How to Enhance the Serendipity of Your Thinking

“It’s kind of a “sleight-of-head” exercise if you will. Because again, we tend to get very narrowly focused in our way of thinking. I’m sure you’ve heard of confirmation bias and availability bias. We tend to think in very narrow paths, and you need to be able to literally kickstart your head in different directions and this is one creative way to do that.”

– Chuck Frey

What you will learn

• What are the origins of mind mapping software? (02:20)
• What are ways to make mind mapping as useful and valuable as possible? (05:11)
• Other than mind maps, what are good alternative visual tools? (07:21)
• What are the most interesting recent developments in thinking tools? (09:43) 
• How do you build up a set of tools to use which works for you? (12:04)
• What is a note? Should it be a sentence? A link? A phrase or an idea? (13:52)
• What are ways to enhance serendipity thinking for the ideas that we find (17:04)
• What is the process to write compelling content on topics outside your area of expertise? (20:52)
• How can you connect ideas to create a narrative? (22:56)
• What are ways to keep focused attention for long periods of time (25:25)
• What are daily practices to improve your information gathering (27:44)

Resources

• Success Magazine
• Miro
• Mural
• Evernote
• Notion
• Obsidian
• SparkNotes
• Napkin
• ContextMinds
• AYOA formerly iMindMap
• Roam
• Evernote
• Notion
• MindMeister
• Second Brain for Content Creators by Matt Giaro
• ThinkerToys by Michael Michalco

Transcript

Ross Dawson: Chuck, delighted to have you on the show.

Chuck Frey: I’m delighted to be here. Thanks for the invite.

Ross: We have a lot to learn from you. We’ll try to dig in and get as much from you as we can.

We want to start with your backstories. How did you get to this? In 2007, you set up the mind mapping software blog, and that may not have been the beginning. Is this something from when you were a child that you were looking at and thinking of? How did you come to these thinking tools, visual concept mapping, and all of these ways of approaching this?

Chuck: Probably in the late 90s, I came across a handheld brainstorming tool in Success Magazine of all places. I’ll try and make this as quick of a story as I can, because I know we have a lot of ground to cover. I didn’t even know that there was such a thing. I reached out to the developer of it, who was from Chicago, and started doing some publicity for him to help promote it. It opened up a whole world to me of tools and resources and methods to think differently, to think better. It seemed to me that even 20 years ago, the pace of change was accelerating and there was a need for people to know more about this.

My background is in PR and marketing. I had the opportunity to join a trade association to help put them on the web. Eventually, I took what I learned and built my own website focused on creativity and innovation, and just happened to be in the right place at the right time, that grew like crazy, to the point where it was the world’s largest site focused on that. I spent a lot of time on tools, thinking tools. One part of that was mind mapping software, which seemed to be growing rapidly, but nobody was covering it full-time. That splintered off from the innovation tools site. Eventually, innovation tools went away. There’s a bad joint venture involved there. That’s a story for another day.

As we were talking before we got on this call, these tools are very powerful, they’re really useful to knowledge workers who need to be able to gather, organize, distill and share information, and doing that in a visual way helps you connect the dots, helps you to see what you’re missing, helps you to get clarity quicker, make better decisions, and to think at a higher level. Since then, that’s expanded to include other types of visual thinking tools. Since COVID, these sticky note-based whiteboard tools, they were around before that, but they took off overnight because suddenly teams could not get access to their traditional whiteboards anymore, and this was a valuable substitute.

As you know note-taking has taken off quite a bit and there’s a whole new sub-genre of that, that are visual note-taking tools where you basically have combined the card base note with an infinite canvas. Now once again, you have the ability to connect the dots and see things in relationship to each other that weren’t possible before.

Ross: Let’s start with mind mapping. As you say what you cover is far broader than that. What are some of the tips or the ways in which somebody who is already minding mapping could enhance their practices? What are some of the ways to make mind mapping as useful and valuable as possible?

Chuck: I actually have a four-step framework that I’ve promoted, and I have a course that I call “The Fast Framework”. You basically need to start out with the right foundation, actually having a goal for what you want that map to be.

One of the challenges comes in that not everybody knows or understands mind maps. As you create a map with all these branches, you understand the context and the thinking behind it but if somebody else is viewing it, if you’ve shared it with them, they don’t have that. You really have to think through it very carefully, what’s the objective of it? What are you sharing? How are you going to make it clear to others? Fortunately, as a thinking tool, it works the way your brain does by association so you can very quickly build out branches and cover a lot of areas.

But again, you have to have a goal. Are you planning a project? Are you trying to make a decision? Are you simply brainstorming and then trying to evaluate all the ideas you’ve come up with? And then from there, step back almost like a painter would from the canvas and look at a high level of what you’ve created, figure out what’s missing, what needs to be added to or clarified. Then there are some things that you can do to enhance the map that a lot of people don’t even bother with; things like icons or symbols, task information, tagging, and things that enable you to visually classify your information.

Then as you’re putting this together, the first arrangement of your topics shouldn’t be the end result, you can move things around, it gives you a great deal of freedom to rearrange your map, and to play what-if with the topics. The interesting thing is, when you move a topic to a new location on the map, it is suddenly surrounded by a constellation of other topics, and you’re able to look at it in a different context, and often that spurs additional ideas. Those are just some of the things you can do to improve a map.

Ross: Fantastic. It points to three major visual diagramming tools, mind mapping, concept mapping, and systems diagrams, each with a different frame for how those connections are made on the page. Other than mind maps, what else would you point to are useful visual tools?

Chuck: Concept mapping, you mentioned. A mind map is very hierarchical. It’s got a central topic, and then branches that come out from it. It’s almost like a visual outline like you did in school. But not all information is aligned with that model. A concept map enables you to show more complex relationships where some topic might have multiple parents or multiple children. You can add notes onto those connector lines, which creates some contexts.

I mentioned earlier, the sticky note-based whiteboard tools that have become so popular, like Miro and Mural, that really enable teams either in real-time or asynchronously to brainstorm, to start working through a thinking process, to do the planning. Again, it’s a very flexible canvas, you can do a lot of things with it.

There are some very popular note-taking tools that have grown to millions and millions of users and billions in valuations, things like Evernote and Notion. But now there’s a whole sub-genre of tools that’s come into play, just in the last year or two, that I call visual note-taking tools where you take the card base note, and now you place it within an infinite canvas once again so you can start moving things around and seeing your ideas in relationship with each other and connect them either implicitly with lines or with tags.

I get really excited about that because it helps you to think better, to think more creatively, and to take advantage of serendipity. One of the things that I’m particularly excited about recently, and I wrote about on my blog is the canvas that has been added to Obsidian. Even before that, the Graph view enables you to see notes that are somehow related, but you may not have connected them yet with backlinks. But you can filter that view to a very high degree and again, see connections between these SparkNotes, these germs of ideas that you can join together and create new things out of.

Ross: You mentioned Obsidian, which is one of the current generations of thinking tools. You said around 20 years ago, you were interested in thinking tools and you just did a post on your newsletter recently saying that the time of the thinking tools has come, which I very much agree with, where suddenly there’s this whole lot of energy and recognition that it’s something we need to do, and a whole bunch of tools are emerging.

What do you see of most interest in the thinking tools landscape at the moment? What’s emerging? What are people taking notice of?

Chuck: In the last year one thing in particular that I’ve seen that really caught my attention was the introduction of AI to these tools.

In the visual note-taking space, there’s one called Napkin, in that as you’re working on one note, it is displaying related notes in the periphery of this canvas. They could be notes that you have explicitly linked to that note, but not necessarily. The AI is doing some semantic analysis and displaying things to you that it thinks may be related that you might want to see. From what I understand when you get up above say 150 or 200 notes, the magic starts to happen, and you start to see things that you go wow, I put that in here a year ago, and I completely forgot it was there but it’s really useful to me now.

In the concept mapping realm, there’s a tool called ContextMinds that has added AI to it. What it does is as you add topics to this map, there’s a panel on the bottom of the screen where it displays related words and concepts. You can drag and drop those into your map. It doesn’t force you to take these things on, and it doesn’t draw the map for you but it gives you the choice to decide what’s related, and what else should be added.

Then in the mind mapping realm, there’s a tool called AYOA, it used to be called iMindMap, it’s been around for a long time, but it transitioned to being a web-based tool and the developers have taken it in some new directions, and they have added AI as well. In this case, if you’ve got a topic in your map, you can tell the AI tool to add five topics, and it’ll create new sub-branches with suggested words on it, again, based on semantic analysis.

Ross: One question is we’ve got all these wonderful arrays of tools available, these are just a handful, the ones you’ve mentioned.

How does somebody choose what set of tools they use? What’s the process of being able to say, I’ll this tool, or I’ll use these in combination? Would somebody use one of the ones you’ve mentioned plus an Obsidian, Roam, Evernote, or Notion? How do you build up a set of tools to use which works for you?

Chuck: Two starting points. Number one, what is it you need to get done? Are you writing? Are you planning? Are you trying to brainstorm things? Are you trying to make decisions? Secondly, what’s your work style? Does it tend to be more visual or more text-based?

In the mind mapping space there has been a great divide for as long as I can remember of people who think it’s the greatest thing since sliced bread, and then a whole other group of people who think it’s frivolous and their documents and spreadsheets and PowerPoint decks work just fine, thank you very much. But at some point, people realize if I want to make a bigger impact, I need to think in some different ways than I’m used to doing because I’m wearing these invisible blinders on my thinking and if I want to reach that next level, I really need to step up my game.

I would start out with something simple. In the mind mapping space, I always recommend one of the web-based tools like MindMeister, where for a very low monthly cost, you can experiment. You can’t really know before you go into it if it’s the right tool, you have to try it, and see if it fits in with your workflow and the way you like to think. There’s a little bit of trial and error, to be honest, but that’s the way to find out what’s going to work best for you.

Ross: Fantastic. A couple of things I want to dig back into. One is this idea of the notes. You mentioned 150 notes, whatever.

What’s the nature of those notes? Would that be a sentence? Would that be a link? Would that be a phrase or an idea? Of course, it could be any or all of those. But what are your suggestions as to the nature of one of these atomic units that are connected in these platforms?

Chuck: I think it’s a very individual thing. Again, serendipity is important. I’m the poster child for this. I’ve been using Evernote for over 10 years. I probably have 6000 plus notes in it. But it ends up being I call it a sarcophagus: ideas go there to die. I’m working full-time. I’m trying to do these things on the side, I don’t have a lot of spare time to write and do these other projects. I haven’t done as much linking and searching back into my archives and finding these nuggets of gold as I should. I’ve been using it right along as a writing platform, I found it really useful in the sense that I have an iPhone, and I use Siri to dictate ideas, I find those can hit me anytime.

I learned a long time ago that it’s wise to capture those immediately, even if it’s just a germ of an idea. Then I can iteratively go back into Evernote and build those up. I’ve been toying around with the idea of moving to Obsidian but I didn’t understand how it would benefit me, particularly as a content creator.

I came across a course recently by a guy named Matt Giaro, called Second Brain for Content Creators, that really opened my eyes to what was possible, particularly with Graph view. The whole idea of working in atomic notes, just taking things down to this basic level so that you’ve got building blocks literally like digital Lego blocks that you can combine in different ways to build up content more quickly than sitting down with a blank note and trying to come up with something and then doing a Google search to try and find more bits and pieces to join with it.

If you’re doing this right, if you’re really passionate about an area and you’ve been doing this collection or curation, and It’s a lightweight system, it doesn’t require a lot of rigor. But again, if you’ve been building up this repository of ideas, you can then dip into them and accelerate your writing process by quite a bit and improve it, coming up with ideas that aren’t just a regurgitation of what everybody else is writing about, but with your own unique perspective.

Ross: Absolutely. You mentioned the word serendipity a couple of times, which is also one of my favorite ideas and concepts. For example, the AI tools you mentioned, facilitate some serendipity, they make connections you might not see.

But more generally, just thinking back as a thinking tool or a thinking process, what are ways that we can enhance the serendipity of our thinking of the ideas that we find? How do we connect them? What are some of the things that we can do?

Chuck: In my opinion, it’s very much a mindset thing. I try and cultivate what I call an inside-out look. As I consume things, I hear things, I listen to podcasts, watch YouTube videos, or read a newsletter, I’m always asking myself, what does this mean? How can I use it? How does it fit in with the rest of what I understand about this topic? Does it challenge it? Is this something I should save?

Just having your radar up looking for things, you’d be surprised at how much you come in contact daily with the things that might be somehow tangentially related to something you’re trying to get done or takes your thinking in a new direction, or helps you come up with a new angle on something you’re trying to write about.

Ross: One of the things I like to do is find different seeds: starting somewhere you would normally start and often a different direction. It’s like: can you find a person or a topic or an idea or a source which is outside, what you normally wouldn’t find? Then use that as a starting point to see where you stumble across that can be relevant to you.

Chuck: One of the things that I’ve been pretty rigorous about over the years is collecting creative thinking techniques. There’s one book I recommend to your audience in particular called Thinkertoys by Michael Michalco. It’s a fun book. It’s not a dry academic read, it’s delightful. It catalogs all these thinking methods that he has come across, and that he has used in his consulting.

I’ll just share with you one very briefly. You talked about a different starting point, one of them is called Board of Directors: Imagine that you’re standing in front of a group of the smartest people living or dead, famous or not, that somehow influence your thinking, say, you’ve got Steve Jobs, Albert Einstein, and a former college professor sitting in front of you, and you briefly explain what your challenges are. Then you wait for their advice. Based on their background, and the way they think, and a lot of this is very public if they’re famous people, there have been books written, and you imagine what advice they would give you and how to solve that problem.

It’s kind of a “sleight-of-head” exercise if you will. Because again, we tend to get very narrowly focused in our way of thinking. I’m sure you’ve heard of confirmation bias and availability bias. We tend to think in very narrow paths, and you need to be able to literally kickstart your head in different directions and this is one creative way to do that.

Ross: I love that phrase “sleight-of-head.” I absolutely agree. Since I was a child, I felt that most people are living their lives with blinkers on. It’s natural, we’ve got things to get on with. We implicitly put our blinkers on and don’t look around. Part of the challenge is to make sure that we take the blinkers off from time to time and look from side to side or outside what’s just right in front of us.

Chuck: It’s ironic, Ross. You write about dealing with overload, we have had to create these blinders just to be able to survive, we have to filter out what’s coming at us by necessity.

Ross: Just coming back to content creation. Your profession is creating compelling content. You mentioned this before, I’d like to hear about how to use all of these wonderful tools or approaches or frameworks to write better. What does that flow look like for you in terms of being able to write some compelling content, perhaps particularly on something which is outside your area of expertise?

Chuck: I have to put my professional hat on here because in the world of content marketing and content strategy as a starting point, we’re all so inundated with information. Step number one is to deeply understand your audience. What are they struggling with? What are their pain points? What keeps them up at night? What are some of their aspirational goals? You can build personas around that, just do a Google search on audience personas and you’ll find a wealth of information out there on how to do this, it’s not hard.

But you’re really trying to get into their head so that you can start writing things that help them solve problems, help them get things done, help them remove blocks from their life, or whatever they’re trying to do. You really need to focus on that first.

Then the real practical things like figuring out where they’re gathered? Where are they talking? Are they in communities? Do some listening to what they’re talking about, and then start to focus content development around those issues. Maybe you survey them, there are all sorts of ways to get that input like one-on-one discussions with people.

I’ve always believed that people like you who are podcasting, you’re talking to so many brilliant people, and getting so many perspectives that you get this incredible generalist view of the world that is so multifaceted just by having come in contact and deep conversations with these folks.

Ross: Once you’ve got that framing as who you’re trying to serve and how you’re trying to serve them, as you’re doing your research, let’s say, it’s a new area, as you’re doing research, how do you piece together all of those things that you discover? And how do those fit together to be able to draw a narrative?

One of the interesting things is that writing is linear. It starts and it continues and keeps on till it ends, presuming people read it that way whereas ideas and the landscapes we’re talking about, there are connections all over the place. How do you take that whole rich lattice of connections of ideas as you pull them together and all of the connections and frames to create a linear piece of writing?

Chuck: Usually, creating the personas and understanding what their journey is as they try and get things done naturally suggests topics to write about. I’m a big believer in either mind mapping if it’s a bigger project, or just doing a traditional outline of what I want to write just to create some constraints on it. Because otherwise, as you said, you could go in a million different directions. You don’t want to overwrite, you want to be fairly concise, because people don’t have much time to read, and frankly if you don’t hook them and keep their attention, you’re going to lose them pretty quickly. Again, it’s part of this filtering mechanism. I don’t want to invest a lot of time in this if I don’t see a payoff.

That’s a good way to keep the writing focused. Within that, you can be fairly creative. It also helps to constrain the research because you can really go down a rabbit hole as you know, doing Google searches and things like that. But it helps you to make some decisions about what’s relevant to the story you’re trying to tell, what’s not, what’s within scope, and what’s outside of scope. Maybe in the process, you find a few new ideas that you just jot some notes on and put them away in your system for future exploration, but it helps to keep the writing focused.

We live in a day and age that if you’re a content creator, the tools that you’re using to publish also provide a whole toolset of engagement. You really need to take the time to look at what people are connecting with, what are they sharing, what are they liking, what are they reacting to, commenting on, and that can give you a sense of if you’re actually meeting those needs, and maybe where you need to go deeper and spend some more time focusing on with your content.

Ross: Are there ways in which you practice focused deep work or focused attention or awareness? Do you meditate? Are there other ways in which you try to keep focused attention for periods?

Chuck: It comes naturally to me because I’ve been writing daily for decades professionally and for my own projects. In terms of my diet of information, newsletters play a big part, I know you’ve talked to other guests about source selection, and for me too, that plays a big role. There are certain things I’m looking for around creativity, change, technology, visual thinking, and note-taking. I subscribe to many newsletters, but then a fairly quickly cull them down. I’m looking for value, and I’m looking for insights that I can share or build upon. If I’m not seeing that, I unsubscribe.

As I said, I’m always in the habit of capturing ideas as they come to me. I just came across something this week that blew my mind. I’m focused a lot on content creation but I was always wondering if a course like the one I talked about earlier could have use for professional content creators, and content marketers working in corporations. Right now, the course that I referred to earlier is mainly focused on individual creators who are trying to write on Medium, Substack, or wherever.

I came across a subject, I’m trying to think of what it was called. The whole idea is that task-based work isn’t the only way to organize anymore, that there’s actually a content-based approach to gathering information and getting work projects done, which I found really fascinating because I never really thought about connecting the two. Apparently, task-based work has reached a point where there are some limitations to it, and the whole concept of teams, permanent teams working together for long periods of time, isn’t as flexible as it needs to be anymore. It’s opening up a whole new rabbit hole for me to go down to understand what people are7 saying about this and how can I connect it to what I’m trying to do.

Ross: Pulling back to this idea of Thriving on Overload, you have a wealth of insight and advice, but just want to distill, what are some of the things that you do, that you think that others might benefit from in bringing into their daily practices?

Chuck: I’m always looking for a better way, I guess that’s the first thing that comes to mind. As I said, I realized I had some limitations in my Evernote approach. It was serving me adequately. But again, I have limited time to work on things, and I need to figure out how to create better ideas.

Mind mapping has been around for over 20 years. I hate to say it, but I wouldn’t say it’s dying but its popularity as a business tool is starting to wane a bit. I’m at a point where I’ve reached a certain plateau with my audience in terms of views and newsletter subscribers, and I’m trying to figure out how to build it up to the next level with better ideas.

I’m trying to improve my information gathering, my writing, curation, all these things, to try and bring more value to my readers and hopefully, to a bigger audience of people.

Ross: I think that the most critical thing of all is that whatever you do, you can improve. I’ve spoken to a lot of people about what they do and some of them are amazing, including you, but I think that everyone can improve, I can improve, that’s the critical thing, is that whatever you’re doing, you need to be able to think about and try things to work out what it is you can do better.

Chuck: Again, we’re real habitual. There usually is some trigger event that convinces people to need to do something differently. Maybe they missed out on a promotion, or they got laid off from a job, or something just didn’t work out right for them, or something they tried failed, and it’s like, well, maybe I need to take a look at this from some different perspectives and different ways of doing things and maybe some different tools to help me do things more efficiently in a more focused way.

Ross: You have a wealth of resources that you share with the world. That will all be in the show notes. But where are the best places for people to find you and your work?

Chuck: Mind Mapping Software Blog is one. It’s mindmappingsoftwareblog.com. I also write on Medium. You can just look me up by name and find my writings there.

About a year ago, I started up a newsletter called CATALYST. Again, every other week, one idea, not fairly concise maybe about six or eight paragraphs, an idea to help creators and entrepreneurs think better, think more creatively and consider new perspectives.

In some cases, I’m just sharing my own observations. In a lot of cases, I come across ideas that just blow me away. Somebody’s got a new metaphor for looking at the world, and I share that in my own interpretation to that. You can find that on my LinkedIn. I also publish it to Medium. Those are the main places right now where you can find me.

Ross: Fantastic. Thank you so much for your time and your insights, Chuck. It’s been a great pleasure.

Chuck: Likewise, thanks for inviting me.