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and you just struggle to get your personality onto the page?
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Definitely something I felt.
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And when I struggle with that, Brie is one of the people who I like to call up.
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And if you've never heard of her, it's because she's been behind the scenes at companies like Figma and Stripe.
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I mean, she basically founded Stripe Press.
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When I think about her, I don't just think about personality, I think about care, I think about craftsmanship, I think about quality, and that's what this episode is all about.
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How do you produce great things while also putting your personality into your work, putting you onto the page?
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So if that is something that interests you, you're really going to enjoy this conversation with Brie Wolfson.
0:38
Let's dive into your years at Stripe.
0:38
You did Stripe Press, you did a lot of internal writing.
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What stands out in terms of what you've learned about writing from your time at Stripe? Two things.
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One is just what a force for clarity writing is. Most not clear.
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Writing is about not clear thinking.
0:55
And if you sort of flip that on it's head, that means that you can get clear in your thinking by getting clear in your writing.
1:06
So I mean, I think this is what you're referring to.
1:06
I'm like taking notes like, "What are my own thoughts?"
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I want to get them clear.
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A lot of my writing is about, I'm just trying to clarify my own thinking on this topic.
1:13
So that at org scale, very powerful, because you're getting a lot of clear thinking on stuff.
1:18
And then the second piece is if we take the Twitter analogy, it's like tapping a tuning fork and seeing what resonates.
1:23
That also on the org level is very powerful, because then you have an artifact of ideas, and now you don't need to translate them or transfer them through a meeting or a one-on-one conversation, they're actually just available to anyone at the company, which is amazing for us for cohesion and resonance and org-wide understanding.
1:40
Not so much for core teams.
1:40
I think core teams do that naturally or functional groups that stick together.
1:46
It's more about the people who are far away on the other side of the org.
1:50
All of a sudden they get unfettered access to your ideas and your thinking in your corner, and that's a really good cohesive force.
1:59
There's like an open email policy, right? Open email policy.
1:59
Actually, I should say, I don't know if this has changed now, but the roots of it, yes.
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Every email is sort CC'd into a group that anyone can read.
2:08
And how much internal writing were you doing?
2:12
What was the nature of it?
2:12
Yeah, I'd say there's two kinds of writing.
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One kind is just general stuff you're doing to advance in your day-to-day work.
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The more interesting stuff is what I like to call a curation layer on top of the work.
2:21
So it's just sort of like a quarterly business review or my thoughts on this or a friction log about this one flow, and then publishing that into the org.
2:32
That's the stuff that's interesting because it's curated for an audience of someone else.
2:35
And I would say Stripe spends a lot of time on that kind of stuff, just reporting on what are we doing? What are we thinking? How are we feeling? What's next?
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So a lot of the thinking work came out through the writing.
2:49
And is that individual, collaborative? All, both, neither.
2:49
Lots of different flavors.
2:54
I think Stripes writing culture is very related to its reading culture, strong stomachs for reading, which means strong stomachs for writing.
3:04
What are the downsides of a writing culture like that?
3:06
It's kind of the difference between doing a research survey when you ask people, "What would you do in this scenario?"
3:11
Versus just observe them in the scenario.
3:11
So I think you can kind of pull yourself out of the work and look down upon it and judge it and talk about it.
3:20
And sometimes actually just doing it is where your answers are.
3:20
So I think you can get a weird relationship between thinking and doing.
3:27
And I would say Stripes was teetering on maybe too much thinking sometimes despite, I think, externally appearing like we ship very fast.
3:31
I think internally it felt like there was a lot of contemplation behind the scenes, which maybe is an okay balance, and I think that thing probably shifts over time.
3:41
But I think you can sort of get over-rotated on thinking or pontificating or predicting.
3:45
You can argue about ideas when actually...
3:50
I think Facebook's got a value that's like code settles arguments or something where you can maybe just settle the argument or the principle's friction through just doing the thing and seeing.
4:01
So yeah, I think there's this relationship between doing and thinking.
4:06
What's principle's friction?
4:06
You can imagine you have two different ideas and you need to resolve the principle in order to get the work off the ground.
4:11
So I'm trying to think of a good example of this.
4:15
Maybe speed and quality or something is the classic trade-off where, should we move faster or should we rev this to higher quality?
4:20
And you can sort of debate which of those values you want to uphold.
4:26
Maybe it's better just to get going and see where you land. Yeah, exactly.
4:31
And tell me about the origins of Stripe Press. How did that happen?
4:35
The origin of Stripe Press, this is actually kind of a funny story I think where John, Stripe's president, had received a manuscript on his desk as a reader, and this was for what became the first Stripe Press book, Elad's High Growth Handbook.
4:46
John loved it so much, he was like, "Every single one of our users should have this.
4:49
We want to empower any entrepreneur to do a great job on Stripe.
4:54
We think this will help them do that.
4:54
Let's send this to every customer."
4:59
So I was charged with the task to turn that into a book that we could get to every customer.
4:59
So that meant sourcing paper and finding the book printer and coming up with a design language and selling physical products for the first time, which Stripe had never done before.
5:08
So it's like all this infrastructure just to get one book sent.
5:11
And I was like, "Wow, I think by doing this one book, we've sort of built enough infrastructure, we're like 80% of the way there for the next book.
5:19
Should we just try a few others?"
5:19
So I think this is my great idea.
5:19
And then it turns out, so Tyler Cohen was one of our first four authors.
5:25
It turns out he and Patrick had been talking about this Stripe Press idea for a long time.
5:29
So classic good leadership, they incept me with an idea so I think it's mine, but really they had the strategy in mind all along.
5:34
But yeah, it turned out we did an experiment with four books and it turned out to be unbelievably effective in ways we couldn't have even imagined.
5:45
One in particular that stands out to me is just in terms of our talent brand, how many people at Stripe said that they joined or got excited to join because of the books.
5:55
And I think what's great about that is that is true to Stripe's culture.
5:59
Stripe, like I said, is a reading culture, it's very cerebral, we're very ideas focused.
6:05
So it was like, great, if you're attracted to this company because we publish books, you're probably a good fit for the culture.
6:08
The other thing that stands out is when you open the books, they open flat.
6:13
So both of the sides- Yeah, I'm so glad you noticed. Thanks, David. Lay flat binding. Yeah. Okay. Okay. So tell me about this.
6:20
I don't know the words, but you sound very passionate about this.
6:23
Well, it's funny, we were just talking before we got recording about reality has a surprising amount of detail, or the things that annoy you.
6:28
And yet this was a thing that annoyed us like, why when I flop something down it will just bounce back?
6:32
So it turns out there's a special kind of binding called lay flat binding where instead of gluing all the paper to the spine, you can actually, you use some threads that has some give.
6:44
So if you lay it flat and you look at it, well actually there's a little rainbow of threads you'll see, and that's like some give in the binding.
6:53
Versus if you just glue it to the spine, it will get stuck there, so it'll pull anything back on the edges.
6:58
Reality has a surprising amount of detail. Yeah.
7:03
So we spent some time getting that piece right.
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And of course it's more expensive to do it this way.
7:07
Well, it's beautiful, right?
7:07
There's a specific design to Stripe books.
7:11
The covers tend to be very dramatic. What are the first four? Let's see. Let's see how I do.
7:17
I think I can do the first five.
7:17
So first was High Growth handbook, Stubborn Attachments.
7:21
Then I want to say it was some combination of Elegant Puzzle, Dream Machine and Get Together. Revolt of the Public. Oh, Martin Gurri. Yes, that one's great.
7:31
That one's actually my favorite color and is my favorite cover too.
7:34
That brand, that is very in style now.
7:39
That brand is really good, and the colors of the Stripe Press books are very saturated, but they're like accent color saturated.
7:44
There's a story behind that too. Tell me. Bring it on.
7:47
It's so funny that you're noticing all of this, because we poured over these decisions and it's cool that they come out.
7:51
So the way a book cover works is actually, it's like a piece of cardboard with paper glued over it.
7:55
And normally that paper stock is dyed just on the surface level, which means when you wear the paper a lot it wears to white.
8:07
But we purchase what's called an impregnated stock, which means it's actually blue all the way through, or gray or whatever the color of the paper is all the way through, so it'll never get that white worn.
8:16
So yeah, this is why they feel very vibrant is because they never wear out like that.
8:22
And the idea was we hope people bring this with them to the coffee shop, we hope they bring it with them to work.
8:27
It's going to be in their backpacks rummaging around, what's going to happen when the corners get bent or pushed or worn?
8:32
We're like, "No, we want them to still feel very high quality and robust."
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So this is why we choose this impregnated stock.
8:42
The other thing that stands out about your time at Stripe is not just that you wrote a lot, but that you managed different writing projects.
8:46
What did you learn about that?
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I just love strapping myself to thinkers and tinkerers and doers.
8:49
And I think what I've learned is that one of my superpowers is being sort of next to creatives or people who have great ideas and sort of pulling out the interesting things.
9:02
So that makes a good partner in a writer.
9:02
So a lot of times it was like I would help people write their...
9:08
Stripe has a big culture of shipped emails.
9:12
When you finish a project, you sort of tell the org about it and you sort of give a story about how it came to be and what you've learned, and it's sort of an internal marketing document.
9:22
So this is one of my favorite things to help people with at Stripe was just like, "Okay, what was the story of doing this great thing?
9:26
What's interesting about it to you?"
9:30
And sort of pulling that story together.
9:30
So yeah, I was sort of like an internal editor.
9:34
Along what axes did you need to push people the most as you were helping people?
9:39
I think when you're in the weeds of something, it's really hard to remember what's interesting.
9:44
Because you're so deep in it you're like, I don't even...
9:44
You know if you say a word a lot, you're like, "What does that even mean anymore?"
9:49
And I think this is a lesson from fiction writing actually, where it's hard to keep in mind what you as the author know, which is how the whole story unfolds, versus what your reader knows, which is nothing.
9:57
So when you're sort of teasing a plot line or doing some foreshadowing, you have to remember, "Wait, how much does my reader really know about this?
10:06
Is this information sort of annoying and it's too much bang over the head, or is it just the right amount that feels like a little teaser?"
10:17
So I think that's the thing people need most help with is just remembering what somebody else knows.
10:23
And hopefully we'll talk more about good editing strategies, especially from the New Yorker.
10:23
But one of Harold Ross's thoughts on profiles was he was like, "I don't want to go for biographical completeness.
10:33
I'm much more interested in humor or intrigue.
10:33
I will sacrifice the full scope of what this person has done just to write a more interesting piece."
10:40
And I think that's actually a lesson for a lot of good writing is we don't need to know everything.
10:45
We just need to know the best bits.
10:49
Get straight to the edge if you can.
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And that's really hard to do when you are an expert, especially if you're a practitioner.
10:55
You're like, "I don't want to leave this part out.
10:55
It's so core to the thing."
11:00
It's just like, "Not memorable."
11:00
I think that the cardinal flaw, the cardinal mistake that Write of Passage students make is trying to write about too much.
11:06
They just try to torch the earth.
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And I'm like, "Don't try to do that.
11:10
Write about less, write about less, write about less, write about less.
11:13
The narrower your scope, the easier it's to write about that thing." It's true. It's true.
11:17
I mean, so much of great writing and great anything is just about obsession.
11:20
And when you're in your zone of obsession, everything looks interesting.
11:25
You're like, "I love it, I love it. And can you believe it?
11:28
This person was married to this person who was the same as this and they went to school with so-and-so."
11:31
And you're like, "What is the point?
11:31
Give me what I need to know."
11:35
And it's really hard to remember what your audience is going to be interested in versus what you as someone who's obsessed with the whole world of it is obsessed with.
11:45
And also sometimes the most things are revealed through the littlest bits.
11:45
Say that you wanted to write something about hotels.
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I think you could do an amazing exquisite piece about the experience of from looking at where the check-in line is to when they give you the card.
12:02
And how do they greet you?
12:08
What does the hotel key card feel like? What does it look like?
12:08
How do they ask for your credit card?
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Do you have to wait in line?
12:14
What are the bellmen wearing or the people behind the desk, what are they wearing?
12:18
And there's so much that's just off the top of my head.
12:18
You could probably say more about the hotel industry just through that little prism than trying to say, "I visited 100 different hotels and I'm going to write the full experience about all these." It's just way too much.
12:32
I'm so glad you brought this specific thing up, because recently I've been digging into Marriott culture.
12:37
And one thing I learned about their culture is that they're obsessed with the first 10 minutes.
12:41
And it's kind of like their equivalent of Facebook's seven friends in 10 days kind of thing.
12:45
They're like, "Okay, we have 10 minutes to get this person.
12:49
They need to be greeted by their name, they need to be acknowledged about their bags, they need to know exactly where the front desk is."
12:55
All these things, they're obsessed with that first 10 minutes.
12:59
So you're right on the money about something. There we go. Yeah.
13:04
The how I write hotel chain.
13:04
Yeah, the how I write hotel chain, the guide to hotels.
13:06
I thought you were going to talk about the napkins.
13:09
I really care about napkins.
13:09
I've actually sourced different napkins, because I like writing my to-do lists on napkins.
13:15
So I've sourced the perfect paper quality to write to-do lists. David, that's so cute. I like napkins.
13:20
You can fold them out easily. Very Anne Lamott.
13:25
You can't do that with post-it notes.
13:27
Anne Lamott with her, she's got these index cards.
13:27
This is an anecdote I love from Bird by Bird where Anne Lamott will just, she sort of is absorbing her world and she keeps an index card of observations in her back pocket and she'll just pull it out, put it back in. But yeah, same thing.
13:42
She's like, "The index card is just the perfect size. It's the perfect stock. That's what I like."
13:46
Let's dive into magazines.
13:46
Let's dive into magazines.
13:50
How in the world has the New Yorker been able to write with so many different writers but maintain the same style?
13:53
So I was founded by this guy named Harold Ross. He is not a New Yorker. He was born in Colorado.
13:58
He dropped out of school when he was 13.
13:58
He actually before the New Yorker edited the Stars and Stripes, which is either the Navy's or the Army's magazine.
14:07
He came to New York with this vision of the New Yorker, but he was very much not in its core audience and he was always sort of afraid of being thought of as a scholar or someone too erudite.
14:18
So he sort of yanked this into place.
14:18
And he is known to be a maniacal editor, sort of not great with words when he was speaking, sort of bumbling, never really able to articulate what his values were, but sort of just endlessly obsessive about tone and style.
14:33
He revered his artists and his creatives, which was sort of not the norm of the day, the more businessmen were thought of as the treasurers in the other places.
14:47
Harold loved the artists.
14:47
He was so into his writers, he gave them real space for expression.
14:52
Harold's known for inventing the Talk of the Town section of the newspaper.
14:58
And they had a meeting that was called the Weekly Talk or something, and everyone would come and pitch their ideas and talk about them, and he would just go bananas on everyone.
15:05
He would be like, "Trash this and take this out."
15:10
And he was kind of just a wild sort of unruly force in that meeting.
15:10
They said it could be very short or it could last almost the whole day.
15:16
And he would just hear ideas, play them through his own heads filter and, "Yes, no, yes, no."
15:22
Even talking about this meter a little bit of just what you say yes to is sort of what ships.
15:26
And so he was really willing to just say, "No, no, no, hate it, hate it, hate it, hate it, hate it, love it."
15:31
And I think that's how a lot of great writing happens is just going through the machine, the machine, and the machine.
15:35
The great stuff we see in the New Yorker is very heavily edited, it's very heavily fact checked.
15:41
So yeah, it just goes through a long cycle of editing and fixing until it's in its final shape.
15:53
Did he have a particular passion for profiles? He did.
15:53
And he says profiles are, they're all about obsession.
16:00
They're about obsession in the person that's covered, and it's also about obsession in the writer.
16:05
So the writer has to be obsessed with the subject and the subject has to be obsessed with their subject.
16:09
And that sort of chain of obsession sort of helps you pick the right people to cover, pick the right anecdotes and stories to pull out.
16:15
And like we were saying before, he was not interested in biographical fidelity.
16:21
He did not care about covering the whole story.
16:26
He just cared about finding the most interesting bits that were illuminating.
16:26
And then maybe the other thing that's interesting about how the New Yorker edits is they really prefer exclusives, which means that they have to write about odd topics.
16:35
And because it takes them so long to put these things out, they sort of have to be kind of sure that they're going to be the only ones talking about this thing in this way.
16:44
And so it sort of forces them to that edgier place.
16:44
They don't want to compete. I love profiles. I know.
16:52
I think that they're just the perfect length.
16:53
I think biographies are often too long.
16:53
What I like about a profile is I can sit down and I can read it in one sitting.
16:58
So my completion rate on profiles is very high.
16:58
And I still remember my first college internship, it was like a Thursday afternoon, and I went upstairs and sat down on one of the beanbag chairs and I read the New Yorker profile of Marc Andreessen. Oh, that's a great one.
17:15
And I remember so vividly how inspired I got.
17:19
And there's something about the length of a profile that I adore.
17:24
There's really something to this 5,000 to 10,000 word profile.
17:24
It is a classic constraints breed creativity.
17:29
It's just like, okay, you're never going to tell this person's entire life story.
17:33
You probably get three great anecdotes. What are they?
17:33
And I think it really pushes you to find the right stuff.
17:40
How do you think these profiles are researched? Is it the same? Does it change?
17:43
Yeah, I'm learning a little bit about this now.
17:49
I think some of them that we read has been years in the making.
17:49
The steps are really, pick your subject, that has its own taste involved, spend time with this person and pick up on their quirks and their anecdotes.
18:01
This is why almost all profiles start with, "I met this person for lunch at the so-and-so."
18:06
You're sort of trying to be in the scene with them.
18:06
But there's just reading and background on them.
18:11
And then the fourth is just getting the words right to express that thing.
18:11
And all of those have deep processes behind them, and a lot of rigor.
18:15
And yeah, I think just the alchemy of getting all those things right, it's tough.
18:22
What are some of the things that you've learned about Vanity Fair?
18:26
Oh, man, I love Vanity Fair so much. Okay.
18:31
I think my favorite thing about Vanity Fair is sort of Tina Brown introduced, in the mid-80s when she took over as editor, and she was coming from a British gossip magazine called Tatler, which for some reason sounds very British to me.
18:41
And she introduced this concept of high-low, which is, I think the way she describes it is we want a little bit of Britney Spears and we want more about public relations in Ghana or something, but we need a little bit of Britney Spears too.
18:56
And in doing so, you sort of elevate the lowbrow stuff and you sort of bring within reach the highbrow stuff.
19:03
And she's the master at sort of introducing those intermittently so that the magazine is sort of full of surprises and attitude and taste. It's not heavy.
19:09
So I think about this all the time, this high-low, I think about how amazing chefs just love junk food, and it's just like, yeah, these snacks are perfectly engineered to make my taste buds go bam. Go berserk. Yeah.
19:28
And chefs just love junk food. It's so funny.
19:32
It's like when they're done with their shift cooking for these Michelin star restaurants, they want a bag of chips. It's amazing.
19:36
So I think highbrow or high-low has these qualities too, where we get to sort of titillate our aspirational qualities, but we're also sort of anchored by the small sort of maybe trashier stuff that actually is somewhat juicy and salacious too.
19:55
So what's the takeaway here, that a brand should run between high and low, or that brand should either be lowbrow or highbrow, or that even the most highbrow people can learn from lowbrow culture?
20:07
What should I be taking away from this?
20:07
As with all cultural things, it's hard to copy someone else's.
20:11
The most brand thing is to just be maximally you.
20:11
But I think the takeaway is, is that the uncanny valley between highbrow and lowbrow is very wide.
20:17
And that's actually, that's the worst place to be.
20:22
And I think this is a lesson for a lot of things.
20:22
And we talked about this already, it's just pulling to the extreme is actually way more interesting.
20:26
And I've been thinking a lot about this, we may be in the end of earnestness phase, and I think sometimes we just need a break from heavy stuff or big feature launches.
20:37
I love when brands are funny. That's hard to do.
20:43
And I think it seems like I'm serious or something.
20:43
But we're all people, we like to laugh, we like to have a joke.
20:50
Like the New Yorker cartoons, an iconic part of that magazine.
20:55
And it's just a little break from where you got pages and pages, and the New Yorker is dense, the text is small and just like, "Oh, now I get this cute little break. Fun."
21:09
Well, this is what is truly exceptional to me about the New Yorker is that they took all these writers, Gladwell and all these other people, and they somehow retained a distinct voice that always hits. It's magical to me.
21:24
This was actually true in the beginning too.
21:31
Harold Ross says this a lot.
21:31
It was all about being a talent magnet for the right people.
21:35
So actually by upholding this very sort of weird and specific set of standards, the people who wanted to write that came to him.
21:40
So I think when Malcolm Gladwell, I don't know him, I don't know his process, maybe he'll go on this podcast at some point, but my guess is when he's writing something for the New Yorker, he's like, "I'm writing something for the New Yorker."
21:53
His spine goes a little straighter than if he was just going to publish something to his Substack.
21:57
I don't think he has a Substack.
21:57
But you got the point, it's aspirational.
22:03
What else should I know about Vanity Fair?
22:03
I haven't really read Vanity Fair.
22:06
What else should you know about Vanity Fair? Okay.
22:06
And this is true of the New Yorker too, obsessed with the packaging around the whole thing.
22:10
This is why I love magazines.
22:10
There is a text, visuals, attitude.
22:16
It's like all of it at the same time.
22:16
Tina Brown from Vanity Fair has this thing, you should be able to throw the magazine on the floor and it opens to a random page and you know which one, you know what magazine we're in.
22:25
Tina was obsessed with the covers.
22:25
Do you recall maybe Demi Moore on the cover sort of naked and pregnant?
22:33
She fully curated this whole thing and it just made a huge splash.
22:38
She was obsessed with what the cover looked like.
22:38
Harold from New Yorker, he says himself that he got the look right before he got the content right.
22:44
And this is definitely something that I learned from Figma, sort of brought to the Kool-Aid factory, which is my first big writing project online, was actually the packaging of it really matters.
22:56
It helps you arrive at the content in a certain way. This beautiful sign.
23:03
How I Write logo, I spent a long time on that.
23:03
Yeah, I think it matters.
23:03
And great writers set the scene, or we eat with our eyes.
23:09
There's a lot of precedents for this kind of thing.
23:09
I think giving that sort of design love and attention helps a reader arrive at your writing in a certain mood or mindset.
23:20
And no shade on Substack, I think it's doing an amazing thing for the internet, but I kind of lament that they all look the same.
23:26
I'm like, "What is the wrapper around this thing?"
23:30
Outside of just the words themselves, which maybe it's nice to have some sort of purity, just like how should I...
23:35
I don't know, how should I feel when I show up here?
23:35
Certainly different if I'm reading a theology Substack versus yeah, a funny one, versus a profile, versus something else. I want the look.
23:44
One of the things that I find is sometimes in the editing process, I can reduce my personality in the name of perfection.
23:49
And I've really been trying to counter that instinct. Yeah.
23:54
I think this is Chris Taco who said this, I don't know, but I think it's like, "Be your authentically weird self, that's why your friends love you, that's why your reader will love you.
24:02
It's just because you're kind of weird."
24:09
So I try to pull those out if I can remember. Yeah.
24:09
And having a compass towards that weirdness.
24:14
You're talking about the New Yorker profiles.
24:14
They want to do something in a way that hasn't been done before.
24:18
You want to write things in a way that's like, "Where's that coming from?"
24:18
And even a lot of what we admire about other people, it's like these funny catchphrases that almost are like, "Huh, where'd you come up with that?" Yeah, totally.
24:29
Because I mean, we're inundated with so much volume of everything, what will cut across?
24:34
What is inertia not doing?
24:34
That's memorable, that's what's interesting.
24:40
And that's the thing that's so hard to write, because it seems weird and it looks weird and you're like, "I like this.
24:45
Is anyone else going to like it? I don't really know.
24:49
It's sort of off in some way."
24:49
But I try to, yeah, what we were saying before about turning the dial up on the inner voice.
24:54
To me, writing is very much just a practice in listening to myself and trying to put the microphone close to things that I think should get more attention.
25:06
And we were talking about this last night that in periods where I am low belief in myself, I don't want to write because I don't trust that inner voice as much.
25:17
It doesn't seem as believable or reliable or as interesting to me.
25:17
And I think that's a sign that, yeah, it goes both ways.
25:24
When I'm not feeling myself, I don't want to write, because I don't want to listen to the inner voice, and it's sort of a cycle.
25:28
But I do think there's something there about trying to do those self scans and understand what is going on in here.
25:37
Yeah, the analogy that's coming to mind for me is you know when you're at the doctor's office and they take that thing and they make it touch your chest or something, and the doctor's like, "I'm going to listen to you breathe now." And I'm like, "What?"
25:47
And I've never used one of those, so who knows if it even works.
25:52
But then they're like, "Okay, everything sounds good, now take a deep breath." And I'm like, "Okay."
25:57
But you're talking about putting the microphone to your inner voice.
26:04
That's the analogy that's coming around for me.
26:04
Yeah, I think that's right.
26:04
It's just my insides are making some noise and I just need to hear what they're saying. Yeah.
26:09
There's probably a bad interpretation of that too.
26:16
But you know what's funny, my partner is a neuroscientist and he does computational neuroscience.
26:21
And an analogy that he uses is, imagine all of our neurons are in a loud noisy stadium.
26:28
And what we used to be able to do in recording, so reading out from neurons, is we would hold the microphone above the stadium so we would get the collective sound of what all the neurons were making.
26:38
And slowly with advances in technology, we can actually bring the microphone down to individual people and hear the individual conversations.
26:43
And I think that is a version of what I'm saying when holding the microphone to my inner voice, which is like, okay, I'm feeling anxious, or when someone's talking to me about leaning out of work, I'm feeling grumpy.
27:00
What's going on in there?
27:00
I want to know, I want to unpack it.
27:00
So I'm just slowly lowering the mic so I can get to the real stuff.
27:06
What have you found in your editing process for things that work?
27:12
You talk about redlining and other things like that. Yeah. Ugh, editing.
27:15
Why do you say, "Ugh, editing." ?
27:18
Because I remember my high school lit teacher was like, "Great writers edit eight times more than they write."
27:23
And I was like, "Those people sound very inefficient to me.
27:23
And they don't sound like very good writers."
27:29
That was how that landed on me.
27:29
I was like, "I don't think those people are very good."
27:34
And then I used to also have this meme in my head of the percentage of things that were in first draft to final draft.
27:38
I wanted that to be as high as possible.
27:42
Now I'm at 0% first draft to last draft most of the time.
27:42
So the editing process is really, yeah, it's the whole thing for me.
27:50
I would say the parts of the editing process that might be interesting to others is one, just an enthusiasm for editing.
27:55
I'm just like, "Yes, I want to be edited.
28:01
I want to be resonant, and in order to be resonant, I need to bounce this off many other people."
28:06
So my editing process is very much in person versus getting comments in a doc.
28:14
Another thing I do in my editing process is I have a doc called Darlings, and it's because sometimes I fall in love with a paragraph or the way I said something, but it just no longer has a place, and I don't want to kill them.
28:24
So I put them in the Darlings doc.
28:24
And every now and then I'll go and read it.
28:30
And that's sort of some kind of pump up mechanism.
28:30
But I like having a place for cut stuff to go.
28:36
Another thing I do in editing is I will read the writing into a recorder and then I will play it back to myself.
28:44
And this is part of, that doesn't sound like you.
28:44
Something about saying it with words instead of just reading it on the page and translating into my head is really helpful. Wait, hold on. So you read it out loud? Yeah, I record myself.
28:57
And then you listen to it back? Yeah.
28:59
And you feel like you get different things from versus the listening? Yeah, both.
29:03
I'm just like, this feels weird coming out of my mouth, or this feels weird hearing, it doesn't sound like you.
29:08
And I think my style is awfully lyrical, so that helps, just hearing how it sounds.
29:18
Or if I'm getting stuck saying it, I'm like, "There's probably something wrong with the text."
29:23
You do that too, don't you, a version of it?
29:23
You say it out loud or something.
29:28
Yeah, towards the end I'll sometimes do that.
29:28
In the final draft, just talking out loud, you do get a lot from it.
29:32
But I've never spoken and recorded it and then listen to it.
29:37
I want to try doing that.
29:37
It's a little crazy, but it works for me.
29:37
It helps me stay in the authentic place.
29:44
An experience I had growing up as an athlete is always watching tape.
29:50
So you play in a game and then your coach sits you down and you have to watch yourself be like, "Too slow to the ball or not shooting on time or making the wrong decision."
29:55
You are just constantly watching yourself at work.
29:59
When I worked in sales, we would record ourselves doing the pitch and meticulously critique.
30:03
I think I have a real comfort with that, a real comfort with being coached, being critiqued.
30:09
And I think there's something about finding a way to watch tape of yourself, whether that's in meetings or just reading your own text that's in the critique taste, self-editing zone, that's worth trying to cultivate.
30:19
So I think that's part of the enthusiasm of being edited is just getting comfortable being critiqued.
30:25
I have a musician friend who's the same way, who's just been like, "Reps, coach.
30:30
Yeah, doesn't sound right. Do it again."
30:35
And having the energy to do those reps and to elevate the thing, yeah, that's only going to come from inside you, but I think you can get practice at that thing.
30:48
How much of it do you think is watching game film versus the coaching?
30:51
I think the combo is helpful.
30:51
Someone who knows what great looks like, and that person can be you.
30:57
It's just like it's so hard to see the right pass in the middle of the soccer game, but when you watch it on tape, you're like, "They were wide open.
31:02
I can't believe I missed them."
31:02
And then next time you're like, yeah, the head on the swivel, that's the soccer word.
31:07
You're just like, "Keep your head in the swivel."
31:12
And you're just like, "I'm so crushed I missed the game-winning pass." You really pay for it.
31:17
And then when you see it from bird's eye view, you like...
31:17
So yeah, that's inherently obvious, but having the coach there to help remind you, "Let's watch tape, this is what good looks like. Did you miss?"
31:28
So I think some mentorship in that regard is helpful.
31:33
Another thing that, this isn't quite editing, but in periods when I'm writing a lot, I'm also reading a lot.
31:38
There's something about the loop of taking good words in and also producing them.
31:42
And I heard you mention this on a other podcasts with someone that you have someone in your life that memorizes scripture and you feel like he has a deeper- I do. I do.
31:51
I memorize a ton of scripture. Yeah, yeah, yeah.
31:51
So I also, I have paragraphs that sort of live in my head that I have read them 1,000 times because I just love how they sound.
32:01
And I think this is all part of the process of the poetry of it.
32:01
I want to hear it, I want it to be sing songy, I want it to be music.
32:06
Yes, I have a note in my Evernote that is just my favorite paragraphs.
32:13
And then what I'll do if I'm feeling, "Ah, there's something off with this."
32:18
I'll just go back in there and I'll say, "Okay, what's going on here?
32:18
What do I like about the vibe of these ones that I'm not getting in mine?"
32:23
And the thing is I think that there's certain emotions that I find it hard to capture in writing that are totally part of me.
32:28
And I think that there's a sort of a sweetness and a melancholy that I can get when I'm just talking to somebody or out and about.
32:42
Whereas writing really activates the logical factual...
32:42
But there's just certain things that I'm like, I sort of have to work for certain parts of my personality in writing.
32:54
Something same thing for me happens when I translate from my brain into my hand, is it comes out kind of in a teacher voice or something, where I'm trying to be like, I don't know, be really explicative or something or I'm really trying to explain.
33:08
It's annoying and I have to sort of pull it back.
33:08
Teacher voice is such a thing.
33:08
People all of a sudden start talking like this. I know. I'm just like, "Why?"
33:18
But people do the same thing with writing all the time.
33:18
I have so many friends who are brilliant when they're speaking, they're good orators, and I'll be like, "Nice, you should turn that into a piece of writing."
33:27
And then when they send me back, I'm like, "This is how you write?"
33:32
And it's timid and it's fearful, and there's no humanity behind it.
33:32
I'm like, "You're not being a human being.
33:39
You are giving me an assemblage of facts and figures and that's not what I want."
33:45
Maybe this is another good editing tip, and this comes from a straight practice too.
33:45
I really try to imagine a person reading it that I want to, not people, not a B2B marketer at such-and-such, like a specific person with a face.
33:57
So that's another part of editing that I think helps with this human thing.
34:03
If I was across the table from Stewart Brand, for some reason he is one I think of a lot.
34:08
If I'm across the table from Stewart brand, am I going to get that twinkle in the eye or is he going to be snooze?
34:12
What's good about Stewart Brand as a person to write for?
34:15
I think he's smart and he's funky. Funky. That's a great word. Yeah, he's funky. That's a great word. He's a cool guy.
34:21
And he's also, he's seen a lot of ideas. He's high-low I think.
34:28
You know what's underrated? What? Why'd you do that? Because I like it. Yeah. Super underrated. Totally. Because I like it.
34:38
Because if you don't trust that, you end up with this regression to the mean. Yes.
34:41
George Saunders says the mark of good writing and someone wants to read the next sentence.
34:48
It's just like, yeah, what's going to make me lean in?
34:52
Because you like it, because you want to, that's the only way.
34:58
And that funkiness, because it is the antidote to that homogeneity that is so common.
34:58
And you talk about reading a lot.
35:05
I think that you need to be careful about the influences that you're pulling from and moving towards funkiness, or just things that certain writers do that you want to emulate and bring into your own work.
35:15
The hard part then is how to do that in a way that's real and authentic and not some sort of fabrication of other people's writing.
35:25
I was reading something the other day and somebody had tried to do a joke, and it was not funny.
35:29
And I said, "That joke's not funny."
35:29
And she was like, "But I'm trying to pull from here."
35:36
And I was like, "But look, it doesn't feel like you."
35:36
And it's sort of like early on when you're trying something, I learned this when I was playing tennis, you sort of start and you're trying to emulate what's right, but you still look ridiculous.
35:47
And over time, people who are very good at tennis, they look very natural as they're doing it.
35:54
And the same thing happens in writing.
35:58
You're kind of trying to emulate that thing or this thing, and it's just not landing.
36:04
And over time there's a fluidity that emerges. It's true.
36:04
We were talking this morning about how writing is not really about the words itself.
36:08
That's not what I land on.
36:08
It's just like how do you tap into the place or the vibe?
36:13
So I think reading things with the vibe you like can help yank you.
36:17
But I think yeah, there's something to just copy pasting stuff that is just never going to stick.
36:22
Yeah, you want to hear something funny?
36:22
One of my biggest inspirations for writing that I've seen recently was I went to stay with some friends, and they live in Opelika, Alabama.
36:33
And I went to stay with them, and the wife of my friend, she said, "Hey, you're coming in."
36:40
And she takes pride in being a tremendous hostess.
36:40
And she sent me the most, well-written, warm, caring, what do you call it?
36:46
A questionnaire about my preferences, "How do you like the pillows on your bed? Hard, soft? How many do you like?
36:54
What sort of drinks do you like?"
36:59
This was the best, "When you wake up in the morning, are you like a 'Woo, let's get up.'
37:03
Are you like, 'Don't talk to me for three hours.' Kind of person?" Great question.
37:07
And the vibe of the way it was written, I felt like she was sitting right next to me and she was laughing at the top of her lungs, and that vibe just swept through the questionnaire.
37:14
And I was like, far inspiration, that is such a well-written questionnaire. That's so sweet.
37:23
And there's a real lesson in there about caring about your reader or your audience.
37:28
And this is kind of to the similar point of having a single person that you're writing for.
37:36
Something I bemoan about a flavor of writing, and I think there's maybe more of it today is just this kind of view from nowhere.
37:42
And I think it became pretty cool to be like, "I'm writing for an audience of one, me."
37:51
And I think that's actually a noble place to start is just like, yeah, what sounds good to me? What do I like?
37:55
And then I think the next level of writing is just like, what is in here for my reader?
38:01
What question am I answering for them?
38:01
What am I helping them see that nobody else can help them see?
38:06
But just a real care for the person who's on the other end of the page.
38:10
What I'm reacting to in that story of your friend is she was so aware of you, you were inside that story with her.
38:16
There was no note unless you were reading it, it'd be purposeless.
38:22
So I think that relationship between writer and reader, you just cannot forget it.
38:28
Tell me about this view from nowhere.
38:28
So you're writing to an abstract audience, is that what you're saying? Yes, exactly. To no one in particular.
38:35
It just might be interesting to someone.
38:35
Why do you think that became common?
38:39
I feel like I'm ripping on Substack, and I don't mean to, but I think it's a little bit of this just like, I write for an N of one, it's just my brain to this page to hit publish.
38:42
There's no editing process required.
38:49
Yeah, I think there's something in that filter process between ideas and audience that it's pretty easy not to think about on Twitter.
38:56
I'm just like, "Tweet to all followers and all feed."
39:02
I mean, this is the marketer in me of just like, who is this for?
39:02
And what will they get from this?
39:06
There's something to hold there that we've lost a little bit.
39:12
You know what validates this, is how many great books going back 100, 200, 300 years are just letters from one person to another.
39:20
Rilke wrote Letters to a Young Poet. And they're beautiful. Yeah.
39:26
That Walt Stegner book, Angle of Repose. I haven't heard of it. Oh, man. Same thing. It's based on letters. They're so nice. Yeah, they're so nice. They're so intimate.
39:36
Yeah, they're so intimate.
39:36
Yeah, we keep saying this, slice of life, the small things, the real inner parts.
39:41
I think it's pretty easy to do teacher voice if you're like, "I'm speaking to an auditorium of people."
39:46
There's so much distance between reader and writer.
39:46
I'm just like, I think the act of pulling them together is you just have to imagine someone who's real, not like someone on the other side of their computer, faceless, but a real person.
39:58
And I will say, this is a beautiful thing about writing on the internet is the people that come to you after, into your inbox.
40:03
And that's all done privately.
40:08
I guess Substack did just release DMs, which I saw someone cheekily was like, "Substack's got a dating network now."
40:13
But yeah, I've met amazing people in Twitter DMs or something in response to pieces.
40:18
Cultivating that deeper relationship between reader, I think you have to hold them while you write.
40:24
We're going to cue some trumpets. Iconic idea here. Iconic idea here.
40:31
We have to talk about your taste piece.
40:34
Oh yeah, that's a great piece.
40:36
Because this is the section of the show.
40:36
Out of all the things you've written, this is my favorite.
40:42
And I think we can spend some time here talking about taste.
40:42
How you wrote it is where I want to start, because you wrote this out of a lot of conversations with people, right? I did. Yeah.
40:53
I was like, "What was the seedling that was like, you really need to spring on this now?"
40:58
And to set the stage, at the time I was doing a lot of company consulting and I was having a meal with a CEO of a company, and he said that he has taste in his hiring criteria.
41:03
And I was like, "Amazing. What a cool thing."
41:13
The way he arrived at getting taste in the hiring criteria is he had a recent experience where somebody executed perfectly on the spec and still somehow got to the wrong implementation.
41:25
And I think it was about implementing some kind of candidate tracking software or something.
41:31
It was just like, "I feel like it was the wrong choice.
41:31
It hit all the things, but there was no taste.
41:36
It was no real understanding of the experience.
41:36
So we put it in our hiring criteria, we want taste now."
41:40
And I was like, "Yes, amazing. We love taste.
41:45
Surely if we're going to hire on it, you've defined it."
41:45
And he was like, "Not really."
41:45
It's one of those, we got rid of culture fit because we're like, "What is it?"
41:50
And then I was like, "Oh my God, I think taste is the new one where I want taste here and taste there and this person's got to have good taste."
41:59
But no one knew what it meant.
41:59
So I was like, "Okay, I'm going to just..."
42:04
I became obsessed with it.
42:04
And I think it was a pretty fun dinner party topic, because everyone's got a thought, an idea, and it was pretty fun to watch people work through it, because it's such a ubiquitous term now.
42:15
I feel like people were just throwing it around.
42:15
They're like, "Wait a second, what do I mean?"
42:19
So anyway, it was sort of a fun collective curation kind of thing.
42:26
And talk to me about the piece, because the structure is very specific too, that it's basically numbered to say, "Here's 28 different things that I believe about taste." Yes.
42:37
So this format is just stolen with pride from Susan Sontag.
42:37
She has a famous essay called Notes on Camp, and it's the exact same format where she's like, "This is a slippery term.
42:44
I don't really know what it means.
42:48
If I try to force it into the structure of some narrative that makes sense, I won't be able to do it.
42:52
So here was just some thoughts on this term."
42:52
So I copied that format for the taste piece, because I think it had the same quality.
43:00
It was so slippery, the phrase, I didn't want to flatten it, but I didn't want to miss the whole point, which was to give us a way to think and talk about what it is.
43:08
So yeah, I'll credit my friend Malanica with this idea.
43:14
She was like, "We've got to write it like Notes on Camp."
43:14
And then the editor that I was working with at Adarina, who's blog we published it on, she was incredible.
43:18
I mean, I probably started out with 50 and she was like, "Girl, we got to get to the good stuff."
43:23
So she was just sort of a relentless curator with me and picking what are the great ideas.
43:31
And something that was actually freeing about the format is because it was pretty easy to pull out, "This is not the core thing.
43:41
This is not the core thing."
43:41
How do you go about cultivating your taste?
43:46
Fran Lebowitz has this concept that I think is really awesome, which is that the reason theater was so good in the '70s was that the audience had high expectations.
43:51
And she calls us connoisseurship.
43:55
She was like, "The people coming, they needed something good."
43:55
So all the artists had to deliver.
44:00
And I think I'm a good critic or watcher or reader, like how you are with the Stripe Press books.
44:06
You're like, "I noticed the paper and I noticed the lay flat. I appreciate it."
44:11
So when people do it, I love it.
44:11
So I think I'm a good consumer.
44:11
When I watch TV, I want to talk about the episode with everybody and what I saw and noticed and the allegory and the colors, and so I think I'm a good, or I try to be a good consumer, really think about what I'm ingesting.
44:27
One of the things that I think is very important in training your taste is recognizing what you love and what you hate, and being okay with what you love and what you hate being different and de-correlated with what you are supposed to love and hate. Very much so.
44:44
I guess this is going to be the meme of the whole thing, it's just listening to what's going on inside you.
44:47
But this is in the taste piece too, but this idea comes from George Saunders where just putting a positive or negative meter on everything and just being like, "I like this, I don't like this, I like this, I don't like this."
44:57
And just continuing to just watch how you like and how you feel, and just picking a few lanes to do that in.
45:02
I think it's just too exhausting to have that for everything.
45:09
And I think it would make you quite annoying.
45:14
And so I think just picking the things that you're like, "It's going to be fashion or it's going to be coffee."
45:18
I definitely have one for coffee and I have a scale and I measure the beans and I grind them to the perfect amount.
45:22
If I did that for everything, I would be a monster.
45:28
Susan Sontag says that taste is very domain specific.
45:28
It's sort of vertical in lanes.
45:28
Is that something that you agree with or do you think that there is global taste that can be increased?
45:40
I think the knowledge of what comes with trying to improve your taste, which is sort of more observant, more appreciative, listening to your insides more, noticing this reality has a surprising amount of detail.
45:52
I think the insight that cultivating taste brings to you is that sort of has knock on effects where you're like, "Wow, somebody chose this rug and those curtains and those books, like this paper for the menu."
46:04
Even if it wasn't tastefully done, that unlock like, wow, everything is a choice that somebody made somewhere.
46:10
That is something beautiful to know about the world.
46:15
That person chose to put that on even if it's not the most tasteful thing.
46:15
So I do think it has some knock on effects.
46:21
I think of it as a virtue for that reason.
46:21
It helps you appreciate more and see the world differently. Yeah.
46:26
Why did you use the word appreciate?
46:31
Because there's a set of things that I don't have great taste in, fashion is one of them.
46:31
And I love when I see someone that does, I'm just like, "Wow, I know the Delta between me and that. And thanks."
46:45
Tell me about some of the similarities between taste and cultivating it, and then the writing and the editing process.
46:50
I think editing, especially editing yourself, is sort of the same as the process of cultivating taste, because you're doing that, to go back to Saunders' PN, positive-negative meter, again, you're sort of looking at the stuff you've already done and assigning that PN to it.
47:06
It's sort of the same process is just like, "Yes, this is doing it for me, no, it's not."
47:12
And that's the same process of cultivating taste like, "Yes, I like that outfit, no I don't.
47:17
Yes, I like this coffee, no I don't." And why?
47:21
How do I get it to the place of, yes.
47:21
So I think editing is about sort of evaluating things at face value and deciding how you're going to move them into the better place, which is kind of the same as the taste thing where you're like, "Okay, I don't quite like this, or I don't like this top with these pants.
47:39
How do I move it to the better place?"
47:39
And it's that same like, "Okay, no, I don't like it.
47:43
I'm trying to understand why, then I can improve it."
47:47
I love what you said about and why.
47:47
I think that's the core thing.
47:47
It's not enough to just be like, "Yes, no, yes, no."
47:52
But to somehow over time, it does take a while, to put words to your emotional landscape and say, "What are the things that I like?
47:58
What do they have going?"
48:03
I think you said something in there that I really liked that was either articulating or explaining your emotional landscape. It's so hard.
48:07
And it's really worthwhile, because that's how you sort of turn the dials of your life to get yourself surrounded by beautiful things or make more beautiful things. So I really liked that.
48:17
Yeah, I'm thinking of the New Yorker again, because Harold was so bad at articulating this.
48:22
There was just no style guide.
48:27
There was only the writer's room and him being like, "Yes, I dislike it.
48:27
Do more of this, do more of that."
48:32
And I do think there's, like you said, it takes a lot of time.
48:32
You have to just put a lot through the machine to see.
48:37
And then I think the style guide comes out.
48:37
It's sort of like it's emergent, but if you try to pin it to terms too early, you can lose some of the magic.
48:51
So a lot of times it's just like, "It's not right, but I don't know.
48:51
I'm going to search for the words, and I want to find them, but just like it feels off."
48:56
And I think there's a temptation, especially in management or in collaboration, where you want to quiet down that it feels off thing, because you can't explain it and you're like, "I don't know, it's just a Spidey sense."
49:12
But that's going to make me sound ridiculous in this meeting if I'm like, "I don't think we should hire this person because my Spidey sense."
49:15
That's completely inappropriate.
49:15
So we, a lot of times will turn that part of that little quiet meep, meep, meep, something's not working, we turn it off at work because we're like, "I don't know, I can't explain it."
49:25
But I think it's important to try to start listening to it and like you said, trying to put language around it. Yeah.
49:35
You made me think of a good writing prompt when you use the word emergent.
49:35
And one thing to ask yourself is, "Okay, I've spent some time in this area of the world in my work, in a project, what are some of the words and phrases that I've developed over the course of experience that I only saw by really zooming into reality?
49:55
And now let me write about that." Yep.
50:02
And I think this is a great part about having writing as a practice in my life.
50:07
I write a lot that I will never publish, I don't even think of publishing, it's just to understand myself.
50:12
And occasionally these memey things are a thread I want to pull comes out, but I think it's just a great practice to put words around what's going on.
50:22
What are some of the strange places that you've looked to cultivate taste for your own writing or to maybe even pull inspiration?
50:28
Because for example, I think Captain Underpants is genius. Absolutely genius.
50:32
You pick it up, you look at it, its funny, it's playful, it's got a good mix of words and images.
50:37
And even just the name Captain Underpants, it's hilarious, right?
50:43
You get this whole image in your head.
50:43
And kids just sort of fly through it.
50:43
I'm like, "Hey, what's going on there?"
50:47
All this to say, I think it's really easy to be like, "Well, I write about this thing, so I'm going to take inspiration from these people, these other highbrow people."
50:54
How about the most lowbrow stuff all over the place that then you can pull in because it's very human and relatable? Yes, yes, yes. That's a great example.
50:59
I definitely appreciate more children's or YA texts than I would expect along these lines.
51:11
There's something so simple about it that I really like.
51:11
Maybe this is less on the topic, but something I'm terrible with is naming in general.
51:17
I think I'm really good with the long version of the idea.
51:22
I'm pretty bad at the name of it or the memey phrase for it.
51:22
And weirdly, I think sometimes science gets this really right.
51:29
So I try to, lately I've been reading a lot about NASA and amazing naming.
51:35
All the missions have great names.
51:35
All the robots have great names. They're so aspirational.
51:42
So anyway, that's been an example of something I'm like, "Okay, I think we have something to learn from science."
51:46
Oh, this was another one I came across recently.
51:51
The American Heart Association's periodical is called the Circulation. Isn't that so good? That is really good.
51:56
I was like, "They're clever." That is really good. They're clever.
51:59
Clever is another word I aspire to in writing.
52:00
And I think the New Yorker does a great job.
52:04
Clever is one of those things that is really nice to be a little bit clever and so annoying when somebody tries to be too clever.
52:08
The best pieces for me come from, I'm trying to say something true about my experience or I'm trying to understand something about what's going on.
52:18
So I'm trying to get to some kind of truth there too.
52:18
And I think I just have to keep banging until I feel like that's right.
52:25
I tried having a Substack where I published regularly to it for a while.
52:30
It just did not work for me, because I couldn't give it that time.
52:30
And then I wasn't proud of what I produced.
52:36
So I think it's just being willing to put a lot of time into things like enthusiasm about being edited.
52:41
Just I want people's feedback.
52:41
I cannot publish anything without it.
52:51
I want everyone to help me make it better.
52:51
And then yeah, some of these little tricks around recording to myself or whatever, I want it to feel true.
52:56
And because my bar is just honest or true, I just really, I cannot stop.
53:02
I mean, it's completely all consuming.
53:10
When I'm writing a piece, I don't run with headphones because the thoughts are so active. Really? Yeah.
53:15
I'm just constantly reciting and reciting, "Not that word, not that word."
53:16
So there's a mania involved I think.
53:16
Other people are such a big part of my writing process.
53:22
I think something I've learned over the years is sort of who to go to.
53:26
You need an editor that's on your side.
53:26
You need sort of the yes and, which a good writer will intuit as no to all this other stuff.
53:32
And something I've noticed in editors is there's the critics and their curmudgeons.
53:37
The curmudgeons hate everything.
53:37
Everything is trash, everything is garbage, everything must go.
53:43
Nothing is good enough for their discerning eye. And that is exhausting.
53:47
And it is also a fool's errand.
53:47
And I think we've all had managers like that or colleagues like that, or even maybe parents like that where it's just like, it's not good enough. Curmudgeon.
53:59
We don't need them in the editing process.
53:59
What we do need is critics, people who are great appreciators, they want to find the interesting thing.
54:02
The whole goal is what gets the spark lit up, and all they want to do is pull that out the most. That's who I like.
54:08
I don't want the curmudgeons, it's too exhausting.
54:16
But the critics, we love them, leaned in.
54:21
I feel like there's a Steve Jobs thing here.
54:21
I don't know what it is, but I think a lot of people look at who Steve was and then they say, "I'm not going to think anything is good enough.
54:27
I have the highest standards in the world.
54:31
Nothing will ever meet my bar."
54:31
But you keep using the word appreciator.
54:36
And Steve was an incredible appreciator.
54:36
He had a real passion and a real heart for great art, for great design, for things of craft and excellence.
54:43
And when he saw it, he was able to say, "That's good." Yes. Yeah.
54:51
I think the thing with their curmudgeons is it's never good enough actually.
54:56
There's no examples of it being great.
54:56
And I think Harold Ross had this quality too. He was excitable.
55:02
It's like when he saw the right thing, it was like, "Yeah, we got it."
55:07
And so pulling towards that place of the we have title, yes, I love it.
55:17
There has to be that phase of the critic process or else it's just, it's no fun.
55:22
I think Elon probably has some of this quality too.
55:22
It's just like, "This is hard.
55:29
I'm going to say no a lot.
55:29
But when we get it, we get it.
55:29
And that is a celebration."
55:29
So I think you sort of need both parts of that process.
55:36
I want to talk about cultures of excellence, because when you first found Stripe, you wrote, "I could immediately tell that Stripe was different."
55:47
What stood out to you then, and how has that culture of excellence shown up in your writing?
55:51
I think in order to get that kind of culture, you have to fund it, quite literally.
55:51
You have to say, "Okay, actually the entire marketing and product team is going to spend a whole extra week on the launch blog post."
56:05
And that's a week of time they're not building.
56:05
So you have to actively fund that kind of care.
56:10
You have to be willing for your people to spend time on it.
56:10
And I think a lot of people want the outcomes of the polished stuff, but they won't fund it.
56:16
And I'm working on a project now that's sort of a big swing at something, and it's like, "Okay, this swing requires you got to hire a whole other person and maybe even two people.
56:26
And we're going to have to take time away from the existing team to do this.
56:33
And that means this stuff that's also a priority falls off this month. What do you think?"
56:38
And you have to say yes to it if you want the big thing.
56:46
So I think a lot of people want to skip funding the hard work.
56:46
Or Steve Jobs is another great example.
56:50
He funds the time to do the last 1%.
56:50
And we know this law, 80% of the work is in the last. Yeah.
56:59
And so you either fund that part of the work or you.
56:59
It can never be the best version unless you fund it, and it's really hard to fund it.
57:06
And maybe some advice to early writers or early people that want to see their best work is just to find a place where the last 20% is funded.
57:19
Find a boss that will do that for you or give yourself all of Sunday to write something, but you have to find a place to fund the last 20% or else you're never going to get it.
57:30
I wonder if this is your experience writing some of your great pieces. They take a while. Yeah.
57:34
I've been thinking about the Steve stuff a lot now that we have the headset.
57:34
And every time a new Apple thing comes out, you wonder, "Is this what Steve would've produced?"
57:38
Or sometimes when I see the laptops with all the different charger things, I'm like, "Would Steve have allowed this?"
57:44
And there's probably some great technical reason why we need all the different charger holes, or the strap needs to be big, or whatever it is.
57:52
I wonder if someone funded continuing to push on these edges, if we would've gotten something different.
57:58
How has the fiction writing that you've done seeped into your nonfiction?
58:03
I think I'm trying to beat a little of this out of myself now.
58:07
I said this before, I have a more lyrical style that I think is well suited for fiction and some narrative nonfiction.
58:14
I could be a little verbose in my business writing.
58:14
That said, I think the most important thing I learned from the fiction writing is two things.
58:22
One, I much prefer writing nonfiction.
58:25
I've always felt kind of weird in my fiction era, because I was living with all these fake characters in this fake world, and I just felt odd.
58:30
I like being in the world and learning about real things.
58:35
Not that fiction can't do that.
58:35
And then the second piece is we talked a little bit about holding our audience.
58:40
You have to be very cognizant of how you're moving and in control of how you're moving your reader through the story.
58:51
So I think that piece has stuck with me.
58:51
The thing that I would posit is that there's a lot of life in your writing, and I wonder how much of that comes from fiction. Yeah, I think so.
59:03
Like world building and building up characters, I'm interested in that piece of writing.
59:08
You know what also writing my novels taught me, is that I could do a big thing all by myself. Oh, wow.
59:15
A lot of our work is just collaborative and you never really know what your individual contribution is.
59:20
It's just it's hard to map.
59:20
I wrote every word in that book and I spent all my days and all my nights thinking and developing that story, and what's in there is really mine.
59:34
There is of course help along the way, but that was my first big project that I did by myself.
59:38
One of my favorite Brie-isms is, I want to get it right, "Not even a simple message can survive a game of telephone." Oh, yeah.
59:45
Oh my God, speaking of things that I poured over for way too long.
59:49
This, maybe you recognize it, this is from the application to Tyler's Emergent Ventures program.
59:54
The question is, "What is a consensus view that you agree with?"
59:58
Which is weirdly harder than feeling contrarian.
59:58
So this was my answer, not even a simple message can survive a game of telephone. And it's true.
1:00:04
I have a much, much younger sister, so we used to play telephone with her a lot.
1:00:08
And I mean, it is truly funny that even a simple phrase, and even without a five-year-old involved, it's really hard.
1:00:19
And that applies to writing because you have to write things down so that writing keeps things stable, steady and concrete or something. Yeah.
1:00:24
Yeah, it codifies the idea.
1:00:24
The other thing I think about writing is just trying to produce a lot.
1:00:29
I've been talking a lot about how I pour over everything and edit a ton.
1:00:33
And I'm trying to channel a little bit more of this energy that just producing a lot actually helps you get to the best stuff.
1:00:38
Probably means you have to throw a lot out too.
1:00:43
But Seinfeld again has this quote in the same interview where he says, "It's just a matter of tonnage."
1:00:47
You're just producing a lot, saying no to a lot, but the stuff that's left is great.
1:00:54
And then sort of another thing in conflict of this that I've been thinking a lot about is my colleague Patrick O'Shaughnessy is always like, "If it works, it works fast."
1:00:57
And just like if it's flowing, it's flowing.
1:01:03
I think Morgan Housel said this on the podcast too, it's just like he knows when it's flowing and then he just lets it rip and move on.
1:01:08
But I think I resonate more with the sort of comedian's way, just writing a katrillion jokes, performing them on stage, refining them, getting them right, but there's just a sheer volume of words that you just have to go through the sludge to find the magic kernels. The sludge. I know, the sludge.
1:01:31
David and I were walking last night and a friend who's working on a piece text me, "Writing his pain."
1:01:35
It was at the perfect moment, just like, it is pain.
1:01:41
It is the sludge just getting junk and junk and junk out there.
1:01:41
And it's funny, because my median second when I'm writing is, "Oh, I am doing such a bad job."
1:01:47
And then you know when it hits me, that writing, that I've actually made progress by writing is once I've stepped away from what I've been doing and I start talking to somebody else and I realize how much depth and dimensionality I've discovered through the process, I'm like, "Whoa." I know.
1:02:10
You're evolving as you write and your thinking is evolving.
1:02:10
This is why I kind of think it takes a while.
1:02:14
You got to put it under the bed a while and come out.
1:02:14
You have to revisit your own ideas a lot.
1:02:18
This is also from that Seinfeld interview, a tip that I like is to reward yourself after you've done the hard work.
1:02:25
So it was like, okay, I did the morning pages or I sat for four hours, or I mailed that intro, I'm going to go.
1:02:30
I think that what you're uniquely good at is, I don't meet a lot of people who have a combination of being able to observe well like you do, and have the patience to nurture a good observation and be able to write the personal component.
1:02:48
I think that really distinguishes you.
1:02:48
Most people I know are good at writing personal, but their observations aren't all that interesting, or the opposite.
1:02:55
Yeah, I'm always trying to hone that. I love Joan Didion.
1:02:55
She's an amazing observer.
1:02:55
Yeah, Tina Brown says this about Vanity Fair too, "I can teach someone to write a lead, but I can't teach them what to notice."
1:03:08
And maybe this is also what intersects with the taste thing is just like, I want to be an active metabolizer.
1:03:12
When I walk down the street, I want to see the buildings, I just want to know what's going on here. Noticing. Noticing.
1:03:24
Yeah, and speaking of Steve Jobs, one of my favorite anecdotes from the new book, Make Something Wonderful, is how he would, as a young boy, he wanted to take apart a radio with his neighbor.
1:03:35
He just wanted to see all of its guts.
1:03:35
And I don't have that with tech, I don't have that with cars, but I do have that with people and I do have that with ideas.
1:03:46
That's what the show is about. I guess so, yeah.
1:03:48
I want to know the guts of the writing process.
1:03:48
I want to see the ugly stuff.
1:03:48
I want to know how something is written, how things are edited.
1:03:54
I want to deconstruct this entire thing and I want to make it ugly and gross, and then through the reconstruction, divine and beautiful.
1:04:04
Yes, yeah, I can deliver the ugly parts of the process.
1:04:06
You're like Song Exploder, but for writing. Yes, exactly.
1:04:06
When you're stewing on an idea, is there anything you're doing besides conversation?
1:04:13
I'm just still caught on this, I've thought about it for nine months, thing. Oh, yeah.
1:04:17
I mean, I'm just talking to myself about it constantly, reading constantly. I'm chewing on it.
1:04:20
It's chewing on me actually is what's happening.
1:04:27
I feel physically uncomfortable. Really? Yes, I do.
1:04:32
I feel physically uncomfortable until it's sorted.
1:04:34
How is that process different when you're trying to understand something that you've experienced like the Stripe piece versus be a cartographer of a new landscape, like the taste piece?
1:04:45
Yeah, I think we talked about this when I came to Write of Passage, but there's a quote I love that's like, there's two kinds of creativity, one is Einstein where you explain the world how it already is, and the other is like Walt Disney where you are bringing new ideas into the world.
1:05:01
I think I'm much more of an Einstein.
1:05:01
I'm nothing like Einstein, but I like explaining the world how it already is.
1:05:09
And I would put the taste thing into that category.
1:05:15
There's almost no original thoughts in there.
1:05:15
I'm just trying to curate what I'm experiencing or what I'm seeing or observing.
1:05:22
And I think even the personal essays are a little bit like that.
1:05:27
I'm just like, "What am I seeing inside me?
1:05:27
How do I describe that in a way that's true?"
1:05:34
But yeah, definitely more of the explainer.
1:05:34
I don't think I have anything new to say really.
1:05:40
Brie, I'm glad we did this. Me too.
1:05:40
Thank you so much for having me, David. This was really fun.
1:05:42
I feel like there is so much in your head and I've read a lot of it and I was like, "This needs to be in audio form." Oh, that's really kind. Yeah.
1:05:50
Hopefully there's something helpful in there somewhere. Lots of good stuff. Thank you. Thank you.