2] BO: Yeah. Well, I’m full-time with Ryan and so I try to read for a couple of hours first thing and then I go straight into work with Ryan. So, whether it’s – like he has his next four books are in various stages, so I am carving out time to – things I need to do for those and then daily [inaudible 0:36:34.1] is kind of a daily like we have a document full of emails that are ready to go but we’re constantly trying to add to that buffer.
So, I’m either looking for stories for him to use or he’ll often send me something that he’s come across in his reading and I’ll be like, “Hey, could you just draft up an email on this?” and then I’ll send that to him. I tried to, like three or four hours every day is dedicated to that kind of work and then the evenings are kind of back to my own stuff. It’s interesting because there is a lot of overlap now like I’ll think –
[0:37:06.6] JU: Yeah, I was wondering about that. It’s like you find a story about Seinfeld or whatever, how do you know where it goes? Is it very fluid? Is it like, “Ryan, you can use this?” or I might put it in the newsletter. With ideas, who owns them so to speak? How do you think of that?
[0:37:20.0] BO: Yeah, like I know what Ryan is looking for and the books he is working on. A lot of the things I find are not a good fit for what he’s working on but I still might be reading a biography that he asked me to read and I’ll come across a story and I’ll know like, “This doesn’t work for anything Ryan is working on but I like this, so I am going to keep this for myself.” That’s kind of the weird thing where like I think I’m working on Ryan’s stuff but I actually am doing a lot of work that I can use in my own content or whatever.
[0:37:48.8] JU: Yeah, that’s cool. That’s cool.
[0:37:50.1] BO: I’ve been working with some other creators I guess where I’m doing a similar like they might ask me to help them with research. Again, I think I’m looking for stuff for them and I’ll come across something that’s perfect for what Ryan’s working on. So, there is a lot of overlap in these things, so it’s truly hard to say how much of my time is spent on any one thing. Like there is a chance I am working on everything at once.
[0:38:13.6] JU: Right, right, and I think making peace with that and being unapologetic about it. It’s like if maybe one way to say just to answer my own question is like, if you are in a position where you have to be apologizing then you are not doing the right thing, right?
[0:38:27.1] BO: Yeah, and it’s also really cool because now, Ryan, he reads my newsletter and he’s been a huge supporter of it and he’ll often – now he sends me stuff that he comes across when he is reading and he’ll be like, “I’m not going to use this but I thought it would be great for you newsletter.” So, it’s been cool where now, he is kind of like my research assistant sometimes.
[0:38:49.9] JU: That’s great. I mean, it takes a village to raise a newsletter, right?
[0:38:53.9] BO: I’ve never seen anyone read as much as he does, so he is always coming across stuff that he sends my way, which has been really cool.
[0:39:00.4] JU: I have kind of two questions before we wrap, we’ll try to wrap by the top of the hour but two things kind of still in my mind. One is, how, and this is a question on everybody’s mind right now but what role if any does ChatGPT play in your life?
[0:39:13.6] BO: I don’t use it ever. If I am like working on a piece and I need update or something, like I know trying to think about – for example, I’m working on something about Shaun White right now. I’m trying to tell a story about how he came back after losing in the 2010 Olympics or 2014. So, this is exactly what I mean like, I know roughly that he lost in one of those Olympics. So, I might pull up in ChatGPT and be like, “What year did Shaun White lose to so and so?”
[0:39:44.4] JU: Got it, so it’s kind of a research tool.
[0:39:47.1] BO: Yeah, and like prior to ChatGPT, I’d use Google obviously for that but like Google just populates stories where I might be able to find that date. So, it just kind of expedites the process a little bit but that’s really my only used case for it.
[0:40:01.3] JU: Wow, okay. Okay, that’s good, that’s cool, and then the other question and I just want to kind of circle back to metrics. You talked about leading metrics, lagging metrics, what do you measure?
[0:40:12.9] BO: I actually do measure how many notecards I make a day. I like tally them, I know like so much of my output is reliant on those notecards and I can feel pretty – like I often will write something and I’ll be like, “I don’t know what I’m going to write next” and that thought is kind of terrifying for me. Am I going to find a story that I’m not as excited about writing about? So, I measure how many notecards.
If I am making three or four a day, I feel pretty good that I’ll be able to be consistent with the newsletter and those things.
[0:40:45.2] JU: Is there anything else that you measure besides the number of notecards?
[0:40:48.8] BO: Not really, no. Like I only start putting content out on Twitter after a year and a half of doing the newsletter and Ryan was like, “Hey, the newsletter is great but like no one is going to hear about it unless you’re on these discovery platforms” and it didn’t even occur to me to go out on Twitter and like grow the newsletter that way. I just like, I love writing it and there is I think at that point like 500 people were getting it, which was like that felt like a lot to me at the time.
So, it’s been like encouraging me to kind of get out there to get these things to more people but so I almost never – I’m looking at like how many subscribers are there. I know those numbers but I’m not like making any decisions based on them.
[0:41:32.5] JU: I wasn’t thinking in terms of output measurements because that, like you said like the score takes care of itself. It’s more to me, I have this vague idea, I love to just even get your feedback or your reaction to it but I’ve got this vague idea around what I call creative wellness, right? This notion that kind of creativity ought to be a part of our health and wellness equation.
You know how many steps you take with your watch, you know how you sleep well with your whoop, like if you’re tracking your macros or diet or things like that. It’s a wild kind of health picture generally and maybe there’s spiritual practices there or maybe there is all sorts of things, right? But if I were to ask you, “How is your creative health?” you probably are more attuned to it than many.
But I think for many people, they’re like, “I have never thought about that my entire life” you know? And is it growing? Are you getting healthier? And so to me, that’s one thing that I have been thinking about measuring, I’d be curious to hear notecards per day is kind of an interesting measure of creative health you could say, it’s a measure of inputs that have been processed. Anything else come to your mind as you interact with that phrase?
[0:42:35.6] BO: I mentioned the dopamine hit for me of drawing connections between things that I am consuming and I do think the creative process is largely just connecting dots. Like I was listening to Danny Meyer, the restauranteur on Tim Ferriss's podcast I think.
[0:42:54.3] JU: ABCD, is that what you’re about to say?
[0:42:56.9] BO: Yeah, yeah, ABCD to ABCD, always be collecting dots to always be connecting dots and this is kind of like a little bit name-dropping. I’ve been doing some work with Rick Rubin, the music producer, and I was with him and he starts his day by he goes out to his pool and he treads water, and listens to an audiobook for an hour and then we would meet every afternoon.
I’d walk over to where we’re meeting and he had a stack of books beside him. So, he just finished reading and then every evening I’d walk over to dinner and I could see through the living room that he had paused like a documentary that he’s been watching and he’s just always consuming stuff. I ask him about this and he calls it looking for clues, always uses that phrase that he’s looking for clues and I would ask him about that.
And he was like, “It’s all I do” and then he said, “But not because it’s my job.” He was like, “My job is my job because the person I am likes to do those things.” I really resonate with that because it’s like I will spend Sunday afternoon reading and watching stuff that I might be able to use. We might have friends over and my girlfriend will have to be like, “He’s always doing this. He’s always working” and she says that I’m – and it’s like it doesn’t feel like it's work to me.
This is like what I’m choosing to want to do, so like the creative health thing is like what’s the thing you would just be doing anyways and can you –
[0:44:18.0] JU: Oh, that’s cool. Okay, so wow, I really appreciate that because where I was going or where I thought you were going was creative health is that collection maybe but it sounds like what you’re saying is collection is evidence of creative health maybe for somebody like Rick Rubin because that’s what’s natural to him or that’s what he wants to be doing.
[0:44:37.6] BO: Yeah.
[0:44:38.1] JU: But creative health is not necessarily the collection. It’s knowing the thing that you want to be doing and making space to do it.
[0:44:46.3] BO: Yeah, exactly. So, maybe there’s a lot of people that treading water and listening to an audiobook sounds like a chore but that’s how he wakes up and looks forward to doing that. So, like creative health would be, the way I’m thinking of it is what is your version of that kind of looks like work to other people but you enjoy it and how can you carve out the time for that and if it is not directly contributing to your work like I think if you are carving out the time to do those things, it somehow finds its way into the other things you do.
[0:45:19.5] JU: Yeah, yeah. That’s a perfect note to end on. We could go for another hour but this is amazing.
[0:45:24.8] BO: Yeah.
[0:45:25.2] JU: And make sure Billy, will you tell people how they can find you? We’ll drop links to all of your stuff in the show notes but let people know where can they find you if they want to follow your work.
[0:45:33.3] BO: I’m at billyoppenheimer.com and I think the newsletter is slash newsletter, billyoppenheimer.com/newsletter. I think that’s where I would – I’d send people first. The newsletter is my favorite thing to do, so if people want to check out something, that’s where I would send them.
[0:45:46.6] JU: Yeah, folks, I cannot recommend Billy’s newsletter highly enough. It’s the reason to open your email on Sunday night. Everybody, thanks for joining us on LinkedIn, we’re going to end the stream here, and hope to see you on Monday as we talk with another hero of innovation, Amy Edmondson, who just won her second Thinkers 50, number one management guru award in a row, which is pretty incredible. So, hopefully, we’ll see you on Monday.
[END OF INTERVIEW]
[0:46:12.0] JU: By day, I’m a professor but I absolutely love moonlighting as a front-row student next to you during these interviews. One of my favorite things is taking the gems from these episodes and turning them into practical tips and lessons for you and your team. If you want to share the lessons you picked up from this episode with your organization, feel free to reach out. I’d be thrilled to do a keynote on the secrets that I’ve gleaned from creative masters or put together a hands-on workshop to supercharge your next offsite adventure. Hit me up at jutley@jeremyutley.design for more information.
[END]
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