The Long and The Short Of It

Episode 174 - Timelines

Transcript:

Jen: Hello, Peter.

Pete: Hello, Jennifer.

Jen: One of my clients said something so casually in passing last week, and I can't get it out of my mind, so I'm going to definitely need to unpack this with you. Okay, are you ready?

Pete: Yeah, I'm ready. I love the casual mic drop. Hit me.

Jen: "There's a difference between a deadline and a timeline."

Pete: Ooh. Deadline, timeline. Okay. Yep, yep, yep, yep, yep. I follow, I follow. This is The Long and the Short Of It.

Jen: Okay, now-

Pete: Give me some context.

Jen: She says this in passing as we're talking about how we want to improve what we're putting out there this year, like how to make good on our promises to ourselves, how to show up as a better version of ourselves, etc. And she says, "Well, this year, I'm going to accept that timelines are out of my control." And I was like, "Wait a minute...what?" "Deadlines are in my control, but timelines are out of my control." And that kind of blew my mind as a person who loves planning and who comes from an industry that is extremely deadline-driven, and I think we've probably conflated deadlines and timelines.

Pete: Yeah.

Jen: I kind of need to untangle this.

Pete: Yeah, I think I need to hear you untangle it. How do you think about the distinction between the two? Like, what is the deadline versus what is the timeline?

Jen: Well, a deadline is something that is self-imposed based on the information that you have. And a timeline is how things actually play out based on everything else.

Pete: Mmm. Do you think it's also not true, though, that deadlines can be imposed by other people?

Jen: Oh, sure. But they're...

Pete: Yeah, okay.

Jen: Okay, maybe a better way of describing that is deadlines are imposed and timelines are what actually play out.

Pete: Yeah. So in that sense, is a deadline like a goal?

Jen: Yes. I mean...

Pete: Or a lofty vision, or like a best-case scenario?

Jen: Absolutely. And I think deadlines are created, at least when they're created in a useful way, they're created based on logic and data and history and reason. Whereas a timeline might meet up with your deadlines, but there are certainly times when the timeline of how things actually play out does not meet up with your deadlines, and it has nothing to do with you.

Pete: Yeah.

Jen: So that just like really...ooh, as a person who really likes to think ahead, that rocked me a little bit.

Pete: Yeah. It's funny, maybe that's part of the questions I'm asking, and me trying to untangle this myself versus you trying to untangle this yourself. As a super-planner that you are and me working on being a planner, I wonder if that's why we're coming at this from slightly different places. Do you think it's something to do with...this is what's coming to my mind. Is, when we create a deadline or someone else creates a deadline for us, like you said, we think logically, we think, "This will lead to this, which will lead to this, which will lead to the deadline." And I feel like we do that in a way that's kind of linear. But then life, and timelines, and projects (creative ones, in particular), the reality is they're just not linear. They're all over the place. They're like...have you ever seen that diagram (I'm going to try and find it and put it in the Box O' Goodies) that's called the creative process? And it's like, basically, the line starts here, and then it kind of goes across the page, and then it just turns into this huge squiggly line, and then it comes out the other side as a line again. Like that's the nonlinear reality, which is the timeline.

Jen: Yeah. And it's like...this distinction is making me bounce off of a million different ideas. So maybe I'll just say them all, and then we can pull on some. Planning Fallacy, which is, you know, the phenomenon that we think things don't take as long to complete as they actually do. And as you become a person who's better at tracking your time, you can close the gap on the Planning Fallacy. So, that's one way to bring deadlines and timelines closer together. I also think about some of the ways we've unpacked in the past, around the way people hide. And one of the ways people hide is by setting unrealistic deadlines and then saying like, "Look, the timeline rolled out that way, so I should never show up in anything ever again." And then the other thing is, experience...well, I guess this pings off of the Planning Fallacy idea. Experience creates more accuracy. Like I was mentioning, I'm in a very deadline-driven industry. When we in the theatre industry set a production schedule, unless there's a global pandemic, we meet our deadlines. When we say, "Opening night is such and such a day," that's when we open. When we say, "You have eighteen days of rehearsal," you don't get nineteen days of rehearsal, the show has to be ready on day nineteen to move into the theater. But the reason we're able to be that specific about deadlines and timelines is we have so much experience to back it up and say, "This is actually how long this thing takes." So it makes me think about, you know, we're toward the beginning of the year and people are setting all of these new goals and pursuing new paths, and how many people (I'm sure I'm included in this) might be doing things they don't know how to do, so they don't actually know how long it's going to take to do that.

Pete: Yeah, so true. You know, it reminds me bizarrely of when I (but I think a lot of people) was at university, and I would have a deadline for an assignment. And I think often in the classes that I took, they would say, "Here's a recommended timeline for completing the assignment. You spend a week researching. You spend a week doing your first draft. You spend a week getting feedback. And then, a week doing it. And it's about a four week process." And I was like, "Oh yeah, that timeline makes sense." And then, inevitably, twenty-four hours before the deadline, you're like, "Oh my god, I need to get that essay done." And you're researching and you're writing and getting feedback all at the same time. And it's like the reality, because of the deadline that's not going to change, it changes. Which...and then even that reminds me of Parkinson's Law.

Jen: Yep.

Pete: Which is that idea that a task will shrink or expand based on the time we allott to it. And, yeah. So I just, I don't know, I'm like throwing these ideas around as well. Is, is the takeaway that we should just not bother with the timeline because it's just going to take however long it takes? Is the takeaway that we should get better at setting deadlines? I don't know, I'm trying to untangle.

Jen: No, no, no...that's my immediate response. No.

Pete: No.

Jen: Because if we don't put any edges on the sandbox, we can just flail forever. But I do think it's like really interesting to think about when you set a deadline for yourself and you meet that deadline, but the larger timeline that your goal fits into takes longer. Like as an example, if you are someone who is seeking a new job, and one of the things you need to acquire for said new job is a proficiency in a certain skill. And you set a deadline like, "I will know this programming software by February 1st." And you meet that deadline, but then the dream job doesn't even become available to send an application in until September. So there your deadline, you met it, it was in your control. But the timeline was out of your control. So how do you reconcile those things and then use whatever learnings you gained from meeting your deadline to continue to move yourself forward, even if the timeline isn't in your favor?

Pete: Yeah. I think that distinction, naturally, I'm obsessed with because I've talked about it a lot on this podcast, of the things that are within our control versus the things that are outside of our control. And I think I heard you say this earlier, but it's like only clicking for me now. Which is, the trap that we might get into, in that example that you just raised, for example, is, "But I did my piece, I hit my deadline. And so like, now I just hide because the timeline is now outside my control. I'm going to get the job or I'm not." And we don't do anything to maybe move it forward. Like we don't check in with the recruiter to say, "Is there anything else you need from me at this point?" Like there are ways that we could perhaps nudge, or stay accountable to, or keep others accountable to a proposed timeline, even though a lot of it is outside of our control. There's this idea that there's actually a trichotomy of control instead of a dichotomy of control, which the stoics have written about. Which is, there's this middle one, this middle ground, which is things of which you have some control. And the example that's often used is a game of tennis. That you could control the way you show up, the way that you execute your tennis game, but you can't control how the other person is going to react. And so you have some control over the outcome of said tennis game, but not full control. So there's this interesting middle ground. Which, I wonder if too many of us (probably myself included) think, "I've done the thing in my control. Now, it's out of my control. So I'm just going to forget about it, hide from it, not talk about it." We've talked about nudging before, or checking in, or reaching out. There are, I'm sure, little tasks that we can do in-between that are within our control, that give some level of input to the thing that's outside of our control. I hope I'm making sense.

Jen: Yes, and my mind is melting. Because I think this is such an important area that we haven't fully ever dug into on this podcast, which is this middle ground of what is like kind of/maybe/almost in your control, but also kind of/maybe/almost out of your control. So interesting, Pete. So, this is like...wow, I'm just all over the place right now, pinging off of every possible dot that I can connect. It's making me think about opening yourself to the fact that other people have different priorities than yours.

Pete: Oh yeah, mm-hmm.

Jen: That feels like an important piece of this.

Pete: Oh, that's good.

Jen: That given circumstances are always changing, and the only thing you can do is make educated guesses based on the information you have at the time you make the decision to set the deadline. And we know that constraints breed creativity and progress, so to relinquish deadlines wouldn't necessarily be productive. Oh, it's also reminding me of an episode that we recorded a while ago but that people found really helpful. And it was called Patience, Episode 54. And in that episode, we talked about the difference between waiting, which is like sitting around twiddling your thumbs and not doing anything to move yourself forward, and practicing patience, which is an active choice on your part. And you can fill that patient time with other things, if you choose.

Pete: Mmm. Yeah, I think the other takeaway or the other thing that feels obvious to me now, is it emphasizes the need to learn from our process.

Jen: Yeah.

Pete: Because if we are (which I think a lot of us are) historically notoriously bad at perhaps estimating our time required to complete something...so we say, "Oh, I'll get that done by next week," and then we like get into it and we go, "Oh my god, actually, I need a month. This is a big process." And if that is a theme that just keeps happening and happening and happening, I think what's being missed is (I mean, to reference another episode that we've done, Reflection Scripts) this idea that we pause and reflect on the things that we just learned based on the project we just did and the outcomes that happened, so that we can get better. So I feel like there's an important learning process that happens when we set a deadline and go through the timeline to hopefully hit the deadline. There's this like necessary reflection after that, to go, "Okay. What information did I have when I set the deadline? Cool, cool, cool. What actually transpired? Great. And then what can I learn from that so that in the future, I either get better at hitting my deadlines, or I do the same thing because I went really well so I remember to do that same process again?" And so I just, I think there's this...rather than letting things happen and continue to happen and become a theme, which is, "I set a deadline and I went way over the deadline. I set a deadline and I went away under the deadline." That's the two of many different possible scenarios. But if there's a consistent theme, what I'm saying is, let's learn from that and get better at trying to align the two. It feels like what we want to do is get those two as close together as possible, the deadline and the timeline.

Jen: Mm-hmm. Yeah. You know, this is making me think of something Seth Godin has said many, many times about what it means to be a professional, that professionals ship their work on time.

Pete: Yeah.

Jen: Eek. And it also, though, makes me think about a friend of mine who, I think it was in 2019, published a book. And it was not the first book he had written, and so he had based his writing deadlines with his publisher on how long it took them to write the other book. But this book took so much longer, and it ended up being turned in more than a year late because the content was just so much more complicated, required so much more research that couldn't be done at the level that was needed with the original deadline. The timeline to collect the research took a lot more. So they ended up publishing it late, but it was worth the weight in that case. And then the other thing that it's making me think of is, you often talk about your Five-Minute Journal, part of your daily routine. That same company, Intelligent Change, also has a product called the Productivity Planner. And one of the elements of the Productivity Planner is when you name a task that you're going to complete, you estimate how many Pomodoros you think it's going to take. (A Pomodoro being a twenty-five minute segment of time in the Pomodoro method, and then you would take a five minute break, and then do another Pomodoro. But after you've completed the task, they ask you to acknowledge how many Pomodoros it actually took. And so that is a daily practice of getting better at acknowledging that there's a difference between your perceived timeline and the real one, and bringing your deadline and your timeline closer together.

Pete: Yeah. I don't know why this didn't occur to me until just now, but this is one of the most hard to bed down, difficult to navigate reasons for cost blowout situations that happen, especially in tech companies, where it's notoriously really, really hard. And many companies, but many developers, many product managers, many, you know, executives or startup founders have a hard time really understanding how long it's going to take to build software. And so they'll make these estimates that, you know, I remember when I worked at a company and they would say, "Oh, that will be thirty days of development work." And we're like, "Thirty days of development work, that sounds outrageous. All we want to do is change the checkout process in this particular transaction. What do you mean," and then it might actually only take them two days. Or sometimes they say, "It's two days," and it ends up being thirty days. So this like need to learn from and get better at measuring how long things take, it's really, really common in software development.

Jen: I'm also seeing that a benefit of getting better at this would be more time off.

Pete: Right.

Jen: Like if you really can figure this out, you could plan your holidays a little better.

Pete: Yeah. And that's an interesting point, because one of the final thoughts I think my brain is extending into is, is it possible that (as a very large sweeping generalization) we're better at deadlines because we're accountable to someone else, whereas timelines are often internal? And so, if I commit to Jen that, "Next Wednesday, I'm going to have a blog post over to you," (I'm making up an example), and I know that that's something you and I have agreed, well, the timeline between me and myself in terms of when I'm going to sit down and write it, I'm not accountable to anyone other than myself for that. So as long as I hit the deadline, which I'm accountable to, it's easier for me to break the contract with myself, being the timeline. Does that make sense? Like is one solo and easy to hide and mix around, whereas the other one is like you're accountable to someone else?

Jen: Well, the thing that's so fascinating about that (and so meta, Pete) is you and I are working on a project right now...which, listeners, we'll tell you about when it's ready. What we're coming up against is we have a timeline but we have no deadlines, and that is proving to be quite the problem. So I think we might have just perhaps nudged ourselves forward by acknowledging we need to add some deadlines to our lives so that we can actually ride the wave of the timeline that we've proposed.

Pete: Yeah, we're missing deadlines. I think we need to re-listen to this episode-

Jen: Yeah, I think so.

Pete: -and take our own advice. Oh dear. Okay. So based on that, working backwards, I guess one of the main things I'm taking away from this is, I think we need both both deadlines and timelines. I think they're different, because of many different things that we've talked about. Sometimes they're outside our control, some are within our control. I think deadlines are often more accountable to other people. Timelines are often more internal. And so I think there's a really important and necessary distinction to make when starting a project, when creating anything, between, "What's the deadline," but also, "What is my timeline?" What are you taking away from this thread?

Jen: Yes, to everything you said. And I'm going back to the original inspiration for this episode, which is to remember that the timeline is out of my control, so I've got to hold it very lightly. But the thing I can control are the deadlines that I or someone else might assign to me, and that is how I'm going to move the needle forward, by focusing on the deadline rather than throwing my hands in the air because of the timeline.

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