The Long and The Short Of It

Episode 99 - Milestones

Transcript:

Pete: Hey, Jen.

Jen: Hi Pete.

Pete: Guess what?

Jen: What?

Pete: We have a big milestone coming up for The Long and The Short Of It. Episode 100.

Jen: Oh my goodness, yes. Next week is Episode 100.

Pete: And so, I thought it might be worth pausing pre-Episode 100 to talk about milestones.

Jen: Hmm. Let's do it. This is The Long and The Short Of It.

Pete: Alright, so it feels a little meta. But, you know, we love meta. So I was thinking about like, what, what might we talk about in the lead up to Episode 100? What might we talk about in Episode 100? And I thought maybe a good place to start would be: what is Episode 100? And if we think about why it feels important, I guess the topic at hand (like I mentioned in the intro) is milestones. And I'm just kind of curious to unpack milestones a little bit. So maybe your first question is like, when you think about milestones, what do you...like, what are they for? What is a milestone for?

Jen: Okay. Well, I had just two competing thoughts come to mind. So, one...

Pete: Ah, share them both.

Jen: Well, one is like, a milestone is marking an accomplishment where you've reached some pivotal moment. But then, I also think of like, a milestone just tells you where you are.

Pete: Yeah, it's interesting because I...like, part of me thinks milestones are overrated. In that sense of like, "It's just another episode. Or, it's just another birthday. Or, it's just another event, or thing that you've done, another notch in the belt, if you like.". And yet what I think, especially about most, you know, generous folks (like you) doing meaningful work, who are kind of so often head down, focusing on the work and the process...sometimes we don't celebrate enough, or we don't pause to like, recognize and accomplish and pat ourselves on the back for the work that we've done. So, I feel...I, too, feel conflicted. Like you, in that I feel like it's always worth in a milestone, whether it's a birthday, or a number of episodes or blog posts, or a revenue goal that you set for yourself, or a number of clients that you wanted to help get from A to B, whatever it is, I feel like there's an importance in pausing to reflect and pat yourself on the back in a way. And the conflicting thought comes because I guess you don't want to get complacent, right? You want to keep focusing on the work, and not...I guess what I'm trying to say is you don't do the work for the milestone. And so, it's like trying to keep that in mind. Of, what really are we doing here? We're not really trying to record a hundred episodes. We're trying to focus on creating change through the work that we do.

Jen: Yeah. I mean, yes to everything you just said. I also recognize that if we just kept recording and recording and recording and recording, and never gave ourselves a moment to pause and ask, "What have we actually accomplished," we might just be doing it by rote. And so the idea that, "Okay, we've gotten to Episode 100," now we have to raise the bar.

Pete: Ooh.

Jen: Like, expect a bit more excellence. So, that feels important to me. But then the other thing that I was thinking about is the corresponding question to "what's it for" which is "who's it for". Now, you and I could have like a private Slack message of like, "Hey, Happy 100th!" But instead, you chose to make this episode about it. So, who is that for? Well, that's for the listeners. Some of whom have been with us since day one, or week one, one hundred weeks ago. And that feels important to be like, "Listener, if you are an OG listener, my goodness. Thank you for being on this journey with us, and we can celebrate together." So, maybe a third idea around a milestone is it brings people together around a specific event.

Pete: Ooh, I love that. It's generous to your community, because it brings people together. Huh. I can get down with that. I wonder if...I mean, the other milestone that comes to mind that we all have is like a birthday. And so, if I think about a milestone birthday...often it's, you know, to mark the decade, whether it's 20, 30, 40, 50, whatever. And I think the same logic applies, right? Is, for the person whose birthday it is, often it's kind of like, "Eh, it's a milestone, and it's my birthday." But it's the bringing together of your family, or your friends, or your community that's the real fun part, the real joyful part. It's not necessarily the fact that you wake up and you're, you know, a year older, or a day older. It's actually, it's an opportunity to bring community together. Mmm.

Jen: Mm-hmm. Yeah, I like that. That feels really good. And that makes me pleased that you decided to celebrate this milestone today. Okay, so here's like a total tangent, but like, sort of related. I am super unsentimental about most milestones. Like, it's not that I don't care. But I find so many things that we celebrate to be so arbitrary that I'm like, "Do I really need to mark that occasion?" So, it's interesting from that perspective to sort of look at, "Well, what am I particularly sentimental or nostalgic about? And why?" Because there are so many things that I'm like, "Meh."

Pete: That's why, I mean, I kind of...I know this about you because you're a Questioner, right? You don't necessarily have attachment to milestones. So, I figured this would be an interesting conversation.

Jen: Well, I don't know why, this is...this is so weird where this is taking me, but it immediately brought up my wedding.

Pete: Alright. Let's do it.

Jen: My husband and I got married in 2008. So, you know, we've been married for a while. And my friends who were at our wedding commented about how weird our ceremony was. Because first of all, I walked...well, I didn't really walk, I sort of ran down the aisle to the theme from Superman.

Pete: You ran?

Jen: But besides that...

Pete: What?

Jen: You know when you go to a wedding and everyone is sort of putting on this very ceremonial vibe, and like the bride starts to walk down the aisle and she doesn't really make eye contact with anyone. She just sort of like walks in this straight, very, I don't know, very expected way.

Pete: Mmm.

Jen: And at my wedding which was a major milestone, (you know, committing to spending your whole life with someone), I sort of like ran down the aisle to the Superman theme and then stopped along the way to say hi to people.

Pete: [laughter] I love that. I mean, you know I have to ask on behalf of all of the listeners: what was with the Superman theme song?

Jen: I should, I should...woah, I realize that might have painted the wrong image. It was the love theme from Superman, not the like flying theme.

Pete: [laughter] I was like, "What? Is that why you were running, because it was symbolizing you were flying? Like, what is happening?"

Jen: It was the Can You Read My Mind theme. But what's really funny is my husband's best man turned to him and was like, "Superman, really?" [laughter]

Pete: I mean, I guess the learning there, or the idea that comes to mind there is really kind of intentionally making a milestone something that resonates with you. And that feels like kind of an obvious thing to say. But I feel like, to your point about weddings and brides or that kind of ceremony, I think the same can be true of milestones like reaching a number of episodes in a podcast, which is like this expectation of what you're meant to do, what you're supposed to do, what society expects you to do. And just like pausing for a moment to add some intention behind, like, what does this mean to us? I really like the idea that we kind of landed on, which is a celebration of the community that we've built. Like that, to me, is so much more inspiring than us holding up our mics and being like, "Ah, 100 episodes. Look at us. We are amazing." Because it's not about us at all.

Jen: Yeah, my brain is just like flipping through memory lane. But I'm like trying to validate this idea I have that there are like certain...I think, to your point, it's like the unique expression of what a milestone means that makes it important, rather than the presumed idea of what it's supposed to mean. And I'm just relating this right now to the COVID universe that we're living in, where there's just all expectations have been completely destroyed. Any milestone has been completely altered. You know, anyone who had a wedding scheduled-

Pete: Yeah.

Jen: -either had to cancel it or do it virtually. People who are marking the milestone of the passing of a loved one are having to rethink what does a memorial service look like? And I just, I wonder if there is something in there. That like, we're learning from this moment about how to celebrate the important moments in life, and how to sort of craft them into something that's really worth remembering or worth celebrating. I don't know, there's something there. I can't really like articulate it quite yet. But there is something in this idea of a milestone. The milestone of a hundred episodes, as an example, is going to be what we decide it is.

Pete: Yeah. Yeah. I'm curious about something you said earlier, too, which was this idea of raising the bar.

Jen: Hmm.

Pete: And I guess maybe just to hear you unpack that a little bit more. As to, what is it about a milestone and what is it about the number 100, in this example, that makes you think, or makes you want to put the flag in the ground and go, "This is now where we raise the bar." Tell me more about that.

Jen: I mean, it's just such a nice round number.

Pete: [laughter] It really is. It really is.

Jen: And it's, there's so much significant input in 100. Like, the fact that we've had 100 conversations, about 100 different things, in 100 different ways.

Pete: Hmm.

Jen: There's enough there to dig into and say, like, "What are the best parts of that? And how do we elevate that moving forward?" So, I mean, I guess we could do it on Episode 101. But there's something so clean about 100.

Pete: Totally. No, I'm with you. I like the clean number. So, I think what I hear though, is this idea of reflection.

Jen: Mm-hmm.

Pete: Which I think is something that is very common in kind of all milestones. I mean, you think about the milestone of turning over a new year, and everyone decides to do new year's resolutions or reflect on the twelve months that was. And so, I feel like that almost built into a milestone, for most people, is this point of reflection, and maybe gratitude for what was and what has been. And then to your point, knowing all of that, what might we do moving forward knowing all of this good stuff, and knowing all of the learnings that we've had along the way?

Jen: I'm sort of having a half-baked aha moment.

Pete: Yes, this is my favorite.

Jen: Which is, it's the idea of when you reach a milestone...it's easy as you're aiming toward something to believe that once you reach it, like something magical is going to happen as a result of having reached that milestone.

Pete: Mm-hmm.

Jen: And the truth is that reaching a milestone, the only change you're going to experience is the one that you actually create.

Pete: Yes.

Jen: I'm thinking back to when I made my Broadway debut in 1998. I remember how elated I was that night, and my whole family was there. It was like a whole big thing. But once we took our bow, I was like, "Oh, I'll just do the same thing tomorrow night." And I had this sort of like aha moment of, "Oh, well, I've done that. And nothing's changed. Like, there's...if I want more, I have to want more. I have to find more. I have to change something in me."

Pete: Yeah. I love that. I mean, it's like a, it's a reminder that everything is a story, essentially. Everything is about a story we tell ourself. And often, I mean, I guess a lot of this podcast is about trying to unpack some of the stories we tell ourselves that might not necessarily be that productive. And I guess this is, in a way this is the inverse. Which is like, a milestone is an opportunity to look at the story we tell ourselves about milestones and use that in a way that is productive. And so, it's almost...it is arbitrary. In that, it's just another number. And if it feeds a positive change, if it creates a story that we can tell ourselves that makes us reflect and then, to your point, raise the bar, then like, that's awesome. That's success. That might be what the milestone is for, is celebrating our community and giving us a reason (a ratchet, if you like) to think about how we might change the story in our head about what this podcast needs to be, should be, can be.

Jen: Oh, that is so beautiful, Peter. So this idea that a milestone is a moment for you to seize the opportunity to do even better, to be even more, to dream even bigger, to serve with even more generosity. That there is something about a milestone that gives you permission (if you take it) to show up even more.

Pete: Yeah. Yeah. I mean, I think about that with new year's resolutions, right? Like, to me, it's...I know various people have various opinions about it, but I've always thought of it as like a "Yes, and." Which is a reflection on what happened last year, and acknowledgement. So, "Yes, look at all this cool stuff I did last year. Look at all these opportunities for growth." And, "Here's how I'm going to build on that next year. Here's how I'm going to make it even more generous, more generative, more aligned to who I want to be in the future."

Jen: Well, I have to say, I'm pretty grateful to you for pointing out that we have a milestone coming up because this has been a wonderful opportunity for us to reflect and recognize that one, my goodness, community of listeners, we celebrate you and this journey we've all been on together. And two, it's time for us to raise the bar.

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