Gretchen Rubin joins guest host and Infinite Books CEO Jimmy Soni to discuss her journey from Supreme Court clerk to bestselling author, the creative obsessions that shaped her career, and the daily habits that fuel her work.
They cover her transition from law to writing Power Money Fame Sex, why she often ends up writing the book before the proposal, the art of editing until the final hour (even during pass pages), her 5:30 AM writing routine, and why "know thyself" remains the foundation of all her books - from 40 Ways to Look at Winston Churchill to Life in Five Senses.
We’ve shared some highlights below, together with links & a full transcript. If you like what you hear/read, please leave a comment or drop us a review on your provider of choice.
Links
Highlights
Are You an Opener or a Finisher?
Jimmy Soni: I have the challenge of sometimes you’re sort of, you know, you want to dance with the girl that you brought, but then you have this other project. Like there’s always the other projects that you’re like…
Gretchen Rubin: ... A hooky book. That’s what I have.
Jimmy Soni: That’s a great... that’s a great one.
Gretchen Rubin: I often have a hooky book. Yes. Now my... when I was writing Better Than Before, my book about habit formation, my hooky book was a book that turned into Outer Order, Inner Calm.
Jimmy Soni: Wow. So how do you prevent yourself from going to... and turning the hooky book into the daily driver?
Gretchen Rubin: Right, right. Yeah, that it is. You’ve got to remember it’s a hooky book. For me, it’s all about note taking. So note taking is a big thing for me. So I will let myself take notes on it. Like, and I’ll... I might read for it and take, put notes into it, but I would never allow myself to begin to structure it. Because once I’m structuring, then I’m like, “Okay, now I’m really tackling it as a book.” But because I always start with a bunch of notes, having a bunch of notes, then when I’m ready to start writing, then I have this huge head start. So it’s a good use of my time. But you’re right, you’ve got to make sure that it doesn’t swallow up what your main project is.
Jimmy Soni: Sometimes, by the way, hooky books can yield something amazing, as you put it. You can have... I find that it’s tempting because the beginning of these projects is some of the best. Yeah.
Gretchen Rubin: Okay, so there’s beginners... there’s openers and finishers. Okay, so openers are people who love to open a project. So they love the beginning stages. They love to start something new. Like, I talked to a professor, and he’s like, “I have seven half-finished, you know, new curricula for new classes,” because he loved to open. But then there... and then finishers are people who love to end. They love to finish. And both of them have pros and cons because openers sometimes don’t finish. And so they don’t get the benefits of their work. And they can get distracted because they’re pulled in so many directions. But finishers, sometimes they just want to be done so badly that they might rush at the end because they’re just like, “Okay, I just really want to get this crossed off the list.”
But a lot of times it’s that last work that’s really painstaking and difficult that can really make something go to the next level. And sometimes they are too cautious about what they start because they think, “Well, if I can’t finish it, maybe I shouldn’t start it.” But sometimes with creativity, you kind of have to say, “Well, maybe I’ll start it and maybe it won’t go anywhere, but I need to just kind of get it started to see.” And so I think it’s good to know which one you lean toward so that you kind of can try to offset that.
Jimmy Soni: Are you an opener or a finisher?
Gretchen Rubin: I’m a finisher for sure.
Jimmy Soni: Okay.
Gretchen Rubin: I’m a finisher. I love to cross things off the list. And it is... it’s like towards the end, I feel myself being... let’s just... let’s just say it...
Jimmy Soni: Done.
Gretchen Rubin: Oh, here’s an edit. But I’m just going to decide I don’t agree with that edit. It’s like, I actually do agree with that edit. I just want to be done.
Jimmy Soni: Want to finish.
Gretchen Rubin: Yeah, I want to finish.
Why Do People Throw Their Possessions Away?
Gretchen Rubin: I went through a serious period of being absolutely obsessed with the question of why people destroy their own possessions. And I wrote a law school paper about it, then I wrote a novel about it. And then I actually published a book called Profane Waste as a collaboration with an artist, which is all about this question of why people destroy their own possessions. So I tried it every which way, and then I just ended up with nonfiction.
Jimmy Soni: So this is why you will now... you are now and will forever be one of my favorite people. Because these are the kinds of rabbit holes that I go down. Right. I’ll just find myself lost in some question that possesses you.
Gretchen Rubin: Yes.
Jimmy Soni: And then you ask...
Gretchen Rubin: So delightful.
Jimmy Soni: Yeah, it’s the best. I think Wikipedia scratched that itch for people who are satisfied with, like, you know, 10 to 20%. But then there’s a whole other level. So if you... if you rewind the clock and it may... I don’t know if you can remember this question of why people destroy their own possessions. How did you even get to the question itself?
Gretchen Rubin: Oh, I know exactly. I was again, I was in D.C. I was walking on my lunch hour. This is why it’s important to go for walks because you have all these ideas. And I went to the... one of the... I forget the exact title of the museum, but you know how the Smithsonians, you can just... they’re free. You just walk right in. So I walked in and it was a display about potlatch. And potlatch is a tradition of kind of exorbitant gift giving. It’s like the big man will give extravagant gifts and kind of give away everything as a... and there’s a lot of research about why the custom of potlatch existed. And then when trading came in, these groups of people became... had so much wealth that they literally couldn’t give it away fast enough.
And they were throwing goods into the ocean too, because they just... anyway, but this idea that people would destroy something as a way to show their possession of it just messed with my mind. Okay, then there’s another thing that happened. So this is in my mind. Then something happened. Where? Okay, so I was in law school. I was first year law school, so in love with the guy who’s now my husband. He was a summer associate at a law firm. And because I was so in love, I’m like, I’ll go with you and just do my own thing while you’re doing your summer associate thing. And on our way there, we stopped at a corner store and he bought a couple snacks. I got a couple snacks.
And one of the things he got was a piece of cheesecake wrapped in plastic. Why? I don’t know. So we get there, he does his work, we’re getting ready to leave, and I look in his trash can and I see there’s the unopened piece of cheesecake. And I say, “Oh, I’ll fish this out. You never opened it, like, you know, it’s still good.” And he goes, “No, I don’t want it anymore. Just throw it away.” And this rocked me to my core. I’m like, what are you talking about? What just happened? Right? You just threw it away.
Jimmy Soni: Right.
Gretchen Rubin: And I can... I mean,
Jimmy Soni: Did you have an explanation or did…
Gretchen Rubin: He was just like “Well, I thought I wanted it, now I don’t want it.”
Jimmy Soni: Oh, wow. And there was some part of you that was disturbed by this.
Gretchen Rubin: Absolutely baffled by it. And so that... and then the potlatch, this guy... and then when I got to law school and we were talking about property rights and all the bundle of rights that are property, I wanted to write a paper about it and a lot... and one of my law professors said, “But people don’t want to do that. That doesn’t make any sense. Why would somebody want to destroy their own property?” And I was like, that’s exactly my point. Why do people do this? It doesn’t make any kind of economic sense anyway. So I would talk about a rabbit hole. I went deep down there.
Transcript
Jimmy Soni:
Well, I have an amazing privilege today, which is I’m here with not just one of my favorite writers, one of my favorite people in the world, Gretchen Rubin. And to set the scene for people, this is you and I get together semi-regularly for lunch and to talk shop, catch up. And the way I describe these lunches to other people is I always tell them that they are like a Gretchen Rubin vitamin B shot of energy and ideas and inspiration. And you push me to think more critically about the platforms I’m on or what I’m doing or talk about this or that. And so I’m hoping that our conversation today captures some of that energy, because I do think of you as one of these great pushers of ambition and creativity.
Gretchen Rubin:
Well, I’m so happy to hear you say that. I feel exactly the same way. I feel like I leave our conversations with homework because I have to go home and look something up and figure out how to do something.
Jimmy Soni:
See, that’s way less nice than the version I did.
Gretchen Rubin:
No, that’s the highest praise. Like, I’m actually going to do what you tell me to do.
Jimmy Soni:
Amazing. So I thought what we would do just to give people a sense of where your career started and where your writing career started. You were a recovering lawyer, you went to law school. So can you just walk us through kind of how you got from law school to the formal work of doing books, but just from your legal career to your authorial career?
Gretchen Rubin:
Okay, so I went to law school for all the classic wrong reasons. It was a great education. It’ll keep my options open. I can change my mind later. I’m good at research and writing, so I’d probably be good at this. My father’s a lawyer. So I went to law school. Did very well in law school. I was editor in chief of the law journal, and then I went on to clerk for Sandra Day O’Connor. But at that time, I was sort of starting to realize that I didn’t know what I wanted to do next. And simultaneously, I have this habit of asking myself theoretical questions, just, I don’t know, kind of conversation starters with myself. And I was out on my lunch break.
I was looking up at the Capitol dome, and I thought, what am I interested in that everyone else in the world is interested in? And I thought, well, power, money, fame, sex. And it was like, power, money, fame, sex. It was like this one big idea. I instantly got incredibly preoccupied with it and started just doing masses and masses of research and note taking, which is something that happens to me all the time and has happened to me since I was a child. So this was very familiar. So I was doing all this research, doing all this note taking, and then finally it occurred to me this is the kind of thing a person would do if they were going to write a book. Maybe I could write that book.
So I went to Kramerbooks and Afterwords in D.C. and got a book called something like How to Write and Sell Your Nonfiction Book Proposal.
Jimmy Soni:
Oh, wow.
Gretchen Rubin:
And then, you know, cut to, I followed the directions and that’s how I got my first agent. And that was my first book, Power, Money, Fame, Sex: A User’s Guide.
Jimmy Soni:
Got it. Okay.
Gretchen Rubin:
So that’s how I switched from law to writing.
Jimmy Soni:
Got it. So what I find interesting with that is theoretical question piece. How long has that been a habit? Because you’re one of the great studiers of habits. Have you always done that? Is that something that...
Gretchen Rubin:
Yeah, often it will be a question or it might be a word. Like I went through a period where apocalypse was a word that I was really preoccupied with. And I ended up writing this really bad novel that I have locked in a desk drawer. Or when I was very young, I was really interested in the Salem witch trials. And so I have this little notebook that’s just my nine-year-old handwriting of sort of facts about the Salem witch trials. Now for some reason I have this incredible antipathy to any plot having to do with unjust accusation. So probably as a result of that, I would never study the Salem witch trials now. But yeah, so I will...
And then I got really preoccupied with the subject of color, in a way that I really couldn’t explain. I was just... did enormous amounts of research and I even wrote a little book called My Color Pilgrimage. And I showed it to a couple editors and they were like, “Well, you really had fun with that, didn’t you?” It’s like, that’s not the answer I’m looking for. You know, like you’re a child. So I turned it into... this is, okay, Jimmy, you’ll appreciate this. Like this is very much a today’s solution. I was like, I’ll adapt like 30% of that material and I’ll make it into a bonus for paid subscribers on my Substack.
Jimmy Soni:
There we go.
Gretchen Rubin:
Because nobody seems... so far, nobody wants the entire My Color Pilgrimage. But there’s really good stuff in there. So it is something that’s happened to me. Or like I remember with Churchill when I just all of a sudden was just like, oh my gosh, all I wanted to do was think about Churchill morning, noon and night. And so when I get... that’s when I usually, when I start a book, that’s amazing.
Jimmy Soni:
You reminded me of something, which is there are all of these creative people I admire, yourself included, who have projects that they have taken, let’s say 40, 60, 80, or even 100% of the way, and then haven’t had them see the light of day. And I remember either reading or talking to you about novels that you had unfinished. So that is tantalizing. Like, what are those projects?
Gretchen Rubin:
Okay, so they’re all finished, they’re just bad. But one of the things I would warn anybody doing a creative project is that if you suddenly lose interest, like call it 80% of the way there, if you’re all of a sudden like, “Oh, I just, I’m not interested in this project anymore,” it’s often a failure because if you finish, then it becomes like, am I going to try to get an agent? Am I going to show this to my agent? Am I going to show it to anybody? Like, am I going to admit that this is the best that I can do? And sometimes I think people turn away from it out of self-protection. And so once you get to a certain point, I’m like, take it all the way and then let it succeed or fail.
And like My Color Pilgrimage, like, let’s just say it did not succeed in what I wanted for it.
Jimmy Soni:
But it got a second life now.
Gretchen Rubin:
I found a... as you say, you find a second life for things. You never know. What do they call it? Saving string where things can end up paying off. But any kind of... I think for people who are doing creative work, anything that you’re interested in doing, it’s like, if nothing else, it’s doing scales. If nothing else, it’s practice. If nothing else, it’s learning and not, you know, every... you know, the more failure, the more success means probably the more failures too, right?
Jimmy Soni:
Did the novels come before the nonfiction work or did you... like how, when, in what sequence were the novels? The unfinished, and I’m sure better than you think novels...
Gretchen Rubin:
No they’re finished, they’re just bad. You know what it is? Growing up, all I read was novels. I was an English major. I just read novels all the time. And I didn’t really... so they were novels of ideas, because I didn’t really understand that what I wanted to do was write nonfiction. So I was trying to channel ideas that I had through fiction. That’s very hard to do. Most good novels are really about character. And so once I switched to nonfiction, then I sort of stopped writing novels because I found the right vehicle for the ideas I wanted to express. Yeah, I wrote a novel in law school. I wrote a novel about... because I went through a serious period of being absolutely obsessed with the question of why people destroy their own possessions.
And I wrote a law school paper about it, then I wrote a novel about it. And then I actually published a book called Profane Waste as a collaboration with an artist, which is all about this question of why people destroy their own possessions. So I tried it every which way, and then I just ended up with nonfiction.
Jimmy Soni:
So this is why you will now... you are now and will forever be one of my favorite people. Because these are the kinds of rabbit holes that I go down. Right. I’ll just find myself lost in some question that possesses you.
Gretchen Rubin:
Yes.
Jimmy Soni:
And then you ask...
Gretchen Rubin:
So delightful.
Jimmy Soni:
Yeah, it’s the best and honest. I think. I think Wikipedia scratched that itch for people who are satisfied with, like, you know, 10 to 20%. But then there’s a whole other level. So if you... if you rewind the clock and it may... I don’t know if you can remember this question of why people destroy their own possessions. How did you even get to the question itself?
Gretchen Rubin:
Oh, I know exactly. I was again, I was in D.C. I was walking on my lunch hour. This is why it’s important to go for walks because you have all these ideas. And I went to the... one of the... I forget the exact title of the museum, but you know how the Smithsonians, you can just... they’re free. You just walk right in. So I walked in and it was a display about potlatch. And potlatch is a tradition of kind of exorbitant gift giving. It’s like the big man will give extravagant gifts and kind of give away everything as a... and there’s a lot of research about why the custom of potlatch existed. And then when trading came in, these groups of people became... had so much wealth that they literally couldn’t give it away fast enough.
And they were throwing goods into the ocean too, because they just... anyway, but this idea that people would destroy something as a way to show their possession of it just messed with my mind. Okay, then there’s another thing that happened. So this is in my mind. Then something happened. Where? Okay, so I was in law school. I was first year law school, so in love with the guy who’s now my husband. He was a summer associate at a law firm. And because I was so in love, I’m like, I’ll go with you and just do my own thing while you’re doing your summer associate thing. And on our way there, we stopped at a corner store and he bought a couple snacks. I got a couple snacks.
And one of the things he got was a piece of cheesecake wrapped in plastic. Why? I don’t know. So we get there, he does his work, we’re getting ready to leave, and I look in his trash can and I see there’s the unopened piece of cheesecake. And I say, “Oh, I’ll fish this out. You never opened it, like, you know, it’s still good.” And he goes, “No, I don’t want it anymore. Just throw it away.” And this rocked me to my core. I’m like, what are you talking about? What just happened? Right? You just threw it away.
Jimmy Soni:
Right.
Gretchen Rubin:
And I can... I mean,
Jimmy Soni:
Did you have an explanation or did…
Gretchen Rubin:
He was just like “Well, I thought I wanted it, now I don’t want it.”
Jimmy Soni:
Oh, wow. And there was some part of you that was disturbed by this.
Gretchen Rubin:
Absolutely baffled by it. And so that... and then the potlatch, this guy... and then when I got to law school and we were talking about property rights and all the bundle of rights that are property, I wanted to write a paper about it and a lot... and one of my law professors said, “But people don’t want to do that. That doesn’t make any sense. Why would somebody want to destroy their own property?” And I was like, that’s exactly my point. Why do people do this? It doesn’t make any kind of economic sense anyway. So I would talk about a rabbit hole. I went deep down there. Yeah, it’s such an interesting subject.
Jimmy Soni:
That is totally fascinating on a number of levels. And did you... at that point, you knew you had this curiosity and you knew you had this kind of... you had wanted to sort of take ideas and make them packaged in some way. Novels weren’t going to be it, because novels are based on character, so... but you also achieved the highest heights of like, legal... of what someone could do with a legal education, like clerking for Supreme Court. That is the... that is the NBA of law school graduation. Right. And so... so were you ever at any point in your career, like surely were torn to like, what might be considered more practical, like go down the law, like make partner or all of that. That track against this following every, you know, your curiosities. How did you, how did you deal with that? Sort of in the tail end of law school and then immediately after.
Gretchen Rubin:
Well, right after law school, I went to work for the Federal Communications Commission. So in there I was really acting as a lawyer. I just, I didn’t know what I wanted. I noticed that when I would look, you know how you read your alumni notes, you get that magazine or whatever. And I realized.
Jimmy Soni:
By the way, I don’t think most people read their alumni notes. I think people like you and I read...
Gretchen Rubin:
If one reads.
Jimmy Soni:
Do you know why I read it, though? Do you know the real reason is because I always read it for the... it’s a... it’s a reminder. It’s like the, you know, memento mori. Because it covers people who are gone.
Gretchen Rubin:
It does, right? Sure does.
Jimmy Soni:
And you have this connection to them. Like I look at my Duke.
Gretchen Rubin:
You know they’re your exact age.
Jimmy Soni:
Exactly. And you go back to the end. And I always look for the people who are the untimely deceased, the ones who are close to me in age, where we have the same experience, we lived the same four years at Duke. And you know, for some one reason or another, they’re here, they’re not here, and I am. Right. And it kind of invests your time and your life with a bit more significance. That’s the reason I do it.
Gretchen Rubin:
That’s a great... that’s a great... that’s a great reason. That’s a great... I’m going to start doing that too, because I know exactly what you mean. For me, it was just curiosity, but I noticed that when people had really interesting law jobs, I felt sort of like mild interest. But when they had really interesting writing jobs, I felt sick with envy. So that was one data point. But one of the things that really made it easy for me is I think a lot of times people know they want to leave, but they don’t know where they want to go. And for me, it was less about leaving law and it was more like wanting to write. And it wasn’t even that I just wanted to be a writer where I think some people are like, “I’d like to be a writer.” I’m like, I want to write a book called Power, Money, Fame, Sex. And I have done like a thousand hours of research and note taking about it. And I really want to do this project. And so it was very clear what it was I was aiming for. And I think that made it easier in my mind. So you know the scene in the original Star Wars where they’re in the Millennium Falcon, they’ve got the tractor beam on them, and Han Solo says, “We have to stop pulling back because we’ll rip the ship apart. We have to allow ourselves to be drawn to this destination.” And I’m like... I just felt like I was in the tractor beam, and I was just being drawn so forcibly toward it. I thought, I’d rather fail as a writer than succeed as a lawyer. I have a project in mind. I’m moving to New York City. This is my time to take a shot. And if I fail, then I’ll figure out what I want to do later. But if I take another law job now, it might be too hard to switch. I will have started to invest so much.
Jimmy Soni:
Yeah, because there’s already... I mean, you’d gone and gotten a degree, you’d run the gauntlet.
Gretchen Rubin:
No, I know, right? If I... any more investment in it starts to become something that you just can’t step away from.
Jimmy Soni:
Yeah. I like this metaphor of the tractor beam as a way of thinking about creative influences and things that pull you in. Is that something you’d consciously thought of in the past, like the idea of what’s pulling you creatively in a certain direction or another?
Gretchen Rubin:
I mean, I don’t know about you, but for me, there is a compulsive element to it which is incredibly gratifying, but sometimes inconvenient for people, or it’s not what they want. I think sometimes people feel compelled to do things even though they kind of rationally know it’s not a good idea, but they just can’t resist it. I definitely know that feeling.
Jimmy Soni:
In your case, though, the writing of books happens to be a compulsion, but also a positive compulsion.
Gretchen Rubin:
It’s been very positive for me, but, like, let’s say I couldn’t afford to take a risk.
Jimmy Soni:
Right.
Gretchen Rubin:
Then maybe I would have had to make a different choice. And then it would have been extremely painful for me not to have been able to write the books that I wanted to write.
Jimmy Soni:
Right. So we’re going to bounce around a little bit chronologically. But, you know, one of the things that is true of the writers I know is at one point or another, their childhood was consumed by books. Right. Not everyone, but I would say there’s a pretty high overlap. Like, it’s like 90 plus percent. What was your childhood relationship to books like, how did you...
Gretchen Rubin:
I read all the time, but I... but I read nonfiction. I mean, not nonfiction. I read fiction all the time. No, I was a huge reader.
Jimmy Soni:
Did anybody spark that in you, or was that... how did that start for you?
Gretchen Rubin:
My whole family are readers, and so it’s like a very... like, we would go to the library every week, and it was a really big deal, but so I saw people reading for pleasure. We had a lot of books in our house, but... but it was... yeah, I remember, like, they had to tell me I had to go outside for a certain amount of time when I was little, because otherwise I would just stay indoors and read all the time. So they were like, no, you have to go out for, you know, 45 minutes every afternoon after school. Yeah.
Jimmy Soni:
Did you have favorites growing up? Do you remember some of your favorite readings?
Gretchen Rubin:
A bazillion. And, you know, I still have a love of children’s literature and young adult literature. I’m in adult groups where we read young adult literature and children’s literature, so... but then... but I was also one of those kids who started reading adult books very early. Jane Eyre. You know, I remember Jane Eyre being the first sort of really adult book that I read, and then, you know, all of the trashy novels that you’re not supposed to read when you’re young. But... yeah, even, like... and not even really understanding books like, you know, David Copperfield, but wanting to read adult books.
Jimmy Soni:
And so for me, the books that changed or that engrossed me, I mean, I had a bunch, but it was the Mossflower and Mattimeo series by Brian Jacques was one that stood out for me. And I remember just being able to lose myself in them for hours. And, like, sometimes I’d look up, and all of a sudden, like, day had turned to night, and I didn’t even realize... what were the... do you have... if you have titles in mind from when you were a kid, what were those for you? Did you have anything that stood out?
Gretchen Rubin:
It’s such a basic answer, but I have to say Narnia.
Jimmy Soni:
Oh, really?
Gretchen Rubin:
Yeah.
Jimmy Soni:
That’s not a basic answer.
Gretchen Rubin:
Yeah, yeah. Yeah, I love...
Jimmy Soni:
That’s amazing.
Gretchen Rubin:
And the thing is, I still admire C.S. Lewis tremendously as an adult writer, too. So, I mean, one of the things I love about children’s literature is that a lot of them are masterpieces of literature on their own terms. And it’s, you know, great writers doing... you look at something like Charlotte’s Web, it absolutely will stand up to any adult novel. You know, and just like his adult work does, such as his children’s work. Yeah.
Jimmy Soni:
So fast forward. Actually, this is a bit of a tangent, but you’re... you, you know, you became a parent. How did you encourage this in your daughters? What’s their relationship with reading? Like, how do you think about the parenting... parent as reader trying to inculcate a love of reading into kids?
Gretchen Rubin:
That’s such a great question.
Jimmy Soni:
Asking for a friend.
Gretchen Rubin:
Asking for a friend. But your child is a big reader already.
Jimmy Soni:
She is already and she reads obsessively.
Gretchen Rubin:
You don’t have to fan those flames. I kind of think a little bit people have to find their way to it. But it’s interesting because my two daughters who now are in their 20s, I would say didn’t read a lot for pleasure, but now they are much more. And even my 21-year-old came home from... for college break and was like, “I want to read. I want to spend the summer reading classics. I feel like I haven’t read enough of the classics.” So maybe people come to it later.
Jimmy Soni:
But I feel like you didn’t do any... there weren’t active steps you took other than having books around and being an author and all of that and talking...
Gretchen Rubin:
About it and having people talk about... my husband’s a huge reader too. He reads a lot of policy. He reads a lot of very contemporary fiction. So it was always that people were always talking about it and, you know, but I think the more you sort of try to make people do, then you... I worry about igniting the spirit of resistance.
Jimmy Soni:
Right.
Gretchen Rubin:
Because it’s supposed to be fun. The reason you do it is because it’s fun. But one thing I will do is like, I will be like, “Have you read The Secret History?” You know, like, give them something that you know is going to be really high payoff. Like a really good book.
Jimmy Soni:
Did you write as a child? Did you write stories?
Gretchen Rubin:
No, I didn’t do that .
Jimmy Soni:
Write for the school paper.
Gretchen Rubin:
Well, I wrote for the school paper, but only just in a very perfunctory way. Not like, “Oh, I’m going to be a journalist” or anything. I’ve never had the desire to be a journalist.
Jimmy Soni:
Got it. So it was always ideas and just rabbit holes that you were going down.
Gretchen Rubin:
Yeah.
Jimmy Soni:
And then sort of how to work backwards from there.
Gretchen Rubin:
Yeah.
Jimmy Soni:
Okay.
Gretchen Rubin:
Just on my own.
Jimmy Soni:
So let’s go through the first book in some detail, the process of the first book. Because I think... we’ll recommend your books and people should check them out and we’ll talk more about them toward the end of the interview. But the... the question I have is the first book is like the big threshold. You don’t really... these are like... so you sort of have these book objects, you know that theoretically somebody is behind them. Right, like somebody does something.
Gretchen Rubin:
Yes.
Jimmy Soni:
So you went and bought a book called How to Write Your First Nonfiction Book
Gretchen Rubin:
Book proposal. Because, as you know, like, one thing I think a lot of people don’t understand is writing a proposal is very different from writing a book. And getting an agent is probably harder than actually getting a book deal. So it’s very... the challenge of being a sort of traditionally published author is very front loaded.
Jimmy Soni:
Yeah, but you’re doing this in an era of... so I had the equivalent experience. So my story of the first book is I googled “how to write a nonfiction...”
Gretchen Rubin:
Right.
Jimmy Soni:
But you had to go to Kramers and buy…
Gretchen Rubin:
And buy a book.
Jimmy Soni:
Right. So what was that... what was that like? How did you know that the idea had merit? You know, now you can test ideas. You can put things on Substack, you can put things on Medium, you can put things on LinkedIn. Right. How did you even know to go down that road?
Gretchen Rubin:
Just the utter commitment. Like, I just... it just felt irresistible. But, you know, one thing that’s happened to me over and over in my career is I’ll have an idea and I’ll be like, “This is an amazing idea. This is so fascinating. Everybody’s going to love this idea.” And people will be like, “Yeah, I don’t really get it. I don’t really think so.” And so I often end up writing almost an entire book...
Jimmy Soni:
Oh, wow.
Gretchen Rubin:
Before I write a proposal, because I feel like I have to have it so well developed in my mind before I can describe it in a way that other people see its potential. Like The Happiness Project, my current project, Power, Money, Fame, Sex. I really had to do a huge amount of... it’s very hard to describe what you’re going to do, I think. So I often end up... which is... then I often end up throwing out just a gigantic amount of material because I may have completely changed my entire structure. You know that. That has happened to me many times. I have many versions, almost complete versions of things that then I was like, “No, this isn’t the right approach.” And I’ve had to recast it.
Jimmy Soni:
Have you ever taken a project that far and just abandoned it entirely? Like…
Gretchen Rubin:
No.
Jimmy Soni:
So something’s always netted out from the work you’ve done.
Gretchen Rubin:
Yeah. But I think sometimes... well, I wrote a book called Life in Five Senses, and it’s about life in five senses. And at first…
Jimmy Soni:
Beautiful book.
Gretchen Rubin:
Well, thank you. Thank you. I loved writing that book. But so first there were nine senses. And I wrote it for nine senses. I’m like, “No, actually there’s 11 senses.” And I wrote it for 11 senses. And I was having all this trouble and I was like, “Do I divide it into sub things? I’m like, what about this? What about that? Which ones are alike, which ones are different?” And then I was just sort of like, you know, sometimes you can intuit by extroverting. And you just... I was just talking it out with somebody and they said, “Maybe you just want to do five senses.”
And I was like, “Oh my gosh, this is the big insight of all time.” Like, went home, like, really just threw away everything that didn’t fit. Just did five senses. Which if I had gotten a board book for a three-year-old, it would have been seeing, hearing, smelling, tasting, touching, the five senses. And that was the structure I ended up with. But it took me so long.
Jimmy Soni:
It took you this…
Gretchen Rubin:
But you do have to write through that. Like, you have to understand, like, why is this? What, you know, why am I writing about this and not that? How does this all, you know, how does proprioception... what are my thoughts and feelings about proprioception? Turns out, yeah, I don’t have to go into that so much.
Jimmy Soni:
So when you open up this book, How to Write Your First Nonfiction Book Proposal, what was the process like between that and getting an agent? Just like, you know, brass tacks, because you’re not just, you know, now, if you and I were to work on a proposal, we’ve seen it done. We know what we’re doing. We can kind of approach certain... we know what the method is like, but you’re doing it for the first time.
Gretchen Rubin:
There is a strange variety. Like, I do feel like there are many different ways people do proposals. There’s like, do you do 40 pages or do you do four pages? Do you do, you know anyway? Yes, but we know that those questions exist.
Jimmy Soni:
Right, but you were... you’re dealing with unknowns then, or at least sort of semi-known unknowns.
Gretchen Rubin:
I knew nothing and I knew no writers. I remember when it was a huge thing for me. I’m like, it was like on my list of, you know, like, life goals. It was like, make friends with writers. Of course, like, now I know so many writers, I can’t count them.
Jimmy Soni:
Now you’re like, I need friends who are not writers because they annoy me and invite me to do podcasts like this.
Gretchen Rubin:
This is so exciting. No, but, yeah, I felt like... but I was lucky. I had a few friends from college who were just starting off in that world themselves, very early. But they were able to give me lists of names. And so I did have that. Like, I had... I had who would I send it to? Cold.
Jimmy Soni:
And then did you... was it sort of the first... you had already written a lot of material and then condensed it into a proposal and then sent it off?
Gretchen Rubin:
Yeah.
Jimmy Soni:
And so what was the moment like when you had your first agent conversation or when the agent said yes?
Gretchen Rubin:
Oh, my gosh. It was the hugest moment of my life. I mean, I think it is probably the most important moment because it is the moment where you are... you’re not an amateur anymore. Because even before I got paid, I was like, time is money. And this person saying they’ll represent me means that they’re putting their time in me. This means that I am... I’m on the first rung of being a professional writer. So it was huge. I still have the same agent now.
Jimmy Soni:
Still the same agent all these years later.
Gretchen Rubin:
All these years. All these years. Yeah.
Jimmy Soni:
Did they... do you remember any of the specifics of what they kind of told you after they read the proposal? Like, or did they make changes? Like, how much of a gap was there between what you pitched to the publisher and what you ultimately did with the book?
Gretchen Rubin:
I think it was pretty close. It was pretty close. In general, my agent is really good at saying something’s not good enough, which is a very useful thing. It’s not always the most welcome thing. I’m not always eager to open her emails, but she... you know, I remember with The Happiness Project, I remember her writing something and she was like, “I’m sorry to write this, but I just don’t think it’s there yet.”
Jimmy Soni:
Wow.
Gretchen Rubin:
Yeah. Wow.
Jimmy Soni:
And has her feedback generally as a tuning fork been pretty useful for you?
Gretchen Rubin:
Absolutely. Yeah. No. I think she’s got a really good sense of what’s missing, which I think is often hardest to see as the writer. You don’t see what you’ve left out because you’ve left it out. So it’s... for some reason, it’s just like, that’s something that’s in your vision or tone problems. Sometimes you get the tone wrong. Like you’re trying to be funny, but it’s not landing or you’re not seeing that you need to find a moment of lightness. So I think that’s where her... that’s... and then she’ll do line edits and stuff. But... but yeah, it’s more those big picture things.
Jimmy Soni:
Did you talk to multiple agents or did you kind of find one that really understood you?
Gretchen Rubin:
I did talk to multiple agents. I was just thinking... I was just telling somebody the other day. Do you remember Judith Regan?
Jimmy Soni:
Yeah. The Judith Regan.
Gretchen Rubin:
Okay. Yeah, yeah, yeah. Like, you know, like, huge, big personality. And so my first book is called Power, Money, Fame, Sex: A User’s Guide. And it’s kind of like if you imagine The Preppy Handbook being combined with Machiavelli. Right. And it’s written like a how-to guide. It’s very much... and I’ve always been sort of enchanted by the how-to format. So it’s written and it’s kind of right on the line between, is it satire?
Jimmy Soni:
Yeah.
Gretchen Rubin:
Or is it...
Jimmy Soni:
Or is it real?
Gretchen Rubin:
Like, you know, and so anyway... but it’s very dense because it’s written in this how-to guidebook format. And Judith Regan said to me, she pointed to a page and she said, “Too many ideas.” And I remember thinking, that is the most preposterous thing. It’s like that scene in Amadeus where he’s like, “Too many notes.” I’m like, what do you mean, too many notes? You can’t have too many ideas. That’s what we all want. But now I realized that was actually a really profound insight. Like, I write too tight, I cut too much, I need to loosen. I need to open it. Ever since... that’s something that I’ve... so, no. So I talked to nine agents, I think, at that time.
Jimmy Soni:
What made you want to pick the one you went with? Just to get very tactical, if you can think back.
Gretchen Rubin:
I think she just felt like she understood what I was trying to do. Like, she got why it was funny, she got why it was interesting. She wasn’t trying to fundamentally change it. You know, sometimes my sister writes for Hollywood, and there are these moments where they’re like, “We love it. It’s wizard school, but let’s set it on Wall Street.” You know? And you’re like, “Okay, I don’t really see...” So sometimes you do get... or just their taste. Like, sometimes people have a taste where you’re thinking, I don’t want to be fighting their taste. So I just felt like we were the most in sync in terms of her response and everything.
Jimmy Soni:
So, and so you send a proposal to the agent and I remember this process. And they then, you know, at the time especially, it was much more of a black box. Like, you just don’t know. You don’t know what they do.You don’t know what cocktail parties they’re going to.
Gretchen Rubin:
I think it’s still… It takes forever.
Jimmy Soni:
It takes forever. What was it like? Did you... how did you land on the publisher you found? Like, what was that process like? Like, did they... did you have multiple offers? Like, how did you... do you remember back to what happened?
Gretchen Rubin:
Gosh, isn’t that crazy? I don’t even remember if I had multiple offers. I’m still really good friends with my first editor, Greer Hendricks, who now herself is like a very, like, you know, like a number one bestselling author of psychological thrillers. So she’s still in my life as well. I might have only gotten one offer for that. And I remember, like, you know, somebody said, “Well, how much did you get?” I’m like, I would have done it for free. I would have done it if they had said, “We’re paying you $0, but we will publish it.” I’ll take that deal. Yeah.
Jimmy Soni:
I always tell authors to just write the proposal. Like, it’s not... you don’t really lose that much. If you’re trying to put a nonfiction book project together and you know, you could go one of two ways. Your way is far... it requires far more... it’s actually much more admirable in some ways. You sort of write the book fully through.
Gretchen Rubin:
But I will say, like, I’m not in... I don’t have to do things like traveling to do interviews. Like a lot of nonfiction authors, there’s a huge financial thing, whereas I’m really writing more of an essayistic thing where it’s my time and it’s like money that I don’t have in my pocket now. But I’m not paying, you know...
Jimmy Soni:
Paying to do the proposal because a lot...
Gretchen Rubin:
Of people, they have enormous expenses associated with actually writing the book.
Jimmy Soni:
But I tell authors too, that the proposal does help you clarify. Like, even if you’re going to self-publish, even if you’re going to do anything.
Gretchen Rubin:
100%. Right. No, you, everybody wants to skip that stage because you’re like, “Why should I waste my time on a proposal? Let me just skip to the book.” But you’re right, it can save you. A lot of times, I think people write a proposal and they realize it just doesn’t... just doesn’t hold up. And then you’ve saved yourself tons of grief.
Jimmy Soni:
You actually are forced to get the structure down. I mean, you’re forced to do much of the book.
Gretchen Rubin:
Yes.
Jimmy Soni:
You know, even getting style and tone.
Gretchen Rubin:
Such good advice. Pacing. Like, you can look and say, “Oh, this book is really out of pace. Like too much of it is in two chapters. But I’m saying there’s 10 chapters. Like, I have to...” That’s... you can’t have a book like that.
Jimmy Soni:
And I would say even the comp titles then force you to make the argument about why your book is different. And I was going to ask you about that project in particular, because it’s not like you’re the first person to write about those four themes. Right. What, in your head back then, what were you trying... how were you trying to position it to make it different?
Gretchen Rubin:
Well, part of it, that it was this really how to....
Jimmy Soni:
Yeah.
Gretchen Rubin:
And it’s written and it is... it’s written in a particular tone. It is very distinctive whether or not you like it. It’s a distinctive book. Yeah.
Jimmy Soni:
When you go back, what was the... so you get the deal? Do you remember any of those moments, like when you find out that you’re going to do it and then... because there is a moment where you figure out you have the deal and you’re like, “Oh, I’m like the dog that caught the car.”
Gretchen Rubin:
Right, right, right.
Jimmy Soni:
Did you have that feeling at all?
Gretchen Rubin:
Oh, no, just so happy to be... just... yeah, but, you know, I mean, to your point about the kind of the confusion around the process, one of the things I, and I often will say this to people who are on the publishing side. I’m like, people know how to be a writer, but they don’t know how to be an author. Like, they don’t know what trim size is. They don’t know what trade publishing is. They don’t know what a pub date is. They don’t know what first run is or first serial or promo copy. You know, there’s all these things that you don’t understand. And I think a lot of times they don’t know what you don’t know.
And I do remember a lot of it just feeling like, “Oh, I’m supposed to know so much more about this process” and feeling like I shouldn’t just say, “Oh, I don’t... I really don’t know what that word is, or I don’t know...” You’re asking me a question, but I don’t know that I don’t know the implications of my answer.
Jimmy Soni:
Right.
Gretchen Rubin:
Like, I remember somebody who was... who self-published and they changed the number of pages and then when she got the book, the quality of the paper was lower than they had agreed to, and they said, “But you raised the page count and that meant the quality of the paper had to change.” And she’s like, “But I didn’t know the implications of that decision.” So you don’t know again, you don’t know what you don’t know. So now I try to really just admit, like, “I don’t know what you’re asking. I don’t know what that means.” Even now.
Jimmy Soni:
It’s an interesting... you know, I had a similar experience, because I don’t know if you felt this way. I certainly felt this way. You get the first deal and you do feel a bit like you’re like, “I got away with something.” Right. Like, I sold this thing to you. You’re about to give me money and you don’t know...
Gretchen Rubin:
Yeah.
Jimmy Soni:
That I have no idea what I’m doing.
Gretchen Rubin:
Right.
Jimmy Soni:
Right.
Gretchen Rubin:
Here I go.
Jimmy Soni:
So then, so then you start doing it and they will ping you with things or send you terms of art within the publishing world and you don’t want to reveal to them...
Gretchen Rubin:
Yes.
Jimmy Soni:
You have no idea what you’re doing.
Gretchen Rubin:
You just try to fake your way through.
Jimmy Soni:
Just like, “No, good.” And then you’re furiously trying to look up what the answer to the question is.
Gretchen Rubin:
Yeah.
Jimmy Soni:
I think this actually drives a lot of authors to drink like...
Gretchen Rubin:
It’s a pub day for a reason.
Jimmy Soni:
Well, it’s a good thing you... you do find yourself having to fake it, especially if you’re getting started. You don’t know what you don’t know. And then worse is you don’t know... you always have this persistent fear, at least I did with my first book, of if I say the wrong thing, they will wake up to me being an imposter, take the deal away and say, “What business do you have doing this kind of work?” Right. Yeah, did you... was any of that part of your experience of writing the book? So once you go through the deal, you’re done with the deal. We’ve gotten past the deal, now you’re in the writing. What was that process like? Like, how did you... because this is your first time out.
Gretchen Rubin:
It was my first time out, yeah. Like, I remember not understanding something like first pass. I don’t... I still am like, “Remind me, what about first pass?” For me, a huge thing. And I didn’t know this until I was on my third book. So this is... this is the kind of thing you learn the hard way is there is... there’s a point at which you can make lots of changes. You can change anything you want. You could add an entire huge chapter. You could change the ending. You can do anything you want. Then there comes a point where your window is starting to close. Then there comes a point where you’re looking at it, but they’re only going to fix a mistake, a typo, a factual error, and they might charge you even for that.
And then there’s a point where they’re like, if you do, it is the hugest, biggest deal. And what... and I also learned is every time you go into a draft and make a change, you introduce an opportunity for error because something goes wrong, there’s a stray punctuation piece that doesn’t get caught. Or you use the same word two sentences above, but you forgot to check because you just added this one thing and you didn’t realize you just used the word “pageant” or whatever. So one thing I’ve learned is you need to watch... I need to watch that very carefully. Like, what... what stage of editing am I in? Because I will edit every single thing up into the last minute. I would never just say, “Oh, it’s done, pencils down.” Oh, here’s a question for you.
Somebody just asked me this question. Let’s say you submit a draft to your editor, okay? So it’s with your editor. Are you like, “Okay, now I’m going to take a break from the book while it’s in their hands”? Are you like, “I will continue to edit myself and then I’ll just incorporate their edits into whatever I’ve done”? It never even occurred to me to stop editing my own work. I’m like, of course I’m going to edit every single day. I’m not going to wait for them, right? Somebody was like, “That’s... why would you do that? That’s bonkers.” I’m like, “Okay, what’s your thought?”
Jimmy Soni:
So this is the thing, is that you and I are wired very similarly in this way, but it is also an editor’s nightmare to have this happen, right? Like in the sense where the diverging... where the diverging... well, because I’m like you. As soon as I turn it into them, you’re immediately thinking, “Okay, let’s go back and revise every chapter and blow things up and twist...”
Gretchen Rubin:
Things around because you got this time. You can’t wait.
Jimmy Soni:
Yeah, you can’t wait. And the thing so I would say one is I know you probably feel this way as well. No one is going to invest the time into my book that I will, full stop. My name’s on the front. I live and die by the words in it.
Gretchen Rubin:
You’re thinking about it morning, noon and night.
Jimmy Soni:
I can’t tell you. I mean for most of the books I love, I probably couldn’t tell you who published them with a couple exceptions. I know sometimes, like just because of the way we’re in the industry, I know some of the editors that are putting out the work I like. But for the most part, most listeners aren’t going to know who published the last great... unless they looked at the spine of the book. I know I’m going to live and die by the words and I know that I’m going to obsess over them like nobody’s business. And here’s the thing. I think there’s... there’s the way publishers tell you that the editing ought to go, which has a rhyme and reason, by the way. Like there’s a reason why they do things the way they do.
And I have found that process is actually first rate. Everything kind of post-copy editing production with traditional publishing is actually phenomenal. Right. But I have found that we’re ultimately dealing with a PDF and in 2026, making those changes is not that big of a deal. Like there’s ways to work around it. I edit right up until the goal line. I edit until I can edit no more. If it were possible to edit in the hour before it was sent to China to get printed...
Gretchen Rubin:
I would too. Because you’re constantly... like that verb is kind of, you know, vague. I can strengthen that. Or like, “Oh, I thought of a...” Or like for me I use a lot of examples. So if I... that I get from real life. And sometimes I’ll just get a much better example from life. So I’m like, “Well, I want to swap this example for that example because it’s just a stronger, more interesting version of the point that I’m trying to make.” Or you just have an original idea and you’re like, “Oh, I want to layer that in” and...
Jimmy Soni:
I would frame it differently. And this is true of all creative work for me. It’s just a touch different. The specifics matter what you just said about word choice and about... but I actually think what happens is if you have a deadline where you’re supposed to send something into an editor, you pour an enormous amount of energy into everything leading up to that moment, right? And you sort of give it your all. It can be this whole body experience of editing. Your friends can’t talk to you. You sort of can’t communicate with the rest of the species. Your family starts to resent you a little bit. You drive and drive and drive. And let’s say it’s like a Monday at 5 o’clock and you press send Monday at 5 and you send them the draft.
You’re so fried, at least for me, I’m so fried at the end of that process that if I take a day or two, the editing I do after that is better often than the editing I did at the tail end of that crazy marathon. So I take a day or two break, but then I get right back at it because I’m bringing better energy to it than I was before. So I actually think of it as super important to go back and dive into the draft as opposed to walking away from it. Because in that state, I don’t know what I was doing in the 72 hours leading up to the deadline. Maybe it was good, maybe it was bad. I frequently find it wasn’t that good. And so I think it’s an energy management thing.
My energy goes all the way to empty right up until the deadline. And then it sort of fills up in the day or two after and I’m ready to look at the project with fresh eyes. And ultimately... the line I always use... everybody wins. Like, we’re gonna sell books.
Gretchen Rubin:
Yeah. No, no, no. It’s better to have a better book, always. Well, one thing I want to do too is read the book aloud. And that takes a lot of time. And so that’s the kind of thing that’s good. Nobody’s gonna do that other than you. And so that’s the kind of thing also that you can do when you’re sort of in that downtime. Because it takes a lot of time to do it and a lot of focus, but you can kind of do it in that period.
Jimmy Soni:
So you go right back into editing as soon as you turn it in and start to dive right back in.
Gretchen Rubin:
Well. And I don’t even really have a deadline. So what I’ll say to my editor is, “I will edit right up until the time I’m ready now. What I have now is a complete draft, but I will continue to edit it. So when you’re ready to read it, tell me and I will give you the most up-to-date draft.” Because if you’re not going to read it for a week, it’s already going to be changed by the time... so for me, the deadline is always, “Okay, I’m ready to read it now. Send it to me.” And then, so they’ll have the most up-to-date one. And then... and then... so I... so for me, the deadline is just
Jimmy Soni:
A suggestion.
Gretchen Rubin:
It’s... it’s like now I’m... by when do you need to have it be ready for you? And a lot of times I find editors really aren’t ready. Like they might say, “I’ll be ready early this month,” but then they have something that came in that needed a lot more work than they expected. And so they’re not really ready right then. So I always feel like it’s good to say... and I think, when are you ready for me?
Jimmy Soni:
Well, and I think the publishing industry is pretty accustomed to delays, right? Like it’s... it’s like you can always move it back. You can’t move it forward. I followed that rule sometimes in a reckless way. Like I... I actually got charged for additional editing. I was one of those people because I edited during my first and second and third pass pages.
Gretchen Rubin:
Oh, okay...
Jimmy Soni:
But then, but then here’s the thing. Don’t do it at home. Really don’t.
Gretchen Rubin:
Yeah, there’s a point where they get very, very cranky.
Jimmy Soni:
Yeah, I would say that being on the other side of it, I understand why they get cranky. And at the same time, there’s a writer I really admire, Erik Larson, who talks about how he edits his first and second and third... and I was like, you know, if it’s good enough for Erik, it’s good enough for me. Like, because there is something... what I would say is the reason that authors edit the first and second and third pass pages, sometimes more aggressively than a Word document or Google Doc or something else, is because we’re finally seeing it laid out on page.
Gretchen Rubin:
It makes a huge difference.
Jimmy Soni:
I don’t know if you’ve had that experience. You have.
Gretchen Rubin:
No, I... funnily enough, I think anything that you do that changes the way it looks... if you print it out, you’ll pick up completely different things. If you read it out loud, you’ll pick up different things. You can put it in a different font. Because I feel like my font kind of looks like my handwriting and if I even... but there is something hugely psychological when it’s laid out and it looks like a Xerox of a page of a book. No, in fact, that’s a really good point. I mean, I’m sure now we could easily do that ourselves.
Jimmy Soni:
Oh yeah. It’s much easier.
Gretchen Rubin:
That’s a really good idea. I want to do that.
Jimmy Soni:
It’s much easier. And I actually...
Gretchen Rubin:
Just because as you say, you pick up a completely... you have a completely different sense of your book.
Jimmy Soni:
Well, you do. And also, by the way, the simplest example, and it happens all the time, is you write a paragraph and you think it’s short, but it turns out to be really long. The only time you realize it’s really long is when you see it in your first pass pages. You look at it and you’re like, “This is a giant block of impenetrable text that nobody is going to want to go through in 2026.” Right. Like this is... we don’t... we don’t have these kinds of attention spans. I need to take this, create an indent. And I’m only going to know that when the first pass pages come around.
Gretchen Rubin:
Yeah. Where your line edits fall. I mean your line breaks fall. Whether your headers are working. I think a lot of things do become... you... just a lot of stuff sort of... that’s a really good idea. I’m going to do that. Like figure out how can I make it look like... maybe they can do it just... well, we’ll just do it to you as a favor.
Jimmy Soni:
Yeah.
Gretchen Rubin:
Like just to kind of fake it.
Jimmy Soni:
A fake first pass.
Gretchen Rubin:
Half pass pages. That would be real. That’s a really good stage.
Jimmy Soni:
It’s a great stage. And it’s also... it’ll save them time. It’ll save them time later. It’s also an important stage. Like it really is. Like you look at it differently, you feel differently about it. I’ve... I’ve actually cut chapters in half.
Gretchen Rubin:
You’ve got to publish... you’ve got to introduce the half pass pages.
Jimmy Soni:
We’ve got to introduce. Yeah this will be our... among our many innovations, another one. The... the thing about it though, if people don’t realize that when you’re... when you are... have stared at something as often as your own words on the page, the change in form matters a great deal. It is the only way to see them afresh. You don’t... otherwise you’re just looking at the same document the same way. And so for me, I do this thing, I have a tracker for every chapter of a book and it has “read aloud, question mark,” “printed, question mark,” “printed edit, question mark” and like what was it? Oh, mobile. So I read on my phone. So I also...
Gretchen Rubin:
I’ve never done that.
Jimmy Soni:
So let’s nerd out for a second.
Gretchen Rubin:
Wow.
Jimmy Soni:
So here’s why there’s two or three reasons why. The first is people are reading on smaller form factor devices.
Gretchen Rubin:
They are, that’s 100% true.
Jimmy Soni:
So you have people who will download the book to Kindle, they’ll have their Kindle synced to their phone.
Gretchen Rubin:
But even a Kindle is a smaller format than reading a book. So you are... they’re multiple sizes.
Jimmy Soni:
So that’s one reason is people... my readers are reading that way. The second reason is an interesting one. If you’re working in Google Docs like I am, but I’m sure this is true of any software you’re editing on. You can find a mobile version. When you’re in your phone. You actually... because of the way we text and because our thumbs are doing a lot of thinking, I find that I write differently. And so when you’re reading something on a phone in Google Docs, you’re kind of having this experience of, what if this was being... what if this passage is being texted to a friend? Does it work?
And so it’s actually... it’s a way to sort of look at it and be like, you know, this could be tighter, this could be shorter, this could be more succinct. It pushes you in the direction of being succinct. That’s reason two.
Gretchen Rubin:
That’s really... because a lot of times I might... this is the training as a lawyer that I always have to push back is a lot of times my first is really kind of long and wordy and it’s like pull it back. Be more succinct, speak more clearly. That’s a really good point.
Jimmy Soni:
The reason is if you turn off your notifications, which you should anyway, you realize that on a computer it’s much easier to be distracted because you have to make an affirmative choice to open up a new tab or change software to... it’s a real choice for some reason to me on a computer to go and be distracted. I’m sorry, it’s not... it’s a much easier choice on a computer to be distracted than it is on a phone. Because with a phone, I find that if I’ve got the notifications off and I’m looking at that document on my phone, there’s something about it that’s much more... it compels me to focus on it as opposed to, “Oh, I could just drift off and do this, or drift off and do email or anything.” The final reason is simple.
I have my phone with me all the time, so I can always be editing. Like, you’re on the subway, you can edit. You’re waiting for a friend at a restaurant, you can edit. You can edit in all these little confetti minutes, right, that you just sort of track during the day. And I find that for me, editing on the phone has actually become a big part of getting books to just be snappier, be more succinct. It’s a totally different way of looking at it.
Gretchen Rubin:
That is such a good idea. I’m gonna... I’m gonna instantly do that. I never thought of that because I know I always read books on paper, right?
Jimmy Soni:
Same, and I’m old school in that way, I love my paper books.
Gretchen Rubin:
I love my papers. So it just... it didn’t occur to me, but 100% I know you’re exactly right. And it’s just any... anything that switches it up reveals new problems, basically.
Jimmy Soni:
One question I have. Not about just your first book, but about projects in general. There are lows in projects, right? So you and I have talked about the highs, right? We covered the highs. Did you have with your first book or with subsequent books? Do you have a method or a way of dealing with the moments when you feel stuck or when you’re like, “I don’t know if this is going to work” or that kind of thing, or do you just breeze through?
Gretchen Rubin:
No, if I feel stuck, I... I will just get up and walk around. So I won’t persist in something that I’m stuck. And I’m a big believer of the unconscious mind will be working on something. So like, let’s say... let’s say I’m in a late stage of editing. And so I have five problems left to solve. And these are the hardest problems because I did all the easy ones first. So I might just look at them and think about them and then walk away or, you know, let a day go by and try them again. And then if I still can’t solve them, sort of repeat. So I’m in the problem and trying to... and trying to... and really pushing myself to try to solve it.
But if I haven’t solved it, then I’ll get up, walk around. I’m also really a morning person. So I get up at 5:30 and from 5:30 to 9 is the best time for my thinking. So anything that’s hard, I do then. So if I have a hard problem, I’ll sort of skip it and save it to do it first so I can do it first thing in the morning. Because that’s my, by far, my best time. But yeah, I think there’s always problems. There’s always things when you’re like, “I don’t...” This is something I should incorporate, but I don’t see how or where it should go or how you would even broach it or it’s a complicated idea that’s hard to succinctly convey.
Jimmy Soni:
You know, when you’re in the middle...
Gretchen Rubin:
Some kind of pervasive issue you gotta tackle when you’re in the...
Jimmy Soni:
Middle of a project. I have the challenge of sometimes you’re sort of, you know, you want to dance with the girl that you brought, but then you have this other project. Like there’s always the other projects that you’re like…
Gretchen Rubin:
... A hooky book. That’s what I have.
Jimmy Soni:
That’s a great... that’s a great one.
Gretchen Rubin:
I often have a hooky book. Yes. Now my... when I was writing Better Than Before, my book about habit formation, my hooky book was a book that turned into Outer Order, Inner Calm. Yeah. Yeah.
Jimmy Soni:
Wow. So how do you prevent yourself from going to... and turning the hooky book into the daily driver?
Gretchen Rubin:
Right, right. Yeah, that it is. You’ve got to remember it’s a hooky book. For me, it’s all about note taking. So note taking is a big thing for me. So I will let myself take notes on it. Like, and I’ll... I might read for it and take, put notes into it, but I would never allow myself to begin to structure it. Because once I’m structuring, then I’m like, “Okay, now I’m really tackling it as a book.” But because I always start with a bunch of notes, having a bunch of notes, then when I’m ready to start writing, then I have this huge head start. So it’s a good use of my time. But you’re right, you’ve got to make sure that it doesn’t swallow up what your main project is.
Jimmy Soni:
Sometimes, by the way, hooky books can yield something amazing, as you put it. You can have... I find that it’s tempting because the beginning of these projects is some of the best. Yeah.
Gretchen Rubin:
Okay, so there’s beginners... there’s openers and finishers. Okay, so openers are people who love to open a project. So they love the beginning stages. They love to start something new. Like, I talked to a professor, and he’s like, “I have seven half-finished, you know, new curricula for new classes,” because he loved to open. But then there... and then finishers are people who love to end. They love to finish. And both of them have pros and cons because openers sometimes don’t finish. And so they don’t get the benefits of their work. And they can get distracted because they’re pulled in so many directions. But finishers, sometimes they just want to be done so badly that they might rush at the end because they’re just like, “Okay, I just really want to get this crossed off the list.”
But a lot of times it’s that last work that’s really painstaking and difficult that can really make something go to the next level. And sometimes they are too cautious about what they start because they think, “Well, if I can’t finish it, maybe I shouldn’t start it.” But sometimes with creativity, you kind of have to say, “Well, maybe I’ll start it and maybe it won’t go anywhere, but I need to just kind of get it started to see.” And so I think it’s good to know which one you lean toward so that you kind of can try to offset that.
Jimmy Soni:
Are you an opener or a finisher?
Gretchen Rubin:
I’m a finisher for sure.
Jimmy Soni:
Okay.
Gretchen Rubin:
I’m a finisher. I love to cross things off the list. And it is... it’s like towards the end, I feel myself being... let’s just... let’s just say it...
Jimmy Soni:
Done.
Gretchen Rubin:
Oh, here’s an edit. But I’m just going to decide I don’t agree with that edit. It’s like, I actually do agree with that edit. I just want to be done.
Jimmy Soni:
Want to finish.
Gretchen Rubin:
Yeah, I want to finish.
Jimmy Soni:
There’s a... there’s that expression, once you’re lucky, twice you’re good. Right. And the first time I did a book, I really did feel like I was... I mean, I knew the book was good, but I felt like I got lucky. It was the second time where I was like, “Okay, I can actually... this is a real thing. I know how to do this.” Did you have a similar experience? Like, how was it... what was the process like from the first to the second project? Because you also changed.
Gretchen Rubin:
Yeah, I changed style. My second book was a short, unusual biography of Winston Churchill.
Jimmy Soni:
Which is... it’s a fantastic book. It’s really great.
Gretchen Rubin:
No, I love that book for me, and this still is a thing which is, are you going to be able to write your next book? If you’re a traditionally published person, that’s a concern, which is, are you going to get published again? Are you going to get a deal again? You know, is somebody going to want to publish you again? So I do feel like that. And I’ve never done a two-book deal, so I’ve always faced that, which is, I’m going out there again.
Jimmy Soni:
Right. And so how did you go from power... from the power book to... to Churchill? Like, what was that process like?
Gretchen Rubin:
Well, when I was studying power, I kept coming across these references to Churchill. So then I became very preoccupied with Churchill. And then a lot of my books have sort of an origin moment. And so I was standing at the corner of 69th and 3rd Avenue and I said to my husband, “You know, you could write a book about Winston Churchill that would just be the most adulatory thing of all time. And you could write a book about Winston Churchill that is so critical of him. And both of them could be completely factually accurate.” And he said, “You could write that book.” And I was like, “Oh my goodness, I am 100% going to write that book.” And I had been reading all these biographies, so I had all these thoughts about the nature of biography.
That’s another unwritten book that I have. I have this enormous collection of quotations about the nature of biography which I could work into something which I actually... I forgot until this minute I had. I should go back and look at that because it’s very cool. But anyway, so 40 Ways to Look at Winston Churchill is both about Winston Churchill and it’s also about the nature of biography. But how this connected with Power, Money, Fame, Sex... like in my mind, they’re very closely associated. From a book publishing standpoint, they’re not closely associated with it, but I was just able to pull that off.
Jimmy Soni:
Yeah. And how did... did you have to convince, coax, cajole, like, you know, because you’re one of the rare people and this is a true gift that you’ve managed to jump from idea to idea. But they’re very... they can be very disparate. Right. Like it... they’re... to quote the… the pudding has no theme. I know it has a theme, and I kind of know that you’re following your intuitions and your curiosities, but it’s not as though you’re a sort of...
Gretchen Rubin:
They’re all about human nature. To me, that’s the thing is they’re all about how do you... and one of the ways you understand human nature is you look at someone like Winston Churchill or JFK, and they’re just so huge and there’s such a vast quantity of information about them that you can study them in a way that you can’t study somebody who’s just more... a more modest player on the world stage. So to me, they feel very connected. But you’re right, but from a publishing standpoint, they’re incredibly disparate.
Jimmy Soni:
But I’m surprised that nobody pushed back to say, “Could you do another book on, you know, power? Or, hey, could we take one of the verticals and really go deep?”
Gretchen Rubin:
I know, I know. It’s... yeah. Now to me... yeah. Because once I started writing about happiness, I have... they’ve all been sort of connected with how do you have a happier life?
Jimmy Soni:
Right.
Gretchen Rubin:
And it is nice to sort of be building around a core subject now with 40... so when I wrote... so I wrote 40 Ways to Look at Winston Churchill, it did pretty well. I wrote 40 Ways to Look at JFK. And you know, when a book flops, they tell you. Or at least my team tells me. “Your book didn’t find its audience.” My book didn’t find its audience. I wanted to write 40 Ways to Look at Richard Nixon. Oh, and that wasn’t going to... just like, this just wasn’t a form. I probably would have kept going. I wanted to do Ben Franklin. I wanted to do Leonardo da Vinci. I wanted to do Saint Thérèse of Lisieux. It just wasn’t supported by the market.
Jimmy Soni:
Why do you think Churchill worked but JFK didn’t?
Gretchen Rubin:
Okay. So I think I have a theory about that. Let me tell you what I think. So I think the people that... that are interested in JFK are... they are either they adore Kennedy and admire him tremendously and everything that he stands for in their minds, or they think... they really... this... you know, they think Kennedy was such a fake and he was doing all this stuff and it’s like this dark underside and what was he getting up to? And so a book that talks about…
Jimmy Soni:
Either camelot or conspiracy.
Gretchen Rubin:
Yeah. Exactly. That’s perfectly... well, that would be great cover copy. Yeah, you’re thinking like a publisher.
Jimmy Soni:
People are getting a window to basically what we do at lunch.
Gretchen Rubin:
So they don’t want to see the other side. They want one or the other, they don’t want to see both. And so people would look at this and they’re like, “I don’t want that.” Whereas I think the people who come to Churchill... so when I wrote the Churchill... and this is a good example of the fact that when you write a book, you never know who the true audience for the book is. You don’t know who it’s really going to appeal to. So when I wrote the Churchill book, I was thinking, there are all these people in the world who have no idea that Winston Churchill is the most fascinating character in history and I will be the gateway drug. They will read my short book and then they will go on to the eight-volume biographies, which I think is absolutely fascinating.
But they don’t yet know that they want to read. Yeah, but that wasn’t who the audience for the book was. The audience for the book was the people who had already read every single Winston Churchill biography. They knew tons about him. So they were interested in my take, because my take was, look, 40 Ways to Look at Winston Churchill. So it was looking at him through all these different lenses, often which were very much in opposition or very surprising. And they’re meant for paradoxical. They were meant to sort of show you what you could... the limits of biography. So people who knew a lot about Churchill were the people who were attracted to that and who... and with whom it resonated. So it was not at all the audience that I thought I was writing to. It was like the opposite.
But I think that audience didn’t exist for JFK because the Churchill people, I think that was an audience that understood the triumphs and tragedies. You know, I think that’s even the title of one of the big... yeah, they got it that his flaws were his weaknesses and his weaknesses were his strengths. And you know, so part of it, I think had to do with the nature of the audience for that figure.
Jimmy Soni:
Yeah.
Gretchen Rubin:
But somebody told me, they said to me, “Gretchen, when most people read a biography, they want an authoritative account with some new information. And that’s not what you’re writing.” And it’s like, it’s not what I’m writing. It’s like I was writing a book that people weren’t that interested in.
Jimmy Soni:
It was more of an impressionist painting almost. Right.
Gretchen Rubin:
40 Ways. Right. So it’s like a Monet... the haystack painting.
Jimmy Soni:
Yeah. And then, you know, I have a million questions that could get into about the Churchill book. But the... one of the... I imagine a criticism or I imagine pushback that you could get is “Gretchen, I mean, the shelves groan under the weight of Churchill’s stuff...”
Gretchen Rubin:
Yes. No, Churchill himself said...
Jimmy Soni:
Exactly.
Gretchen Rubin:
That’s... that field has been plowed. I mean, even when he was still alive.
Jimmy Soni:
And he himself was prolific and...
Gretchen Rubin:
Oh my gosh.
Jimmy Soni:
So you’re competing against your subject and people who have written about your subject ad nauseam.
Gretchen Rubin:
Yeah.
Jimmy Soni:
For 50 years, 60 years. So how did you... did you have to deal with that, any of that?
Gretchen Rubin:
I mean, I... I dealt with it in the introduction. I just said, “Yeah, I get it, but...”
Jimmy Soni:
But your publisher still went for it.
Gretchen Rubin:
Yeah. And it’s just like... but there’s always a new way to understand him and his own account of himself. The biggest problem with the Churchill book was that Churchill himself is such an outstanding writer that I felt like whatever he wrote just jumped off the page. And then my stuff was like, “Eh, this is... yeah, meh.” So... but I learned so much as a writer from Churchill. Like, that was a thing I didn’t expect. It’s just like, because I would type out all these, you know, these... my favorite speeches and things that he would write, my favorite passages. And there was so much as a writer that would be a really fun book which is writing lessons from Winston Churchill because he was a master.
Jimmy Soni:
I think there is a book like Churchill as Writer.
Gretchen Rubin:
I’m sure there is. Right?
Jimmy Soni:
Churchill as Painter.
Gretchen Rubin:
Yeah. The wit and wisdom. No, I’m sure I probably have that. Yeah, yeah.
Jimmy Soni:
You made a really important point and it’s an interesting one for anybody who’s listening, who is a creative. And there are many that you... I... the way I’ve heard it described is you have to leave a reader-sized hole in your work. Right. So you never know... to what you said. You never know who is going to find your book and use it or treat it or think about it in a way that you’ve never anticipated. Right. So for you it was, “Oh, this is the gateway drug.” And it turned out to be actually... this is the... this is the finishing course for this particular meal.
Jimmy Soni:
I had a similar experience with my first book, which was about an ancient Roman senator named Cato. It was called Rome’s Last Citizen. And I remember thinking, “Well, I’m writing this for people who are super nerdy like me, really enjoy Roman history. They probably read about Caesar. They might have read about Cicero. This fits that spot on the bookshelf. Great. That’s the audience.” And it turned out that Cato was one of the patron saints of Stoicism. And Stoicism had a renaissance among different people. And people like Tim Ferriss read my book, loved it, let me blog on his site way back in the day and it took off among the sort of contemporary Stoicism set. Right. I heard a story about Michael Lewis when he did Liar’s Poker.
He said he thought he was writing kind of a message in a bottle for people to stay away from... to stay away from Wall Street. And what he got were hundreds of letters like, “I read your how-to guide for how to succeed on Wall Street. Like, is there other things you left out?” I do think you have to leave a reader-sized hole. Like it’s one of the challenging things actually about doing this work is when you see it misinterpreted or you see it kind of... and it’s not always a bad thing because if people are reading it, you’re happy. Right. But I do find that there’s a little bit of, “What about that little thing that I put in there that everybody missed that I was so happy about?” Have you had moments like that?
Gretchen Rubin:
Yeah, you have to let go of that. You have to let go of that. Well, it’s funny because in writing about happiness, a lot of times people will say to me, “Well, I know you wrote in your book, blah, blah, blah.” And I’m like, “I never wrote that at all,” you know, but I’m just like, if you brought that to it that’s fine.
Jimmy Soni:
That’s fine.
Gretchen Rubin:
You know, it’s because I think once people start thinking... one of the nicest things that anybody said to me about my work was somebody, it was either Better Than Before or The Happiness Project. They said, “I’ve never read a book about somebody else that made me think about myself more.” And I’m like, that’s exactly what I’m going for. But when people are reading a book and they’re trying to understand it for themselves, of course they’re going to start seeing things in the book that you never put there.
Jimmy Soni:
Never intended. And it’s actually also one of the... books are great randomness machines in this way.
Gretchen Rubin:
That’s a great... that’s a great way. It’s just throw a bunch of ideas. You know, when the student is ready, the teacher appears. But the question is, how do you put yourself in the place where the teacher can appear?
Jimmy Soni:
Right, right.
Gretchen Rubin:
Yeah.
Jimmy Soni:
And it’s... but it’s also one of the most gratifying. Like, I’ll... you get random notes from people about some little ingredient you included you didn’t think was a big deal or a footnote you threw... a stray footnote that ends up being a thing.
Gretchen Rubin:
Wait, can I tell you an example from our podcast? Okay, so I have the Happier with Gretchen Rubin podcast, which is my sister. So sometimes people would send in... and this is to the point of you never know what ideas are going to land deep with people. So somebody had written in and said, “I lost my engagement ring. It was really important to me. We can’t afford to replace it. I am just sick about it. I don’t know. I looked everywhere. I just can’t find it. I just can’t find it. And my question is, how do I make my peace with this? How do I find happiness when I have just so much... and I’m just so upset about this?” So the question isn’t how to deal with a ring.
The question is, how do I deal with the negative emotions that I have around the ring? So we had our own answer. Whatever. Then a listener wrote in and her answer... people to this day are like, “What was the episode where the woman talked about this answer?” We’ve returned to it several times because people just... it struck a chord. She said, “In Japan, we have the belief that a precious object might sacrifice itself for you, that to save you from a bad fate, it might lose itself.” And she said, “It’s totally a myth. But it might be help... comforting for her to think that this precious possession had lost itself to save her.” And to us, this was so strange because it’s just a reframing, right? Nothing in the... none of the facts have changed. It’s just the reframing in your mind.
And people to this day are like, “What episode was it where that woman talked about the ring losing itself?” There’s just something about it to just... and then I was in Japan and I was having some... I was with a guide and I mentioned this and she looked at me and she said, “It’s very Japanese.”
Jimmy Soni:
That does sound… you told me this story without cultural context, but that sounds Japanese.
Gretchen Rubin:
It sounds Japanese. And because the reader herself is in Japan. This is... we have this thought, but... so that was an interesting example where to us this was just like, “Oh, interesting insight from a listener in response.” And we... we have these all the time. And then it was just... it just reverberated for years. And sometimes you just don’t know. And I think for creative people, this is why sometimes it’s good to just throw a lot of ideas out there, because you don’t always know that you’ve hit a deep seam, because, like you said, there’s so many rabbit holes that you’re going down all the time. You know, sometimes it’s really... it’s really illuminating to think, “Oh, this is an idea that people are really... that somehow is really striking a chord.”
Jimmy Soni:
It’s also one of the reasons why I tell people, whether they are authors or just readers, to write in. Like, to tell the person who created the thing what specific things stood with you. Like, I just have that as a default habit now. If I walk around the world...
Gretchen Rubin:
Do you really do that with books you read?
Jimmy Soni:
With books I read, with statues I walk by.
Gretchen Rubin:
That’s so nice.
Jimmy Soni:
I remember I walked by Jane’s Carousel in Brooklyn, and I was so... my daughter was riding it a lot. And I remember thinking, “This is a really nice carousel, and it’s nicer...” and I could get in trouble for this. “It’s nicer than the Bryant Park, the SeaGlass, the Central Park one.” It’s the nicest carousel in New York. It’s very beautifully maintained. And so I started going down the rabbit hole. And I remember thinking... I was like, my habit is, I’ll find it, find the creator, write them some kind of note so that they know.
Gretchen Rubin:
This is such a lovely practice.
Jimmy Soni:
And it just became a default thing. But what’s great is I know how I feel when I get those notes. And so I wrote to Jane of Jane’s Carousel. One thing led to another, we became friends. And then I ended up doing the coffee table book with her about Jane’s Carousel. Because of that note. All because of that note. So I always tell people, if something strikes you, if it enters your life’s conversation in some way...
Gretchen Rubin:
Yes.
Jimmy Soni:
Let the person know.
Gretchen Rubin:
That is really...
Jimmy Soni:
Because then you and I don’t have any sense of what’s working or what’s not.
Gretchen Rubin:
We don’t. We don’t.
Jimmy Soni:
We have a vague sense, but not really a concrete sense.
Gretchen Rubin:
Okay. And here’s what I would add.
Jimmy Soni:
Yeah.
Gretchen Rubin:
There’s so much AI slop of all these AI agents saying all of these flattering things that it’s like, can I tell the difference between somebody who’s faking it and somebody who’s actually resonating?
Jimmy Soni:
100%?
Gretchen Rubin:
100%. Or even people are like, “I loved your recent podcast episode where you talked about...” I’m like, “Yeah, that’s fake.” Because I can tell when somebody’s really, you know, says, “Oh, I was thinking, you know, we have this...” But you can just sort of tell the difference in terms of how people are, you know. For 2026, one of the items that I wanted to do was to rate and review podcasts and books more, because as somebody who’s a creator, I know how much it matters. It just matters for the... for all these things, it really matters to people, and it’s gratifying, and... and I haven’t even really been keeping up with that as much. And you’re going way beyond that, which is to actually track down the contact information. But that’s so much more meaningful.
Jimmy Soni:
It is. It’s also... it’s not that hard to do. So here’s the way I think about it is...
Gretchen Rubin:
Also to sharpen your gaze.
Jimmy Soni:
Oh, absolutely. And the other thing is you know, you... everybody lives a life where you try, I think, on balance, to leave the world... hopefully you live your life this way... a little bit better. A little... just a wee bit better. Right. And you can do that in a lot of ways. You can raise your kids well. You can do creative work. You can just be a human. You can volunteer. And I do think that this is my way of the karmic scales.
Gretchen Rubin:
Yeah.
Jimmy Soni:
Like, I need to keep them in balance. And, you know, my work requires a lot of borrowing on karma from other people, whether it’s editors investing in you or time away from certain friends or... I kind of think of this as my way of restoring the karma scales. But then the other part of it is it’s not a long exercise. You know, I finished a book a couple weeks ago, and it took me, what, a minute or two of Googling to find the person’s contact info. I had two sentences that I wanted to say to them because there was one chapter that really stood out to me. Drop a note. Send it off. It’s not like I’m not laboring over this for years and years. This is just very quick.
Gretchen Rubin:
So keep it easy.
Jimmy Soni:
But keep it easy. And also, it then sort of puts you in the position of, I may never have contact with that person again. Ever again. But they know that something that they spent years on had some kind of effect in the world. I think that’s one of the things that, you know, it’s... you do spend years of your life on these projects. And I’m sure, especially when your first few books came out, anytime anybody wrote you, it was the greatest. It was the greatest moment ever.
Gretchen Rubin:
No, it really was.
Jimmy Soni:
I think you can be world famous and these things still affect you. Right? Like, you can have fans galore, but it’s somebody identifying something specific in your work that still makes a massive difference. A massive difference.
Gretchen Rubin:
No, I think that’s really true. And I think there is something about putting out those... the appreciation for people’s efforts..
Jimmy Soni:
And I would say that it extends as well... as I said to physical things or a product you really love or... it doesn’t have to be a book. It doesn’t have to be some... some work of art, it can be something very simple. I also find the other effect of this. It gets you to find the origin story of the thing itself. So you... because you look at something and you’re like, “I really like that.” You have to then go dig and figure out how did this thing come into being. Right. And for people who love rabbit holes, that’s catnip, you know, there’s nothing like that feeling. How did you... just... because I want to be conscious of your time. How did you go from JFK and Churchill to The Happiness Project? What is the origin story? The kind of, you know, pre-story on The Happiness Project?
Gretchen Rubin:
Again I have been... I know exactly when and where it happened. So I was finishing up... it was probably just after first pass with my JFK book. So I had this... and at that time, because writers didn’t have all this other stuff that we were doing, there is kind of a period of inactivity because you can no longer actively edit, as we were saying, and they’ve ripped it out of your cold hands. And the book hasn’t been published yet. So there’s kind of this... and for me, it was... so I just sort of had this open time in my head. So it was during that period and I was stuck on the crosstown bus on 79th in the pouring rain. It was going really slowly and I didn’t have anything to read or distract myself with. And I just...
I looked out the window and I thought, “What do I want from life anyway?” And I thought, “I want to be happy.” But I... and I thought, “Well, but I don’t spend any time thinking about whether I am happy or if I could be happier or what is happiness anyway?” And I thought, “Well, I should do a happiness project and figure all this out.” So... and I instantly became super interested in the idea of happiness. So I ran to the bookstore and the library and got a giant stack of books. Stoics, you know, novels, nonfiction, research. This was right at the time when sort of the positive psychology movement was just getting going. So there was a lot of interesting research that had just kind of emerged at that time. And at first it was just...
For me, it was just like, what do I... what could I do to be happier in my own life? And... but as I got into it, I just... my note taking, my research got deeper and deeper, and there were so many things that I wanted to learn and so many things I wanted to try in my own life. Yeah. That I thought, “Oh, maybe this could be my next book project.”
Jimmy Soni:
Yeah.
Gretchen Rubin:
And then I’ve sort of been writing about happiness one way or another ever since. And it’s funny because I don’t know about you for titles, but for me, titles either come right away or extremely slowly. And people, many people, said, “You shouldn’t call it The Happiness Project because that sounds like homework. Nobody likes to do it.” And I was like, “But I love homework. I love...” No, I love a project. Homework for long periods of time. Seriously, give me a course. I’ll sit down. I love a curriculum. But... but I was like, but that’s... that’s... it was... I was like, it... just from the very first minute, I had this idea it was The Happiness Project. Yeah. Yeah.
Jimmy Soni:
That’s great.
Gretchen Rubin:
Yeah.
Jimmy Soni:
Did you have trouble selling it at all, or was it a pretty easy sell after... because you said JFK didn’t do well.
Gretchen Rubin:
No, it was not an easy sell. First of all, I was talking to people about it, and they didn’t get it. Like, somebody’s like... because I was like, “Oh, yeah.” I kind of mentioned Benjamin Franklin. Because if you’re talking about, you know, he’s, you know, OG in this... in this space.
Jimmy Soni:
No, he is. He’s the Godfather.
Gretchen Rubin:
Yeah, he’s the Godfather. And they would be like, “Well, maybe you should do a thing where you follow all of Benjamin Franklin’s rules.” And I’m like, “No...” This was a time when doing sort of what... what you could dismissively call stunt nonfiction was... was more and more. And so kind of the...
Jimmy Soni:
The more august name. Right. Was the gonzo journalism a long time ago.
Gretchen Rubin:
Exactly, exactly right. And so, yeah, everything just keeps being reinvented. Auto-fiction, it’s like, yeah, they’ve been doing that for a long time. No, so first people didn’t really get it. And that’s part of why I thought, I think I just have to really write a lot of it because people aren’t understanding and this wasn’t me officially pitching it, but just more me casually talking to smart people to sort of pick their brain and they just... they just weren’t responding the way I thought that they should in my vanity. So I basically wrote a huge thing and then my agent was just like, “Yeah, it’s not good.” And then I wrote it again and my agent was like, “Yeah, I’m sorry, it’s just still not good enough.”
And then... and then I kind of figured out how to break it. And then... and then that’s when I went out. And then there was a reasonable amount of interest. But not like wild enthusiasm.
Jimmy Soni:
Not enthusiasm commensurate to what the book eventually became.
Gretchen Rubin:
No, not at all.
Jimmy Soni:
Because now that’s your best known...
Gretchen Rubin:
For sure. Yeah, I mean it was, yeah, it was number one. It was on the list for two years. Yeah, no, it was... no, nobody... but the one thing that I had done so I had a blog that I had been doing for years, a daily blog. And I did it because when I was writing the book, one of the arguments that I was testing, because it was all a test on me, all self-experiment was novelty and challenge make people happier. And I had thought, “Well, I’m not that kind of person. Maybe that’s true for most people, but I like familiarity and mastery.” But I had to test it for the purposes of the book. So I decided I would start a blog because I’m like, “This is novel, this is challenging. I don’t know tech, I don’t write for deadlines.”
I’ve never been a journalist. This is going to be really hard and, but I’ll do it and just sort of report. And I thought, “Oh, I’ll do it for a month.” But then it really worked. And so I was fortunate in that at that time, not that many people had done something like that, which is to create an audience for a book before the book was published. And use it as a way to try to get people interested in a book. Now of course, preorder campaigns are a huge thing. And people are constantly talking about this thing. But at that time it wasn’t as common and I didn’t do it strategically and cleverly. I did it accidentally and for my own reasons. It just sort of ended up that way. But I think that was something that made... that really helped.
Jimmy Soni:
I want to bring things kind of... wind things to a close, but I, you know, we talk a little bit about your writing habits. You write in the mornings.
Gretchen Rubin:
Well, I write all day, but I write hard things in the morning.
Jimmy Soni:
And so how do you, yeah, how do you structure your creative life now? Like what’s... what is a typical week, a day and then a week kind of in your life look like.
Gretchen Rubin:
So in my dreams, I’m a Benedictine monk and every day is exactly the same and I know exactly what I’m doing at 10am every single day. But it’s not like that because now I have a podcast... I have podcast Happier with Gretchen Rubin, I have a newsletter, I have a newsletter in Klaviyo, I have a newsletter on LinkedIn, and I have a newsletter on Substack, all of which are different. I do social media, I have products, I do speaking. So I... so the one thing that I… I go to the Met every day...
Jimmy Soni:
Right yeah, which is probably one of my favorite things in Life in Five Senses.
Gretchen Rubin:
Part of my creative practice. So as much as I would love to have a very routinized life, I can’t because it’s just... it’s just, it’s constantly, I have to constantly shift things around. And I think that’s one of the reasons why I like to do my hardest reading first thing in the morning is from 5:30 to 9. Rarely changes. I... except for walking my dogs. That is very much... I can count on that. And then everything else, it’s like, I may or may not be able to do it. I might not be able to do it until 4pm by which time I’m not at my best. I might only have an hour. Instead of having a big block. One thing I have learned to do is not to have a big block. I think when you’re starting out in writing, you’re kind of like, “I have to have a whole day or I have to have half a day.” And now I’m like, I have all kinds of writing tasks and some of them I can do if I... I’m just sitting down for a few minutes.
Jimmy Soni:
So does the morning time always go to the biggest, most important project? Is that what you try to do?
Gretchen Rubin:
Yes, that’s what I always try to do.
Jimmy Soni:
And do you miss that? Like, do you... do you miss it when you’re on the road? Do you sort of give yourself breaks, or is it seven days a week?
Gretchen Rubin:
I try to do it seven days a week.
Jimmy Soni:
Wow okay. Yeah. That’s great.
Gretchen Rubin:
Because it is just so precious to me. Yeah. Yeah.
Jimmy Soni:
Look, I’m...
Gretchen Rubin:
But I’m rigid. Yeah.
Jimmy Soni:
You know, I’m rigid in the same way. And honestly, I feel off on the days I don’t have that.
Gretchen Rubin:
It doesn’t feel like... it doesn’t feel like a treat.
Jimmy Soni:
Yeah. It feels like the way I described it to friends. It’s like, if I don’t have that time in the morning where I’m doing a... whatever the creative or editorial or writing task is, that’s the most important. It feels like I didn’t brush my teeth.
Gretchen Rubin:
Yeah, no, that’s... it’s such a good analogy. Exactly.
Jimmy Soni:
Something is off…
Gretchen Rubin:
It’s not that it’s really a big deal or that it matters in any kind of way or that anybody else cares, but you just feel...
Jimmy Soni:
Just feel off.
Gretchen Rubin:
Yeah.
Jimmy Soni:
And then those grooves, they get... they get to be the place I’m happiest. Right. Is when I’m in that... that particular groove.
Gretchen Rubin:
Yeah.
Jimmy Soni:
Do you... have you ever tried to change up the schedule or has this been the schedule for time immemorial?
Gretchen Rubin:
I haven’t always been able to get up this early. And when I had little kids, of course, I had much less control over my mornings. So then I... but at that time, I had fewer other commitments. You know, I didn’t always have the podcast. I didn’t always have the newsletters. I didn’t have... it just... I feel like as a writer, the kinds of work that you might do just as part of your ordinary writing life have really expanded. So I feel like I was fortunate that when my kids were younger and they were taking up a lot of my sort of unpredictable time and predictable time. I was just more focused.
Jimmy Soni:
When do you read? If you read?
Gretchen Rubin:
I love to read. This is a huge question in my life, it is a huge mystery because I read books, at the end of the month, I have the stack and I post a picture of it. And these are the books that I read. And I see that I read books. I’m always like, I feel like I’m never reading. I’m constantly fighting to find more time to read. My favorite thing is the same day book where I start and finish a book in the same day.
Jimmy Soni:
That’s where my...
Gretchen Rubin:
So delicious. I love that feeling. I have to do a lot of work for reading. If I’m doing work reading, I’ll do that during a work day. Kind of at the end of the day when I’m tired. If I’m just reading for pleasure, then I feel like I have to read it in sort of my leisure time. But... and I... I feel like I’m not reading nearly enough. For the podcast, we always have a challenge tied to the year. So 25 for 25 was read 25 in 25. So you had to read 25 minutes a day?
Jimmy Soni:
Oh, 25 minutes a day.
Gretchen Rubin:
Yeah.
Jimmy Soni:
Okay.
Gretchen Rubin:
That... and that was... yeah, I... I just, I don’t know. How do you get enough reading done?
Jimmy Soni:
It’s hard.
Gretchen Rubin:
It’s... it’s something that’s very easy to find... push to the bottom. You have to fight for it.
Jimmy Soni:
You have to fight for... what I do, you know, part of it, I think... and this is sort of occupational hazard. I read... I am reading always, somewhat opportunistically. If I’m in the middle of a book project, I’m reading things that are tied to the thing I’m writing. So I feel like it’s real work. Right. So then I always have a reason.
Gretchen Rubin:
But does that feel different. Oh, yeah. That’s... that’s a different category.
Jimmy Soni:
There were years when I actually... I talked to a friend about this the other day, that I, at one point, I lost the ability to read for pleasure. I was... I... because you write books and you’re obsessed with books and you’re working on books all the time, and all of a sudden I wake up and I’m like, “I don’t actually enjoy reading anymore.” So I had to go back and start with fiction again and revive my childhood love of reading and wonder. The wonder of discovery. I lost all of it because it was all so utilitarian now.
Gretchen Rubin:
Exactly.
Jimmy Soni:
And then I would say, I... I try to do... if I... if I’m going on vacation, I try to take only novels and I’ll read stuff that has nothing to do with work. Right. But it’s actually hard. It’s actually hard to carve out. There was a period where I was trying to do 15 to 20 minutes every morning before anything else. That lasted for several months, and I finished a bunch of great books in that process. But I... it’s a challenge. Like, I... I will find that... actually, one thing that’s helped is my daughter has 30 minutes of required reading time every day for school. I just read side by side.
Gretchen Rubin:
Yeah, that’s a great...
Jimmy Soni:
So it’s like...
Gretchen Rubin:
That’s a great...
Jimmy Soni:
That makes it actually very easy.
Gretchen Rubin:
Because you have that accountability. One thing a friend of mine told me, and I’ve completely followed this, is that when she’s traveling for work, she reads for pleasure. So she never tries to work on a plane or review a document or something. It’s like, if you’re traveling for work, you just read for fun. And she’s like, that way, you know that you have that time and it’s just the most delicious. I love reading on airplanes because you’re just so focused.
Jimmy Soni:
Yeah, no, I finished... I finished a number of books on airplanes that I wouldn’t have finished in any other form or because you always feel like you’re robbing Peter to pay Paul.
Gretchen Rubin:
Right.
Jimmy Soni:
It’s like, do you work on the Substack or do you read? Do you work on X or do you read? Right. And I find that the other... the other bit, for me, it’s much more around choosing books. If it’s in project mode, I’m choosing books that I have to read anyway. Hopefully they’re enjoyable. But if I am, I try to portion out vacation time and choose my books there so that it’s pure pleasure.
Gretchen Rubin:
Pure pleasure, yeah. I think people don’t sometimes expect enough. Put down a book that’s not good, find something that’s really... then what I often do is I’ll pick a book. I’ll pick something to read for the summer to give my summer a theme. So I had a summer of Proust, because I had never read all of Proust. I had a summer of rereading, because I love to reread. And there were a bunch of sort of difficult books that I wanted to reread, like The Varieties of Religious Experience. I’m like... I’m like, when am I going to reread that? So I’m like, “Okay, I’ll have a summer when I just reread these books.” And then my summer this year, which will start June 1, is the summer of Virginia Woolf’s diaries. Because I love Virginia Woolf. She’s my favorite author.
But I have never read her diaries, which are extensive. And I’m like, when am I going to get around to that? Like, I had to turn it into sort of a project. So... so that’s what I’m gonna... so that’s... so I will often do that with the summer if there’s something that I kind of want to tackle. Yeah, that’s how you’ll tackle it. Yeah. Yeah.
Jimmy Soni:
So one of the ways all Infinite Loops episodes end with this question, which is, you’re made emperor for a day. Which, by the way, I actually think you’d make a great emperor.
Gretchen Rubin:
Thank you.
Jimmy Soni:
Like, if you ever... you ever decide to campaign for that office, let me know, because you’ll have my vote. And you... you have a magical microphone. You’re allowed to share two ideas that everybody in the world will wake up, and those two ideas will be implanted in their minds, and they will... they will believe that they are their own. Right. They’re not coming from Emperor Gretchen. They’re coming from their own psyche. And they... people live by and adhere to them. What... what are those two... you’re... you’re somebody that’s thought about this question extensively across...
Gretchen Rubin:
I’ve never thought of it in this iteration.
Jimmy Soni:
What are the couple of... Couple of ideas?
Gretchen Rubin:
I would say, know thyself and do unto others as you would have them do unto you. I think that could go pretty far.
Jimmy Soni:
Yeah. So on the know thyself, that’s been your life’s work, right?
Gretchen Rubin:
It’s on the Temple of Apollo at Delphi. Yes. Yeah.
Jimmy Soni:
Is that... is it fair to say that your work is kind of an extension of that question?
Gretchen Rubin:
Yes, I think that’s a... I think that’s... yes.
Jimmy Soni:
I think that’s why it has resonance. Like, it’s... it’s why even...
Gretchen Rubin:
It’s a great challenge of our lives. Yeah.
Jimmy Soni:
And in the intro to Life in Five Senses, you write about how this is... these books are very personal for you.
Gretchen Rubin:
Right.
Jimmy Soni:
That one seems to be the most personal. You have this kind of moment. And I won’t spoil it, because I think people should go check out that book. But you have a moment that leads you down these rabbit holes. It’s about knowing yourself.
Gretchen Rubin:
Yeah.
Jimmy Soni:
And the other one is do unto others…
Gretchen Rubin:
As you would have them do unto you. And you can quibble and you can say, “Well, but sometimes they don’t want you to do unto them. They want you to do unto them the way they want it to be done unto you.” I was like, start from there. Start from there.
Jimmy Soni:
Amazing. Well, Gretchen Rubin, you are... you remain... and you are one of my favorite authors. I love your work. I want everybody to check it out. Where can people find you? And just give us... give us the list so that we have...
Gretchen Rubin:
GretchenRubin.com. It’s all... everything’s there. Yeah, yeah.
Jimmy Soni:
Okay.
Gretchen Rubin:
Yeah. Oh, this is... this is such a pleasure.
Jimmy Soni:
Thank you for coming on. Thank you for taking the time to do this wonderful work and until next time.
Gretchen Rubin:
Until next time.
