The Long and The Short Of It

Episode 87 - Legacy

Transcript:

Pete: Hey Jen.

Jen: Well, hello there, Peter Shepherd.

Pete: I heard something in a podcast recently that blew my mind as it relates to legacy, I think. And I would love to share it with you and for us to unpack it.

Jen: You know that on my Brene Brown list, legacy is one of my two words. So, I am into it. This is The Long and The Short Of It.

Pete: Alright. So I've been bingeing a series of podcasts by Derek Sivers, who we've mentioned on this podcast quite a few times. He is an author, former entrepreneur, really, really interesting thinker, and challenger of basically any mental model you can imagine. He has imagined what it's like to be the opposite of that. So, I find him refreshing to listen to because he just challenges every single story that you tell yourself, I find. And so, in a recent episode of a podcast he was interviewed on, he talked about...well, they asked him about how he thinks about legacy and, kind of, I think they were trying to go down a philosophical path of like, "What happens after you die?".

Jen: Mm-hmm.

Pete: Like sort of heading towards that direction. And he sort of paused and thought about it for a second, and then said something to the tune of, "Well, my personality lives on in the work that I create, and put into the world. And so whenever I'm creating something (i.e. a book, or a podcast, or a blog, or doing an interview, or giving a keynote), I try and think about, 'Is my personality reflected in this?'. Because I know that when I die, people can get a taste of my personality in the work that I've put into the world.". And I had to rewind and listen to it about five times. It blew my mind. And it seems so simple, but I just like have been thinking about it for about two weeks now. So, what like...talk to me about what you hear when I even just say that.

Jen: I mean, that just...it strikes a very deep and resonant chord in me.

Pete: Mmm.

Jen: And it immediately made me think of a podcast that I was listening to today, where the person being interviewed was actually our mutual friend, Caitlin Fahey. And she was talking about the confusion she feels around people who devote so much to work they don't believe in, don't care about, don't love.

Pete: Mmm.

Jen: And so, my immediate thought when I heard that Derek Sivers quote is, "And oh my goodness, what about the people who aren't putting their personality into their work? Does that mean that they're doomed to be misunderstood for all time?".

Pete: Mmm. Wow. Wow. Yeah. I mean that, that thread was kind of my first reaction. So when I heard this quote (and paused, and rewound, and listened to it six times over), I then just went down the like rabbit hole of, "What is the work that I'm shipping into the world? And is it a reflection of my personality?". And I found a bunch of stuff that I could proudly say, "Yeah, it is.". And honestly, I found some stuff that I was like, "I don't think it is.". So, that's a cool moment to pause and think either, "Do I want to stop doing that? Or do I want to inject some more personality into that, and what does that look like?". So yeah, that was the, that was the first direction I took it too, is, "Am I not...or, where am I not injecting personality, and Pete into the work that I'm putting out there? And if not, why not?".

Jen: Okay, this is bringing to mind a conversation you and I literally had ten minutes before we started recording, where I showed you the latest Instagram post I made about our Learning Lab.

Pete: Yes.

Jen: Which I think is kind of funny.

Pete: [laughter] It's ridiculous!

Jen: But I was saying to you that because I feel like I'm speaking for both of us when I talk about the podcast, I put things in there that I think are reflective of your sense of humor, because I want to make sure that we're both accounted for in what I'm posting.

Pete: Mmm. That's so interesting, because you mentioned it was reflective of my personality. And so I would ask...in doing so, do you think it's also a reflection of your personality, or our collective personality?

Jen: Yes. I mean, so what I...full disclosure here, listeners. I feel like I have to have a punch line in something I'm posting, if I'm posting on behalf of the two of us. Because I remember you saying that one of the things you try to do with Instagram is make people laugh or smile.

Pete: Hmm.

Jen: So, that's what I try to do when I'm posting on our mutual behalf. So, I just thought that was an interesting side note.

Pete: Mmm. I love that. Because I think like, honestly, that's the...I mean, we don't have to go down social media rabbit hole. But the, the place that I referenced where I have caught myself not necessarily being a reflection of my personality is on various social media platforms.

Jen: Hmm. That's funny.

Pete: Yeah. Like, Instagram. In the past, honestly, is I have thought about it so much, or overthought it so much that I haven't posted something even though I'm like, "This is hilarious. I should post this.". And I'll be like, "Oh, no, no, no, no, no. No one needs to see that.". And so like, talking myself out of sharing a version of my personality is definitely something that I've done in the past. And, I agree with you around the podcast. It's, if and when we're sharing anything to do with The Long and The Short Of It, I'm always like, "Well, it's going to make people laugh. Let's just add a little, a little bit of Rule Number Six, a little bit of humor in here.". Hmm. And before you can even explore Derek Sivers' amazing quote, there's a level of self-awareness that one must have of like, "Well, what is my personality? What are my values?". You know? "What are the things that I want people to notice in my work and say, 'Oh, yeah, that must be something that Pete did, or that must be something that Jen did because of the tone, or because of the humor, or because of the question, or the insight.'". So, I think there's a level...it's almost like a step before this, which is really a values exercise, a self-awareness exercise of which there are plenty out there.

Jen: We do this exercise in one of my classes, based on an analysis book, that we call the Personality Profile, or the Character Profile. And basically, we look at the behaviors, or the actions a character takes in a story, and we create (from an outsider's perspective), a character trait profile of how that person might be described. So, we might call a character short-tempered, or pouty, or hopeful. You know, we accumulate all of these words. And then we, we sort of talk about how it was the actions that led us to label people in this way. And then we reverse engineer it on ourselves. It's like, "Okay, well, if I know...I, I believe myself to be hopeful. And I want other people to see that. What actions do I have to take? Or what behaviors do I have to exhibit in order to earn the adjective 'hopeful'?".

Pete: Ooh, I love that.

Jen: And I just wonder how you can look at that in terms of putting your own work out into the world. Like, what, what do you have to do to earn people seeing what you want them to see?

Pete: Yeah, that's so good. I think just in the way we communicate, as humans, as business people, as freelancers, as CEOs, as leaders, whatever position you hold...where I notice so much inconsistency, I think, in someone's personality versus how they're sharing their work is like, honestly, in a really simple example, is like an email.

Jen: Mm-hmm.

Pete: If you were, if you were to read a bunch of internal emails in a company from an individual, I would, I would wager (pulling figures out of nowhere), that almost like 85% of them are not a reflection of their personality. There is a certain like corporate tone, there is a certain culture from a company that is like, "This is the way we do things around here. This is the way we communicate.". And it's often quite formal, and rigid, and corporate. And, email being one example. Leveraging off that, the other example I've seen so much in my work and in my previous work, is in something like a proposal. So if someone asks you and your company to pitch a piece of work for a project they're working on, there are some proposals out there and some messaging out there that is so off-key, so tone deaf sometimes that it's no wonder that the proposals don't necessarily go anywhere. And I often wonder, and think about (and I've done a bunch of projects and work myself with businesses, and companies, and in my own business around proposals, as you know, and...) communicating in a way that is a human to human. You know? Like, there is a human reading this email on the other side of the computer screen. There is a human reading this proposal on the other side of the computer screen. So what would it look like for you to show up as you, the human, with your personality injected into the way you're communicating that message? And see if you might connect with the human on the other side of the screen.

Jen: I think that is such a great call out. And it immediately brings to mind other tools that we use, like resumes.

Pete: Yes.

Jen: I know we've done multiple episodes where we've discussed resumes.

Pete: I think there's a, there's a connection worth calling out here, too. Honestly, so many of the things we've talked about in the past...which is firstly, like, when communicating, when sending an email, when creating a CV, it's like very, very worthwhile thinking about it through an empathetic lens. Which is, "Who is the person that's going to be reading this? What do they need to know?".

Jen: Mm-hmm.

Pete: Like, I think that's the starting point. And then, to me, it's like, "How might I inject a little bit of Pete's personality, or Jen's personality, or my personality into this?". Still communicating in a way that's going to resonate with them, but doing so through the lens of like, "Oh, plus there's like a hint of, a hint of my personality in that.". Versus...what I'm not saying, and what we've talked about in the past, is showing up "authentically", without regard for who's on the receiving end. And then just being like, "Oh, but I was authentic. You should have just got it.". So, I'm not saying that. I'm saying, still start with empathy. And then think about, "How might I inject some personality into this?". So I have an example, actually, that involves you and I, that might be worth sharing.

Jen: Oh, really?

Pete: It's kind of funny, yeah.

Jen: Okay.

Pete: So, I've not shared this with you before. [laughter]

Jen: Okay, I'm a little nervous...

Pete: So this will, this will be funny. So when we very first started collaborating together, I came to New York, and you asked me to speak at your studio in front of a bunch of really interesting and amazing creative artists.

Jen: Right.

Pete: And there was some other work we did together. And our relationship at that point was...I was kind of your coach. And so you asked me, like, "Send an invoice.". Or like, "What's this, what's your, what's this fee? Like, what's your fee, basically?". And I agonized over this for hours, days maybe. And...

Jen: Really?

Pete: Yeah. And I actually...the short version of this story is I sent a draft response to our mutual friend and changemaker in Adelaide, Kirsty Stark. And it was this like, you know, over-manufactured, beautifully written, here's corporate Pete showing up, like, "Well, Jennifer. Based on the opportunity you've presented, I propose that we do this, and this, and this.". And Kirsty wrote back like one line, I think it was, which was basically like, "Where's Pete?".

Jen: [laughter] That's Kirsty.

Pete: Like, "You're not...this is not, this is not Pete. This message, yeah, this message is not Pete at all.". And I was like, "Hmm. Great point.". So I basically blew the whole message up, and just wrote this, like, I don't know, very casual one or two sentences, and within thirty seconds you replied, and were like, "Great, let's do it.". And I was just like, "Oh, of course.".

Jen: That's really funny.

Pete: Yeah.

Jen: Oh my gosh, remember your first trip to New York? We had, we had never seen each other before.

Pete: [laughter] I know, that's so true.

Jen: We had, we had been working together, but we had never seen each other. That was weird.

Pete: It was so weird. I remember it well. It was raining. We were in Greenwich Village, I think, from memory. [laughter]

Jen: I was in the middle of facilitating a workshop.

Pete: Mm-hmm. And in said workshop, to bring this back to the topic, I remember sitting and observing you in the workshop very much delivering content that was quite impactful for the people in the room, based on empathy. And doing so with Jen Waldman very much injected into it. So you were putting work into the wild, into the world, that was a reflection of your personality.

Jen: Wowza. There we go. Back at the start. Well, I have to thank you for this noodle Pete because (and I imagine the listeners are feeling the same way) I intend to step through my work, this week and hopefully beyond, with a new awareness of making sure that I am in it. That I am in my work. It's a beautiful thing.

Pete: Yeah. Because, I mean, at the end of the day...not to get morbid. But at the end of the day, when we pass, our personality lives on (this was kind of Derek's point) in the work that we create for many, many, many years beyond us.

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