Embracing the discomfort of self-reflection with Buster Benson

Welcome to the first edition of Mindful Makers, an interview series where we ask highly creative people how they manage to do great things while taking care of their mental health. The first guest is Buster Benson, writer, entrepreneur, thinker, and overall wonderful human being. It’s a bit of a special interview, because I’ve known Buster for a long time—but we only connected recently.

Buster is one of these people whose work you have probably interacted with several times without realising it was created by the one and same person.

In my case, the first time I benefited from Buster’s work was almost ten years ago, when I was participating in my third NaNoWriMo—which stands for National Novel Writing Month, a global challenge to finish the first draft of a novel during November.

While looking for an uncluttered writing tool, I stumbled upon 750 Words, a platform that merges the privacy of writing on a notebook with the convenience of online writing. Such a user experience sounds so obvious today, but bear in mind it was ten years ago!

750 words is about three pages. By writing three pages a day, you can definitely finish the first draft of a short novel in a month. This is probably why 750 Words quickly became popular with NaNoWriMo participants.

750 Words was initially free—I was one of the first 200,000 people to register before the paid accounts were created—and is now available for $5/month. There are now almost 500,000 writers who signed up to 750 Words.

Don’t miss it: Buster kindly offered 3 free months of 750 Words exclusively for the readers of the Maker Mind newsletter. Make sure to subscribe to receive the code in the next edition!

Years later, while I was looking into cognitive biases, I found this incredibly useful cheat sheet. I feel comfortable saying it’s useful, as it received more than 50,000 claps on Medium and more than one million views. Who put together this beauty? Who took the time to meticulously research this long list of cognitive biases? You guessed it—it was Buster again.

Between his career as a product manager with the likes of Amazon, Twitter, Slack, and Patreon, and his entrepreneurial ventures, Buster has had an eclectic journey so far. So eclectic that he has changed his legal name twice—born Erik Keith Benson, then Buster Butterfield McLeod, then back to Buster Keith Benson.

This interview will cover some of the other times I was lucky to randomly find a great piece of work only to realise later it was Buster who was back at it again, such as his book about productive disagreement. I will share more links after the interview, but for now, buckle up. We will discuss free-flow writing versus writing a book, resolving disagreements, embracing the discomfort of self-reflection, and much more.

“I identify as a poetic naturalist, a term coined by Sean Carroll, which basically means to see the world as it is not as we want it to be, but then to allow a healthy sprinkling of poetry and mythos over it all to make it fit into my brain and become meaningful.”

Buster Benson.
Buster Benson Interview on Writing - Icon
Hi Buster, thanks so much for agreeing to this interview! This feels kind of nostalgic as I started using 750 Words in my early twenties, before you created the paid accounts. I imagine it must be a big one, but can you tell us a bit more about the role writing plays in your life?

I didn’t know you were an early adopter of 750! That’s one of the most unexpectedly rewarding things that happens after building things on the internet decade after decade—we learn that obscure tiny projects that we thought nobody really noticed actually did get used, and even loved in some instances. It’s so great. 

Yes, writing has always played a big role in my life, but in a weird way it has always sat in the backseat relative to my other more practical life goals. I graduated in 1998 with a creative writing major, planning to dedicate my life to the next Great American Novel right as the internet boomed and Amazon popped up down the street. I put down my slow-moving disasters of novels (one was even titled Disaster) and I applied my creative writing instincts to engineering and product management at a time when the internet needed people who were at home in ambiguity and chaos. It was a perfect fit, and I realized I wasn’t the only person like this—Web 2.0 was created by liberal arts people, and then when the scaffolding was up the real engineers and business people moved in and refactored all our code and designs. Granted, what we built was not meant to scale. I digress!

I was an early blogger on Diaryland and Livejournal and even built a few of my own blogging tools, trying every new tool that came out (Blogger, Greymatter, Movable Type, Typekit, and so many more) because I bought into this underdog ideology that sharing our lives online was the future. I think I still believe that, but have a long list of caveats and warnings and hard lessons learned in the footnotes.

We all witnessed blogs and online publishing take off as they found a business model friend in online advertising. As that was happening, I also saw private journaling receding from the zeitgeist. And yet, private journaling has always been how I figure things out in my own head, so that the business-y and status-y milestones can be handled with integrity when reached.

750 Words was an experiment at the end of a long line of experiments that I had for trying to bring Morning Pages into the internet age. I’m sure you’re familiar with this, but for those who might not know, Morning Pages is a habit popularized by Julia Cameron and her fantastic book, “The Artist’s Way”, and encourages unfiltered daily writing as a way to clear your brain of cobwebs and stuck thoughts.

As a lifetime journal and notebook-doodler I have always felt that in order to do my best writing, absolutely nobody should be able to ever see it! Only then can I get the real words down, and once they’re down, only then can I fit the puzzle pieces together and figure out what I’m really trying to understand. 750 Words was built so that the words could be locked up somewhere other than my computer or my notebook, and with that reassurance I could do the kind of writing that I enjoyed most. I honestly can’t say where my life would be without private journaling… so many minor epiphanies and resolutions and new idea sparks have happened there, and could not really happen anywhere else.

I love what Dr. James Fox (creator of the Choose One Word program, which I highly recommend) says about journaling’s unexpected benefit of giving you a chance to get extremely bored of your own internal narrative. Only by hearing it out in excruciatingly verbose detail can we then say, “I get it. Can we move on now?” Without journaling, that task goes to other people in our lives, who will tell you to shut up long before you get bored of hearing what you’re trying to say. 

Writing, to me, is scaffolded thinking. It’s both how we communicate what we believe most important to say, and how we figure out what is most important for us to say. Does that answer the question?

It does! Journaling has so many benefits and writing in general is a superpower. “Scaffolded thinking” is a great way to put it. Now, can you tell us a bit more about your book, Why Are We Yelling?—Seth Godin said it was “a life-changing book” and Adam Grant described it as “funny and relatable.” Why did you write it in the first place, and what was the reception like?

Why Are We Yelling? is a 250-page book with 100+ illustrations and eight “things to try” when it comes to the art of productive disagreement. Each of the 8 things is an approachable entry point to a specific practical tip based on science and personal experience. For example, the first thing is to “watch how anxiety sparks” and talks about reframing anxiety as an opportunity to reflect on a value that feels threatened, and an opportunity to connect with someone around that value. It brings together mindfulness, cognitive behavioral psychology, and journaling and tries to make it simple and useful for everyday conversations. 

The other seven tips are: talking to internal voices, developing honest bias, speaking for yourself, asking questions that invite surprising answers, building arguments together, cultivating neutral spaces, and accepting reality and participating in it. One of the tips that has resonated a lot with people is to host potlucks that invite people to share their perspective on a particularly heated topic. I’ve done them for gun control, ghosts, and a few others, and have found them to be surprisingly insightful experiences each time. Playing to the cliche that most nonfiction self-help-y books can be summarized in a tweet, I tried my best to do so here:  

I wrote the book because it was the question I felt the most blocked by. I’ve always identified myself as a “civil” disagreer, pretty level-headed, pretty open-minded, etc. Rational, etc. But as the years went by, and as the 2016 political upheaval became more obviously central to our public lives, I realized that what I was doing wasn’t working. It wasn’t working to move conversations forward (it was just expertly avoiding them) and it wasn’t leading to stronger relationships, smarter thinking, or a less anxious life. I had a very slow-blooming epiphany after writing the Cognitive Bias Cheat Sheet, which is a 12+ minute read about a very dry subject that somehow sparked a million and a half reads, that our collective instincts for productive disagreement were off. We were doing the same thing over and over again and expecting different results, which is one definition for insanity, or at least an extremely unproductive form of self-medication. 

This book took three years to write because I didn’t have the answers. The first three drafts of the book were all about figuring out what I was missing, and what we were all missing, when it came to productive disagreement. When I finally arrived at the answer, I had to write the whole book yet again, and go through another five drafts on that manuscript. The whole point of the book was to become the person who could write it, and the person who would be able to read it. Even before it came out, my goal had been accomplished, though I’ve also had a lot of fun sharing it with others and hearing how others are doing on this journey. 

The reception has been great, much better than I was expecting, because I know how the attention economy works and also don’t have a whole lot of desire to put myself through that wringer. But Penguin Random House has made it possible to reach many more people than my own voice could reach alone, and they have been super amenable to strange requests like doing a podcast tour instead of a book tour, and not pretending to play the role of expert in a market that only listens to experts.

It’s great you got to work with a publisher who was open to a more original approach. Okay, so, in essence… Why are we yelling?

TLDR—we’re yelling because we only have a few tools in our toolbox for resolving disagreements: using the voice of power to shut conversations down, or using the voice of reason to appeal to a higher truth. When we have a disagreement with someone that doesn’t respond to attempts of force, and who doesn’t trust the same sources of truth, we move into avoidance and frustration and ultimately: yelling. Which is really just a return to the voice of power in its rawest form. But it’s not going to get us out of this pickle. To do that, we need to ask ourselves, and our opponents, what else is possible? What can we do to learn a new path out of this stuck spot? We all want to get out, and that alone is something we should be able to agree on and collaborate on together.

What are some of the differences between free-flow writing on 750 Words and the kind of writing effort you had to put in to write your book?

Ooh, good question. Free-flow writing is one of several different kinds of writing that need to happen to write a book. The first kind of writing, certainly, that one would use in terms of figuring out what you want to write about in the first place. And also the kind of writing that will come in very handy every time you find yourself in a dead end in the more structured, coherent project. And yet, it’s not the writing that will actually appear in the book… which is different in many ways.

The writing that appears in the book is writing that must emerge from a deep, nebulous, organizing principle. That type of writing is iterative, requiring many drafts. It’s minimalist, in the sense that every word and idea must fight for its existence on the page or be ruthlessly cut (or saved in a “I still love you even though I killed you” folder, as the case may be). It must not just be expressive of your own inner truth, but it must also land in the reader’s mind with a high level of predictability, across a diverse set of minds, and have a chance of becoming their truth. 

I found writing a nonfiction book extremely difficult for these reasons. It’s an entirely different beast than writing a blog post, or a product brief, or even a piece of fiction.

Getting past the 30,000 word barrier without wanting to scrap the whole thing and start over felt like the 4-minute mile barrier, or the atmosphere’s escape velocity for rockets. It required me to gather and then burn through all of my sources of motivation as I directed it towards this singular task for a period of many months. It sucked. But it was also formative and transformational in a way, and, I suppose, a much more accessible form of transformation for me than both the running and rocket barriers.

Combining both forms of writing is probably the best approach to complete a project. What piece of advice would you give to someone who wants to write more but is struggling to build a habit?

I’m with you and others who advocate for diving into the deep end. Basically clear some space in your life and plan to binge write for a good long while. Maybe forever. Discomfort is key to our growth when it comes to writing. Reframe discomfort as play-testing a new writerly persona, and go overboard with it. Don’t think of it as a habit you’re trying to start—we often think of habits as things we do automatically without thinking. Writing is the opposite of that: it’s the repeated re-entry into the discomfort of self-reflection, self-doubt, and self-transformation. It’ll never feel like a thing you can do without thinking, or automatically. But it might eventually feel like a home that you can return to and find yourself in, listen to yourself in, and slowly learn to accept yourself within in new ways as you change day-to-day, year-to-year, decade-to-decade. 

Also, even though writing is a pretty solitary pursuit, joining a community of other people on solitary pursuits can help get through the inevitable low motivation and low ability spots without giving up. Find others who are similarly stuck and support each other.

Thank you, Buster, really appreciate the candor. For readers who want to learn more about your beliefs, I want to share your Codex Vitae, which is such an amazing personal project of yours I recently discovered. I also want to give it a try. And of course, there’s your book.

If you’ve enjoyed this interview, please make sure to subscribe to the Maker Mind newsletter. The next edition will include 3 free months of 750 Words, courtesy of Buster!


Anne-Laure Le Cunff

I’m an ex-Googler, entrepreneur, and part-time neuroscience student at King’s College. If you found this article useful, subscribe to my weekly newsletter about mindful productivity.

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