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Episode 165 April 30, 2019 | 33min

Reflecting on Gmail 15 Years Later

Paul and Gina discuss the email service on its 15th anniversary.

Show Notes

Email sucks: On this week’s episode of Track Changes, Paul Ford and Gina Trapani reflect on how Gmail has revolutionized email over the past fifteen years. We recall the many iterations the platform has gone through—going all the way back to the days when it was invite only—and discuss the many flaws that still remain. Is there ever going to be a productive solution to deal with that ever growing pile of emails?

Paul Ford Well, here’s Google gettin’ the next page of search results. You ready? 

Gina Trapani Yeah. 

PF [Very slowly and in a low tone] “Oh. Kay. [Gina laughs] I’ll get ya those search results.” And I mean [Gina laughs]—I wanna die! [Music fades in, plays alone for 18 seconds, ramps down.] Hey, Gina? 

GT Hey, Paul. 

PF How you doin’? 

GT I’m doing great today. How are you doin’? 

PF Me too. I’m doing fantastic. What are we gonna talk about? 

GT I had this really weird thing happen to me the other day. 

PF Ok. 

GT That made me feel kinda old and kinda weird but I—so I was—I’m on my smartphone and [mm hmm] I launch the Gmail app [music fades out].  which is something I do, you know, on a—on a regular basis [mm hmm] and up in that search bar at the top there cuz, you know, Google—all Google products have like the search bar [mm hmm] at the top. There was like confetti and then the Google logo—

PF Mmm! 

GT—and it said, like, “Gmail is 15.” 

PF Ah! Happy birthday! Buddy. 

GT Happy birthday but weird. Old. 

PF I really didn’t wanna celebrate that one that much. I saw it too, I was like, “Oh, cool [disappointed], it’s Gmail’s birthday.” 

GT Do you remember when Gmail launched? 

PF It was really hot. 

GT It was April Fools’ Day—

PF Everybody’s was so excited. They wanted—

GT 2004! No one really believed it. They were like, “This is a joke.” Cuz back in 2004, especially, like, April Fools’ jokes were particularly bad.

[1:24]

PF Well and Google did April Fools’ jokes up—

GT Right! It’s the thing that they do, every year. 

PF But they launched Gmail. 

GT Do you remember what email client you were using at the time? 

PF [Low and holding the ‘r’s] Thunderbird. 

GT Were you like a Yahoo Mail person ever? 

PF I was like a—no [both snicker]. I mean I had an account but I—I was—

GT You were like—you were the IMAP—you had an IMAP and—

PF I liked having my Linux box. 

GT You still do! That’s what I love about you, Paul. 

PF You know what, honestly, I probably was using Outlook Express, on Windows, at that point. 

GT Outlook Express on Windows! 

PF Yeah. 

GT Yeah, I went through that phase. 

PF It was good. It had like—it had like a—

GT Yeah, yeah, it actually wasn’t bad. Express wasn’t bad. 

PF I was freelancing. I had a gateway PC. We’re going—

GT Yeah, there you go. 

PF [Does an impersonation of an older person, raspy] “Yes! That was me!”

GT The cow print. 

[2:03]

PF Ok. So, you know, Gmail [Gina laughs] comes out and suddenly all the cool kids have accounts but nobody else. 

GT Right! It was one of those like invite only—

PF Limited—you had to beg. 

GT—deals. Yeah. And it was so much storage

PF No, they did it like it was—it was like two gigs and then you did it—you could give up to four accounts away. 

GT That’s right! 

PF So it spread virally.

GT Yes! 

PF And, boy, was Google just the belle of the ball that—that month. 

GT It really, really was. 

PF Yeah. 

GT It was—it was the first—that—I feel like Gmail and Google Maps were like the two big Google launches [yeah] that made me go like, “Woah!” 

PF Well Gmail was like, “Hey, we’re actually gonna take . . . the whole world of email and we’re gonna put it right in the browser. So, you know, you mighta been thinkin’ about email clients. Don’t do that anymore. We’re gonna take care of it for you.” [Yeah!] And it was also a moment when spam was really, really bad. 

GT Spam was real bad. Although, I mean, Yahoo and Hotmail were both web based. 

PF Yeah, but nobody—

GT Gmail did conversations

PF Yeah, Gmail did everything real good. 

[2:52]

GT Threads! Like that was like—that was new stuff. 

PF And then Maps was the other one where they just went, like, “Yeah, you know how this is supposed to work and it doesn’t do that anymore. This is now—” 

GT It’s like, “Oh you think MapQuest works? Look at this!” 

PF Mm hmm. “This is an infinite space [Gina laughing] that you can explore and zoom in and out of in a web browser,” and everybody went, “Well, ok.” 

GT Right. “Ok! That’s way better than what we thought.” 

PF Yeah, “I guess we’re not gonna make accessible documents for people anymore [Gina laughs lightly], help them along. We’re gonna do interactive 3D experiences.” 

GT Did you ever find like printouts of MapQuest like—like under your car mats—

PF Yeah, cuz that’s what you used to do. 

GT—that’s what you’d do. You’d print them out, right? Anyway, Gmail’s 15. How you feelin’ about Gmail these days? 

PF  I use it. It’s alright [sounds sad, Gina laughs]. I use everything. It’s alright. 

GT It’s one of those things that gets so good but it really could be so much better, in so many ways. 

PF It’s—I mean there’s—What’s the worst quality of Gmail? 

GT I mean, honestly, email. 

PF Mm. Email is bad. 

GT Yeah, like in 2019. You know like I’m really good—See, I’m in a bad position, right? Because I published a book and it literally had a chapter that was called like “How to Empty Your Email Inbox” [yeah] and my personal email is an absolute mess. [Sure!] It’s like the biggest, deepest, most horrible shame hole [sure!] like in my life. Like I’m on top of my work email cuz that’s what you do at work but part of it is that I just don’t talk to my friends on email anymore [no]. I’ve got like my Twitter DM groups and I’ve got my like Hang Outs and I’ve got my chats across the things, you know? And email’s just super formal. 

[4:11]

PF Well, nobody—nobody writes—Email was like, “I have a lot of big ideas and I need to share them.” 

GT Yeah. 

PF Big ideas I have now to share are like, “Can I get those prescriptions filled?”

GT [Laughs] Yeah I actually have a couple of good emails between you and me, like very early in our friendship. You always—you always did good email. Obviously cuz [I loved to—] you’re a writer. 

PF No, it was wonderful to write emails. 

GT Yes. Yes! So like I can look back and every, you know, one out of every hundred emails is like a meaningful message between me and somebody who I cared about in my life [mm hmm] but very high noise ratio, not a whole lotta signal. 

PF I’ll tell you the worst quality of Google: search. 

GT [High pitched, in disbelief] Really?!? 

PF I just can’t make that search work for me. It’s slow and then it’s like, you know, you’re like, “Has attachment”. I can never figure out what the hell it’s supposed to—

GT It’s got so many advanced operators. [It does and then—[sighs]] That “has attachment” like operator that like makes me feel like a wiz—Like I love it cuz it’s got that command line feeling to it. 

PF Here—here’s some other things—here’s some other—ok. Ok. It’s got the comm—you like that [Gina laughs]. I don’t—I don’t like that. 

GT Well it depends on what you’re into, I guess. 

PF Well, I mean, I just want it to search and show me the search results without me having to—So now it’s like, “Hey, I found you four but there’s 4,000,000 others. You wanna keep clickin’?” And then you get to that next—[Gina laughing lightly] You’re like, “Alright, I need to see the next page of search results.” And it’s like—So that’s a bad—that’s a bad feature. And then, yeah, it’s—you can’t find anything—and you know the one thing—the thing that just breaks my heart is it is a hypertext document on the internet, on the web. 

GT Yeah.

[5:28]

PF And you can’t click on somebody’s email address and see all the emails they sent you. 

GT [Laughs] That’s true. 

PF I wanna do it. I wanna do it so bad. 

GT There’s—- there’s a lot there that isn’t done that should be done. 

PF Yeah! Like thing—cuz you know why? Cuz search doesn’t work. If searched worked you could be like, “Ah! Lemme see—” And you just click and it would be like from this person. You could have—I love the interaction between clicking and searching when like search bar populates with the things that you click on and that teaches you how to explore [yeah] the data set. 

GT Like the different ways that you can explore the data set? 

PF Mm hmm. 

GT I—I—I absolutely hear you on that. I mean, this is the thing, in defense of the search I really like that you can say, “subject, you know, colon is this ‘to’ or ‘from’, ‘has attachment’,” there’s a few others. There are like some date parameters, I could never figure out how to format those correctly though [mm hmm]. Yeah, I just don’t use them enough to—to remember. But agreed, if you clicked on someone’s avatar to show you the history of all of your interactions with them. And contacts. It doesn’t do a great job with contacts. It doesn’t dedupe well or like help you manage those better. 

PF The deduping’s gotten better. I recently did some serious deduping. [Gina laughs lightly] I was combining things and upon—upon my deduplication was surprisingly effective. It was also recommending more dedupes. It’s like, “Eh! You might wanna dedupe this.” 

GT Oh that’s good! That’s good to know. 

PF It’s not really necessary cuz I did the dedupe so it’s like you don’t—you don’t really have to do that but I’m like, “Now I got to.” Cuz you gotta—once they show you what’s dirty, you have to clean it. 

GT You have to clean it. 

PF Mm hmm. 

[6:44]

GT Google Photos does this a lot too. It’s like, “Hey, do you wanna clean out these screenshots?” [Oh yeah] “Or are these two people the same person?” 

PF No, they wanna tidy that up. 

GT Yeah, they really do. They really, really do. It’s true. 

PF [Sighs] Google Photos. That’s the best. 

GT Google Photos is a good product. 

PF A flawless web and mobile product. 

GT Like I stopped obsessing about all the hard drives I kept all my, you know, gigabytes of photos [no. No, no, no.] when Google Photos happened. I just gave up. I was like, “This is too easy.” 

PF Imagine if Gmail worked like Google Photos. First of all, you know what’s amazing about Google Photos? It’ll show your damn photos [both laugh]. Like you can actually get them. Literally. I can’t sear—I can find my—If I search for like ‘daughter’ in Google Photos, no problem. 

GT Yeah! There—there she is. 

PF “We figured it out from her facial structure. We [no, I know] did a bone scan and now we know who your daughter is,” and then you go into Gmail, arguably the most important mail client in the world and you go ‘daughter’ and it’s just like [Gina laughing], “Oh, Russ and Daughter [sic] has a deal on um—”

GT On lox! 

PF Yeah, on lox! Oh good, I love salmon! Um—

GT [Laughs] Google Photos gets to the point where like it will—it will identify that a person has a certain outfit on and haircolor and it will identify the person if they’re turned away [mm hmm] from the camera, like their face isn’t—isn’t in the photo. [Mm hmm] I found this out because my kid’s preschool uploaded a bunch of photos to Flickr and then, you know, Flickr was shutting down so I downloaded a bunch of them but I only wanted the photos of my kid. So then I uploaded them all to Google Photos which was actually a lot easier for gigabyte [God, is it]—like gigabytes of photos. And it went through and identified all the kids in her class and I was like, “Alright, just show me the ones of my kid,” and then it brought up photos of my kid like turned away from the camera and I was like, [low and slow] “Woah!” 

[8:21]

PF I know. Now, imagine—imagine for just a second, Google decides to apply machine learning to Gmail. 

GT [Interrupting] To—to Gmail. 

PF Yeah! [Gina laughs] Ok. They apply it to—to Photos. Ok. Hey, Photos, “Cool, I can show you your child backwards. Put your child upside down, in the—in the tub, just like one foot sticking out.” They’re like, “Oh! Cool.” 

GT Oh yeah. Cool. 

PF “How you doin’? Hey, honey.” But. Ok. [Gina laughing] In Gmail. Same thing. More resources. Bigger. Billions of users. Trillions of users. Like people in space are using this thing, and they have all the same machine learning and it’s text. Much easier. Much easier. Much faster. 

GT It’s true. It’s true. 

PF What do they do? “Good job!” [Gina laughing, music fades in] “Nice to hear from you!” [Music plays alone for five seconds, ramps down]. Hey, Gina? 

GT Hey, Paul. 

PF Ask me what Postlight does [music fades out]. 

GT What does Postlight do, Paul? 

PF Postlight builds amazing digital platforms. We build apps; we build APIs; we build these systems. We’re kind of a premium shop: we gotta be honest. You come to us if you need really good work done and usually [snickers] after you’ve had not really good work done and you go, “Alright—” 

GT And you go, “Ok.” 

PF “I get why.” There’s another thing people should know about: we have a thing called Relay. 

GT We do! 

[9:34]

PF You wanna tell the people about Relay? 

GT This is—Yeah, I do! This is a brand new thing. So, Postlight put together it’s very own flavor modification of a design sprint, and it’s called Relay, as in relay race cuz we build for the hand off. Relay’s a ten day design sprint where we work with you and then we kinda go headphones on and then we come back and work with you some more . . . to get your—your app idea into a build plan and a prototype. 

PF That’s right. So you get to work with our designers; you get—engineers come in and validate; and you get the best of us for about two weeks in order to get that deck ready and to get that prototype built. You’re interested in that, you should send us an email to [email protected] And if you’re interested in anything else [music fades in]. Now, let’s get back to the show. We’re talking about [low and ominous] Gmail [music plays alone for six seconds, ramps down]. 

GT What I really like, though, about Gmail is that [music fades out] because it’s web based it kinda had this like hackable interface [yeah]. So I have—I have this history with Gmail. So, back in . . . whatever, oh six or oh seven, I was running Lifehacker—

PF Sounds cool! 

GT Firefox was like—oh. C’mon—

PF Sorry. Alright, I’m gonna stop—

GT Come with me—come with me on this journey—

PF I’m gonna stop being a Gmail email responder [Gina laughs]. Cuz that’s—that’s what I wanna do for the rest of this podcast is just like—

GT “Sounds good!”

PF “Looks good!” 

GT Man, those like suggested responses sometimes I see them and I’m like, “I actually I would say that and now I hate myself.” 

PF Oh, yeah, no, some of them are really real but a lot of times it’s just sort of like, “Sounds good.” And you’re like, “I don’t need Viagra.” Like what—

[11:00]

GT No, Viagra doesn’t sound good. 

PF Ok. Go ahead. You have a long history with Gmail. 

GT So, I have a little bit of a history with Gmail. So back in oh six, oh seven, when Firefox was “the browser to get”, there was this browser extension called Grease Monkey where you could write like Javascript scripts and apply them to any page [mm hmm]. And people wrote a bunch of Javascript against the Gmail interface . . . to make it better in different like, if you say, “This file’s attached,” when you hit send it would up a little module that said like, “Hey, you didn’t attach it.” 

PF Right, cuz that’s the thing: Gmail’s a webpage. 

GT Right! Gmail’s a webpage. And it’s really cool. Yeah, yeah, so I wrote—I wrote a little program that basically took all these Javascript, you know, these little Grease Monkey scripts and compiled them into like a fully packaged extension for Firefox, I called it Better Gmail. And because I had this big platform on Lifehacker, I posted on Lifehacker. It was like, you know, on Lifehacker was the only place you could download it. And it got like—it had like hundreds of thousands of users. 

PF I remember this. It was just like one of those things on the internet for awhile. 

GT Yeah! Yeah. 

PF “Oh you know if you’re using Gmail a lot, you need—you should go get—” 

GT This’ll help you. And—and it did stuff like that Gmail actually built into the product eventually like, you know, children—you know you could do labels that were kind of like folders. [Yeah, yeah] And  you know snippets and that kind of thing. 

PF Oh that was a rough one. They started with those labels [yeah those labels]. “Yeah, we gotcha—” 

GT Oh no, those are just tags. 

PF Yeah, you don’t need folders. 

GT No—no children. 

PF You put that slash in there and—

GT No subfolders. 

[12:14]

PF Alright, it’s folders. It’s ok. 

GT Exactly. 

PF Gmail is basically 15 years of giving up. 

GT It really is. If you look at the interface, I used Inbox for a long time—

PF Google Inbox? 

GT Yeah! 

PF Ok. Yeah. 

GT And then I switched back to regular Gmail and I was like, “Oh they really compromi—Like they really said yes to everything.” 

PF Oh yeah. 

GT Everything just got like, “Ok fine.” 

PF Were you an Inbox fan? 

GT I liked Inbox. 

PF Ok. Inbox was—Inbox was good for everything except composing an email message to send to anyone. I mean they would like move the box around, I could never—sometimes it would just like not work, and I couldn’t write an email. I found that disappointing in a mail client. 

GT I mean that’s—that’s fair [mm hmm]. I should say that some of my love was purely was a nerdy love of material design [yeah] cuz I was really into Android at the time and like Inbox was the first really like web based material app, you know? 

PF Mm hmm. 

GT And it was just very calming blue—

PF I mean I was using Opera 10 on SUSE Linux. Maybe I should’ve—No, I was using [Gina laughs] Chrome, damnit. [Both laughing] No, ok, alright, so it was your—it was blue. 

[13:06]

GT It was blue. It was nice. It did some like new—although it’s been a—It only shut down a little while ago [yeah]. It did some grouping of messages like the primary inbox and—

PF [Interrupting] Well, this always the goal, right? “We’re gonna organize your stuff.” 

GT “We’re gonna tell what’s important.” 

PF “Cuz email sucks.”

GT “Cuz email sucks and there’s a huge pile of it, we’re gonna tell you what you really should—should look at.” I like that part of it. And then I just went back to regular Gmail. The red. 

PF Yeah, it’s pretty grim. 

GT It’s pretty bad. 

PF Especially now that it has that little animation where the—where the letter opens. And you’re like, “Wow, this is taking 40 minutes to load a webpage that is a list of frickin’ messages. [Gina laughing] But at least I don’t have to do a search today! Cuz I didn’t put that on my calendar.” Which is also frickin’ from Google. Anyway [Gina ramps up laughter] um so you—you were a little sad to see Inbox go? 

GT A little bit but I sort of accepted my fate with like a 43-year-old’s just sort of, you know, resignation [chuckles] cuz I was just like, “Ok. Like I get it. Like I build products.” 

PF No, I know, it died. 

GT It didn’t work. 

PF See, for me, it was like when someone famous that you didn’t like dies and everyone’s on Twitter really sad. 

GT Yeah, and you’re just like, “Meh.” 

PF Eh [exhales intensely]. 

GT Circle of life. 

PF Yeah that’s a tough one, I can see why people are upset. 

GT Yes. Yeah. 

[14:11]

PF But in the background I’m just like, “Fffff, ok. Ok. Life happens.” 

GT Ok. Ok. It’s true. 

PF But [whistles a high pitch]. Anyway, so Google Inbox—I hope the Google Inbox team is listening. You know? [Both laugh]

GT Really sorry that didn’t work out. 

PF Oh can I tell you once something I did? I did change the web for the best ones. I wrote a tweet and it was something like . . . it was just along the lines of like I hope that people who are working on the Twitter mobile web experience can find other reasons to keep living. You know cuz I was just—it [laughing] it was one of those lines—

GT Oh man! That’s rough! 

PF It was rough. It turns out they—they printed those out and made stickers and put them on their laptops. 

GT Wow!!

PF And then they made a much better mobile web experience. 

GT As a motivation! 

PF That’s right. 

GT So you’re the kinda personal trainer that like gets up in somebody’s like face and like really plays on their insecurities. 

PF Oh I’m just like a personal trainer—

GT Versus like the nur—the nurturing “you can do this” like boost your self confidence. You’re like, “Cut em down. And they’ll rise to the occasion.” 

PF No, I’m the worst. I’m a passive aggressive tweeter. I’m a disaster [Gina laughs]. Like, seriously, this is—this is the worst part of my life cuz it was just like I thought I was nurturing. Right? 

[15:16]

GT [Laughs] But it turns out—

PF I didn’t really wanna be like Mr. Tough, Draw the Line. 

GT Right, right. 

PF But now I’m just a passive aggressive—

GT Passive aggressive, somewhere in the middle. 

PF—dick on Twitter [Gina laughs]. Anyway, so the Inbox crowd like clearly me beating up the dead product that Google killed is gonna really lift their spirits. 

GT You never liked it because the performance wasn’t good. 

PF I just couldn’t send email with it. The email box would always slip around them and it like it would just kind of stop and—

GT Thunderbird was kinda better? Faster? 

PF No. 

GT Slicker? 

PF Everything—all email’s bad. That’s the problem, right? No, you know, it was also, too, like you couldn’t indent text or something. It was like—

GT Oh! I re—yes!! Quote replies! Yes! 

PF You couldn’t quote reply. 

GT Where you had to fly the window out like into a separate compose [yeah] and then you could expand. 

PF Oh that was a world of—

GT So this was—this was tough for old school emailers. Like for—me too! 

PF I’m just like, “Really? Is this is now my part time job? To deal with Google Inbox?” Really? Cuz you can bucket. You can tell me my mom is one person and that Toyota is another. 

[16:08]

GT Right, I just wanna be able to respond to this part of the email. 

PF Oh God, I just wanna get outta here. 

GT And then top post your top poster. It made a whole world of top posters. 

PF Yeah, top post—do people know what top posting is? We should—

GT We should—

PF When you hit reply—

GT Yup. 

PF And you just start typing. 

GT Yeah. 

PF That’s top posting. 

GT Top posting. 

PF Why is it top posting? 

GT Because when the email gets sent your reply is at the very top of the stack of messages. 

PF That’s right, so you get underneath that there’s all those quotes from other people [exactly] for, you know, and—and if you—

GT The responsible emailer—

PF Is—engages in a conversation [Gina laughs] and they hit reply and they look at the email and they leave the context. 

GT And they edit out—this is a lot of work and, honestly, I don’t do this as much as I used to anymore. 

PF [In deep, ominous tone] Nobody does it. 

GT There was—there was a time—I had a minute where I was pretty religious about this. 

PF Mm hmm! 

[16:54]

GT Because the—you know, if you—if you interact on open source mailing lists—

PF Oh yeah. 

GT—you are religious about this. 

PF Do not top post. 

GT You do not top post. 

PF There was one particular web accessibility advocate who has been in and out of my world and um [mm hmm] I won’t invoke him but he did definitely like [Gina laughs] don’t top—He’d write me and I’d be like, “I didn’t hear from you.” And he’d be like, “Don’t ever top post.” 

GT So wait, would he do that to the whole list? Or did he just reply directly to you? 

PF No, it was a personal email. 

GT Oh right, well at least it was personal. 

PF Oh it was—

GT At least it was a one to one call out versus [God!] in front of the whole list! 

PF It’s the industry that loves to correct you. 

GT [Nasally] “Look at this noob!” 

PF [Nasally] “Actually!” 

GT [Nasally] “Actually!” 

PF It’s everything’s “actually”. 

GT “Well, actually.” 

PF Rename it. 

[17:30]

GT So I started getting emails from various people in my professional and personal life that had this little footer that said something about this product called Super Human and I was like [mm!] what—what is—finally I said, “What is this?” And I clicked through and Super Human is a—an email client for Gmail. It lives on top of Gmail. What it actually is is a Chrome extension that lives inside the browser on top of Gmail but there’s also a server component. 

PF So Gmail’s in there. 

GT Yeah it—it—

PF I didn’t know this. 

GT It only works with Gmail right now. 

PF But that’s cool. It’s a cult. 

GT No, it’s totally a cult! So it’s a cult, right? Because you have to actually do an onboarding—First of all, there’s like a cue, a wait list, you have to know somebody—

PF Yeah, you have to talk to the guru. 

GT And then you get like a—there’s like the onboarding consultant. 

PF And he’s like, “C’mon wash my feet, and I’m gonna give you access to amazing email.” 

GT Yeah, and it’s 30 bucks a month. Which is three times the cost of—

PF 360 dollars a year. 

GT Yeah that’s like quite a bit for an email—more than Netflix. 

PF I’m tryin’ to think of what I spend 360 dollar—that’s like three Brother printers. I mean it’s just like you could print out all of your email for that cost. 

GT But ok. Here—here we go: it’s the cult. It’s so good. 

PF What’s it called? 

GT Super Human. 

PF This is always the question I ask about, any product, what superpower does it give? 

GT I relate to it because it’s very similar to Better Gmail. The superpower that it gives is all the things that Gmail sucks at, it does really well. So you open an email from someone and in the sidebar you see their Twitter; their LinkedIn; the last few things they tweeted; their avatar; all the conversations that you had with them. 

PF Mm hmm. 

[18:55]

GT When they say, “Hey, can you meet up on Tuesday?” Your calendar comes up. Everything is keyboard driven so you can clear your Inbox without ever taking your hands off the keyboard. 

PF Ok. 

GT You can do stuff like say like—I commute. I’m—we’re here, in Manhattan, New York City, I commute every day and I like to go through my email on my phone. I can say, “Remind me about this email at my desk top.” So I can sort of clear it away and then when I get to my desktop, that email sort of reappears for me, so I can get—I actually can get down to Inbox zero like just on my commute, alone. I can say, “Remind me about this email in a day.” It’s just got a ton of like super power user kind of features. 

GT How’s the UX? Cuz that just sounds like a circus. 

GT See, this is the thing, and you have to be into this. If you’re into this sort of thing, because it’s keyboard shortcut driven, it’s got this like Quicksilver or Alfred-esque like [oh!] you invoke this command line via like command, ‘k’ and then you type like, “I wanna reply all,” or, “I wanna compose.” 

PF But why don’t you just do what I do which is download all your email via Gmail ear [?] in Python and then you use the Emacs mail mode in mail search in order to access it through MU? That way I can look at 20,000 messages and organize them using my text editor. 

GT I mean that would be a lot cheaper. 

PF Mm hmm! 

GT But also it takes some extra time [laughs]. 

PF I mean I understand—I understand what you’re saying. I’m—I’m just. Wow. Ok. 

GT Seriously though, are you—what do you use one of these days? Like what’s your—what’s your email client? Like? 

[20:16]

PF My state of communications is despair! [Gina laughs] I have Base Camp. I have—

GT No, but for email. For email. 

PF No, that’s the thing it’s all one thing. [It’s just everything] I can’t figure what I’m supposed to do or where I’m supposed to be at any given time [Gina laughs]. I have no idea. 

GT What’s the first thing you reach for when you’re like, “I’ve just arrived at work and I have to see what important communications have come my way!” Like what do you look at? 

PF What I reach for is um I mean, obviously, Gmail to start. 

GT Yeah, just the web interface to Gmail, not like Thunderbird or like Mail dot app. People use Mail dot app [I know]. Which I call Mail dot app. Is that even a thing? 

PF Yeah, I think so. 

GT That is it. 

PF Cuz otherwise you just say Mail and it’s too confusing. 

GT I use my email. 

PF I have a real problem which is that the particular job I have right now, the things I’m doing, the number of messaging interfaces in my life is out of control. And even for people—even like the tools where they’re like, “We’ll get all your messages under control,” it’s not—nothin’. 

GT Well, every—every platform wants to get all your messages like all your—like Slack wants you to pipe everything into it and Basecamp wants you to send emails to it and then—you know. 

PF Everybody’s the center and—and there’s two things that work for me. One is Emacs org mode. If I actually have time. But it’s really. I’m so scattered. I got Basecamp CRM, email, Twitter DM because like Signal comes into me in a lot of different ways. So I could triage it and turn it into opportunity for Postlight, right? [Right] And I can’t really control where it comes in a lot of the time. 

[21:32]

GT Right, and this is like external. Well, and Slack. 

PF Yeah, and so—well and then there’s Slack. And there’s about 20 channels that I’m involved in [right] and I get sort of assigned tasks in Slack as well—

GT Right, like, “Hey Paul, can you look at this? I need you to sign off—” 

PF And then you read it and then it’s gone forever. I’m getting better at like, “Remind me about this.” 

GT Remind me about this. Yeah. I do that a lot. 

PF But even there you’re like kind of smashing your thumb on the—on the bus. What is working, I mean, frankly, what’s working is information triage sessions of an hour [yeah] where I come in on the bus, I got an iPad now and I just triage through the five systems. Until I’ve got everything to do. I can’t use my text editor on the iPad so I use Google Tasks. Which is just a—what I’m realizing is when things get really, really out of control, hierarchy actually bec—like hierarchical outlining and structure? 

GT Yeah. 

PF Become your enemy. Because you aren’t really in a place where you are—you’re not working on something hierarchical. You’re just really responding to a feed. 

GT Yeah. 

PF And [sucks teeth] my—the system I have now is, you know, tasks on the right cuz I know where Gmail is. 

GT Right. Tasks are built into Gmail now. 

PF They’re in it. Yup. 

GT They’re in that right sidebar. That right sidebar has actually gotten kind of—

PF There’s a lot goin’ on there. 

GT It’s a whole thing goin’ on there. It’s like the county fair. You’ve got like the big turkey leg; and the like the fried cotton candy—[crosstalking] Yeah, you’re just like, “Oh, oh, ok. Right? Is this the line to get on? Like the—” 

PF “Why is Peter Frampton playing in the—[Gina laughs] the right side—like it’s cool, I just didn’t know he was still a thing.” 

[22:53]

GT [Laughing] No, it’s true. It’s true. It’s a whole thing.

PF Funnel cake. 

GT Funnel cake, exactly. Deep fried Snickers. And you’re just like, “Why are all these icons here? Oh I can integrate all the things, that’s cool. Just get out of my way.” 

PF The thing with Google though is it’s always like, “Yeah, we’re gonna give you like Calendar mini over here.” And you’re like [yeah], “Yeah but I wanna add a room.” And they’re like, “Well, you know, you can open that up over here. That is ok.” Literally they’re like, “You gotta leave the room. You gotta get up. Walk over. Go over there.” And then if you’re not smart, if you pop it up in a tab, I basically—what happens cuz I’ve got my personal email and I’ve got my um and if you don’t pop it up on a tab, I’ve got my personal email and I’ve got my  work email and it’s like by the end of the day I have opened my work email and my calendar and my personal email in like 30 separate tabs in one browser over and over [Gina laughs] and over again. 

GT That’s when you know you’ve had a day. 

PF Yeah! No, cuz I keep opening—cuz you get into Gmail and you’ll be like, “Oh wait, I need to open up Calendar,” and then you’re in Calendar, and you’re like, “I gotta write ‘em about that event,” and it just—everything starts going to the right, just like—

GT Yeah and the tabs smaller and smaller and then—

PF Oh it’s bad. 

GT—you can’t really see the favicons. Do you not do Chrome profiles? Do you not do like—like my—So I have [I do] you know my personal thing is signed in here; my work thing; and then I switch between windows. 

PF Gina, objectively, you are a better person than I am [Gina laughs]. 

GT No, I’m really not. 

PF No, no, like objectively like literally by any scientific, cultural, physical, mental, or an emotional measure, you are a better person than me. 

GT I’m not. 

[24:16]

PF There’s a reason that you were the first Lifehacker. 

GT That I was literally the—I am the worst at this. 

PF Yeah. 

GT We did a show a long time ago about how I used to do text for—for years [mm hmm] and I stopped. I stopped like a year ago. I started using, this is a real cult, I started using  just forgive me for saying this phrase—I’m gonna say it. I started using a bullet journal. It’s real good. 

PF They are really good. Right? 

GT And when I say a bullet journal, I mean a notebook but there’s just a system of writing down tasks and events, and it’s actually very good. It was designed by this product designer here in New York, Ryder Carroll, and he’s got um attention deficit disorder and one of the techniques for focusing is like writing a daily planner, a daily organizer and so like his—the thing that he did for himself and he wound up releasing as a system is the bullet journal and it’s been tremendous for me. Like I sit down with my notebook and I write down my tasks and I cross them out—you and I have this similar thing where I know you like the like pen on paper. 

PF Oh yeah. 

GT Which is why I see you around the office now with your iPad and you’re so happy with your pen. 

PF It’s a pen simulator. 

GT Yeah, it’s a pen simulator. Exactly. 

PF It also records audio which I find really useful. 

GT Yeah. It’s really great. 

PF It turns out that I haven’t been paying attention to anything that anyone has said. Like I’m listening to audio now that I’ve been recording and I’m like, “Oh my God! [Gina laughing] People are saying all of these meaningful things! In the room and in the conversation.” 

GT It’s so tough when you’re like in it. 

PF No, no, no, I’m literally picking up about ten percent. I’m worried that I’m dead. Like I’m worried that I’m actually [Gina laughing] a dead person and this is a Sixth Sense scenario and [no, no, you just] my iPad is alive. You just realize that like neither side was actually listening to each other at all. 

GT Right, right. 

[25:45]

PF It was just this sort of like weird transaction. Even if you thought you were focusing. 

GT Right, you’re like, “I have this.” 

PF You’re like, “When the hell did they tell me about their trip to Nepal?!?” Like I had no idea! [Gina laughs] I had no—wow! 

GT It’s true. It’s true. So you listen back to your meetings? 

PF I’m using text to speech more. I’m ready for way more automated transcripts. I’m look—I continually shop for like the automated transcript service [!!!] of my dreams. I just wanna drop audio in a box and get stuff back. 

GT I see you in the conference room here like kind of talking loud into your phone. You’re using that voice to text a bunch. 

PF Well what happened is Google um created a small version of their English language machine learning data set [mm hmm] that now runs local on an Android device [ok]. So you don’t have to go to the cloud. So it used to be like, “Hey Google,” and then it’d be like, [sings] “Doo doo doo doo doo doo doo hey Google.” 

GT Right the little dancing dots. You’d like wait. Right. 

PF And it would show up. Yeah. 

GT Right. 

PF And now you talk to it and it shows up. 

GT It’s instantaneous. Really?! And it’s good? 

PF [Deep, sensually] Oh yeah it’s real good. It’s crazy good. 

GT And there aren’t like Amazon workers listening to snippets for quality control reasons [nope]. It’s all local. 

PF It’s just a—it’s the robot on your—and you realize how—it’s like what I’m complaining about with search. Local execution of any software is just so ridiculously slow, the network is—

[27:02]

GT Yeah, it’s true. It’s slow. 

PF There’s this amazing—I—I—I don’t have it at hand but there’s this amazing thing where it’s like if you took a nanosecond and turned it into a second, like how long would things take. And it was just sort of like a hard drive’s seek would be minutes [yeah] and memory access is like a minute [yeah]. You know just sort of things like connecting and getting something back over a network is just weeks. 

GT Yeah. This is why clients have Javascript. Like to—having the application live in the browser is just—is just better. 

PF It’s just why it took over, yeah because it turns out that [it’s just so fast] the network just wasn’t that fast.

GT Mm hmm. Mm hmm. 

PF And so we’re still—we’re still working through that actually as an industry, I think people—

GT Absolutely. 

PF People really have this fantasy that we’re done in any way but it’s like, no, the network is actually unbelievably slow compared to everything else. 

GT Yup. 

PF Alright. So you’re happy with your new email. 

GT I’m dig—I’m diggin’ my new email. I’m likin’ it a lot. 

PF How long do you last with a—with a solution like that? 

GT I really try to commit myself to [mm hmm] like a solution. Like I don’t expect the solution to fix me unless I use it, right? So I try to stick with things for at least . . . you know, a few months. Now, I mean, Super Human, I’m paying for on a monthly ba—Or I should say Postlight is paying for. Thank you—

PF Oh good! 

[28:08]

GT Thank you, Postlight. 

PF Good job. 

GT [Laughing] Because I use it to parse [laughs] parse work email. 

PF You’re achieving, that’s fine. 

GT But like that was—that was very much like this has to clear a very high bar for me [right] like to—to pay for this thing. And, of course, I’m sort of delighted by it because I’m like, “Oh this is like way, way, way better Better Gmail [Mm hmm] um going on,” and as long as I’m sort of dealing with like a just large volume of email that’s like directly connected to the growth of our company, like it’s absolutely worth it. 

PF No, it’s sensible. What makes the bullet journal work? 

GT It’s become like a meditative like ritual for me. It’s like less about like it being a superior task management tool and more about me having like a minute in the morning where I sit down—it sounds so inefficient, it’s very inefficient. I copy like my calendar for the day like onto a single page and then I put down my tasks and then I star the ones that definitely have to happen which is only like two or three absolutely, drop dead, must happen before I leave the office, and it [says “calms” slowly] calms me. Like that’s what’s like—and just the pen on the paper and there’s no like blinking lights or Slack or things ha—you know jump—and then I carry my notebook around and it just makes me feel good. And then there’s this like incredible satisfaction of like finishing the notebook. [Mm hmm] I finished—this is my fourth one. I don’t know what about that is—

PF See, this is, in theory, as a leader in this company, I’ve got two major sources of the day. One is Google Calendar [mm hmm] and the other is the set of tasks I need to accomplish [mm hmm]. The problem is as the leader you actually shouldn’t have the second. 

GT The set of tasks? 

PF I should simply be meeting with people and delegating [mm hm]. Like that’s not realistic at this stage [mm hmm]. The mismatch between those is really hard [yeah] because then I’m like—cuz I really can’t—in order to keep the—the company and relationships moving forward, I cannot avoid meetings. Like I need [yeah] to just like—I need to be talking with people; listening to them; and figuring out how to move stuff forward [yes]. Those take priority and then I have like six hours of working time and then—

GT Mm hmm. 

[29:56]

PF It’s tricky. It’s just like [it is tricky]—I can’t find the one system and I’m not looking very hard anymore. So [exhales hard through nose]. 

GT You know there’s—there’s no one true, good, best solution. That’s just true. 

PF No, I mean the best is just not having to work [Gina laughs]. Everyone—I mean everybody always leaves that option out, right? Like the best—

GT The best is like I can walk out of the office and think I haven’t—like I haven’t totally blocked someone today or like screwed something up [no, that’s right] like I enabled things—the right things to happen. Here. Today. And that’s the best thing that you can say to yourself, is anybody walking out of an office, “I did my best to like enable forward motion.” 

PF That’s right. 

GT “In this place.” 

PF Unless I’m the last person leaving the office and then I’m like, “What the hell is—” 

GT “I somehow got caught up in the fact where I [laughs] what I get done—” 

PF I always panic that I’ve left the water on, too. I’m always like, “Oh no, what’s happened?” I gotta—I’ll go all the way down and then I’ll be like, “Nope, gotta go back up again.” Cuz it’s the whole office! [Gina laughing] I can’t—what if I left the window open a penguin could fly in? Anyway. Alright. Alright. What did we solve? 

GT Gmail’s 15. 

PF Gmail is 15. 

GT Email kinda sucks. 

PF Email is—

GT Still kinda sucks. 

PF Email and you and I are about the same age. And  I’ll tell ya, I don’t know how you feel but I think I kind of feel like email [both laugh]. Like I don’t know how either one of us is gonna go out on—like it’s gonna outlive me. That’s what’s weird. 

GT Yeah. It will. 

[31:15]

PF There’s gonna be email like a hundred years from now. 

GT It will. All those Twitter DMs and WhatsApp messages and Facebook chats, they’re all gonna go away but email [music fades in] will be—there will be an IMAP server somewhere. 

PF We won’t be able to serve subpoenas otherwise. 

GT It’s true. 

PF It’s true. Like you always—also like people forget like The Vatican needs email. Like there is like—

GT Yeah. No, it’s real business happens over email. For sure. 

PF Yeah, that’s right. 

GT You should join our newsletter, by the way. 

PF Oh that’s right. 

GT It’s really good! 

PF People should get in touch. 

GT We send an email [laughing] once a week. 

PF Yeah. Go to postlight.com and just bathe in it. Just, just get in there. And see what happens.

GT Check that box. Give us your email address. We’ll be very, very respectful. 

PF It’s true, you scroll down, and you’ll see boxes that you can fill stuff in and get in touch with Postlight. You should do that. 

GT Absolutely. 

PF Absolutely do that. You should also send an email to [email protected] 

GT Bring us your digital challenges. 

PF It’s true and, you know what?—

GT We love to talk about it. 

PF Let’s think about some other things that people should do: they should come to an event on May 21st, mark your calendar—calendars in the evening. We’re gonna tell you. 

GT Yes, we are. We’re gonna announce that. 

PF We’ll tell you a little more. If you subscribe to the newsletter, you’re gonna know about the event. 

GT You’ll be the first to know. 

PF So, yeah, just get ready. Come to our space. And, you know what we don’t ask people to do anymore but they should is give us a good rating on iTunes, it means a lot. 

GT It does. It does. 

PF It really does. It tells the robots that we’re good. 

GT It’s important that the robots know we’re good. 

PF They do. Only you can tell them. 

GT I seek the robots’ approval. 

PF The robots need to know about love, and it’s on you to educate them. So [email protected] and Gina? 

GT Thanks, Paul. This was a lot of fun. 

PF Yeah. 

GT It’s been awhile. 

PF It has been awhile. 

GT Thanks for having me. 

PF I—I’m not gonna use that new email thing because then I won’t—I will get disappointed. 

GT I just wanna show you how fast the search is [Paul whispering under breath], it’s really good because it’s a Chrome extension, [laughs] it caches all the messages locally so that—

PF [Interrupting, listlessly] [email protected]

GT—that thing you’re talking about, the voice thing, it’s like the same thing in email but it’s awesome, Paul. 

PF [Over Gina] Thank you, everybody. Give us a good rating on iTunes. 

GT [Laughs] Bye. 

PF [Deep] Bye [music ramps up, plays alone for five seconds, fades out to end].