Become a Writer Today

Using Prompts and Constraints to Inspire Creativity with Herbert Lui

May 27, 2021 Bryan Collins Season 2
Using Prompts and Constraints to Inspire Creativity with Herbert Lui
Become a Writer Today
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Become a Writer Today
Using Prompts and Constraints to Inspire Creativity with Herbert Lui
May 27, 2021 Season 2
Bryan Collins

Have you ever used prompts or constraints to inspire your creativity? 

Herbert Lui is a well-known freelancer. He’s written for top publications like Lifehacker and Fast Company, and I also know him as the guy who introduced me to the Zettelkasten method, which changed how I research and write books. 

Herbert also runs his own business, helping companies set up blogs and build a name online. 

In this episode, I ask Herbert what it’s like to write for companies like Lifehacker and Fast Company and how new writers can get gigs writing for publications like these. He also explains why quantity should be your number one priority as a creative and how to balance quantity with quality.

I also ask Herbert to tell me more about his new book, There Is No Right Way to Do This.

In this episode, we discuss:

  • What Herbert's latest book is about
  • Tips for starting writing again
  • The types of constraints that authors use
  • Using the three-act structure when writing a book
  • How a new writer can start writing for big publications


Support the Show.

If you enjoyed the show please leave a review on Apple. And if you have any questions you can find me on Twitter @BryanJCollins

Thanks for listening!

Show Notes Transcript

Have you ever used prompts or constraints to inspire your creativity? 

Herbert Lui is a well-known freelancer. He’s written for top publications like Lifehacker and Fast Company, and I also know him as the guy who introduced me to the Zettelkasten method, which changed how I research and write books. 

Herbert also runs his own business, helping companies set up blogs and build a name online. 

In this episode, I ask Herbert what it’s like to write for companies like Lifehacker and Fast Company and how new writers can get gigs writing for publications like these. He also explains why quantity should be your number one priority as a creative and how to balance quantity with quality.

I also ask Herbert to tell me more about his new book, There Is No Right Way to Do This.

In this episode, we discuss:

  • What Herbert's latest book is about
  • Tips for starting writing again
  • The types of constraints that authors use
  • Using the three-act structure when writing a book
  • How a new writer can start writing for big publications


Support the Show.

If you enjoyed the show please leave a review on Apple. And if you have any questions you can find me on Twitter @BryanJCollins

Thanks for listening!

Herbert: Perfection and quality emerge through practice but also through just stepping up to the plate enough times to try to allow it to happen rather than forcefully trying to like deliberately push for perfection to happen.

 Introduction: Welcome to the Become a Writer Today Podcast with Bryan Collins. Here, you’ll find practical advice and interviews for all kinds of writers.

 Bryan: What prompts can you use to become more creative? Could constraints be one of them? Hi, there. My name is Bryan Collins, and welcome to the Become a Writer Today Podcast and the topic of using constraints and also becoming more creative is something we talk about in this week’s episode. I caught up with the well-known freelance writer, Herbert Lui.

He’s written for top publications like Lifehacker and Fast Company and I came across his work a year ago because he’s the guy who introduced me to the Zettelkasten method which has changed how I research and write books. Herbert also runs his own business, helping companies set up blogs and building a name for themselves online. He’s also recently written a new book, which came out a few months ago, and it’s called There Is No Right Way to Do This and it’s for creatives, not just for writers but for artists, musicians, and other types of creatives.

 For writing this book, Herbert used the three-act structure. And if you’re working on a book, the three-act structure is a constraint I recommend you use as well. It’s popular both in fiction and nonfiction because, if you think about it, every good story has a beginning, a middle, and an end. 

If you’re going to use the three-act structure, in the first act of your book, you just introduce the problem or you introduce the story or you have an inciting incident of some sort and, normally, the first act is one of the shorter acts in your book. The second act tends to be quite longer and it’s where you elaborate on the problem or you elaborate on the story or you develop the plot and that tends to be the meat of the book. You know, it will form up to 50 percent of the word count. And then, in the final act of the book, the third act, you know, you bring things to a resolution or you bring things to a close for the reader.

 Now, Herbert organized his book into three acts and he gave them each a visual metaphor which I thought was quite clever. These are head, hand, and heart. In each of the three acts, he has prompts and techniques that people could use. 

So, if you’re struggling to, you know, organize ideas for your book, consider using the three-act structure. Now, there are other methods that writers can use too but this one is pretty simple to apply and, in fact, if you would like to see what it looks like in practice, check out the writing app, LivingWriter, because they have a series of templates that non-fiction writers can use, including one for the three-act structure.

 In this week’s interview with Herbert, I asked him about how he organized the ideas for his book and I also asked him about what it’s like to write for companies like Lifehacker and Fast Company and how new writers can get gigs writing for publications like these. He also gets into why quantity should be your number one priority as a creative and how to balance quantity with quality, but I started by asking Herbert’s to tell me a little bit about his book, There Is No Right Way to Do This.

 But before we go over to this week’s interview with Herbert, remember, if you enjoy the show, you can support the show for just a couple of dollars a month on Patreon. I’ll give you discounts on my books, courses, and also on writing software. And if you enjoy the show, you could also leave a short review or share the show on iTunes, Overcast, Stitcher, or wherever you’re listening.

 Now, with that said, let’s go over to this week’s interview with Herbert.

 Bryan: My guest today is Herbert Lui. I’ve been following Herbert’s work online for quite a while and he’s actually the writer who introduced me to the Zettelkasten method and he has some interesting ideas about an approach to deep work and he also has a new book out called There Is No Right Way to Do This. Welcome to the show, Herbert.

 Herbert: Thanks for having me, Bryan.

 Bryan: So your book, There Is No Right Way to Do This, which came out last autumn, would you be able to give listeners a feel for what it’s about?

 Herbert: Yeah, for sure. So, it’s a really practical guide to creative projects. If you’re trying to learn new skills, if you’re trying to kind of get back into the groove of anything creative, whether it’s writing, designing, art, or problem solving and just trying to step up your creativity at work, that’s what this guide is all about. 

So, I kind of go through a bunch of different people’s insights into how to be creative and, I mentioned this earlier, Bryan, but the intro is really — it sets the stage for the book and it’s important. There’s a quote by this cartoonist, Shaun Tan, who says, “Nobody ever really starts drawing. We all know how to draw as kids already, but most people stop,” and I think that’s the approach I take to the book as well. We already know how to make stuff, we already know how to create, but, along the way, most of us stop or we forget because life happens and this book is a guide to getting that started again into awakening that side of you.

 Bryan: So, what steps would or could somebody take if they’ve stopped, well, I guess, in this case, writing? What would you suggest they start doing?

 Herbert: Yeah, for sure. So I would say — the way I approach it is starting with the hands first, then the head, and then the heart and so I would say like just start putting words on the page. I was talking to this visual artist, Big Mike, who actually has a job being a general manager at a hairstylist place in New York City and he’s been doing that for decades and he just paints at lunch.
And so, one hour a day, he just goes into — I think he uses a hall in the shop as his studio and he just paints. And he just says, “Put the paint on the canvas,” and I feel the same way about writing. You just put the words on the page, and that’s writing.

 Bryan: Is an hour a day do you think enough?

 Herbert: I would say so. I mean, some people don’t even have that, right? Like —

 Bryan: Yeah.

 Herbert: — if someone’s saying, “Oh —” like, if you’re listening to this and you’re like, “Oh, I really don’t have an hour a day,” then I would suggest maybe like starting even just with 5, 10 minutes and scoping the thing you’re trying to do really, really small. So, for example, there are these things on Twitter called screenshot essays, right? 

And I would say if like an hour a day and writing like, you know, 500 words is really intimidating for you or you just don’t have schedule, then try doing a screenshot essay in like 5 minutes so just turn off Netflix 5 minutes earlier or like, you know, 5 minutes before you go to bed or 5 minutes when you wake up, just like write down what you’re thinking and like put it in the screen real estate of your phone and that’s kind of your constraint. So, I would say even starting really, really small is really nice, and then when you’re ready to publish your work, then that’s kind of the next step as well after that.

 Bryan: I like that you mentioned constraints. I think that’s pretty important for creatives. When you were researching the book or with your other work, have you come across any interesting other types of constraints that creators are using?

 Herbert: Yeah. So, time is a constraint and I mentioned another one which is size just now. I would say that those are kind of the two really big ones but really anything in life can be a constraint, right?
I mean, we probably each face too many already. And so I would say — there’s one in the book that I cover which is about chance as a constraint so like rolling dice or like flipping coins, in some cases, you assign a decision to each of the dice’s faces or like each side of the coin and that way you really — like you leave it up to chance, destiny, fate, whatever you want to call it, to decide, “Hey, like here’s what I’m gonna do with this piece of work today.”

 Bryan: Yeah, I like the idea of using a dice. That would be an interesting way to approach this. Have you ever heard of the Oblique Strategies?

 Herbert: I don’t think so. No, but I’m curious.

 Bryan: Yeah, no, they’re prompts for creatives and I know you’ve got prompts in the book. Well, basically, it — a musician, Brian Eno, and his artist friend who’s passed away came up with them. But, basically, it’s like a commandment that you use, so if you say something like, “Turn it upside down,” and you use that as like a prompt to start writing or start painting or, in their case, it was composing music. So, yeah, they’re quite good. I recommend checking them out. What other types of prompts do you have for creatives in the book?

 Herbert: Yeah, I have all sorts, I would say, that, you know, whether — there’s nine different chapters and, in each section, so the hands, the head, and the heart are how I kind of split the book and I would say that change, you know, starts with the hands and so there’s three chapters in that first section, three chapters in the head, and then three chapters in the heart. And the more practical ones are probably the ones with the hands, right? So kind of even, for example, I would have a proposition on showing people your work and that’s like a really big part — I mean, you know, we kind of picked up where we were a few minutes ago, that’s a big part of creativity too is being able to ship it and show people, “Hey, like this is what I’ve been making,” and then they get feedback on it. 

And whether that’s just posting it on the internet, which is the most common way these days, but also like showing a smaller group of people, like not necessarily in public and just, you know, a private e-mail list or like a Facebook group or even just showing someone in the physical world, like maybe a roommate or a family member or a friend and getting their feedback and really listening to it. That’s a part of it. I could go on for a while about the rest of the propositions. There’s a quite a few in there.

 Bryan: So, is that proposition from the hand part of the book?

 Herbert: Yeah. It’s from a chapter called “How to Make Your Market” —

 Bryan: Okay.


Herbert: — and, yeah, it’s just kind of about like — I think it’s really important for anyone doing creative work, especially in writing, to make their own market in a sense and to make sure, “Hey —” you know, like when a publication reaches out to you, it’s best when they’re like, “Hey, we need a piece by you. We don’t really —” Like sometimes they don’t even care what you write.
They’re like, “Hey, like we just want a piece by Bryan and Bryan can just cover what Bryan wants because people like Bryan’s coverage, people like Bryan’s perspective.” So, that’s kind of the end goal of that chapter is like to get someone to the point where they become this really — I think people will approach them for what they want and they don’t have to chase other people’s expectations or what they think those are.

 Bryan: Could you give an example of a constraint from the head part of the book?

 Herbert: Yeah. So, in the sixth chapter, it’s about experimentation and I would say that the example I use there is this author and comedian, her name is Sarah Cooper, and she’s always been super — she’s explored a lot of platforms really well.

So, I mean, back in 2013, she was at Medium already and kind of like went viral there and got a book deal. And one of the propositions from that section is about — I mean, she’s the opening example, I would say, but one of the propositions from there is all about like trial and error. So it’s like, okay, like come up with a remix of one of your old ideas so taking one of your old ideas and either reformatting it or, let’s say, if it’s an article, then we try to like put it at Instagram, put it in a picture format, or to redo it again and post it back at another platform or to re-pitch it to someone else.

So, it’s like things like that that kind of like, you know, involve the, I would say, the more cerebral side of like examining work. Another one is recreating a classic so like taking someone’s work you really like, like taking a crack at trying to make it again, right? To kind of deconstruct, “Okay, how did they do this and what techniques did they use?” So, for me, actually, what I’ve been doing recently, and this is in the book too, is I’ve been doing copy work. So, just taking a book I really like and trying to just type it out and, in doing that, I find that I notice a lot more stuff than I would have if I’d just — when I read it silently or even out loud. Because when you type it out, you really like — your muscles kind of get into it and you’re going at a slower pace, sort of, and you’re like, “Oh, like I didn’t realize that this person used, you know, this meeting, for example, to go through so many different personalities and like, you know, uncovered this business model and stuff like that.” I was doing copy work with Chaos Monkeys so that’s where I kind of picked at the story and could deconstruct things a little more.

 Bryan: Yeah, right. Funny you mentioned that. A writing teacher years ago recommended, when we were studying short stories, that we write out the first few pages and he said it was a good way to learn the author’s sense of style and to take apart what they were trying to do. So, yeah, it’s interesting that you mentioned that. I didn’t realize Sarah Cooper was on Medium. That’s the comedian who did the skits about Donald Trump, wasn’t it?

 Herbert: That’s right, yeah, and those went viral when she tried TikTok, right?

 Bryan: Yeah. 

 Herbert: And it’s super interesting how that happened because her platform, I think the one she usually uses is Twitter. I mean, she’s super popular there now too, but the one she really gained a lot of traction on was TikTok more recently. And so it’s funny how like, you know, as writers, we kind of stick to the form, right? “I like writing so I’m going to write,” but I mean, you doing the podcast is a good example of this too, like we’re using our voices in different ways, not on the written page, and we’re communicating in a different way. And so I think that’s — like exploring different formats as ways to get your ideas out, even still, you know, if you keep the identity as a writer, you know, learning to use Figma to try to like do graphics and stuff and pull out excerpts of your articles and try to rearrange the logic into a visual format, I think that’s a really interesting process too.

 Bryan: Yeah, I’ve used Figma. I’ve never thought of using it that way before. Something I should definitely look at. So, we’ve covered the hand, we’ve covered the head, have we covered the heart? Have you — or have you mentioned that already?

 Herbert: Yeah, I probably briefly mentioned it but the heart is just about like, you know, really — I think it just naturally follows, right? You really start understanding things and kind of getting more focused on the process. And, you know, an example of a proposition from there would be about obsession, let’s say, right? So, there’s two propositions one right after the other and one is like cultivating an obsession, which is get really obsessed about something to the minute detail and try to make it perfect, and the next one is about letting go of obsession, because in order to release anything, you have to kind of let go of any other expectation you might have of it, right? Otherwise, it’s never going to see the light of day and that’s how creative blocks really started happening and so that’s where propositions like that really come in. 

And I think it ties in really nicely. I almost see the process as circular, like you go from hand to the head and then to the heart and then back to the hands again and that’s how I really see the creative process in general. I mean, if I could format the book in a circle, I would try. Maybe there is a way to do it.

 Bryan: Yeah, maybe, there is, with Figma or something. And I’m curious, did you come up with the three acts, the heart, head, hand, when you were writing the first draft or was that something that emerged during the editing process?

 Herbert: So, my writing process for the book was a little convoluted. It kind of came in between drafts, like maybe between like the first and the second, I would say. I was looking for a structure and I knew I want it to be three parts and like, you know, the first draft was — I actually kind of — I don’t even know if I would call that the first draft but, really, I wrote like maybe six to seven to eight essays and I didn’t really like where it was going so I decided to scrap it and go do a new draft and I took material from that first draft, of course, but the new structure involved three parts. I really liked the 3-3-3, like the rule of three but also, in stories, like you have beginning, middle, end so I liked that rule as well and kind of how well balanced it seems.
So, the three parts, nine chapters. I mean, I just found this out recently that, you know, a coach was telling me that everything in coaching has to do with changing what you’re doing, what you’re thinking, and what you’re feeling. And I was like, “Oh, I didn’t really notice that, I didn’t really think of it,” but the hands are the doing, the head is the thinking, and the heart is the feeling and so I think it actually really worked out. And so, when I do a revised edition, I definitely plan on keeping that structure but maybe even elaborating on a little more.

 Bryan: Yeah. Well, the three-act structure works very well for books. I like that you have a nice metaphor for it. I mentioned earlier on that I came across your work because you wrote about the Zettelkasten method so we had the author, Sascha Fast, on the show before. Basically, it involves capturing ideas and writing like your reaction to the ideas and interlinking the notes. I guess there’s a bit more to it than that, but did you use the Zettelkasten method to write your book?

 Herbert: Bryan, you read my mind and that’s exactly what happened. I would say it’s actually probably the biggest thing I changed in the past couple of years and I don’t know if I could have done the book without it, to be honest. I’ve been trying to write a book for a while and that was — I mean, I did a few things differently this time around but that was one of the big ones and, I mean, even to this day, I’m still taking maybe, on average, three to four notes a day first thing in the morning and so I have a thread full of index cards for this particular book and I also ended up putting everything into Notion —

 Bryan: Yeah.

 Herbert: — so that’s what I used to manage my digital version of the Zettelkasten.

 Bryan: Could you maybe elaborate a little bit more on your personal slip box or Zettelkasten? Because you mentioned index cards and Notion so I’m curious about how you get the ideas and organize them and interlink them?

 Herbert: Yeah, for sure. So, I’ll probably come across an idea, it could be when I’m reading, it could be whenever, honestly, as you probably know too well as well, and so whenever I get the idea, I’ll either jot it down, like I’ll try to capture it, like it could be on my phone. I mean, I write them down on like cue cards as well —

 Bryan: Yeah.

 Herbert: — just a list — a very quick list so I don’t forget it. It might be two or three words. From there, when I get the chance, usually first thing in the morning, I’ll end up like elaborating on each of those lines and say, “Oh, like this is what I actually wanted to say.” Sometimes, I find that the lines, you know, weren’t really that great or I’ve already written about it before and so usually what happens there then is I write the card, sometimes I actually don’t even put it in yet, I’ll just write the card out, and I find the hardest part is connecting the card to something else —

 Bryan: Yeah, it is.

 Herbert: — but that’s the most important part too. And so I’ll just write the card and kind of like make it easy for myself and be like, “Okay, one day — like, eventually, I’m gonna get to putting this in there,” and then when I put it in, usually I look through the threads I already have so I have like an index of, “Hey, this is what thread 1 is, thread 2, thread 3,” and then I’ll just start attaching them to the threads and also, every time I put the index card number on it, then I’ll also like put it into Notion as well.

 Bryan: Are you using hashtags to organize the threads or just interlinking in Notion?

 Herbert: I actually have a — I created a database, I think, in Notion and then I created a template and inside each template, there’s like — I think there’s an option to do like a drop-down menu for themes — or not a drop-down, like a keyword for themes.

 Bryan: Yeah.

 Herbert: So, I have like these keywords that I use in addition to the index cards, but, frankly, I haven’t really tried combining my ideas like that yet. I know they’re organized like that but I’ve never looked at it like that before. So, it would probably be interesting to have a look at things like that.

 Bryan: Yeah. I’m using the journaling app, Day One. It’s not built for the slip box but I find it’s quite good because I was using it for journaling anyway so it encourages me to put like an entry in the Zettelkasten as well.

 Herbert: Oh, for sure.

 Bryan: Have you come across Roam Research because that seems to be quite popular these days with people who use this method?

 Herbert: Yeah, I’ve come across it. I’ve actually — I tried exporting everything from Notion into Roam once and it worked and so I definitely — I’ve been meaning to try it out more aside from just like seeing if it would work because I know it — there’s like — I think once you can figure it out, it becomes very powerful but, at the same time, I do think, to a certain extent, like as long as whatever note-taking method, whether it’s Evernote or Notion or Roam, whatever it is that you’re using, as long as you can export the files, then you can go wherever you want with it so kind of — if someone’s listening to this and trying to figure out where to get started, that was something I wrestled with as well for a while. I just decided on Notion because I think Roam was closed at the time then I think just start with whatever you’re most comfortable with. So if you’re already using Notion like maybe picking Notion is best or Evernote then Evernote might be good.

 Bryan: Yeah, it’s better to have one system and use that system rather than —

 Herbert: Yeah, for sure.

 Bryan: — just keep using different things. And do you spend much time going back and looking at older notes or older threads?

 Herbert: I do when I have a new idea to add to it. So I don’t really deliberately go out of my way to have a look but if I have a new idea and I kind of forgot if I’d written a thread like that before or an idea like that before, then I’ll go and have a look. And it gives me an interesting excuse to kind of comb through knowledge.

 Bryan: Yeah. That, for me, I think that’s where the real value is because you’ve — it’s amazing how much you forget when you read something and you file it away.

 Herbert: For sure.

 Bryan: So I also wanted to ask you about your freelance writing career. You’ve written for like a lot of big publications, Lifehacker, Fast Company, and so on. I guess how does like a new writer go about writing for big publications these days?

 Herbert: Yeah. I mean, I don’t know if it’s that different from maybe even 5 years ago. I feel like that process has stayed pretty much the same. For me, I got started freelance writing as a guest poster. So, at the time, I didn’t even get like compensated for it. My first few posts were for like publications I really liked, so like Hypebeast, The Globe and Mail, and Lifehacker were amongst the first ones and that was when I was just graduating from college. I mean, Hypebeast, eventually, like just sent some money on PayPal, I think, on my third attempt or my third, like my third piece with them, but the other ones were just guest posts and then eventually what happened was I kept writing for Lifehacker and they posted these job opportunities so I figured I’d apply and they saw that I’d written for them before and so the editor-in-chief at the time, Whitson, was like, “Hey, let’s give it a shot and let’s see how this goes,” and so that’s how I got my first more steady like staff writer opportunity.

 Bryan: Is your priority these days freelance writing or working on books or something else?

 Herbert: So, I would say my priority right now is focusing on actually my editorial studio so that’s where most of my business is. So we work with software companies to build publications which is like a really businessy way of saying we kind of like help them start — we help their team start to write and we set up their blog and promote it and help them with all of that. And so we’ve worked with companies like Shopify and Twilio and Stripe and organizations like the City of Toronto as well.

 Bryan: Yeah, I worked on a content marketing team before and it’s always amazing that companies have difficulty articulating what their product does into everyday language that customers and readers use.

 Herbert: Yeah, it’s the curse of knowledge.

 Bryan: Yeah, because you’re an expert in what your software does, but to actually turn it into, you know, an engaging, helpful article, it’s quite a challenge.

 Herbert: Yeah.

 Bryan: Is there anything that you do or that your team those to help people clarify their message?

 Herbert: I would say that our process is pretty straightforward, honestly. I think that a big part of it is in actually coaching them through the writing process so kind of like from the beginning, even making the business case for it and all of that, you know, for the most part, it’s recruiting or marketing, all the way down to the nitty-gritty of like, “Okay, like do you have time to write? If you do, then we’ll kind of interview you and coach you through the outlining, the writing, the editing,” and work on the interview and the edit with them but they’ll do most of the writing so that’s more like a training program and then, if they don’t have much time, then we actually work with them as co-writers and we’ll interview them, outline it, do the first draft for them, and then they have a look at the first draft and kind of edit it for voice and style, maybe some substance if there’s, you know, if they want to add code snippets and things like that, we would highly encourage it, and then take it from there and, you know, go through the rest of the process as well. 

Some companies are bigger so they want publicity and legal review. Other companies just want more peer reviews and like, you know, marketing or engineering leadership review. And then we ship it and help them promote it and get some eyeballs.

 Bryan: What works quite well for promotion these days?

 Herbert: Yeah, I would say that if you’re doing an engineering blog, obviously, Hacker News is the place to go. I think a lot of subreddits are really good and there’s a lot of nuance to it in the sense that like you kind of got to have a sense of what does well at these platforms before you write it so you have an idea. It’s not about pandering, necessarily, but it’s more about like packaging and like, okay, like people want to hear this versus what you want to say and you want to find the intersection of the two.

 Bryan: Yeah.

 Herbert: I would also say that a lot of it is about relationships and focusing on relationships first and so I would say that if there’s a newsletter or someone who runs a community, then building relationships with those people who do that, I think, are really, really powerful. And, lastly, it depends on the size of the team, but I would say that like leveraging the company’s internal network is like one of the big parts of it as well. If, say, we did a piece with a company that’s recruiting and it’s about a day in the life of, let’s say, an analytics software engineer, then having the analytics or the engineering software team share it would be super valuable and then their networks at LinkedIn and Twitter kind of see it and it’s kind of more a softer call to be like, “Hey, like come work with us here. We do really cool stuff.”

 Bryan: How do you find the balance between somebody’s voice coming through on the page and in the article versus making sure that it’s engaging?

 Herbert: I mean, I think it really depends piece by piece. I would say that each person — I think it’s really up to the person and their — I couldn’t think of a better word than personality so we’ll just go with that, but kind of their opinion on what they want to say and how they want to say it, right? I do think that a lot of the magic does happen in that second like voice and style edit stage I talked about and, quite frankly, like if we used an app like Otter for live transcriptions and like — and they integrate with Google Meet and Zoom now as well —

 Bryan: Yeah.

 Herbert: — then we literally have the things that the person is saying so you can, as much as possible, like try not to tweak it too much because this is their literal voice and this is, you know, they’re using those words. And so I would say that, like the — from the edit side, mostly, a lot of times, we’ll be looking at structure, we’ll be looking at the headline, we’ll be looking at other algorithms that we’ve — and heuristics we’ve used to kind of determine, “Oh, like here’s what you might wanna open with, like let’s start with something less expected,” right? Or let’s start with a moment kind of starting in the middle and then like jumping to the beginning. Yeah, there’s those sorts of tricks that we use.

 Bryan: You have an interesting take on quantity versus quality and why quantity should be your priority. Firstly, does that work for your clients? And also maybe could you explain about your take on quantity as well?

 Herbert: Yeah. So I would say with quantity versus quality, we usually put them as a tradeoff, right? “Oh, we don’t want quantity, we want quality.” The reality is quantity actually can support quality and there’s — in the field of historiometrics, there’s this professor, his name is Dean Keith Simonton, and he studied creative geniuses for decades and, basically, that was the conclusion he came to is the more hits you make, the more misses you make as well. And this is from the creative geniuses. And so one of his subjects was Thomas Edison, for example, who basically had like — applied for 1,500 patents, got 1,000 of them accepted, but only one of them was the light bulb. And there’s a lot of other examples like this, right? I mean, Picasso’s another example. 

You know, he’s in the Guinness Book of World Records, I think, for the person who’s made the most paintings and the guy has done 10,000, I think, maybe even more pieces of art and so the principle there is just that perfection and quality emerges through practice but also through just stepping up to the plate enough times to try to allow it to happen rather than forcefully trying to like deliberately push for perfection to happen. I do realize that — so, one of the things he mentions is this relationship is probabilistic, right? So there are outliers on either end so sometimes there’s, you know, people who make one thing and that one thing is amazing and then there’s also people who make a million things and none of those million things really breakthrough. But I think the general principle is it’s the most consistent strategy is to try to like do a lot of stuff and to release it and try, like just to keep trying and then allow something good to happen.

 Bryan: Yeah, I think that releasing it is key because if you’re spending a lot of time creating stuff by yourself, you’re not getting enough feedback, whereas if you were constantly releasing and publishing your work, you can use data and readers and reactions or lack of reactions to figure out if you should do more or less of it.

 Herbert: Yeah, that’s true and, actually, another thing too is about combinations, right? Like creativity is really kind of about combining ideas and combining them differently and like, again, with the quantity thing, there might be like really good parts of certain pieces, like if we’re talking writing, there might be really great paragraphs or pieces of research or, you know, structures even in there, but maybe the rest of it wasn’t that great so it’s really important to take — to learn which parts are good but also to just — sometimes it’s just keeping busy and like recombining things, right? So, not literally like, you know, just one or two clicks and you’ve kind of cut a paragraph here and there but literally like, “Hey, like this idea, there’s something really good about this. I have that feeling, and other people have that feeling but not everybody yet. So what can I do to kind of make it better or to recombine it and repackage it so that this little glimmer of greatness like really shines through?”

 Bryan: Yeah, I like that. I like that. Sounds — I think I need to read more of your work. Herbert, where can people find your book or where can they discover your writing?

 Herbert: Yeah. They can find my book at and my blog is Obviously, you can find me at Medium, it’s my first name and last name, and my Twitter as well and I also do a newsletter. So, every month, I send the three best books that I read so that’s And if you’re working in software and you want to start a blog and are struggling, then you can find me at and that’s where my business is and a lot of the work we’ve done and the case studies as well.

 Bryan: Thank you, Herbert.

Herbert: Okay. Thanks so much, Bryan.


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