The Long and The Short Of It

Episode 43 - Planning

Transcript:

Pete: Hello, listeners. We just wanted to take a quick moment to say thank you so much. Jen and I are coming up on the one-year anniversary of The Long and The Short Of It, which is crazy. And none of it would be possible without you, our amazing listeners. So thank you for the way that you've shown up. Thank you for the way that you've listened, and shared, and taken screenshots, and tagged us, and sent us text messages and emails. We really, really appreciate it.

Jen: And in celebration of our one year, we've decided to give you a gift. The Box O' Goodies, starting in August. If you want to sign up, you can receive a weekly email from Pete and myself with that week's favorite podcasts, articles, quotes, books. Anything that we have taken in that we think is worth sharing, we will share it in the Box O' Goodies.

Pete: You can go to our website: thelongandtheshortpodcast.com

Jen: And listeners, we would love it if you would help us share this work with more wonderful listeners like you, by identifying your favorite episode and sharing it with a friend. That would mean the world to us. Thanks so much for sticking with us. And here's to year number two.

Pete: Hey, Jen.

Jen: Hey, Pete.

Pete: It's good to see you smiling. It's good to see you smile. Because last week, last week you and I had a little disagreement, if you like. A little verbal, verbal stash. And so it's good to see you smiling back at me on the Zoom screen.

Jen: It was a disagreement. I wasn't angry at you. I just could not understand where you were coming from.

Pete: Which is exactly why I think we should go back to this topic with fresh eyes, and have a thoughtful conversation. And unpack from the various angles (the long the short), what we think about when we think about planning. Because as it turns out, we have very different thoughts.

Jen: So different, in fact, that we decided to leave that argument on the cutting room floor. So yes, I am happy. I'm happy to start fresh today. This is The Long and The Short Of It.

Pete: Okay so I'm trying, I'm actually trying to remember how this even came up. I believe, and correct me if I'm wrong, you were sharing with me how you've been talking to a few of your clients about long-term planning and time management, specifically in relation, in relation to, like, sort of goal setting. Is that right? Can you paint the picture?

Jen: That is exactly right.

Pete: Oh, wow.

Jen: Yes. I mean you, you painted it perfectly. How does long-term planning impact goal setting, which impacts planning? It's like this circular thing: planning, goals, planning, goals, planning, goals.

Pete: Mmm. And what we uncovered was- you and I both think about long-term planning, in particular, very differently. And so, perhaps to start, would you like to share with us how you think about long-term planning? And why it's important?

Jen: Yes, and this is really a time where our, the title of our podcast feels apropos. But what might surprise the listeners is that in this case, I am the long of it. And you are the short of it. Because I do like to take a very long-term view in terms of how the projects I'm working on right now, and the goals that I'm working toward may have a cumulative effect in the long-term. And what do they add up to? And your perspective is totally different.

Pete: Yeah, and neither is right. But my perspective is...and maybe it's not even a perspective. But my preference for how I think about my work is very much grounded in the short. In that, I don't necessarily get great comfort, or have great skill in thinking twelve months, even six months, in advance. And I've wrestled with whether this is a weakness that I should improve. Or whether it's a quirk in the way that I approach work, or what exactly it means. But I do think there are some things I could definitely learn from Jen Waldman, the long.

Jen: Well, it's funny because right before we started recording, I was lamenting to you that I had this plan for how I was intending to spend my time this summer, and then my husband's scheduled changed a little, and my daughter's camp schedule changed. And my plan sort of got thwarted. So perhaps I have some things to learn from you, as well. But in marinating on this disagreement we had about planning, I was really thinking over the last couple days about: how did I get this way? Like, how did I develop this very, sort of, long-term view? And the thing that I've landed on is that- this is my theater background basically laid out in the form of human behavior. Where it's like, my...in the world that I come from, we set opening nights well in advance, and then we figure out how we're going to get to opening night. And for the most part, we don't miss opening. Like, we open when we say we're going to open. And when I was working as an artistic director, in those scenarios I'm planning five years into the future, with the board of directors. We're, you know, talking strategic plans. And then we're scheduling our entire season well in advance, and setting all of the opening nights. So I'm, I think that that has infiltrated the way I think. For better or for worse, it is...it is very challenging for me to not think of how this due date will impact the twelve months from now due date.

Pete: That's interesting. So, just to unpack that a little bit. So like, your general premise is to have a due date, be it twelve/six months in advance. And then you work backwards from there? Is that right? And, like, create mini milestones?

Jen: Yes. That is how I work. Is- I think about: where do I ultimately want this to end up? Or...not even, like, that there's a finish line. Like, what am I working towards? So five years from now, hopefully I will have finished this book. So it's like- okay, hopefully by that point I'll be on the, you know, the second one. So in order to be working toward completing my second book, how will I have had to be working right now, in order to make that possible? So yeah, I do think about sort of the end state that I want to achieve with a project. And then I work backwards from then, in order to get to today, which helps me in a couple different ways. One, it helps me actually determine if my timeline is realistic or not. If you know the idea of planning fallacy...we're terrible. Just, human beings are terrible at estimating how long something's going to take. And I do think my long-term view makes me much more realistic about how long something takes. And the other thing that it does is- it sort of allows me to see how my concurrent projects impact each other, what the dependencies are. So I can work at, on a lot of things at once, because I'm taking the long view.

Pete: Yeah. Mmm. Oh, this is so good. And then there was one other thing I wanted to ask you to elaborate on, before I talk about how I'm thinking about this. And that is: what became interesting in the, in the, in the conversation that we had last week...I won't call it disagreement, even though it kind of was...was how this links to your tendency as a Questioner. And so for those wondering- when we talk about tendencies, we're talking about Gretchen Rubin has a framework called The Four Tendencies, which sort of talks to, and describes how we respond to expectations, essentially. And so, Jen is a Questioner. And I'm so fascinated by how that plays into what you just described, your process for planning.

Jen: Yes, well, Questioners like to have all the information. We like to question everything. And what's interesting...so, Pete is an Upholder. You are an Upholder, Peter.

Pete: Mm-hmm, I am.

Jen: There are also two other tendencies: Rebels and Obligers. I am so textbook Questioner. I respond readily to my internal expectations. Like, if I can see the logic behind something and want to do it, I will do it. But I'm so textbook, that I really feel no obligation at all to external expectations. That doesn't mean I don't want to do things for other people, or I don't do what someone asks me if they ask. But if I cannot generate an internal understanding of why this thing is important to me, I just won't do it. But my Questioner tendency really requires lots of logic leaps. And so that long-term view helps me before I even start, to make all of the leaps, and to acknowledge ahead of time all of the skills I might need to acquire, or research I might have to do, or network I might have to build in order to make that end thing possible. So it's, it's like I do a, a five-year out pre-mortem for all of my projects.

Pete: Mmm. It's fascinating, so fascinating. So I would agree, actually, with this idea of starting with the end in mind, beginning with the end in mind. I do that, too. I love that. And I think it's from...it's from many books that we've stolen that from- this idea of defining what the "end game" is. I guess where I differ from there is- once I've just, once I've defined it, I kind of...I don't work backwards. It's almost like, I've defined it and so I've internalized it. And so now, as an Upholder who responds to inner and outer expectations, I trust myself to create habits and routines and, and I guess, milestones internally along the way, with absolutely no, like, rigidity other than the trust in myself that if I keep showing up and doing the things that I think will help me get there, that yes, I'll get there. So mine feels more like...it's not a project in that it has an end date. It's like a...this sounds so lame, but it's like a journey or a process of trusting and enjoying showing up each day to do the work that I think is going to help me contribute to where I want to get to. Does that make any sense? To a Questioner?

Jen: Yes. It does. And I, the thing that I feel like is worth calling out is- if you have a ship date, you meet it. It's not like you're working willy-nilly and, like, flimsy about whether or not you ship things.

Pete: Totally.

Jen: And on my side of the coin, when I have a ship date, if I...I'm not beholden to it just because it's in the calendar. Like, one of the things that defines Questioners is we sometimes find certain dates to be arbitrary. [laughter] So if I try to set ship dates for myself that are really based on some good information...but if the information changes, I'll change the plan. It's not like I'm beholden to this plan. The other thing that I feel like is really interesting...you have been called, by some, the Human Periscope. And I have been called, by some, the Human Stethoscope. So when you think about which, which direction that's moving in, that's really interesting to me. Because the stethoscope goes from out to in. And the periscope goes from in to out.

Pete: Wow.

Jen: Which is just sort of right.

Pete: Yeah, that's fascinating. And I think, like, to relate...I was, I was trying to work out, you know, in terms of you realizing that this tendency that you have perhaps stems from your theater background. I've been trying to, like, piece together how I've been conditioned to think less about outcomes, and attachment to outcomes, and more about processes and habits, and, and I guess showing up in the moment and doing the work when I feel like doing the work. As opposed to, like, keeping myself on a strict schedule. And I wonder if it's something to do with that idea of the periscope. Like, I wonder if...so much of my work has been about helping other people, and letting other people determine success and then I help them get there. And so, it's not that I have a certain place that I want these people to get to. It's that I am completely open and fluid to go wherever they want to go, in terms of what success looks like for them. And so I'm able to show up and help them get there. But I show up, as I am, on Tuesday at twelve o'clock, not with this idea that when I get to Friday at four o'clock, I need to be at this particular point. Does that make sense? I don't even know if I'm making any sense.

Jen: Yes, it does. So I'm wondering if you had a similar experience that I had, which...I'm trying to figure out how to describe it. Right now I would call it, like, an empathy explosion, or an empathy implosion. Where, honestly Peter, until you told me you thought about planning differently, I guess it just never occurred to me that people thought about planning differently. Like, I was so startled to hear that your relationship to the future is so vastly different from mine, that it really, like, jolted me into this like, "Wow, Jen. That is a major blind spot. Like, you just assume that everybody thinks the way you think?". I mean, talk about burning the empathy bridge.

Pete: [laughter] Yeah. It's so interesting because I think that was, like, that's the...I mean, that's the "what's it for" of even having this episode, to me. It's, like, realizing that there's no right way or wrong way. That both of us are both incredibly efficient. Both of us get a lot of work done. Both of us are able to show up and record podcasts together, and get a result that is, you know, something we're both proud of. And yet we come at this idea of planning from two completely different angles. And we had an example play out so perfectly, where I had a spurt of creativity. And so I whipped up this idea around the Box O' Goodies that we've been talking about. And I sent it to you. And I was like, "What do you think?". Because that is just how I do it. I like, I had a wave of inspiration. It wasn't a date that I was set to do this thing, and so I did it. And I sent it to you, and you were like, "Okay, so let me work backwards. We're going to send this in August.". [laughter] And I was like, "What? Why are you working backwards? I just sent it to you. It's done.". And you were like, "No, no, no. We need to go back...". And so, it played out right in front of us. Which is so interesting. And I have no doubt we'll get to a place where we release the Box O' Goodies, and we're both really happy with it. But it's just, like, fascinating that we can come at it from two completely different perspectives.

Jen: So then it makes me wonder, because I'm the Questioner...does that make me a bully? Like, did I bully you into not sending the Box O' Goodies, because I wanted to come up with a process for filling the Box? Or was it, was it useful to say, "Yes, we should send a Box O' Goodies. But right now we have no system for filling it each week."?

Pete: I love this question. So, I don't think it makes you a bully. In fact, what you have taught me, and what I have realized in working with you (not just in this example, but in so many others), is sometimes my tendency to quickly get away with inspiration and ship something is too soon, is too early. And I'm not having empathy for people like you, to give them the space and the time to think about it, and plan it out. I'm just like, "What are you talking about? It's done. I did it. Let's move on.". Which is a strength sometimes, but it can be a weakness other times. And what I'm realizing is, in this example, and what you and I have kind of come to discover is- it's almost like when there's a collaboration that exists, there is a level of compromise. And so for me: I sent that, I was excited. And then you came back and said, "Oh wait, let's plan backwards from this.". And I was like, "Huh. Okay, yeah. Of course, that makes sense. Because that's how Jen thinks, that's how she wants to do it. And so my compromise is- I'm going to hold off for three weeks and go through the process of planning it with you.". Because that is how we, Jen and Pete, get success. Not how me, and my system of just shipping stuff is going to help. So I think it's a, it is an empathy exercise, to your point, in collaborating.

Jen: I'm questioning whether I should even say this out loud. But I'm, I'm questioning if I might be robbing us/myself in certain scenarios of...sort of the scrappiness of just doing something without thinking about the consequence of it. So, I'm going to challenge myself to find some areas, and to be less futuristic and more, like, impulsive in the moment. And the great irony of this all, Peter, is that at my studio, when I'm working with artists in some of my classes, we do what I call impulse training.

Pete: Hmm.

Jen: Maybe I need to take a chapter from my own book...

Pete: Yeah.

Jen: ...which will someday be completed. And train my own impulses, to trust my impulses more.

Pete: I like it. And I think it's worth experimenting with, and trialing. But I also don't think, like, we don't have this conversation so that we completely change who we are. I think your strength was evident...to use the example of the podcast, when I, when we first started this I was like, "Jen, we've recorded one episode. Let's release it. Like, it's done.". And you were like, "What if we got ten in the can, and then started releasing them, Pete? That would be, probably a little bit smarter.". And I was like, "Really?". And yes, you were right. Because we got ten in the can, and as it panned out, there were a bunch of weeks where we didn't end up recording, so we needed the can. So like, that was an unbelievable strength that you brought to this collaboration. So, I think it's great to realize that other people have other perspectives. And it's great to see that you can experiment with other ways of approaching planning. But it's also not throwing out your system, because I think your system is...it's been effective enough to get you to where you are today, so.

Jen: Oh, yeah. I mean, it's, it's tried-and-true for me. But I, also, am committed to developing myself and my systems more. So here, here's to growth mindset, my friend.

Pete: Here's to #growthmindset. And I'm committed to us working backwards on our Box O' Goodies. Which is, I think we said the start of August we'll start sending. So, I'm committed to that. Look at us collaborate.

Jen: Oh my gosh, look at this. And hey listeners, while Pete's on the Box O' Goodies situation...if you want to know what we're talking about, we are planning to send out weekly, an email with our favorite stuff from that week: articles, podcasts, videos, quotes, books, exercises, whatever it happens to be that week. And if you would like to be in receipt of it, I'll need Pete to tell you how to do that. How do they get it, if they want the Box O' Goodies?

Pete: I love that. If you'd like the Box O' Goodies...also, I love that used the word "planning" back there. "We're planning on doing this, and we're working backwards."

Jen: Oh my goodness.

Pete: So if you'd like the Box O' Goodies, thelongandtheshortpodcast.com is our website, and you can subscribe (I guess the word is there?). Pop in your email and we'll send you no spam, just a weekly box of delicious goodies.

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