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Here’s a question for you. Oh no. How do you plan for things? Oh God.

Oh, good, good, good. I’ll make sure to start talking slower. Have you ever seen that movie Zootopia?

I’m not familiar with that joke. Could you tell me about it? I hate you. I know

So, so the reason we came up with this episode is we have contrasting planning styles, or at least The tip of the iceberg. What you see as the output of us working on a thing are different planning styles. Nick is very much a, like when we were in Copenhagen. You showed up in Copenhagen with a list of these are the 30 boutiques I’m going to go to. Like, you very much had a plan and you have a system and you have the Leslie No binder of This is what I’m going to do. And I have a different planning style, which you’ve referred to in the past as Kai’s non-planning planning style. And hearing you explain that, like, or hearing you explain your side of it. I think we actually have very similar approaches, but different styles of it and different outputs or different surface level evidence of it. I live by a few key rules. If it’s not in my calendar, it doesn’t exist as an event and won’t happen. So my calendar is sacred. Like If you would like to have a call with me, it needs to be in the calendar. If it’s a project I’m going to work on, it needs to be on the calendar. If it’s a task I’m committing to, it both needs to be an omni-focus or Trello, depending on what project and where it’s supposed to live. And there needs to be time booked out on my calendar for me to work on that as a project. Either as here’s a four-hour block where I’m going to do stuff, or here’s a one-hour block where I’m going to do that specific thing. When it comes to the planning leading up to a project, I mean, I just got my entire Burning Man group onto Basecamp, and there’s 15 messages and something like 20 different to-dos all assigned to different people with dates on there because I very much enjoy the Hey, I’m at the 2,000-foot view. What needs to happen for us to reach our plan? How do we backwards plan from we have departed for Burning Man successfully to it is now today before we depart from Burning Man. On the to-do list, there is literally a to-do item, the final item to check off. Everybody in the car holds their ticket up to their hand before we put the key in the engine. Because you know what the worst case scenario is? We show up at the gate and somebody’s missing their goddamn ticket. So. I very much have a similar approach: I want to map everything out. I have the binder. I mean, I’m putting together the W Freelancing Academy right now and manhandling as much information into place as I can. There’s no way to do non-planning around it. But when I looked at my life, and I ironically did a lot of planning and note-taking before this episode. I realized my planing style is sort of a simmer in the background like you’re making a stew. I take a bunch of inputs, I toss them together, I talk with people, I let it simmer some more. And then I might act fast and decisively with what appears to be no planning, but it’s just because the planning is hidden behind the scenes. Like when I moved to Hawaii from the outside, I had a friend say, You make some really crazy spontaneous decisions in your life and business. You moved to Hawaii and then you moved back six months later. Are you having a midlife crisis? He honestly got to ask me this at 26 years old. Are you having a midlife crisis, Kai? And I realized it was because from the outside, he and genericizing it, they, the world, couldn’t quite see like the thought process that went into it. Like, picking on Hawaiian example. As an example of non-planning, I didn’t necessarily know I was going to move to Hawaii 12 months before I moved, but I knew something was coming up. And so I spent 12 months building up my savings, I spent six months building up a freelancing client base, I spent three months Building up a second stream of income. The iPhone eBay business I’ve alluded to a few times on this episode, or on this podcast, that we should record an episode about sometime. And I didn’t know what I was going to do. I knew I was prepared to do something. And so when I reached the point of I am going to do something, move to Hawaii. The punchlist of what needed to happen for that to be a success was really, really short. Make a budget, sell 90% of what I owned, tell my clients I’m going to be moving and I need to take a week off. Figure out the general area of Honolulu I wanted to live in, ship my car over there, buy a plane ticket, arrive in Hawaii. That was really it, because All of the planning that was necessary has sort of been happening in the background. As I know, something of this general shape and form is going to happen in a couple months or a year. Let me take care of the details now, even if I don’t know what it will be specifically. Similarly, when I visit another city, like we have very different approaches to visiting a city, I like throwing myself into the middle and figuring out Okay, what’s there? What interesting things are there to do here? What’s on my list? What are the things I should see and take it day by day? But there’s been some inputs of thinking about like, well, what type of experience do I want to have in the city? It might not be as. Specific as these are the restaurants I want to go to, this is what I want to experience, but is thinking about it on a mental level or emotional level What do I want to have happen here? So, when I think about our trip to Copenhagen together recently, you went into it with a very, very, not rigid, but a very structured idea of what you wanted to experience and what you wanted to see. For me, it was going in with a very strong emotional idea of: okay, I’m coming off of this conference, I’m coming off of a couple months of hard work. My ideal experience in Copenhagen is to Just rest, to relax, to emotionally recharge, to see some interesting things, to have some interesting events, but not overwhelm myself. And Having that as sort of the guiding idea of my experience in Copenhagen gave me ideas on how to experience and experiencing it. hang out with you for a day, go check out some boutiques, hang out with some other friends, spend a day by myself, hang out in the gardens for six hours and just zen out. And yeah, so I think there definitely is a good contrast between our different styles of planning. But Through it all, it seems like we have that similar thread: it has to be in the calendar. We have to have a general idea. If we’re making a commitment to do something, it’s a commitment. So it deserves to be treated with respect. If it’s not being treated with respect, is it really a commitment? And if it’s not a commitment, why are we wasting brain energy thinking about it?

Welcome to Pie Chat.

No, I agree. I agree. And for me personally, and like I hope the audience connects with these different planning styles, it very much is that measure twice, cut once approach. And I even think about My feature move in that context, where over the past two years I visited Chicago three or four times, San Diego twice, like all the places that are on my shortlist of, I would like to move here. I’m trying to spend as much time there in week to two week chunks as I can just to feel out more of the city and to connect to like our planning on vacation style. When I’ve shown up in Chicago recently, I haven’t had like an explicit plan of I want to see these 14 tourist sites in the week I’m here. It’s been very much a casual. I want to stay in an interesting neighborhood and just wander around and pretend I’m in need. Like, I want to go to Lula’s and then be disappointed that Lula’s is closed on Mondays because I always forget it’s closed on Mondays.

That’s where I fuck up.

Longman is open every day of the week. I just need to always start eating there. But, anyways, uh, uh, just go there on Tuesdays. Exactly. I should have done that last time. But, uh, Like you said, it gives me that impression or that experience of living in the city as a native, which is the measuring twice. Before I look back at my time living in Hawaii and Because it was Hawaii, I made it as one big leap. And there were benefits and costs to doing it that way. And this time I’m being a little more cautious about it and saying, I want it, like you’re saying, like. Visit Chicago in the winter so you know what the winter is like. Visit these different places. I’m just gonna say. Exactly. And, like, It all adds up and it all simmers in my brain. And it might be like, people like, haven’t you done that thing yet, Kai? Well, I’m still collecting data and letting it simmer and figuring out what the right action is. And there’ll be a time, maybe post-Burning Man, maybe in the new year, once I’ve like. Reach that point where something just clicks, and I’m like, I have enough data to make a decision on this. I’m going to make a decision. And then flurry of activity. In four weeks, my life will have changed completely, but It’s a slow, simmering data collection gathering process. And I think it applies to the positioning in my business as well. I’ve switched positions four times. That’s what he said, over the last couple of years. And each time it’s been like a small, carefully calculated risk. It hasn’t been overnight I’m tearing down the website and building a new one for a new audience. It’s what if I take a project for a slightly different target market? What if I do this project that’s a little outside of my comfort zone? Okay, both of those went well. What if I start advertising to that market or adding this as a service? Okay, that went well. And now I’m four months into it, and I’m like, okay, what if I update my positioning to reflect this new direction? Okay, that went well. Okay, what if I shut down the old website and just focus on the new market? Okay, that went well. And it’s been like a two-year process that from the outside might look like he’s walking an inch at a time, make him hurry up. But it’s also me being like very careful and deliberate and saying, let me gather a little data here. How was this experience? Did this go well? Is this a market I’d want to continue to serve? And over time, it’s slow incremental changes, a game of inches, that move up to a transformation in what my business is focused on and what I do. What I do now is Drastically different from what I did two years ago. But the benefit of it has been, I’ve learned so much along the way that it’s led me to this new point.

Like, come on, dude. Come on. But I mean, like, at the same time, I think this is this. The Google, and like we could, we could literally share the Google Doc in the show notes. I think it would be fun too. You sween. It exemplifies. It’s like I put this together 30 minutes before our call started, but I’d been, we talked about this episode maybe three months ago. And I’d been thinking about like, well how does my planning style contrast with Nick’s? And then we were in Copenhagen, I was like, okay, here’s some real world examples of it. And then we got back and I thought about it some more. How exactly do I plan? How do I make these commitments? How do I honor these commitments? What does it look like? What’s my philosophy on this? And it just was all floating around in my head. But because I’d spent so much time like letting it simmer, it was easy for me to be like, okay, what are like the four ideas? Okay, what are all the bullets for this? And like, there’s literally Four five levels of bullets for some of these topics, like five levels deep on sub-bullets, because it all just germinated in my head and came together as like oh, this is what the shape of it is actually like. Had you asked me three or four months ago, what’s your non-planning style like, I would have made scooby-doo noise, and had no response. But my approach is very much that let it simmer and see what comes out the other side.

Hey, by the way, the thing we talked about three months ago, I happen to have built it and launched it. What?

But yeah, I very much file, and again, I hope this is useful for the audience to talk about like these different planning styles. I don’t think either one of us Let me start by saying, I don’t think either of us are necessarily right, or there’s one right mode of planning, and I don’t think either of us are wrong. What’s important is Understanding how you as a person or you as a consultant, dear listener, actually process things or plan things and There’s always room for improvement. I mean, like, Marilyn Mann’s written and spoken a bunch about this. David Allen’s Getting Things Done is a wonderful resource. There’s so much great information you could pour into your brain about. How do I become an organized person? How do I plan things? How do I manage projects? How do I manage my life? Oh, what’s that book about ordering and cleaning up? The joy of tidying up.

Yeah. Yeah. No, I think it’s critical. Like. Own your process. There’s no right or wrong process. There’s your process, and understand that process.

Right. And if anybody says like your process is wrong, well, within that statement, I think it’s important to hear: hey, I have a different process, and I see contrasts and benefits that you might not see. And not to hear it as necessarily an attack, your way of planning is wrong, but instead take it as an opportunity to open a conversation about how planning styles differ or management or project management styles differ and say, What do you do differently? How do you handle this? Oh, that’s interesting. Oh, I learned something valuable there. Like, there’s probably three important lessons I learned about how to take a vacation from you while we were in Copenhagen together. And that those influenced the rest of my trip into Europe and will influence every single trip I take from now on. And it’s not because I was doing it wrong or you were doing it right. It’s because we had different styles and I was saying, oh, cool, you approach this in a different style. Let me look at this and say, oh, wow, these three bits, I love these three bits. I’m going to incorporate them into my style now. And it evolved not to change to mirror yours, but to become something new and different and grow on what I’ve learned.

Not going according to plan. Fuck everything.

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