We'll start with a question from Molly. Molly asks, "Are you a control freak?" She then elaborates, "Is it possible that trying to be on top of everything is a way to tame the anxiety of the uncertainty of our human condition?" Well, Molly, I think what we all probably agree on is that having no organization is stressful.

So if I'm entirely reactive, if I entirely exist from moment to moment, "Hey, what should I do next? What do I feel like? What's urgent? What am I late on?" This is not a great way to live as a human, especially in the modern context where we have such a high cognitive load of various obligations and ongoing tasks.

It's a complicated productivity landscape that the modern human exists in. And if you try to wander haphazardly through that landscape, you are going to get caught on a lot of dead ends. You're going to twist your metaphorical ankle in a lot of potholes. So you have to have some organization.

How much is too much? I would say when you feel like the organization is causing more stress than it's helping. It's a pretty simple heuristic, right? So, you start putting in place some sort of structure so that you have some sense of what you're trying to do and when you're trying to get it done.

You're basically, in our metaphor, drawing a map for this complex landscape. But if you get to a point where you find that you're spending too much time on that map, or the details of the map itself is starting to stress you out, then pull back. Use yourself as the thermostat here.

What I would caution you about is the, I would say, messy sophilism of just saying, "Don't be obsessed with... Everyone's obsessed with productivity and being organized and, you know, the human condition is messy and I'm just vaguely speaking feel some superiority because I can understand that that's all sort of bougie and I'm much more enlightened." That's just a sort of tonologically true, like, "Yeah, you shouldn't be too obsessed with being organized." It doesn't really add anything to the conversation.

Like, you can't run your life chaotically in the modern world. You need some organization. I can't tell you how much you should have or not. Figure that out based on how you feel. But let me give you some tools to draw from. I do think you're right that anxiety levels probably play a role in exactly where that set point lands.

I have quite a bit of structure because I think I would be anxious without it. I don't actually get a lot of anxiety in the classical sense. I don't ruminate on the future or worry about bad things that could happen. For me, and I've talked about this before, the omnipresent anxieties of the type of big stakes things I've been doing my entire life tend to manifest themselves in sleep issues.

So mentally, I feel fine. Like, "Okay, yeah, I guess I'm going on that TV show tomorrow. I guess we just signed that deal." But then I don't sleep. And so I use that as my barometer, and I find when I have some more structure about things are off my mind, I know what I'm working on, my plans are at multiple scales.

Here's my vision, which fuels my quarterly, which fuels my weekly, which fuels my daily time block planning. The relief of having to continually worry about, "Do I have the right plan? Am I missing something? Am I forgetting something? Am I making progress on things that matter?" That relief is helpful, and actually I typically find it helps my sleep, and then I know that's probably about right.

If I got even more obsessive about it, then probably would start to have negative impacts. I would have to rein in. For someone else, and I know people like this, they're at a different set point of anxiety. Maybe much less structure and organization would get them to where they need to be.

And having something like my multi-scale planning maybe would feel like it's too much. I don't know. I think that's possible. So I would say you have to control for yourself exactly how much structure you want in your life. But the only thing I know for sure is that no structure is never going to be the right answer.