John Gruber: A Mix of the Technical, the Artful, the Thoughtful, and the Absurd

John Gruber has been writing the often quoted, ever popular Daring Fireball since 2002.

I had the privilege to interview John via email and ask him some questions that don’t seem to get asked. Of course we talked about DF, how the Linked List began and how he got into Macs. But we also talked about writing, what John eats for breakfast and more.

And yes, I also got a lesson in email bottom-posting etiquette.

The Interview

  • SHAWN BLANC: In 2004 you mentioned in your Something Daring article that developer interviews and software reviews were two of your favorite things to write. When I read your interview with Brent Simmons I think it may have been the longest email interview posted to a weblog I had ever read. Fortunately for the three of us it was good, worth reading and even a few years later I’ve found myself going back to it for reference.

    What are some elements that you think help to make a good interview? What are some dynamics that you hope to incorporate in the interviews you conduct?

  • JOHN GRUBER: You need to be really well-versed, as the interviewer, regarding the work of your interviewee. You must be prepared up-front with questions that you’d like to learn the answers to, but at the same time, I think you have to be ready to let the interview veer into unexpected territory. You want a plan, but you also want to be able to wing it as it goes.

    The mistake I see in most interviews conducted over email is that the interviewer simply emails the subject a single list of questions, all at once. Just a two step process: “Here are my questions,” then, “OK, here are my answers.” There’s no room in a simple process like that to ask follow-ups, or to delve into details or pursue interesting but unanticipated digressions.

  • SHAWN: Funny you say that, because it is the exact scenario for many of the first interviews I ever tried to conduct. I say “tried” because most people I asked were unwilling to participate.

    After reading your interview with Brent I realized that a published interview can and should cause the interviewee to shine. I see it somewhat as the interviewer’s job to draw out information that never would have appeared in a generic list of Q&A.

    I know the reason I attempted the two step process was because I assumed an email conversation would be too much of a time requirement for the interviewee — that the two step process would be more convenient. But based on my experience that is obviously not the case. Why do you suppose that?

  • JOHN: Well, in some ways it is more convenient. Just set aside time to write one email answering all the questions and you’re done. Maybe it doesn’t seem as worthwhile, though. Personally, I’m more interested in participating in an interview that seems interesting than one that seems easy.
  • SHAWN: With the insane amount of email you get why would you prefer to take the time needed to conduct a longer, drawn-out interview such as this rather than the quicker two step style? I’m know you must get hundreds of emails soliciting your attention; how do you handle it all?
  • JOHN: I just say no to most requests. Or, I’m sad to say, I never get around to answering some requests. If I answered all my email, I’d have no time to write Daring Fireball. I really believe that — some days I could spend 8-10 hours just answering emails that come in. Part of that, surely, is that I don’t have comments on the site, so when some reader has a remark they just have to get off their chest, email is their only recourse. That’s cool. But it means I treat email more like comments — I look at them all, but I respond to very few.
  • SHAWN: On your site you say over 50,000 people subscribe to the feed. My guess would be that most of them keep Daring Fireball at or near the top of their subscription list — because they like what you like, read what you read and want to know your opinion. Thousands of them have never met you but feel like they know you in some way. If they bumped into you one day they may give you a good hand-shake and tell you how much they love reading Daring Fireball.

    Some of these guys are developers, some are designers and some are just folks that like their Mac. Whoever they are they read your site and (hopefully) like you; this interview is for them.

    Now, correct me if I’m wrong – and please fill in any gaps – but here’s what your story looks like to me:

    In 2002 you were doing freelance consulting, web-development and tech writing. Meanwhile, after months of picking out the right “slate blueish background color” you finally launch Daring Fireball and begin writing articles for which your wife was the first reader. Two years later you start offering the membership and also end up working at Bare Bones. Then two years after that, in 2006, you quit your day job and now spend your time publish DF from home.

  • JOHN: Your chronology is a bit off. I worked for Bare Bones from 2000 to 2002. I started DF a few months after that. Joyent was the company I worked for while writing DF, from January 2005 through March 2006. When I left Joyent was when I started writing DF full-time.
  • SHAWN: After all that journey, is writing DF what you expected or hoped it would be? I’m curious if you still feel like the same guy who five years ago began a weblog because he really just loved to write?
  • JOHN: Do I feel like the same guy? Yes.

    Is the site what I thought it would be? No.

    I didn’t really have a detailed long-term plan for Daring Fireball. I still don’t. It started very simple, and I’ve changed and added things slowly over time. The plan was just to keep improving it steadily over time. That plan remains in effect today.

    When I make elaborate, detailed plans, I get too attached to the plans, too reluctant to break with them. Plans aren’t a product. I’m only effective when I’m working directly on a product.

    A great example is the Linked List. The Linked List didn’t appear on DF until June 2004, almost two years after the inception of the site. I hadn’t planned on adding the Linked List. My original idea was that DF would consist only of articles. Sometimes short articles, but articles nonetheless. And certainly no more than two or three in a day, tops, and usually just a few per week.

    What happened is that I was frustrated by the number of things I wanted to link to, things I wanted to bring to the attention of DF readers, but which I didn’t want to write a full article about. It was also the case that I wanted an easy way keep the site fresh even during stretches when paying work — remember that this was two years before I went full-time with DF — was consuming so much of my time that I didn’t have time to write articles.

    The other thing was that the Linked List was largely initiated as a bonus for paying members. Originally, the only way to get live updates to Linked List content was through the members-only RSS feeds — the items didn’t appear on the web until the next day. In hindsight, that certainly seems silly.

    Over time, the Linked List has grown from a peripheral gimmick into an essential component of the site.

  • SHAWN: What does your average day look like?
  • JOHN: My day looks very dull. That’s not to say it is dull — to me at least — but I strongly suspect it would look dull. Writing is a lonely endeavor.

    Typical day: I wake up when I wake up. Mid-morning, typically, but if I’m working on a major project or article, I sometimes wake up early because I’m anxious to finish. I get coffee. I go to my office in my home and pick up where I left off the night before. Some days that’s with an article I’m working on, some days that’s with things to read that I might want to post to the Linked List. I’m either writing or reading — or, occasionally, hacking on code for some new feature on the site — all day long.

    Ernest Hemingway said this:
    You write until you come to a place where you still have your juice and know what will happen next and you stop and try to live through until the next day when you hit it again.

    He was talking about writing books, but I find his advice perfectly apt for what I’m doing with Daring Fireball. Without having a boss or editor, I could do anything at the start of the day. Leaving off the day before with something specific in mind for what to do next is an enormous aid to getting going.

  • SHAWN: Additionally, my wife wants to know (a) what you eat for breakfast, and (b) if you like to hug your wife?
  • JOHN: I’m on an oatmeal kick this week, but usually just a banana. The big thing, though, is coffee, always coffee.
  • SHAWN: Coffee black?
  • JOHN: Of course. It’s not really coffee otherwise. And who doesn’t like to hug their wife? Is there an anti-hugging contingent out there I’m not aware of?
  • SHAWN: No. My wife just likes to know how other wives are treated by their work-from-the-home-office husbands.

    About the Linked List: Do you spend the majority of your day reading feeds? Do you skim articles or read every one? How do you decide what makes the cut? Do you have a running tab of sites you want to link to but haven’t yet?

  • JOHN: I get links from a variety of sources. For breaking news, things that have just happened or were just announced, the best source is email. If something big happens, I usually get a few emails about it soon thereafter. Other than that, I read voraciously. I almost never post something to the Linked List that I haven’t read entirely.

    I try not to spend too much time in NetNewsWire. I usually have it open, but I find I’m more productive if I make fewer (but longer) sweeps through it looking for new stuff. As for what I link to and what I don’t, it’s very much like Justice Stewart’s definition of obscenity: “I know it when I see it.” There’s a certain pace and rhythm to what I’m going for, a mix of the technical, the artful, the thoughtful, and the absurd. In the same way that I strive to achieve a certain voice in my prose, as a writer, I strive for a certain voice with regard to what I link to. No single item I post to the Linked List is all that important. It’s the mix, the gestalt of an entire day’s worth taken together, that matters to me.

  • SHAWN: How often do you get requests for a DF link?
  • JOHN: Surprisingly, to me at least, I don’t get that many requests for links. I do get many press releases, which I suppose are implicit requests, and a few times a day people will send me links to things they’ve posted on their own weblogs that they think I might be interested in. I very seldom find anything from a press release worth linking to. A lot of times, though, the stuff people email directly — “I wrote this, thought you might like it” — is perfect Linked List material.
  • SHAWN: Something else Hemingway said:
    All good books are alike in that they are truer than if they had really happened and after you are finished reading one you will feel that all that happened to you and afterwards it all belongs to you: the good and the bad, the ecstasy, the remorse and sorrow, the people and the places and how the weather was. If you can get so that you can give that to people, then you are a writer.

    My point being, at the end of the day it is clear that the bread and butter of Daring Fireball, as well as what you take the most pride in, is the articles. The “Fireballs”. You are a writer.

    You have managed to create a tech-based weblog and build a community of readers that not only looks to you for information and opinions, but listen (or read) to everything you have to say. They actually feel ownership of the elements, content and topics on Daring Fireball. You’re like the E.F. Hutton of the Mac community.

    Khoi Vinh said publishing Subtraction.com has actually hindered him as a writer. Did you consider yourself a writer before you began blogging? Do you have any personal history in writing, or did you find your voice through publishing DF?

  • JOHN: I’ve considered myself a writer ever since college, when I wrote for (and eventually became editor of) the student newspaper at Drexel University. I wrote a regular op-ed column for the paper, and by the time I graduated in 1996, I felt I’d gotten pretty good at it. But then what? A career in journalism? An entry-level job as a reporter working for some publication that I wouldn’t otherwise read? Not for me.

    So I waited and thought about it. Somewhere around 2001 or so, it occurred to me that I’d been thinking about what next to write for five years, which was as long again as the time I spent at the paper at Drexel. That was a bit depressing — but really only just a bit, because for some reason it felt to me that my writing skills hadn’t atrophied at all. On the contrary, I felt like I was a better writer than I was in college, even though I hadn’t been writing at all. That struck me as incongruous, because I was also convinced that the reason I was a much better writer when I left college than when I started was simply by writing and editing so much material for the paper. So while I felt like I was still becoming a better writer, I strongly suspected I was deluding myself.

    At the time, I was working for Bare Bones Software, and there was a question on the Mailsmith-Talk mailing list from a customer asking for help with a script that would count the number of words in all the messages in a mailbox. So I wrote a script that did that, and I ran it against my own outgoing message archives. The script was smart enough to count only words that weren’t in quoted passages, ignored signatures, etc. I forget the exact result, but the result was just preposterously high. Based on some common rules-of-thumb, I’d written several books worth of email messages over the previous five years — posts to mailing lists and a ton of personal correspondence, all of which I tried to write the hell out of.

    Around that same time, it became obvious that the outlet I’d been waiting for was available: I needed to start my own weblog.

    I’ve improved significantly as a writer in the last five years, but I feel as though I’m continuing to hone the exact same voice that I started aiming for 15 years ago in college.

  • SHAWN: Do you have any advice for writers who are struggling to find their voice?
  • JOHN: I honestly don’t know what works for others. The act of writing, like any art, defies description. Some of the best advice I’ve seen regarding how to write essays is from Paul Graham. He says writing is thinking, and, insightfully, that writing forces you to think better. He wrote, “Just as inviting people over forces you to clean up your apartment, writing something that other people will read forces you to think well.”

    My other suggestion (also, I think, stolen from Graham) is to concentrate on writing things with lasting value. I’m not sure I’ve been doing a good job of this at all lately — I think too much of what I write currently at DF is about stuff that’s only relevant right now. I’m certain that what helped me make a name for myself, what built the DF readership, were the long pieces I did in the first few years, most of which are still relevant, or at least still interesting.

    There are a lot of people writing for the web today; but there aren’t that many at all who are trying to do great writing for the web.

  • SHAWN: How has your approach to writing articles on DF changed over years? Have you gotten better at writing something and publishing it or are you more meticulous than you used to be?
  • JOHN: That’s hard to put into words. Early on, I had to think about my “voice”. I was conscious of my style. Now, not so much — I “just write”, and the style seems to come naturally. Part of that is that you get used to anything over time, but a bigger part is that the style changed slowly over time — I kept tweaking it until I found the perfect pitch, at which point it became something I didn’t have to think about to achieve.

    Put another way: early on, I had to concentrate both on what I was saying and how was I saying it. Now I just concentrate on what I’m saying.

    I also find it much easier to write now that I have a regular audience. The hardest thing for me starting out at the very beginning was trying to shake the feeling that I was writing something no one would read. It felt like delivering a speech in an empty auditorium.

  • SHAWN: Are there any other weblog articles which have stood out to you over the years as being an exceptional display of online writing?
  • JOHN: I object to the adjective “online” in that question. Why not simply weblog articles have stood out as exemplary displays of writing, period? The idea that weblogs are a bastard or lesser medium holds many writers back. I find, in fact, that the opposite is true. Most magazines I read are filled with bland, tepid prose. There’s only one New Yorker, and only a handful of other magazines in the same ballpark.

    My two favorite weblog writers are Paul Graham and Dean Allen. They’re the two who’ve written the most things that simultaneously delighted me (as a reader) and filled my heart with jealousy (as a writer).

    Paul Graham wrote:

    My experience of writing for magazines suggests an explanation. Editors. They control the topics you can write about, and they can generally rewrite whatever you produce. The result is to damp extremes. Editing yields 95th percentile writing — 95% of articles are improved by it, but 5% are dragged down.

  • SHAWN: What are a few of your personal favorite DF articles?
  • JOHN: My favorite articles tend to be the ones that seemingly come out of left field. The first “Anthropomorphized Brushed Metal User Interface Theme” piece, for example. Or the occasional personal piece, like “Vacation, All I Ever Wanted“, which I wrote a year ago. I was going for something very specific with that one, very hard to hit, and I nailed it.

    My favorite essays on standard DF topics are probably:

    It didn’t really stand out to me when I wrote it, but “Good Journalism” was recently included in a “Best of Technology Writing” compilation, and looking back on it, it strikes me as very effective criticism.

    I will add this:

    I’ve been thinking a lot that while the overall quality of DF has gone up since I started writing it full-time, that’s mostly because I’ve been writing more items, more regularly. I think the trade-off has been that there have been far fewer extraordinary articles. I.e., I’ve been writing a lot more good stuff than I used to, but less great stuff.

    I think I know how to fix that, though.

  • SHAWN: How so?
  • JOHN: Simply by being self-aware of it.

    Pre-Linked List, when DF only consisted of regular articles, there’d occasionally be stretches of a week, sometimes two weeks, where I wouldn’t find time to write anything. During those stretches, I’d feel overwhelmed with the desire to write something good to break the dry spell. Eventually it’d become all-consuming, and I’d just have to write something good.

    Even though I now post something to DF nearly every day, and articles a few times a week, I’m starting to get that feeling about posting substantive essays.

  • SHAWN: Ah, that’s fantastic. I’m glad you brought up the issue of substantive content. It is something which is constantly on my radar as a writer and a designer.

    William Faulkner said something along these lines that I love:

    It is [the poet's, the writer's] privilege to help man endure by lifting his heart, by reminding him of the courage and honor and hope and pride and compassion and pity and sacrifice which have been the glory of his past.

    I suppose my question to you is this: as someone who enjoys reading and writing tech news and reviews and opinion pieces — which by nature are usually only relevant for a short time — how do you define and create substance in your own writing? And more than that even; as a writer, John, what do you think makes substantial content?

  • JOHN: Something that’s only useful or interesting here and now can still be substantial. The only short definition I can think of is how much talent and time goes into something. The more talent and time, the more substantial.

    For me, much of the effort in writing, especially on technical topics, is in creating a narrative. By that I mean writing a piece that reads straight through, pulling the reader along. A perfect example of this is the way John Siracusa writes his epic-length reviews of major new Mac OS X releases for Ars Technica. What makes them so substantial, and so good, is that he crafts them into a narrative. Most reviews of something like Leopard read like bullet lists — a list of features and what the reviewer thinks about them.

    What graphic design is to a visual idea, writing is to a verbal idea. My goal is to craft my writing in such a way that makes it as easy and obvious as possible for the reader to “get” exactly what it is I’m hoping they get.

  • SHAWN: Speaking of reviews, this leads right to what I wanted to talk about next: reviews…

    It seems whenever I read a review you’ve written it basically states the obvious. But it’s the obvious things I didn’t think to check into and discover on my own. When writing a product review what are the things you look for to talk about in your article?

  • JOHN: That’s an interesting observation. I’ve never thought of it that way.

    Perhaps it’s more “examining the obvious in great detail” than “stating the obvious”. Trying to think about things that don’t get thought about very often.

  • SHAWN: “Examining the obvious in great detail”. Ah yes. That is exactly what it’s like. I didn’t mean to make you sound so dull by the way I described it. I think “Full Metal Jacket” is my favorite DF article. It made me want to keep using my PowerBook until it evaporates, or something.
  • JOHN: That “Full Metal Jacket” piece is one of my favorites — one that turned out exactly how I wanted it to, and the sort of piece I’d like to do more often.

    One of my favorite quotes of all time, probably my very favorite, is this one from Stanley Kubrick: “Sometimes the truth of a thing is not so much in the think of it, as in the feel of it.” A lot of times when I’m reviewing something, what I’m trying to do is capture the feel of it, rather than the think of it.

  • SHAWN: What was the first Mac you ever owned?
  • JOHN: A Mac LC with 4 MB of RAM and a 16 MHz 68020 CPU. My parents bought it for me for my freshman year at college. It had a 12-inch 512×384 display. I always regretted that I didn’t get an SE/30 instead. I was suckered by the color display.
  • SHAWN: What does your current Mac setup look like now?
  • JOHN: A 15-inch PowerBook G4, maxed out with 2 GB of RAM. When I’m at my desk, I use a 20-inch Cinema Display.
  • SHAWN: How did you end up publishing a “Mac Nerdery, etc.” weblog?
  • JOHN: I don’t have an explanation for it other than that I’ve been naturally drawn to computers ever since I was a kid, and when I first started using a Mac in high school, which I think was in 11th grade in 1989, I knew I wanted to own one. If you have an interest in user interface and experience design, I don’t see how you wouldn’t be drawn to the Mac.

    I knew coming out of college that I wanted to be a writer. And the type of writing I always felt most suited to was being a columnist. I’ve always enjoyed the way that with good columnists, it’s not just that their individual articles stand on their own, but that there’s something greater than the sum of the parts when you follow them as a regular reader.

    The problem with wanting to be columnist, in traditional print publishing, is that it’s a hard gig to get. Typically, at least at newspapers, columnists are promoted out of the ranks of reporters, and I had no desire whatsoever to be a straightforward reporter.

    In 2002, when I started Daring Fireball, doing a sort of columnist-style weblog simply felt like something I was compelled to do. I could write whatever I wanted, however I wanted. And, to be blunt, I was certain that I could do it very well.

  • SHAWN: Do you suppose you will write DF for years and years to come until you finally retire some day? Maybe sell the domain and pass the reigns to some other witty tech guru?
  • JOHN: I can’t see ever passing it on or selling it. But, I can’t see more than a few years ahead of me. Will I still be doing this in another five years? Almost certainly. But, say, 20 years from now? I don’t know.
  • SHAWN: Will you for sure continue in a career as an author? Maybe write a book, or movie?
  • JOHN: One way or another, I don’t see how I could be doing anything other than writing. It’s the only thing I’ve done in which I’m endlessly engaged.

    It would seem like a missed opportunity never to write a book. Most novels are just dreadful; I don’t know if I could do a good one, but I know I could do better than most. But it never seems like the right time to start. I just stumbled across an apt quote from Emerson last week: “We postpone our literary work until we have more ripeness and skill to write, and we one day discover that our literary talent was a youthful effervescence which we have now lost.”

More Interviews

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