The Long and The Short Of It

Episode 406 - Perfectionism Trap

Transcript:

Pete: Hey, Jen.

Jen: Hey, Pete.

Pete: I have discovered a new perfectionism trap.

Jen: Oh, yikes.

Pete: I know, and I need your help getting me out of the trap.

Jen: Okay, I am very curious.

Pete: This is The Long and The Short of It.

Jen: Perfectionism traps, yikes.

Pete: Yeah, so, you know, our old friend perfectionism.

Jen: Heard of her, yep.

Pete: I've liked to think over the last few years, I've gotten pretty good at navigating my own perfectionism trap. And what I mean by that is I've gotten better at shipping things, calling things done, putting things into the world that are at a standard that I'm proud of and that are good, but they're not perfect, because perfect is like this nebulous concept that kind of doesn't exist, because it's different to every individual and it's a bit of a hiding place. And I guess we could go on a whole different rant about the fact that perfect doesn't exist, and I'm pretty sure we have in one of our old episodes. So, I feel like I've gotten pretty good at like, you know, putting things into the world and maybe they feel like they're only 95% there, but it's okay because done is better than, you know, not done and constantly iterating and thinking that you're being productive, but actually you're just going round and round in circles. What's the saying? Is it "perfect is the enemy of good"?

Jen: Don't let perfect be the enemy of good.

Pete: There you go. So, all that to say, I feel like I've gotten pretty good at that. I mean, this podcast is a good example of that. I don't think I've ever had a podcast that we've listened to and gone, "It's perfect. Put it into the world."

Jen: No, that's for sure.

Pete: Right. So, I feel like I've got all these little practices and I'm like, yeah, you got to ship that email, that reach out, or that proposal, even though it's not quite perfect, because you got to generate momentum and get things going and blah, blah, blah. Okay, so, enter AI.

Jen: Oh, yeah.

Pete: Which, you know, we've mentioned a few times, everyone wants to talk about, but it is becoming a very big part of my workflow and I use Claude Code, I use Claude Cowork, I use it pretty much every day for a lot of different tasks and it's wild how useful it is at helping me get a bunch of things done and brainstorm a bunch of things and challenge my own thinking, like a thinking partner. And, slash, but, one thing I've caught myself doing of late is saying something like, "Is this a 10 out of 10 yet? Can you help me make it a 10 out of 10?" Or, "I need you to help me make this world class. Here's my rough version. Can you make it world class?" And it'll come back with some suggestions and I'll go, "But how do we make it even better? How do we make it an 11 out of 10? What would that look like?" And I'm like constantly asking AI to help me improve things, which I think is good to the point where you then ship it. But I'm noticing myself in the last few weeks starting a lot of things, improving a lot of things, and not necessarily shipping a lot of things. So, help? Help? Is this common? Do you know what I mean?

Jen: Ooh wee. Well, first of all, Pete, I'm just laughing because the questions you're asking AI sound like the questions AI asks you. So, it's just like, it's circling the airport and not planning to land. Because every time you're done with something, unless you've trained your AI to not do this, it'll say, "And would you like me to offer this? And would you like me to suggest this? And would you like me to make this better for you?" So, it's just funny that you're doing that to yourself now.

Pete: It is. I mean, there is this reality to these tools that I'm getting more and more aware of. That is, their incentive is to have you to keep using the platform to keep burning tokens, because that's their business model. So, of course, they're going to come up with a bunch of useful suggestions. And sometimes I'm like, "Oh, that is a damn good suggestion." I have actually had conversations where I'm like, "Please don't keep asking me to do more things, because I know that that's just going to delay this." So, I feel like I'm getting better at catching the trap.

Jen: Well, I found myself in a similar conundrum, Pete. And if I have not told you this yet, I actually cannot believe I never told you this. I had it create a Ship It skill.

Pete: Okay, I don't know about this.

Jen: So, I went to Seth Godin's Ship It Journal, which Seth gives away online. This is not me stealing Seth's IP. I will actually put a link to the blog post where Seth offers you a free download of the Ship It Journal and encourages you to share it with people. I will put that link in the Box O' Goodies. The Ship It Journal is this amazing journal, really, that Seth created that helps you take something from inception to ship date. And so, I put the Ship It Journal into Claude and I said, "Based on this brilliant thinking by Seth Godin, I want to create a skill that requires me to answer all of these questions in order so that I can actually ship things." And, Pete, maybe it's been a while since you've looked at the Ship It Journal, because it had been a while for me.

Pete: Yeah, it has.

Jen: So, one of the things that you do at the beginning of the Ship It Journal is pick your edges. And that has been so helpful to me in avoiding the perfectionism, because you name right up at the top (it's on, like, page five of the Ship It Journal) what are the things you will not compromise on? But, you know, Seth's point always is, like, if you are not going to compromise on this, you've got to be willing to compromise in other places. You can't be the...I don't know, I'm just going to pull some ideas. You can't be the cheapest and the most luxury. Like, you can't be both of those things. So, anyway, putting the edges on that has been so helpful, as well as all the other questions. But just, like, out of the gate, it will remind you that, like, well, what you're trying to do here is make something that's cutting edge. So, all these directions you're going are now getting in the way of being at the forefront of something or at the cutting edge.

Pete: Jen Waldman, how dare you not share this with me until now? And that is the coolest idea I have ever heard. I'm so obsessed with this.

Jen: It's so great. And the reason, Pete, I did this was because on a couple episodes ago that was titled Occam's Razor, I shared this horrible experience I had spending four hours in a Panera not being able to answer a question. And I was like, "I have to put some fail-safes in place that I never get to this point again." And I thought of the Ship It Journal. So, that's one of the things that I do now.

Pete: That is so good. Okay, I'm obsessed with that idea. I'm going to use it. I'm going to borrow it. I'm going to create my own skill. And we should totally send that to Seth. He would love it. So, one of the things I've done last week was I made a rule for myself that I wasn't allowed to start another project in Claude until I shipped all the ones that I already had going. Because I had, I mean, I had like seven going at the same time. This like proposal here and this website refresh here and I'm building this case study there and I'm having it review all of our podcasts to pull out interesting stories that we've done. I'm doing all these different things and I'm like excited about all of them. And meanwhile, I'm also like, "Ooh, and this one. Ooh, and this. I just thought of another cool one. I just thought of the Ship It skill. I'm going to add that," like all these things. And last week I got to the point where I was like, "This is getting so ridiculous. You need to ship these five things," because they were time sensitive, which was useful, "and only once you've shipped those, you can then start to play around with those." So, I now have like a separate text file that's just called Claude Projects. And I mean, it's getting longer and longer by the day, but I'm only allowed to take from them when I've shipped something. So, I'm like trying to play around with not having multiple things on the go at once. Because that's one of the other things I've found is, I mean, we know humans can't multitask, but AI is pretty good at multitasking. It can do so many things at once.

Jen: Yeah. Oh my gosh, I have so many thoughts about this. First of all, Pete, we have a very long-time listener and a dear friend of mine, Michael, who told me once that when he buys an article of clothing, in order for it to get a spot in the closet, he has to get rid of another article of clothing.

Pete: Love it.

Jen: So, it kind of sounds like you're applying that principle, which is so great. So, the other thing is, Pete, you were calling this a perfectionism trap. And what I'm hearing in here is distraction. And I'm sure we've said this on the podcast before, but I once heard someone say, and it stopped me in my tracks, I literally had to stop moving when I heard someone say, "The opposite of distraction is not focus. The opposite of distraction is traction."

Pete: Oh, how dare you.

Jen: Right. And so, what it sounds like to me is that you have so many plates spinning at the same time that you're actually potentially slowing yourself down by speeding yourself up.

Pete: Oh, that is so good. Slowing yourself down by speeding yourself up. Because I agree. I actually think that both things are true and both things are happening and both things are slowing me down. One is, on the projects that I am saying I'm going to ship, I definitely am doing like three or four extra, "Are you sure this is a 10 out of 10? Are you sure this is world class? Are you sure this is as good as we could possibly do?" I'm definitely doing that. So, that perfectionism trap, I think, is still there. But maybe the bigger point is the one you described, which is I'm so distracted and honestly excited. But I mean, I have not been this energized about my work and the ideas that I have for, I don't even know how long. Like, years. Not to say I wasn't energized, but just to say at the moment, I cannot stop thinking of like new ways to help my clients and use these tools and try interesting experiments. So, it's like a victim of that plus the victim of the fact that, like we mentioned, these models are deliberately, I'm sure, influencing that, because they're encouraging me to keep thinking about new ways of doing things. Is making me, yeah, lose traction, get distracted, because I'm coming up with all these different thought bubbles. So, it's a combination of the two, which to your point, slows you down, even though, my God, it feels like we're moving so fast at the moment. And I'm like doing all these cool things and I'm, "Oh my God, I just did this thing that I would never have done if I didn't have this tool." And I was just crazy, but it's the filter of, yeah, is that actually speeding you up or is that actually slowing you down? And could you be moving even faster if you focused on, I don't know, one or two things at a time?

Jen: Yeah, well, it's bringing up yet another thought for me, which is making sure that you know what it's all for. So, like, "I'm having Claude read all of our podcast transcripts," so that what? And maybe the things that have a clearer "so that" are the things that could get the focus and the things that are like, just for fun, could maybe be for not work days.

Pete: Yeah, that's a good point. I mean, I'll tell you and our listeners, I've had one of the Claude Code models mine all of our 400 plus episodes for what it thinks (and I guess that's an objective, interesting parameter in and of itself) are the best stories and the best frameworks that we've shared across these 400 episodes. So that I then have essentially a repository of our frameworks and our stories, because I forget so many of them across 400 episodes. And so when I'm designing a keynote or a workshop or thinking about an idea, I want to be able to say, "Hey, have we talked about this before? Or is there a framework Jen and I have mentioned before? Or is there a story I should use to start this keynote?" And it will go, "Yeah, Pete, here is literally what you and Jen said verbatim." So it's wildly useful.

Jen: So useful.

Pete: I just find, I mean, yesterday, this is so real. Yesterday, Claude's like, "We released a new model that's more powerful than every other model." And I'm like, "Well, does that mean I need to do that entire thing again? Because it'll be better?"

Jen: I had that message pop up today for me and I said, "Skip."

Pete: Oh, good for you. I'm such a sucker for, "Maybe I could do all these projects that I've been currently doing, but even better, because it's more powerful now."

Jen: Right. I'm sure it is. But like you, I can get sucked into it and go like hours. It's like the nerd's version of scrolling.

Pete: Yeah, I don't do much scrolling anymore, but my God, I do some prompting. I do some conversation.

Jen: Oh, I do so many prompts. I'm burning some tokens over here. I love it. Oh my gosh.

Pete: This is, I guess, a classic case of everything that we spruik and talk about, which is, it's so helpful to say this out loud, to call myself out for getting stuck in these perfectionism traps. I know it's happening and my AI probably knows it's happening, but I'm like, "It's just our little secret." So I got to tell Jen, because if I do that, then I got to do something about it.

Jen: Yeah, it's making me think, Pete, that maybe you could build a skill where after you've asked certain kinds of questions, it says to you, "You're falling into the perfectionism trap."

Pete: "Yeah, you're doing it again, Pete. You're doing it again."

Jen: Yep.

Pete: Like, if I ask you, "Is this 10 out of 10?" for the fifth time. Also, sidebar, I love these different little benchmarks we give AI. I've had a chat with a friend yesterday who sent me, like, one of the things he'd been doing and he's like, "Oh, you know, I gave it the prompt to do this world class, blah, blah." And I was like, "Oh, you say world class too?" And he's like, "Every single time." I'm like, "Me too." I say everything's going to be world class, because why would I do otherwise?

Jen: Right. Whoa, I just had a thought, Pete. I hope this does not send us down a dark, stormy, spiral situation. But I run into this with clients a lot, that they seek feedback from all sorts of sources, and they may get from one source negative feedback, which they will trust, but then that same person will give them positive feedback and they don't trust it, or vice versa. And then every so often, they bring someone into their life who they really do trust on both sides of that coin, where it's like, "I trust you to tell me when something needs work, which means I will also trust you when you say that something is ready to be shipped." And I do believe it is a trust issue. So what I am hearing is that you might not trust your AI.

Pete: Do I have trust issues?

Jen: Yeah, me too. But then I guess the question is, why are you then trusting the robot to tell you when something is good enough to ship?

Pete: Because, Jen, I guess I like validation.

Jen: Okay, fair enough. Although the validation, it sounds like, isn't actually getting the projects out of the door.

Pete: And maybe it's not validation. Maybe it's...you know what this probably is? It's Pete's tendency to get the A. And I feel like before I send something to a client, I want someone, something, some entity to say, "Great job, Pete. You did it. You got an A, and now it's ready to go." But to quote Benjamin Zander and Rosamund Zander from one of our favorite books, The Art of Possibility, maybe, just maybe, I need to continue to get better at giving myself the A.

Jen: Yeah, maybe. And you know what else you used to do that you could do again?

Pete: What?

Jen: You could send something that you're planning to ship to one of your human friends who you trust will tell you if it needs work.

Pete: I do that too, by the way. But I could get better at doing that, for sure. Noted. Noted.

Jen: I don't know why I suddenly feel like I have to tell you my advice for how you should be doing your work.

Pete: I'm getting called out, team. I need to wrap this right up.

Jen: But the reason, Pete, is because your work is so good and so valuable and so impactful that the thought of it, getting stuck on the hamster wheel of Claude, is giving me agita. I want your work out there in the world where it can make the difference that it's supposed to make.

Pete: Okay, well, excuse me while I go and tell Claude to stop, and I'm going to go ship some stuff.

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