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Full transcript: Author Jessica Weisberg on Recode Decode

Her new book, “Asking for a Friend,” is about the history of giving advice.

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The book “Asking for a Friend” by Jessica Weisberg Jessica Weisberg on Twitter

On this episode of Recode Decode,hosted by Kara Swisher, writer and audio producer Jessica Weisberg talks about her new book, “Asking for a Friend: Three Centuries of Advice on Life, Love, Money, and Other Burning Questions from a Nation Obsessed.” Starting in 1690s London, Weisberg examines how advice became a cultural force in America and how professional advice givers presaged the internet by creating the first platform for people to ask difficult questions anonymously.

You can listen to the whole thing in the audio player above. Below, we’ve also provided a lightly edited complete transcript of their conversation.

If you like this, be sure to subscribe to Recode Decode on Apple Podcasts, Spotify, Pocket Casts, Overcast or wherever you listen to podcasts.

Kara Swisher: Hi, I’m Kara Swisher, editor at large at Recode. You may know me as someone who loves giving free advice, especially to people who don’t ask for it. But in my spare time I talk tech, and you’re listening to Recode Decode from the Vox Media podcast network.

Today in the red chair is Jessica Weisberg, an award-winning writer whose new book is called “Asking for a Friend.” It’s a tour of three centuries of advice givers who have made their names, and sometimes their fortunes, by telling Americans what to do. She also works at Gimlet Media and previously was a producer at Vice News Tonight, and on the hit podcast Serial. We have a lot to talk about. Jessica, welcome to Recode Decode.

Jessica Weisberg: Thank you so much.

What an interesting career you’ve had. Why don’t we go through that, because we always ask about people’s careers and how they got to where they got.


I want to understand how you got to your advice-giving book, essentially.

Sure. My advice-giving book, the way it started was, I was at the New Yorker a number of years ago.

Doing writing?

I was a fact-checker and I was writing a lot for the website. I was also writing those sort of anonymous book reviews in the back of the book. In case you wondered who wrote those, it’s fact-checkers.

Okay. Why did you want to become a fact-checker? It was like, “Oh, you gotta work at the New Yorker”?

It was my first job, and basically, I thought it would be a great way, I had never gone to journalism school, and I thought what better way to learn about journalism?

Is that a hard job to get, a fact-checker at the New Yorker? I bet it is.

Yeah, I think so. I mean, I feel like I lucked into it, but everyone there has to speak a couple languages.

Oh, wow.

Because they want to be able to fact-check in other languages. So yeah, it’s a really smart group of people, and I’ve kept in touch with all of the people I fact-checked with, and now they’re my editors and my colleagues, so it was a really nice community. It was like grad school without having to pay for it.

Sure, perfect. So you were there, and ...

So I was there, and I was ... there was a book coming out at the time, by Cheryl Strayed, called “Tiny Beautiful Things,” and I said to my editor, “Oh, hey, I’d like to review that one. That one’s interesting to me. I read it on the website,” and my editor there, who I have a lot of respect for, was like, “Oh, we’re not gonna review an advice book. That’s not what we do.”

Right. It was from her column. “Dear Sugar.”

“Dear Sugar.” So it was a really popular column at the time, on The Rumpus, and I had read it and thought it was really beautifully written.

Explain The Rumpus, for those who don’t know what it is.

The Rumpus is a website that’s sort of for literary types, I would say, and it’s a really nice website. They have some original fiction, but it’s mostly sort of interviews with writers, and profiles of writers, and Cheryl Strayed had anonymously written this advice column called “Dear Sugar,” and people had written to her often. I think it started with sort of questions on writing and questions from aspiring writers, but it turned into questions about all sorts of things — mourning, love, loss, divorce — and I just thought that she created this really incredible community online.

Right, very funny.

Funny and wise and really poignant.

Yeah, and she had a tough life, too, so she had a lot of advice to give, or a lot of experience.

And it was the kind of advice column that really is where the person giving the advice is revealing more about themselves than any of the people asking for it.

Which are the best columns.

Definitely, and I thought it was interesting, and she’s a really well-known writer, and so I said, “Hey, I’d love to review this book,” and the editor was like, “No, we’re not reviewing that.” And I was like, “Well that’s interesting. Why wouldn’t we review an advice book?”

This is something that has a huge history in our culture, and it’s ... Advice givers are people who have, who wield a lot of power. So I didn’t write a review, but I did end up writing a piece for the New Yorker’s website about advice givers over time, and I wrote that piece, and a couple people had said to me, “Hey, this should be a book,” and I was like, “No, I’m not writing a book right now.”

But it was an idea I just kept coming back to, over the years, and then a few years later I was like, “You know what? I would like to write a book about that.”

Right, about advice givers. Then you went to Serial, which obviously was this enormous, that’s why we’re all here.

Yeah, yeah it’s true.

What did you do there?

So I was a producer on Season Two of Serial. I came to Serial through a film production company called Page 1 that was founded by Mark Boal, and basically ...

So you had left the New Yorker and gone ...

I left the New Yorker. After the New Yorker, I started grad school at Iowa, the writer’s workshop, and while I was there, I was working part-time for Mark Boal as a researcher, and it was just a great gig to have while you’re in grad school. And then he started a production company and asked me to come on full-time, and I thought it was a really interesting idea, this idea of taking specific journalistic projects and sort of creating the most blockbuster treatment of them possible.

Right, right, which is common, which is ... all the magazines do that.

Yeah, and it was sort of this nimble organization that was going to be able to do that, so that really appealed to me. It was like combining narrative and journalism, which has always been the two things that drive me, and so I joined that company.

And one of the first things I did at Page 1 was try to track down Bowe Bergdahl. So we had done about a year of reporting before we went out to Serial, explaining what we had, and then once we showed them our materials, they were like, “Let’s partner,” and so then I spent the next year of my time pretty much borrowed by Serial.

Right, borrowed by Serial, working on the second part. Talk about that experience. What happened with that? Why was that so interesting?

The Bowe Bergdahl story? Well, I think for a bunch of reasons. One it was that he ... I think Bowe Bergdahl is a person who has a very lofty idea of himself, and he sort of felt like what he did was standing up to something much bigger. And when you see what he did, it seems just like a really scared kid who was in a situation he didn’t know what to do with, and I think what the series did — and hope it did — was just take that contradiction and apply it to the whole war in Afghanistan.

What was really appealing about it is that we could take one person’s story and tell a story of an entire war.

Sure, and you were doing it through audio. Did you have any podcast experience?

I had done radio in college, so it was really ... it was such a fun, wonderful homecoming for me, to be able to come back to it.

Right, and so you worked on that. And went over, then, to the next project, which was Gimlet, or I’m sorry, Vice Media. Vice News Tonight, where you were the head of features.

Yeah, I was the head of all the feature stories there.

Yes, and that was sort of fast and millennial news, kind of thing.

Yeah, it was, I mean it is.

It is. It continues.

It continues. Yeah, we did some stuff that was ... yeah, I think the department I worked in worked on things that were a little bit slower, and a little bit more ... took a little bit more time to come out, but I think the thing that was really exciting to me about Vice News was that it was a nightly news show where they were gonna really curate the news, and that’s something that I think The Daily, for instance, has done so well. That at a time when we get one million news stories a day, to have a source where it’s like, no, you only need these stories. This is what you need, to be an informed citizen right now.

Right. Like a magazine, though.

Yeah, but like a nightly magazine, and so that really appealed to me, ’cause I think that’s such a useful service in news right now.

It’s super high-concept. It’s the high-concept, which is interesting. I’m always wary. I’m much older than you, but I was on a ... there was a show called “West 57th” that CBS, I think it was CBS, and it was all the young reporters. And the beginning of it, you should go find it on the web, ’cause the opening scene is like ridiculous. They go running, grab copy, and run right in front of the camera. It was like Meredith Vieira when she was very young, and stuff like that. It was a similar thing. It failed, ’cause it was the idea that young people like news differently than old people kind of thing, which I always am sort of wary of.

I don’t think that’s true.

I don’t either, I don’t either. But it’s designed, Vice News is designed that way, and that’s the way it’s told, which is interesting, and untucked shirts, and everything else.


And I find myself thinking, “Would you please tuck in your shirt?” Which is a terrible thing, when I’m watching the news, but I sound like a crazy old lady, shaking her fist at the internet, but it’s an interesting thing of where news is going, and stuff like that, and how we get our information.

So I want to get into this, the concept, because everything like what your book is about was something that was a staple of news products, and it’s the same thing, but it’s online. So how did you get to the book? You just decided it’s time to do this?

Yeah, so I had written that article, and then a couple years later I wrote another article about two marriage gurus, and after I did that article, I realized that I really did want to delve into this subject in a deeper way. I think part of the reason why I wanted to was because I felt like the internet was really making advice ... advice was everywhere. Suddenly it seemed like all of the content people consumed — whether in podcasts or online — was, in some way, a form of advice. I didn’t think we had put a name on that yet, and so I was like, this is part of a tradition, and this is more popular than ever, and I wanted to examine that.

Right, exactly. So you went back. So let’s talk a little bit — and we’re gonna get into it in the next section, of the history of this — but let’s talk a little bit about the history of advice. Because again, it’s something, when I was making the point about Vice, it’s like the same as it ever was. There’s an expression, “There’s nothing new under the sun,” it’s Euripides. A good piece of advice. I think it’s Euripides, I’m pretty sure it is, but the idea that this has been around for a long time, that people have been doing this in whatever format it takes shape in, forever. Forever. So talk a little bit about that. The idea of how it’s been delivered, these advice, or what the history of it is.

Yeah, so the thing that you see, if you go back to the earliest advice givers, is that they were using anonymity as technology. They were saying like, “How do I ...”

That’s a good way of putting it. That’s a great way of putting it.

They were trying to really make this system where people can just have complete freedom to say whatever they wanted, and also complete freedom to sort of both ignore and idolize the person giving advice. The way to do that was by everyone being anonymous. That technology has been perfected by the internet.

Of course, yeah.

I think that’s why it’s so popular today. But if you go through history, there’s a lot of adaptations to that system.

All right, talk about the first commercial advice giving, I guess.

The first commercial ... So the first chapter in my book is about a guy named John Dunton, who was giving advice in the 1690s in London. He was a guy who had a career as a publisher, nothing ever took off, and then he decided to start this magazine that was only advice. He started it with his two brothers-in-law and this guy he was 50 percent sure was a doctor, but they pretended they were like 26 wise men.

Oh, okay. So wise men, the concept of wise men.

Yeah. They pretended they were the best astrologers and the best mathematicians and religious scholars in all of London.

So there’s always fraud.

There’s always fraud involved, and but people didn’t care. And even though it seems that people were pretty suspect of the actual quality of these people’s resumes, they didn’t mind. They just really wanted to have their questions answered, and also really wanted to see their questions in print, I think, is also a real appeal. So the first chapter of the book just looks at what kinds of questions were people asking when presented with this new opportunity to ask them anonymously?

So what were they?

They were a lot of the same ...


Yeah, the same questions as people have today. It’s really hard to figure out if someone likes you back. It was really hard in 1690, and really hard today. Really hard to figure out marriage, really hard to figure out sibling relationships, really hard to figure out parent-child relationships. And then because there wasn’t Google then, there was a lot of sort of informational questions that we would now pose to Google, like “Can you throw a witch in a pond and she’ll die? How does that work?”

Yeah, that’s a big one. The other day, I was Googling that.

Yeah, you know, like now we have Google to answer these silly questions we have. Things about food and diet, things about the stars. And the bathroom. There’s lots of questions about horse excrement.

What about it?

Like why it has a certain shape.

Oh, right.

You know, just the kind of random questions we’d put to Google now.

People. Yeah, well, we’ll get into that later. I’ll have a good story about Google and when I first went there.

Oh, really?

Yeah. So this was just printed and then there would be answers? Hugely popular.

Mm-hmm, hugely popular. So that’s the first chapter of the book, and then the second chapter of the book is about a guy named Lord Chesterfield, and he wrote ... he didn’t mean to become an advice giver, is what’s interesting about him. So he had a child out of wedlock and he wrote his son letters, basically every day, to sort of try to make up for the fact that he wasn’t present in his life. And then when ...

Right. These are “be a man” letters, right?

Yeah. It’s like be a man, this is how to be in society, and his advice is very strategic, and very ... a little bit heartless. It’s like, never say what you think, never say what you mean, always adapt to the situation, never reveal too much of yourself.

And then what happened was when Chesterfield died and left no money to his son’s widow, she was like, “I’m gonna get back at him by publishing all these letters,” and the letters took off in America, and people were ... when I say they took off, they were popular, but they were also hate read. People were really upset about it, and you can read letters between John Adams and Abigail Adams about how morally horrifying these letters are.

Because of the advice itself?

Yeah, ’cause of the advice itself. Because of the idea that people wouldn’t be themselves, and the idea that the best way to be was to hide who you are. But the book was really popular, in large part.

What’s it called?

The book was called “Letters to a Young Man.”

Ah, yeah, yeah, that’s right.

Yeah, I think that the book was super popular because it was giving people access to sort of think about things that nothing else was really giving them access to think about. This was the time when most books were religious texts, and this was a book that was talking about things that people were thinking about, even if people weren’t writing about it.

And then it morphed into Benjamin Franklin.


So we’re gonna get to that when we get back, who I think was the biggest advice giver of all time.


We’re here with Jessica Weisberg. She’s got a really great book called “Asking for a Friend,” and it’s about advice givers over three centuries, which has sort of reached a new height, with the internet.


We’re back with Jessica Weisberg. She’s the author of “Asking for a Friend.” She’s also had a million fantastic jobs, the last one ... now she’s working for Gimlet, part-time, correct? Another podcast company, they make lots of great podcasts. We’re talking about advice givers over the centuries and we’re way back in the Ben Franklin times. So Ben Franklin was anonymous and he gave advice, and that was one of his most popular things he did.

It was absolutely the most popular thing.

He did a lot of other things we might want to thank him for but ...

Yeah, he was a productive guy. Yeah, what he did is he wrote advice and very smartly decided ...

This is “Poor Richard’s Almanack.”

“Poor Richard’s Almanack.” And what I didn’t really appreciate about “Poor Richard’s Almanack” until I really wrote the book was how funny it is. He did have the good sense to present really earnest advice with sort of a sarcastic tone.

Give me an example.

Well, because Poor Richard ... It was the idea ... It was like he didn’t know how to make any money, and he didn’t have a great relationship with his wife. And the idea of taking financial advice from a guy who calls himself Poor Richard is a little ridiculous. And I think that he just saw ... We all bristle a little bit with too much earnestness, and I think that’s why there’s a bit of embarrassment about the idea of consuming advice today. And I think Benjamin Franklin just had the sense to be like, “Oh, if I couch this in a sense of satire and humor, they’ll be more digestible to people.”

And he took the persona of who? I forget.

Well, it was Poor Richard. But then before that he had other personas that he sort of played around with before he got to Poor Richard.

Of women and lots of ...

And it was like he was very interested. He wrote about how — very ahead of his time — he wrote about how the message doesn’t come across to a reader unless it comes from the right author. And instead of trying to find the right author as editors would do today, he was just all of the authors.

And so when he wrote about abortion, he wrote about it from a woman’s first point of view. And similarly with Poor Richard, he’s like, “How do I get people to actually read the advice and not feel like they’re being preached to or spoken down to or just feel uncomfortable with the earnestness? I’ll do it from a guy you kind of want to make fun of.”

Right, right. There’s so many aphorisms.

So many aphorisms.

Go through a couple of them because they’re ...

Oh, God. There’s early to bed ...

Early to rise.

Makes a man healthy, something and wise.

Wealthy and wise, yeah.

There’s a lot about not overstaying your welcome.

Fish smells after three days.

Fish smells after three days. There’s so many. There’s a lot about hard work being more important than intelligence. There’s a lot about ...

And did he answer questions? No, he just put it out. All kinds of tidbits in “Poor Richard’s Almanack.”

Yeah, they were all just like aphorisms. They were not responding to questions.

And his point being ... This was a business for him, he sold this. He sold “Poor Richard’s Almanack” so it was a good business for him.

Yeah, absolutely.

And did it set the tone for advice giving? Because he really had such an impact on ...

Yeah, absolutely. I think that there are other advice givers who followed him who followed on the line of satire. One, for instance, was this guy who wrote a book about efficiency in the 1950s, CJ Parkinson. I think I got that name right ...

That’s okay.

It was a book about business efficiency that was taken very seriously but he sort of wrote it in a satirical way. He the one who said the quote, “Works fills to the time you have to complete it.”

Oh right. Yeah, yeah, yeah.

And there’s another guy, Michael Korda, who wrote advice books. One was called “Power” and one was called “Success.” And similarly they’re funny, funny books, but they’re treated as sort of serious advice book. So he definitely set America on that. He definitely gave a lot of advice givers the idea that their work needed to be funny. And Ann Landers and Dear Abby are also really known for their pithy one-liners.

Right. All right, let’s get to them because to get to them, there were all kind of advice givers.

Yeah, a lot people ...

There’s a lot of people who ... Dale Carnegie. It just goes on and on and on. And “Who Moved My Cheese?” It goes all the way up through and between. Is it an American thing? Or is it ... I don’t feel like Europe has a lot of advice givers.

They don’t. They exist but they don’t ...

They have their fables and then there’s German fairy tales, which are advice in some way.

Yeah, absolutely, but the figures themselves do not reach levels of prominence that advice givers achieve in American. There’s no equivalent.

Why is that? Do you know?

Well, I think it’s a few things. One, I think that if you ... having a country without a centralized religion has created space for gurus and created space ...

That’s a fair point.

... for people with unique ways of seeing the word that people want to follow. I think that Lord Chesterfield, just to go back to an earlier example, was popular because he came to America right around the Revolutionary War and there was just people really open-minded to different ways of living and sort of wanted to break tradition with the U.K., and this was an opportunity to think about different ways of existing and different ways of being around people. And I think that tradition can be used today. One of the things I write about in the book is that the popularity of this form just really reflects the fact that the American Dream really exists in people’s imaginations.

Imaginations and heads, because that’s what it’s a lot about. So we go from Ben Franklin, what’s the big next thing before we get to Dear Abby and Ann Landers.

There’s a few more in the sort of early America. And then I skip to the 20th century. And the 20th century, the section that Ann Landers and Dear Abby are included is a section about how women were starting to get these roles and why they were starting to get these roles.

So why were they?

People were sort of interested in advice givers who weren’t authority figures as much as someone like Benjamin Franklin was or Lord Chesterfield was. They were interested in people who seemed like friends. Who seemed like they could relate to the problems that were being faced by the people asking the questions. And when that transition happened, suddenly a lot of women got those jobs because they could traffic in empathy moreso than other men could.

And every newspaper had one, correct?

Absolutely. And so I talk ...

They were staples of the offerings, pretty much.

Yeah, and incredibly popular. There was one columnist at the turn of the 20th century, Dorothy Dix, who people said had more influence over cultural norms in America than absolutely any other force.

Why was that? And she was conservative, right? Correct?

She was actually quite liberal. She was a suffragist.

There was one that was conservative. Anyway, go ahead.

She was a suffragist and she didn’t use her column to talk about feminism in a direct way, but it definitely informs her advice. And yeah, I think she was just like the ... There’s a sociologist couple named Robert Linns, who were sort of studying trends in America. And what they found was that Dorothy Dix could influence popular culture more than anyone.

Give me an example of that.

Like, when she said .... Like, her ideas about marriage and divorce and when a girl should start dating and all these things was how people glommed on to what was right and what was wrong.

Because they weren’t getting the signals that you said from religion or ... which they were, but they weren’t. They were seeking other ways to do it. Now, she did this in a newspaper form. Now, were these questions made up? I mean, most people ... that’s how you think about it when you look at a lot of these things, that they’re sort of made up, essentially.

I mean, I’m sure that’s the case. I’m sure that some questions are made up, but I also think that one of the reasons that I wanted to write this book is I felt like all of the narratives about advice-givers — like “Miss Lonelyhearts,” for instance, that great book — is about these people as frauds. And there’s a lot of ...

Talk about “Miss Lonelyhearts” so people understand the context.

So “Miss Lonelyhearts” is a great book. It’s about a man who is pretending to be a woman in order to write an advice book. Not an advice book; an advice column for the lovelorn. And in reality, he’s sort of neurotic and a chain smoker and a little bit of obsessive compulsive and a depressive, but in his words he offers a lot of consolation to the people who seek his help. And the questions he gets are a mix of things that are presented to him by his sort of drama-seeking editor and questions by real people. And the people have questions about all sorts of really heartbreaking things and that sort of strikes the reader that this is the man whose been sort of authorized to give them advice.

So I feel like that, because there were so much about the fraudulence about the advice giver, I was sort of interested in another question, which is like the power of the advice giver and the popularity of the advice giver. So I don’t look so much into the question of how many of these questions were made up, but I’m sure it’s a lot.

The authority is an interesting question, but it does go back to the shaman idea. Like, the idea that there is a priest or a shaman or ... The advice was, as you said, given by religious figures, often men. And this is the way you behave, essentially. You followed along to them even if you’re seeking other versions of advice. So there were lots of people like the pre-Ann Landers. All kinds of columnists. The Sob Sisters; there’s all kinds. They went on and on and on. But we get to Ann Landers and Dear Abby; Dear Abby being the more important one. And they were sisters, correct?

They were twin sisters. They were twin sisters and what happened was they ... The woman who would later become Ann Landers got the gig first in Chicago. Her first months on the job, she and her sister co-wrote the columns because she was really overwhelmed. She had never written professionally before.

How’d they find her?

She applied and there was a test. Basically, Ruth Crowley, who had been writing the column before her, died unexpectedly and they had a big test to see who wanted to fill her shoes. She applied and got the gig, but she had never written professionally before. And she was really overwhelmed and she roped in her twin sister to help her. And her editors were like, “We can’t have someone outside the paper reading all this confidential information. Sorry, that’s not going to happen.”

And then Dear Abby was heartbroken because she really loved the job, and then she sort of just browbeat editors at the San Francisco Chronicle to give her a column of her own. And so, within six months, they were competing with each other and they were the two main advice columnists in America. And they weren’t speaking for many years and they were always trying to sort of get gigs out from under each other. And they had a very contentious relationship because they both took the same path.

What’s interesting about them is they have very similar advice, even though they were so competitive with each other. And what interested me about them is they were giving advice for such a long time, they really see the norms change over the four decades that they were giving advice. They start off feeling one way about gay marriage ...

Against it.

... and interfaith marriage. Yes, against all those things. And by the end, they have quite progressive positions.

Was that dictated by the newspapers? Or by them themselves?

By them. One thing I will say is that I’ve found that giving an advice giver ... advice giving has sort of a reputation for conservatism, of saying like, “This is the right way to behave here.” And that’s why a lot of people bristle with the idea that there are norms and people are censoring you to achieve those norms. But one thing I will say is that if you look at advice givers who stuck with the job for a long time, it has an impact of making people more progressive. Dr. Spock, for instance, who I write about in the book, started with a very strict idea of how parenting should work, and by the end of his career had a much more progressive idea.

Had evolved himself.

And part of that is times change, but part of it is, I think, they were just exposed to so many different ways of living by the questions that were being asked. Yeah. I think it did, sort of, garner more empathy than they had at the beginning.

Do you ever see that the idea of advice giving is a way to control society? Because a lot of the more ... “draw within the lines, stay within the rules, this is the way you do it. You can’t do this. You can’t do that.”


They do that. I read them. And I’m like, “I can’t believe I’m listening to this.”

Yeah, I mean, it’s horrifying. Their early columns, by Ann Landers and Dear Abby, when they’re saying that a women should stay in a marriage even if she’s being hurt by her husband is quite disturbing. And that’s certainly a trend of advice givers. And the desire to have that role, the role of being the arbiter of what’s right and wrong in America, I think inspires some interesting power-hungry people. And you see that there’s a tension in all these people, between wanting to help and wanting to achieve a very unique kind of power, and I’m interested in seeing that sort of balance.

Were any really awful advice givers who really were like that?

Yeah, I mean, there were ... None of the people I wrote about in the book, I think, are unilaterally awful, because I just didn’t think that would be a very interesting book. But I would say there are advice givers who, I think, are saying very irresponsible things in very public places, and that’s been true throughout history.

Such as?

Well, for instance, I ... like as contemporary example?


Like, I see a lot of things on Goop and I’m like — the Gwyneth Paltrow site — and I’m like, “Oh, that seems pretty dangerous.” Like a lot of medical ...

So she wants you to put things in your various body parts.

That seems pretty risky.

Well, there’s health stuff and then there’s personal stuff. Emotional stuff.

And then emotional stuff, I think that there’s ... I mean, especially today when anyone can become an advice giver and there’s not as much of a centralized role as there was with Dear Abby and Ann Landers. If you go looking on the internet, you can find some ...



And we’re going to get to that in the next section, but I want to finish up with Dear Abby. So, what happened to them? They syndicated these columns, they were everywhere. My grandmother used to read them.

Oh really?


And my mom used to read them too. Helen Gurley Brown was much bigger for my mom, but ...

Who was at Cosmopolitan.


She was more like, “Everybody have sex.” “Sex and the Single Girl.”

Yeah, that’s really interesting to think about her advice now in the era of MeToo. Because her advice was like, “If someone makes a pass at you, it’s a compliment.” And she was also such an inspiring person for people like my mom who didn’t know that many women who worked. And it was like, “You should work. Women should work. But if your boss makes a pass at you, it’s fine.” So you read that today and it’s sort of horrifying.

Well, nothing ever holds up, does it? So you can watch societal norms change with the advice givers.


That’s what’s interesting about it in lots of ways. And it’s interesting that they’re not accountable for what they said in some cases. Like, what you’re talking about with Ann Landers, about staying in a marriage that’s dangerous. They’re not necessarily accountable.

Yeah, it’s a slippery role. Because they’re not politicians and they’re not academics. They’re just people people are seeking out for advice. So it gives them a lot of flexibility, a lot of moral flexibility. And you see people sort of shifting their values over time to reflect those of the time they’re in.

Absolutely. All right, we’re here with Jessica Weisberg. She has a new book called “Asking For a Friend, it’s about advice givers over the centuries. When we get back, we’re going to talk about the internet and how that’s changed that.


We’re here with Jessica Weisberg. Her book is called “Asking for a Friend.” It’s about advice givers. Let’s finish up talking about the internet, because that’s sort of changed everything.


It’s one big advice-giving platform, essentially. You start with Google, really, which is an advice giver as far as I’m concerned. How do you look at it now because it seems like ... I remember there were tons of companies that started. I don’t even remember the names of all of them. Epinions ... Yelp is even .... People giving advice about restaurants. It’s everywhere, essentially.

What’s interesting about the internet as an advice giver as opposed ...

It’s an oracle, really.

Yeah, it’s an oracle. One of the things I have found throughout my book is that it took a century or longer for women to be able to get platforms for advice and much longer for people of color to be given opportunities ...


... to give advice for a public ... a public platform to be offering advice. So an advantage of the internet is it’s much easier to find people whose experiences resemble your own, and the democratic nature of it benefits advice givers the way it benefits a lot of different parts of our communication. And then the other side of that is that we’re all seeking advice from different people in a way that sort of changes I would say what advice, it changes a little bit about what advice was originally intended for.

Like when Benjamin Franklin wrote “Poor Richard’s Almanack,” he wanted to give individuals advice, but he was also thinking about rules to make society better. He talked about how his book was making ... He hoped that “Poor Richard’s Almanack” would make the economy thrive and would make people harder working.

Now that the internet gives us a more segmented idea of how to live and what’s appropriate, it doesn’t have that quality. And then the good thing about that is that we’ve talked a lot about norms and how a lot of the norms the advice givers provided over time were quickly outdated, were somewhat oppressive, and obviously, we live in a time when because we have fewer centralized norms, it’s somehow easier to avoid those sort of oppressive ideas of how you should live.

Right. Is that a good thing? Because again, when I think about Google, it’s just literally, it’s everything.


The story I was thinking about is when I was there ... I was there in the early days when they were doing it, but one time I was sitting there, and they started to do this ticker where things would come through, like what people were asking about. I used to think about it as the database of human intentions. Like what are they intending to look for? And so they would screen out the porn stuff, which was quite a lot, and the queries and things like that. I would always be fascinated by why people were stringing words together. What did they want? I think it was searching. I mean, I know it’s ... They are search, but advice is searching for an answer kind of thing. I was always ... Like, there was one that was like “Clydesdale horse, Mars” and some other thing. I’m like, “What do they want? What are they looking for?”

And so I started to ... I remember sitting there in this lobby, going ... It was a really interesting moment of asking questions, people asking questions. One of the things that was interesting is Google also had a globe where it would ... They could see where the queries were coming from and what languages, and beams of light would come off this globe of where questions were being asked all over the world. The U.S. was English. It was in white. Russia was in red. They were being funny about the Communist countries. So you’d see lights coming off of cities and everything else.

When they spun around, interestingly, to Africa, because they didn’t have connections there, there were no questions. Of course there were questions there. Everybody has questions. But the ability to ask questions was a really interesting phenomena, but now it’s gotten noisy, right?

Very noisy.

Now, there’s too many questions or too many answers, really.

But I think that’s a really, that’s a really good point about what are people seeking when they seek advice. Like, are they seeking a straightforward answer? Are they seeking someone just to tell them that everything’s fine and the decision they made is valid? Are they just seeking a community of people who maybe share their experiences?

What do you think?

I think it varies. I think one of the advantages of the internet is that it can be all those different things depending on where you go. If you look at Dear Abby and Ann Landers, a lot of people of our time were really using their columns the way we use a chatroom. They were asking questions and then hoping that another reader would answer them. Not necessarily Dear Abby or Ann Landers. I think that’s what the internet provides. It provides community ...


... and connection in a somewhat anonymous setting.

Why that, though? Because it used to be your town was like that, and everyone knew what you were doing, but then you were limited by the people in the town and their prejudices or their experiences, essentially.

Yeah, I think it’s that. Like we all, none of our communities are perfect, as much as we might love them. And then I think what you see over time is that being anonymous is a really freeing tool and that there’s something about being able to escape your own identity that allows you to ask questions that hit a different place than they would otherwise.

At the same time, though, it does keep you from other things, which is behavioral.


Let’s talk about that, because the internet’s gotten out of control, I think a lot people feel, not just the stuff that’s happening falsely, the false news part of it or whatever, the abuse of the platforms, but the idea that it’s a cesspool, really. It’s a noise. Like Twitter, I’m thinking of that, there’s tons of advice on Twitter.

Yeah, I mean, one of the things that sort of raised the stakes of the book for me was when — or made me relate to the people I was writing for — was when President Trump was elected. I thought a lot about how there was suddenly people in real life and on the internet saying things that were just so bigoted and so hateful and that these advice givers, while they were trying to censor people, they were trying to create ... Like it was in the name of people treating each other civilly. One of the people I interviewed for the book was Miss Manners.

Mm-hmm. Judy Martin.

Who’s wonderful.

Writes for the Washington Post. I know her.

She’s great. She talks a lot about how ... Like, she wishes people were a little less honest online and that she sees sort of etiquette as a way to combat bigotry. I think that just the changes of online, just how big of a cesspool it became, made me sort of relate more to the formalized ideas of advice that older people gave, even if it was very strict in terms of how people should behave, that the intention of creating those standards of behavior was a good intention, if it also did restrict the way people ... It made people feel bad about themselves.

But is there any way to take the, to put the ...

Good with the bad?

You can’t put the top back on, right?

No, you can’t.

It’s interesting, because I think it has degenerated conversations, degenerated advice, and people are confused almost continually. I feel that way, and I’m an older person, but my kids, they ... It’s a very ... There’s no central advice situation anymore, or there’s no one you trust to give good advice. Maybe Oprah. I’m trying to think. I often quote Oprah. I don’t know why. I just do because she makes sense, but is there, in this noisy cacophonous situation we’ve gotten ourselves into, where does advice go? What happens to it?

Yeah, I think it’s very, very individualized. You go online and you type in whatever search terms that you are inspired to type in, and you go down the rabbit hole that you found for yourself. What’s interesting is that, on the one hand, it’s this idea of you can be connected to anyone in the world, but it’s such an individualized experience, you’re not necessarily ... The answers you’re seeking aren’t necessarily corresponding with the answers anyone else with the same problem is seeking, because there’s such a cacophony.

So what do you imagine happening? Because then, you could think of AI, all kinds of things, they can give you advice too. Like computers can give you advice and probably better advice than people in lots of ways, or statistically speaking, if you do this or you do that. Where do you imagine advice going?

I think the history of advice is also the history of media. I think it’s headed in the same direction that media is going, which is chaotic, and that this sort of standards and taste are just becoming more fragmented in terms of what people are seeking and what we consider “good.” I think that’s happening in every way in the media.

Is there a big advice giver now online, you would say? Well, there’s all the YouTube stars, there’s ...

There’s the YouTube stars, and of course there’s Oprah, and then there’s all the advice givers who sort of fall of like under the Oprah umbrella, but other than that it’s YouTube stars ...

Dr. Phil.

Dr. Phil, Martha Beck, who I write about in the book. So there’s Oprah, but other than that, it’s just everyone. It’s celebrities who offer advice on their Twitter feed, and YouTube stars who offer advice in a variety of formats. It’s Quora where I think people ... It’s like a, it’s really for advice.

It’s an answer site. Yeah. Answers, they’d say.

But yeah, I think it’s become more and more fragmented. That’s the way the media’s going, like not just ...

Do you imagine there ever being a big advice giver or big central anything for humanity? Or the country or wherever?

I think that that’s ... It’s harder to imagine now. I think that because of just the ... It’s harder to imagine one person being trusted by so many different segments of the population, which isn’t to say that everyone trusted Benjamin Spock. A lot of people thought he was ... I mean he got a lot of ... People really disliked him and thought he was too liberal. But he was very, very trusted by huge swaths of the population. The idea of one person achieving that sort of ... for people to circle around one person, it seems somewhat impossible in our society today. What do you think?

No. I don’t think so. I think computers will be giving the advice — and probably good advice, probably better advice than people in a lot ways — but then you lose the heart of it. Like AI can really mimic people really well over time.

Better how?

They will have ... In terms of just information, it’ll be better. In terms of information, it will understand your patterns. It’ll understand what you want. I think you can get to points of machine learning or advanced artificial intelligence that will be quite strikingly sympathetic or at least mimicking sympathy or something. And then you wonder if there’s a feeling computer, like if there’s a feeling ... Or there’s parts of your brain that you can access. There’s all kinds of ...

I just did read Michael Pollan about LSD and how to change moods. That might be the way it goes. It might be chemical and digital, the way we feel better about love or whatever. I don’t know. I don’t know. But you could start to think where it could go.

Yeah. Absolutely. I think what’s sort of ... We started the conversation with Cheryl Strayed as a person who divulged so much about herself, and to me, like that ... AI will not be able to achieve that, the sort of connection with another person, the sort of deep pen pal-type relationship that some advice givers were able to give their readers. That seems unachievable with AI, even though there is an understanding, like a sense of connection, that people can have with AI. But the idea, that learning about someone else’s experience and seeing yourself in their experience, that, I feel like that will not be available.

All right, all right. We’ll see what happens. Last question for you, Jessica. What’s some of the best advice you got doing this? Do you have any advice for anybody?

Sure. Do I have any advice for anybody? Let’s see. The best advice I ... I would say that one of the pieces of advice I wrote in the book that I think about the most is this Dorothy Dix who was writing for women at the turn of the 20th century. Someone wrote to her feeling really stressed out about all sorts of things, about her marriage. She said something about like, “It’s amazing what a walk around the block will do.” I was like, “That’s really good advice.”

Yeah, it is.

It’s really applies to almost every situation.

It’s absolutely true. It’s 100 percent true.

Yeah, so that’s probably ... That’s one giveaway.

That is a good piece of advice. One the things I’ve been using a lot is, speaking of digital, is a thing called WeCroak.

Oh, interesting.

... which I talk about all the time. It was 99 cents. Allegedly, in Bhutan, they think about death five times a day, and so this ... I consider it advice. They send you quotes five times a day.


Death-oriented quotes. Yeah. It’s fascinating. This one is, this one is Seneca, so there’s five of them a day. They pop up. They’re quite good. A lot of it’s Joan Didion, Euripides. This is Seneca. It says, “The whole future ...” This came up this morning. “The whole future lies in uncertainty. Live immediately.” I think that’s a good piece of advice.

That’s a very good piece of advice.

It’s interesting. It does stop you for a second and makes you not ... When you’re upset about anything from work to love to whatever, you’re like, “Eh, it’s a fair point. I’m going to die.”

Maybe not think about that ...

I think the best advice I’ve ever seen was Steve Jobs’s speech on dying.


I think that was ... I think about that all the time. All the time, and I don’t know why. I can’t tell you why. I was surprised by the source, I’ll tell you that. That was ... And I think we do get our advice from technology giants in a way we probably shouldn’t, which is interesting. In any case, would you have any advice for us?

Other than the walking around?

Walking around. I’m going to walk around!

Take a walk around the park.

Walk around the block. Got it. It was great talking to you. Jessica Weisberg’s book is called “Asking for a Friend.” It’s available now. It’s about advice givers and how it’s changed over centuries and where it’s going.

Thank you for coming on the show. It was really great talking to you.

Yeah, thank you for having me.

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