Steve Portigal is an independent user research consultant. He is the author of Interviewing Users and Doorbells, Danger, and Dead Batteries. Steve and I both have new books, so we thought it’d be fun to compare notes on writing non-fiction. In this, the second of two episodes on the subject, we focus on the process of writing. If you haven’t done so already, listen to our previous conversation, which focused on our motivations. But now, here’s Steve Portigal on the process of writing.

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Jorge: Steve, welcome back to the show.

Steve: Yes, it feels like no time has passed at all. It’s great to see you again.

Jorge: It does. And I have to say, I always feel that way when talking with you. So, the last time that we talked, we focused primarily on our motivations and general approaches to tackling nonfiction writing. We talked a lot about second editions and standing the test of time.

The Mechanics of Writing and Organizing Ideas

Jorge: But what I was hoping we would do in this conversation is talk a bit more about the mechanics of writing processes and tools, and not just for sitting down and putting words to paper, but also for making sense of the ideas. When we finished our last conversation, we were talking about this kind of miasma of ideas that we have at the beginning of a book project; you have all these things circling around in your mind. How do you go about putting those down in a format where you can start playing with possible organization schemes?

Steve: As always, I’m not going to give you a direct answer, but I will try to reflect on that. I think the hardest and also most interesting thing about writing a book is figuring out how to write that book. Or maybe it is figuring out how you write that book at that time in your life.

So, I’ve done three of these projects, and they have been… like, how I’ve approached it has been completely different. I think it’s because the material is a first edition of a book, as we talked about last time; that’s ten years of teaching. I had a book from scratch that was built up by aggregating dozens of stories from other researchers. Then, revisiting a book from ten years ago that already exists that has a structure, but with new ideas and stuff floating around.

Each of those are very different. I think information organization, storytelling activities, and it takes a while to crack the nut. Like, how am I gonna go about this one?

The Challenges and Joys of Writing a Book

Steve: Extremely painful for the first two books. Extremely joyful for this book. I don’t know why this was much easier. I think I don’t like figuring out the structures of things. It makes my brain break. And I know not everyone… like, I can’t necessarily do it.

I did have the chance to review… I won’t name-check anybody, but a UX researcher that people know had written a book or was writing a book. They asked me, as part of the process, to review the outline, and the whole book was in the outline. It was a table of contents where everything was properly named, and then there were three deep-nested headings. So, there was an incredible amount of structure but no text, but the title showed you the whole book. I imagine, in my mind, they just wrote that outline and noodled on until they got it. So that, if that’s true, that’s like an amazing brain to me to be able to use an outliner to come up with that book.

I think most of us have to muddle around and write stuff out to see what it wants to be. And this is true in fiction as well as nonfiction. You have to write to figure out what your ideas are, how to structure them, and how to sequence them. And that isn’t always fun. I think maybe some people will take to that differently than others.

So, for me, writing this second edition, the book was there so I could revise the structure as opposed to coming up with the structure. Maybe the biggest change I made was the original edition flowed in a weird way, and having done all of these workshops that are linear; they take place in time. You put together an agenda so the day flows. And you teach things that kind of build.

The Role of Structure in Writing

Steve: And I’ve changed that, and changed that, and I could finally go back to the sequence of chapters in the book, and I changed the container label and changed the flow of the container without even thinking about, “Oh, I want to say completely different things about planning.” Even just to work at that structural level. And so, this is all before we even get new information. And it’s just to figure out how to go about it.

And it shouldn’t be surprising, given what I’ve said before, that I had stuff in a lot of different places to do this, but eventually, I created an outline. I did it in Google Docs because it was done originally to share with not only the publisher but also the editor. And so, to get a sign-off on what I thought it was going to be. So, I started expanding it, and then I had a miscellaneous section. So here’s an outline.

I think I copied the table of contents from the original book and then kept marking it up, changing things, and moving it. I did try to work at that outline level. But then, as I was going through material that I had in other places or seeing something in the world or thinking about something on a dog walk or something, I had this huge, almost like a punch list, section at the end at the bottom of just stuff. Every once in a while, I would go through and tag those as to where I thought they would go, as the top part of the document was the sort of evolving structure with headings and subheadings and an outline of the book.

And then this sort of stuff that needed a home, and then eventually, I would move it into the right part of the table of contents. At the same time, the editor that I had been working with had the Word documents from the original edition, and they were going through and re-editing them and making some stylistic changes because the voice — the publishing voice — had changed. Marking dated references. So, they were doing a pre-edit of the existing content and then sending that to me. So, at that point, I could start going into Word, which was the tool that I used, and moving stuff around or adding comments to myself that were directives. And it sounds messy because I was working on the book and also the outline of the book.

And then, I think as I got further along, there was even like another metalayer, which was more actually like a punch list, like instructions to myself. I even had a table — I probably did this in three different forms because I kept starting and stopping it — which was new content to get that I wanted to reach out to people about. There’s a lot of stuff that I’m not an expert in that I think is important. So, just trying to make a list of other people’s expertise that I might ask them to write. I might ask them for a quote; I might link to them. Like, the actual implementation of bringing someone’s voice is varied, right? I asked you to write about note-taking, which is a great topic in user research and a great topic of yours. And I think you and I went back and forth, “Is there something you’ve already written that we want to just link to,” or is there… I quoted people in one sentence; I quoted people who had been on my podcast.

So, I was pulling in other people’s voices in a lot of different ways. That’s why I started off as a table of who and what. Who could talk? What’s the thing I want someone to talk about, and who would be the person to talk about it? And then, eventually, that gets refined, and once you get into that chapter, you’re like, “Oh, this doesn’t need…” Right? We call them sidebars, like a little short essay. It doesn’t need a sidebar. It can just be this short piece. It doesn’t… we don’t want to load it up with this other stuff. So, figuring out how to implement that.

There are all these things that are messy and have some structure that you keep revisiting and going through and making a decision or taking an action. And then, you can check them off or close them from an open decision to a decided thing.

Using Different Tools

Jorge: Were you tracking that punch list and table in Word as well, or did you use something else?

Steve: It started off in a Google Doc, and it stayed in a Google Doc. There was almost something comforting about having the… Because the book was in separate chapters, so you end up with all these documents. And then, as you go through the revision process, you create new versions of them that get sent off, so it becomes a complex document management thing. To have a Google Doc, it’s in the browser, not in Word. It works a little bit differently; just having this meta piece sitting in a different tool, I think, was comforting for me. It helped me. You’re in writing and editing mode, or you’re in planning, deciding, or project management mode. And I think to have both of those open at once and be able to go back and forth; it’s an artificial distinction, but it gave me some structure.

Jorge: I’ve tried, I will say unsuccessfully, to merge those two worlds by using Scrivener. I don’t know if you’ve had experience with Scrivener, but Scrivener is billed as a tool to get at some of these issues, right? Particularly the “Not being so attached up front to one particular structure” because it lets you reorganize the outline fairly easily and bring the text with it so that you know the structure and the text are somehow managed in the same tool. And you can also do things like annotate and keep reference materials and stuff like that.

I used Scrivener for the work on the fourth edition of the Polar Bear book. And funny enough, I used it again in part of the work I did for Duly Noted. And in both cases, I found myself eventually gravitating to other tools to manage. The structuring and thinking through what was pending and where things should fit were part of the process, and to your point, it’s a different mindset. I found going back and forth between the tools helpful in helping me think differently about what I was working on.

Steve: Are you are you a wall-of-sticky-notes-book-writing person?

Jorge: I’m a wall-of-virtual-sticky-notes, so I use Tinderbox. And I was actually going to reference that I had Mark Bernstein, the designer of Tinderbox, as a guest on the podcast. One of the things he said, which I think is relevant to our conversation, is that he thinks of Tinderbox as a — I’m trying to recall back — but it was something like he thinks of Tinderbox as a tool for writers. And by writers, he means thinkers because you think through writing. The process of writing is a thinking process. This process of thinking about the structure of the work is an important part of the writing process. I think that for a book, it’s the critical part of the writing process, right? Or at least one of the critical parts of the writing process.

And the great thing about a tool like tinderTinderboxat is that it lets you… visual. I’m a very visual person. So being able to see all these ideas spread out in little boxes that I can move around. And in the case of both Living in Information and Duly Noted, I ended up with a matrix. And the matrix had… you think of a matrix as having two dimensions, right? So, the x-axis, the horizontal dimension, was the chapters. I had the flow, chapter one, chapter two, and chapter three, and those were columns. And then, the y-axis, I had this notion that I wanted in both of those books; I wanted all of the chapters to have a similar length.

So I’ve read some books where, like, you’re reading chapter one, and it has, I don’t know, fifty pages. And then you get to chapter two, and it’s fifteen pages or twelve pages or something. Then, you get to chapter three, which is thirty pages. When I read those books, I always find myself struggling a little bit because I’d like to know the cadence that I’m going to be getting them the information at. So, for me, it was very important that all the chapters have a similar length.

I was also very concerned about the chapters in both of those books having a similar rhythm. So, there’s this notion of cadence, but there’s also a notion of a certain rhythm. For example, I wanted them all to open with — now I’m talking about Duly Noted — I wanted them to open with some kind of story or an image, a memorable story or a memorable image that exemplified what that chapter was about. I wanted to have certain beats in all chapters where I was teaching the reader something useful, like a tip, technique, or idea that would be applicable to their work. I wanted some parts in the chapter where I’m summarizing what the chapter was about, as you might imagine, that comes at the end.

And all of those would get listed. I had rows in this matrix for each of those types of beats. Then, if you have this two by two, not two by two, but this two-dimensional matrix, you can start populating the ideas in the book. Imagine you have the stickies; you can start moving them around and say, “Oh, this is a good story for opening chapter three.” Or, “This is a good way to close chapter eight,” or whatever, right? It also becomes a punch list because then you start thinking, “I don’t have a good exercise for the user to do in chapter five. I need to think about that one.”

So, that’s how I’ve gone about it. And for me, it’s been primarily Tinderbox. Although, because I actually wrote about this in Duly Noted, I wanted to experiment with other tools. So, I also used Apple’s Freeform app. For part of that book project, I used Tinderboxr for the first draft, and then I used Freeform for the second draft. And that was just to force myself. I’m very comfortable with Tinderbox, but I wanted to force myself to use a different tool just to have the experience of doing it and seeing if these ideas are valid with a different tool. And it worked. It worked fine.

I’ll add one more thing to that: something that resonated with me with what you were talking about earlier was that you found the experience of working on the third book much more. I don’t know if you use the word pleasurable, but you certainly said that the first two were more painful, right? That resonated with me strongly in that I think I was lucky and very unusually lucky in that my first writing project was a new edition of an existing book in that that project started with a text: an existing text that you can point to and you can have these conversations, and you can imagine this process I’m describing, you can start with the matrix pre-populated because you have an existing text.

And I think it’s much easier to start with something that exists than to start with a blank canvas, right? One of the insights for me, particularly in Duly NotedDuly Noted is the most pleasurable experience I’ve had in writing a book. I’ve enjoyed all three. Frankly, a lot of people talk about writing as painful. For me, it’s actually the opposite. I really enjoy writing books. But Duly Noted was especially useful or pleasurable for me. In part, it was because I wrote the book twice. I wrote the first draft of the book, and that’s the draft where I figured out what the structure was going to be and how it was actually going to flow.

So, when I took a pause between writing the first draft and the second draft and when I started the second draft, I was not working from scratch, but I was also willing to jettison a lot of the first draft, which I did. And I now started with a much better understanding. It’s almost like I was working on a second edition, and that made it so that I’m much more confident in the structure of the final product because it’s gone through this revision process where I’ve thought through how it might be communicated and then I reread it, and I thought, “No, that’s not quite right. Let’s now do it right.”

That’s something that I would encourage anyone who asks me what I would recommend for writing a nonfiction book I would recommend: have in your mind the idea that you’re going to be writing the book twice if not more than that. And I think it goes much better.

Steve: Yeah. And that comes up a lot in fiction writing as well. And I think many people say this, but I read it in Annie Lamott, who talks about shitty first drafts, and that’s the phrase that gets used and that you don’t know what you have until you write it. And I think it goes back to your matrix because the question that was coming up for me with the matrix… I think someone could hear this and think first, write the matrix, and second, populate the matrix. But I don’t know how it is for you. To me, some of that structure comes from writing a chapter and seeing, I don’t know, what it wants to be. And it doesn’t mean that you stick with that, but at least you prototype by writing, and then you can…

I think we’re talking about going back and forth with the meta and the specifics. So, you write a chapter, and then you can extract that structure and put it into the matrix and then try to write another one and see, “Oh yeah, that structure breaks, and we’re talking about this other thing. So, let me add another anecdote to close it out. And oh, let me go back to the first chapter.”

Like, now the structure of the matrix kind of changes. So that sort of top-down, bottom-up exploration, I think. There’s stuff that you have to figure out by writing. And I say you, but I don’t mean everyone. Like I said, that person sent me an outline that kind of had everything. Maybe they wrote to get that outline, or maybe they just worked at that level. But I think that I hadn’t thought about writing and then treating it like a second draft. I think putting that pause in there is really good for you. You walk away from it, and you come back to it with a second project.

Jorge: This actually relates to the work of design, like my work in design and information architecture. I think that one of the most valuable skills in doing this kind of work is being able to zoom up and down between different levels of abstraction. You used the word “prototype,” and that felt to me spot on in that when you’re working at the outline level, you are thinking about it in a very abstract plane. And it’s not until you actually start writing text to flesh out those sections, subsections, or whatever that you actually figure out what the main idea is, right? And once you’ve figured out the main idea, the place where you thought it fit might not be where it fits anymore.

The same thing happens to me when working in an information architecture for something like a website. Oftentimes, after doing the research, I start at a very abstract level, working on conceptual models and content models and stuff like that. And then, when I start sketching out the implications of the hierarchy that is implied by those models on the user interface, I realize that some of the things that I thought made sense in the model come across that way when you actually see them on screen and that causes me to go back and revise the model.

So I think that you’re right: it’s a back-and-forth between these levels of abstraction. And it’s important, at least for me. I’m sure that there are people who work differently. Jack Kerouac, didn’t he write just stream of consciousness, just dumping it all out?

Steve: That he was a chronic alcoholic, so maybe that’s something there. You’re right; I think what I’m hearing is that there are some sort of larger principles here, like zooming in and zooming out. But we all have tools that we use in the work that we do, and those are probably the kinds of tools that work with our brain because I think you and I have a lot in common, but I think we have very different ways of organizing the world that we live in or not organizing it. And your matrix thing makes sense to me, but it also sounds painful, and I would never want you to see the messiness that I struggle with because I think you would be fascinated but horrified, I think. I don’t know; I’m presupposing judgment.

But our approaches reflect us. And so, it’s cool to hear how an information architect zooms in and out, and how an information architect writing a book zooms in and out, and how a visual person zooms in and out. And those are things that I’m not, and I totally buy into the sort of model that you’re describing, even if the implementation of it is different.

Reflections on Writing

Steve: I think there are some best practices here, some guiding principles that you and I are unpacking that look different to everybody, but not that we’re giving advice here, but if I was to put on advice voice, find your way of doing, hear how we’re talking about doing the same thing differently, and find what that looks like for you. And don’t forget the power of zooming in and out or moving between modes or between moving between tools. And the specifics; the specifics are up to you.

Jorge: I’ll highlight another principle that’s coming up as you’re saying that. And I definitely think that being able to shift your attention between the different levels of abstraction is one. And I have to put in a sidebar here: One of the very first interviews I had on this podcast was Gretchen Anderson. And she had just come off. Writing a book, she talked about how she basically took over — she commandeered — her living room and her dining room and stuff and covered it in sticky notes. And we talked about this idea, which is to say, the tools don’t matter as much as the mindset that you are going to be doing this; you’re going to be thinking at different levels of abstraction.

But the other thing is, and you said it explicitly, but I want to name it, that different people have different ways of going about it. And it’s important for you to discover which one works for you. When I read your book, it comes across as very conversational to me. And it might be because you and I are friends, and I can hear your voice in my head when I’m reading it, but it’s also written in such a way that flows very naturally. And I think that might not come across, or it might not be as successful if you went through the process, like the one that I did of saying, I’m going to have this beat at the beginning of each chapter and this beat at the middle of the chapter. And it might be like a forcing function that might make it sound unnatural to you. I think that everyone has different voices. Part one of the principles here is to find the processes, tools, and methods that let your voice come out. Don’t let anyone tell you that there’s one size that fits all.

Steve: And I would add to that these change over time. I’ve written three books, and as I’ve said, they’re all totally different… at some remove, they’re totally different processes, and at some level, they’re the same. We talked before about pain and pleasure. I think the painful part was figuring out what process was going to work for me at that time for this book. Once I figure that out, then it’s really exciting because I now know how to work on this.

And I’m three in. Were I ever to do a fourth, I’m extremely intimidated about how I would do a fourth book if I was going to start from scratch again. How would I do that? So, I’m actually getting some inspiration from this. Like, I could see your matrix thing or my version of it, right? This wouldn’t look like your version because I think you can use format and structure to… like, you need some scaffolding.

Even the idea of a book was extremely intimidating to me, as I was starting to work with an editor and an outline and then having them send you to go off and work on a chapter. A chapter is still an incredibly intimidating construct, but to take a break from working on the book, which is overwhelmingly uncertain, to work on a chapter and feel your way bottom up or dictate top-down what those beats are going to be, what that structure for that chapter is a way to get there. I don’t know; I’m intimidated by trying to figure out how to do it again.

But now I think, oh, maybe, maybe a matrix would help me. Even if I don’t use it the way you would use it, I don’t build it out. If I don’t want to adhere to it the same way as you, I think it’s good guidance because that’s there. And I’m sure we could go and map out my book with my conversational tone, and you could see, we could create, we could map it in retrospect and see what that matrix is, even if I didn’t use it. I think that it’s just where you end up.

Jorge: Keeping with the theme of what’s next, would you ever do another one? It’s very hard for me to think about starting a new book right at the end of writing one, right? But like I said, I really enjoy the process, and I do have more stuff that I would like to share in book form. So, I suspect that I will, at some point, tackle another book project. For me, one of the hardest things about it is that I first make sense of that first information dump so that I am not starting with a blank canvas.

And the one thing that has changed over the last year, and we talked about this a little bit in our last conversation, the big thing that has changed for me in the last year is the popularization of LLMs. And I don’t believe in having the AI write for you, but I believe in the AI as a very useful partner in the writing process, and particularly in these early stages where you’re trying to make sense of this morass.

What’s the first approach to organizing this thing? How might these ideas be laid out in a logical sequence? These are all things that you could bounce off someone else and get some feedback. And in the absence of doing it with another person, LLMs can take you pretty far, I think. I don’t know because I haven’t tried it for a book project, but I would be very excited to try something like that, seeing how an LLM can help me — not so much in the writing process, at least crafting the actual sentences and paragraphs, but in the, “How am I going to tell this story? What is a good way to structure this so that it comes across to people?” The tools available now are super exciting. So that’s something that I would look forward to so that I don’t have to stare at a blank canvas.

Steve: I like that you’re thinking ahead to content but also process. Because we are talking about process and how it thwarts us and enables us, but that’s cool, I think, maybe if we can unblock anybody who’s listening to think like there are a bunch of different approaches, and that even a seasoned author, third in the can, fourth on the horizon, maybe you’re still thinking about process and experimenting it.

And again, I just want to keep hammering home, like this changes. It changes, the technology changes, and it changes as we mature. I suspect that if you were to go back and if you could be the person who looked at the Polar Bear book version four, you would probably do it differently now because you’ve matured in doing this. You’ve written two additional books, and so you have some sense of what works and what some best practices are for you. I think they’re personal, and they evolve over time. So you’re at this interesting stage where you’re considering what other sort of structural support is there, and you also like to experiment with different tools, right?

I think you and I are opposites in that way. You’re experimenting with, within the book. You’re changing your tactics within the book to see what works. And so I think that that curiosity and willingness to experiment and fail, I don’t know… for me, I admire that. I don’t feel like I’m that person. And again, if you’re listening, hopefully, the contrast between how you and I approach this stuff is illustrative that people could find their own path through this.


Jorge: I think it comes back to this notion of making it your own, finding your own path, and finding the path that brings you joy. Because ultimately, writing a book entails sitting your butt down regularly and getting the work done, putting actual words on the screen. And if you find the process painful, if you find the tools painful, if you struggle with the ideas, it’s going to be much harder to build the momentum necessary to carry it through to completion. Yeah, make it your own; find joy. And it sounds like you’ve done it, Steve. Congratulations on the second edition of Interviewing Users. And I’ve done it to a degree as well. Where can folks follow up with you, find out more about you, and buy the book?

Steve: So to find me, two places: my website is You can find out about my work and any speaking that I’m doing, and I tend to… like, I’ll post this podcast on there. You can see some of that stuff. And LinkedIn is a good place to connect with me. People are welcome to connect and talk about what we’re all working on. I’m fairly active on there these days.

And the book is available, the best place to — let’s support small businesses and support authors as well — from the publisher, Rosenfeld Media. They have a page for the book, and there is a discount code for twenty percent off the second edition of Interviewing Users. And the discount code comes from the name of this podcast; the discount code is INFORMED, one word.

Jorge: Fantastic. Thank you so much for that. Again, I encouraged everyone in the previous episode to get the book, so I’m not going to repeat myself. But get the book, even if you don’t think of yourself as a researcher. Thank you, Steve, for sharing with us.

Steve: Great to chat with you, and good to learn from you in this conversation. I really enjoyed that opportunity.

Jorge: Same here.