Episode 23 - White Space


Jen: Hello, Peter Shepherd.

Peter: Good morning, Jennifer Waldman.

Jen: Well, it's been a little while since we've recorded because I was out of town off the grid last week at a writer's retreat.

Peter: Yeah. I'm so curious to hear from you on how all of this went down, because you know, it was difficult for me, you being off the grid.

Jen: It was difficult for me, too. I learned so much, and I thought maybe I would unpack some of the learnings and get your take on it.

Peter: I would love to do that. This is The Long and The Short Of It.

Jen: Okay. So I feel like first we have to talk about the genesis of the writer's retreat, because that in and of itself was a learning experience. I actually wrote a blog post about this last week after reflecting. So last summer in July, I was having dinner with my husband's family, and my mother-in-law said, "We're going to play this game called 'Questions,' and I'm going to ask everyone a question, and everyone's going to contribute to answer - things like, 'Where's your dream vacation? What piece of advice would you give your younger self, et cetera.'" And one of the questions was, "If you could have a conversation with anyone alive or dead, who would it be?" And I immediately went to Stephen Sondheim, and then began the shame spiral because I was like, "Jen, Stephen Sondheim is alive. The only reason you haven't had a conversation with him is because you have been too scared to reach out and ask him to have a conversation with you. You fool, change your answer." So by the time it got to me, I picked a different one of my heroes, Martin Luther King, who I obviously could not have a conversation with, although I would like to, and it went on. But this tape started playing in my head of "who else would you like to have a conversation with who is very much alive walking around this earth?" So I said to myself, "Okay, I'm going to pick the people who have been most influential in my recent past and start with them." So I landed on Douglas Stone and Sheila Heen, who are the authors of Thanks for the Feedback -

Peter: Great book.

Jen: - A must-read book for any human being walking the planet. Like, if you haven't read it, what are you doing? Push "pause." Push "pause" right now, read the book, and then come on back. So, I wrote them this gratitude letter basically saying, "Your work has been so influential, not only on me but all my clients, you should know that there were people on all over Broadway tonight who got there in part because of their ability to process feedback thanks to you." So I went to their website to try to find the contact page, and then I saw that they were hosting - and it was just in tiny little writing - that they were hosting a writer's retreat. And then I called you -

Peter: You did.

Jen: - and I was like, "Peter? Peter, should I do this?" Like, "Should I go on this book-writers' retreat?" And you said, "Yes." And I said, "Okay," something to that effect. So I changed the letter, I rewrote it to express my gratitude, and then say, and I'd love to be a part of this writers' retreat. I got accepted to the writers' retreat, and I just got back from spending a week - a week - with them and thirteen other people who are working on books.

Peter: Yes!

Jen: So the whole reason I was able to go there is, first of all, because of the lord of all things, Stephen Sondheim -

Peter: It's always about him.

Jen: - my internal shame spiral, and then my desire to get myself out of the shame spiral by taking action.

Peter: And also, you never know unless you ask.

Jen: Boom. Truth, truth-telling by Peter Shepherd.

Peter: That's some Jen Waldman truth. I'm just regurgitating an an older episode.

Jen: True. So I go to the writers' retreat, and how it's, I could impossibly unpack everything, but let's just say it was mind-blowing. Everyone was so interesting. Everyone was so supportive. It turns out writing a book is a creative process - who knew - and very similar to the other creative processes that I use. So a lot of what I call "impulse training," like throwing an idea out and then quick-firing back an answer, so we had these amazing writing exercises to do, lots of community-building where, you know, we're having these group conversations. Anyway, there were so many learnings, but a couple key points that I think would be really important for our listeners. So I want to share them. One was so obvious, but like, duh, why hadn't I put it in these words before? Sheila said, "When you embark on any creative project, you must make white space in your life." And she said, she went on to say, "This means that you have no idea what's going to fill that space, but you've left the space open, and you protect it with everything that you have. No calls, no emails, no texts, no social media, no music," -

Peter: No meetings?

Jen: And, nothing.

Peter: So this is like a blank calendar.

Jen: Yeah. So this is similar but different from what I call "magic time," because the white space is totally devoted to this one project. So then she used a phrase which I am obsessed with, which I'm going to steal and apply to all sorts of different situations, that "When you are outside of your white space and just existing in the world, you look at the world through book-colored glasses," where - so you know the phrase or the saying, "you look at the world through rose-colored glasses," like, you see everything, you know, as a better version of what it is; she was saying, "Look at the world through book-colored glasses, where everything you see, figure out how it connects to the book, figure out how it can inspire the book, figure out what it has to do with the book." And those two ideas of creating white space, and then when you step outside of your white space, to be intentional about how you are taking in the world around you have been really, really empowering. So I'd love to hear your thoughts on that.

Peter: Naturally, I have a lot, but I'll start with these two thoughts that spring to mind: so on the first one, the "creative project needs white space," it is like, it is one of those ones where you're like, "Obviously," but also, so few - it's so rare for people to legitimately execute on that. I think it's, I think there's a story from Warren Buffet where, it might've been Bill Gates was like, they caught up and he said, "What's your secret?" and Warren Buffett handed him his calendar and was like, "Have a look at that." And he - Bill Gates - opened it up and flipped through it, and it was just blank page after blank page after blank page after blank page. And Bill Gates was like, "Where are your meetings? Like, how are you, are you talking to investors, or are you, like, what are you doing?" And Warren Buffett's like, "No, I just, I have no meetings, no appointments. I sit around, and I read, and I study the businesses that I want to invest in, and look at and understand the market. And that is, like, my number one pro tip is, create white space." Which, while you might not think of investing as creative work, I think the logic is, is the same. So there's that. The other thing I would say about creative white space is, hang worked with and working with a number of very high-performing individuals that I am lucky enough to coach, it's a really common thread for so many of them to have so many projects that they're working on, not enough white space. So it's, it's easy to understand, like you said, like, obviously, but what's really hard to execute is to create, deliberately create this space for ourselves so that we can either look at things through a rose-colored lens or a book-colored glass or a podcast-flavored lollipop, whatever you want to call that thing - I don't know why I went with lollipop? That was weird. But moving on to that point real quick before I throw back to you for some thoughts is, when you described book-colored glasses, and looking around you for things that relate to your book and connecting the dots, I just realized in this moment that that's what Jen Waldman does every day when you listen to a podcast and you figure out how it's going to apply to the work that you're about to do, which you've talked about in the podcast before. Or when you read a book and you realize that one of the concepts in it can be applied to performing artists, or whatever, like, you do this really well already. So I'm wondering if you realize that in a moment when she talked about it.

Jen: I did. However, what I had failed to recognize is that the way I had been looking at the world through my book-colored or project-colored or "Aha!" moment-colored glasses -

Peter: No lollipops.

Jen: - was, was leading me to the book I was opposed to write, which was not the book. I thought I was going there to write, so I came in with an idea that I had had over the summer that came to me in a flash of inspiration in my sleep.

Peter: Of course.

Jen: Oh, there's the sleep situation again. And I thought the idea was so good that was very committed to writing about it. And I still believe the idea is so good; however, when I put on my book-colored glasses and looked at the world, the thing I was supposed to be writing about was basically staring at me from every possible angle, and I had been ignoring it because I had been so married to this other idea. So on the third day of the retreat, I threw out everything and I started over with this new idea. And once I committed to it, I was in such flow; I couldn't stop writing. It was, like, pouring out of me. At one point they said, they referenced Stephen King's book on writing in that he said, "twenty-five hundred to thirty-five hundred words is a good day," or something like that, and there was one day where I wrote five thousand words.

Peter: Oh my gosh.

Jen: I just couldn't stop. It was like, it was just, I dunno. I had been, I guess, so committed to this previous idea that I was going to shove all my ideas through that filter. But then once I said, "Oh wait, I am actually seeing the world this way," it made it so much easier to flow. So I'm grateful that she said that, because you're right, that's exactly how my brain works, and I was trying to ask it to work a different way.

Peter: Yeah. And so I guess the, the thing that sticks out to me now is the white space and the rose - the book-color glasses, I keep going to say rose-colored glasses - is that feels like a posture that's easy to take when you're on a writer's retreat, and it's literally what you're there to do, but what happens when you come back to New York or wherever it is you're from, and you are balancing various other creative projects, too? Like, how do you wrestle with this idea of, you know, there's a great book by Greg McKeown called Essentialism, and he basically says you need to figure out what the essential thing is to work on, and work on only that. Which I love and I understand, but for so many of us have so many other things that we're also working on. So, like, how do you grapple with that?

Jen: Well I only have an answer that is less than one week old, but I will tell you that I have made a couple of adjustments since returning. One is, I'm waking up an hour earlier -

Peter: Wow.

Jen: - and writing in the morning.

Peter: Oh, welcome.

Jen: Yeah, welcome to your world.

Peter: Yup. The world, 5:30 in the morning. What's up, Jen?

Jen: That's right, that's right. And honestly, it's not hard for me cause I'm a morning person. I imagine for someone else, that might be challenging. But for me I just am waking up earlier, and it's fine. I realize that the day that I stop writing every day is the day the book is going to stop being written, so I have to write every day. This is a commitment that I'm making to myself. And the other big "Aha!" moment was with some of their quick-fire exercises, the amount of writing that could get done in thirty minutes. It was really mind-blowing to me, because my assumption was that I would have to sit down in these very long multi-hour chunks to get my groove. For some people who are at the retreat, they talked about that, that the quick-fire actually disturbed their groove, and they really need those longer sit-down moments. But for me it was like, wait a minute, I've got these thirty minute chunks throughout the day that I often just fill with, like, administrative stuff. But if I repurposed those as writing time for right now, because my schedule is pretty - I, I'm in the middle of a three month project, I'm basically right in the middle, so I've got until the end of March on this pretty big project that I'm working on, I don't have the flexibility in my calendar that I will have starting in April, so I need to make the most of the time that I do have. So I'm taking all these little half-hour chunks throughout the day and devoting to writing, and then come April, when my time frees up, I'll actually be able to carve in more of my magic time, more of my white space time, but this has been really helpful to learn that I can work in spurts.

Peter: Yeah, not only the spurts, I like the spurts and the beautiful constraint of time, but I want to double down on this idea of, you have to write every day. You have to keep that chain going, otherwise the book stops. I think it was, in fact it was Jerry Seinfeld who talked about this.

Jen: Yes, it's Jerry Seinfeld. You're right.

Peter: He used to have a calendar, and every day that he wrote jokes, he would do like a cross, and his comment is, "Once you get enough of the crosses in a row, you have a chain, and so like, psychologically, you just don't want to break the chain, and you have to show up and write every single day." Which also reminds me of, of course, Seth Godin, who just - this line that he said casually in a podcast has stuck with me for so long, because everyone always says - so Seth releases a blog every day, one blog a day, sometimes two, and the question he always gets asked is, well, "How do you always have something to say? Like, what is it? What is it that inspires you to write?" And he says, "I don't write because I have something to say. I have something to say because I sit down to write." That the art and the practice and the the work is showing up and opening your laptop and putting the blank page in front of you and just typing, and eventually you'll figure out that you have something to say through the work of showing up and writing.

Jen: I love that so much. I think about that often, that so many of us wait for the inspiration to do the thing that we think we're meant to do, but if we just do the thing, then we will eventually be inspired by something. Yes. There's another thing that I feel like I have to point out, which was very much the thing that compelled me to want to be a part of the retreat is that, you know, coming from an arts background, one of the things that I know to be true is that an artist without technique is not sustainable. That you need some sort of technique to rely on - some sort of structure to work within a framework so that you can, constraints. You can have constraints, you can measure your progress, you can also assess your excellence or lack thereof. And as a writer, I have no technique, because I've never taken writing classes. You know, I'm very good at analyzing scripts; I can help writers, script-writers improve, you know, playwrights, improve their plays because I really understand dramatic structure and understand what needs to be in a play. But in terms of a personal development book, I have no technique. And what was really interesting is, every night we did some sort of technique-based exercise, and the second I had something to rely on that felt sturdy and that was not interpretive by me, it was actually like a legitimate craft technique-based idea, the writing became so much easier, so much easier. And I realize that part of the thing that I had previously called "Fear of Not Being a Writer" was actually lack of technique, presenting itself as fear.

Peter: Interesting. And you know, I have to ask you to share briefly, your favorite, well, my favorite technique that you shared with me.


Jen: Oh my God, it's so funny. We spent an evening talking about voice, finding your voice as a writer, and that not every book that you write will have the same voice because not every book you write will have the same audience. And the, the voice you use is the voice that best serves the audience that you're writing for. So that was very helpful, because I realized I was writing in this very academic professororial voice, which - that's not me. I can, I can speak in that language, but the people I'm really talking to, you know, "real talk."

Peter: Yeah.

Jen: That's, that's the voice I settled on. But in order to get there, we did this exercise where they gave us a bunch of ideas of potential voices to use, and we took a piece that we had already written, and rewrote it three different times using three different voices just to experiment. And so one of the options is what they called "angry voice." And I chose that because I thought it was going to be very hard for me.

Peter: Really?

Jen: And it turns out, yes, I think I talk in angry voice a lot, like, in my classes, but I couldn't imagine writing in it. But it turns out, Pete, it was so easy for me. Basically the key was, if I'm feeling stuck, all I have to do is start a sentence with, "Listen, asshole..." and then the idea comes out. And I can always cut, you know, the "listen, asshole" part. But then the thing that I was trying to say follows it, and then I can recraft that into a voice I would feel proud putting out into the world. But it's kind of amazing how tapping into your anger can bring you clarity.

Peter: Oh, it's my favorite. I haven't tried it yet, but I am committed to trying that technique because I just love the idea of untangling yourself from the fear of writing, which you just reframed really well actually as no technique. It's not necessarily a fear of writing, it's that you don't have a technique, so it's like, what if the technique was, start every paragraph with, "Listen, asshole..."

Jen: And what's really funny is, we do this exercise in a couple of my classes that we call "Catchphrase," where we basically put the same phrase at the beginning of every line, which sort of forces the the actor to clarify point of view. And usually the phrase we use is - you might need to bleep this one out with a car horn - the phrase we usually use is, "Don't f*** with me." So it could be in any context, and it seems like it wouldn't work. Like, if you logically play the thought process, and you're like, "No, how could that work?" But it does. We do it with dramas, we do it with comedies, we do it with pieces that have romance. It's amazing how putting, in that case, the angry voice, before every line helps people find clarity of their point of view.

Peter: There's so much wisdom in this. I just wrote down, like, the preface, or the, the almost disclaimer, in a way. I don't know the, the prompt of, like, having something to say before you say it is so useful, and I just realized that I do this in a bunch of other contexts. So as a coach in the altMBA, for example, we have this idea of "real talk," which you mentioned earlier in the podcast, is like, so if I start a sentence with "Real talk" (#realtalk), we know that I'm about to say something that is like, from a deep, generous place that might be hard to, hard to hear. "This is the honest truth of how I feel about the situation." Having that as a preface for what you're about to say feels so much more genuine than just saying it. Like, just coming out with a, you know, it's something that someone might go, "Oh, that's a bit offensive." And the other one I have with a friend of mine who's also a client of mine, which is along the same lines. We, we both have a mutual friend who is like, real talk king, just, will very openly and bluntly give you an opinion on a matter. And let's say their name is Joe, which it's not. We'll say to one each other. We'll say to one another, "I'm going to give you some Joe feedback," and what that means is like, "Listen up, I'm about to give it to you straight. Don't be offended." This comes from a beautiful, general, generous place, and so that to me is like, a version of what you're doing with, you know, "Listen here, asshole..." or, "Don't f*** with me."

Jen: Yeah.

Peter: Little tricks for the brain.

Jen: That's right. That's right.

Peter: Also, before we wrap on up this episode, I have to double back to what you said about the book, and the idea of speaking in a voice that resonates with the audience. Like, we've talked about empathy, we've talked about sonder, but we could not talk about it enough. If you are out there and you are a performer, if you are out there and you are an entrepreneur, a freelancer, a creative, like, whoever you are, there is so much wisdom in this idea of understanding who you seek to serve, understanding the ways they think, the ways they act, the ways they communicate, so that when you communicate to them, you do so in a way that resonates with them. Like it's just, I just love that you casually mentioned that as part of the retreat, but that is a fundamental part of building, of writing, of creating anything that matters. So that's my final rant.

Jen: And that is The Long and The Short Of It.