Hello there, friend!

When it comes to planning your work, what's your approach? Do you rely on structure a lot, with weekly reviews, time-boxing, and thinking through the order of your priorities, or do you go for spontaneity, working on whatever feels the most fun or the most urgent, and wondering what the hell is a weekly review? And more importantly, how stupid and anxiety-provoking does the opposite approach seem to you? If you feel comfortable with both, you can probably just skip to the Dig-ups section, but if you have a strong preference, let's explore what are the pros and cons of each.

Control vs. Energy

So: structure helps ensure that you're on top of everything, but it can feel boring or self-oppressive. It optimizes for control. Spontaneity helps you get in touch with a more natural rhythm of working, but it can be too chaotic and volatile. It optimizes for energy. As always, the right balance is somewhere in the middle, but it's not that structure comes at the cost of energy – in the right amount good structure actually gives you energy.

When you break big, faraway goals into smaller, more proximal ones, you benefit from the feedback this unlocks – whether you see you're on track or that you're falling behind, you're getting more energy than you'd get with just the ultimate goal scheduled sometime in the vague future. Smaller goals are also more actionable, giving you guidance on where to start. And when you make decisions about what to work on in advance, you avoid the need to make the decision in the moment when you're trying to start working, which can again make it easier to get started.

On the other hand, creating structure is extra non-essential work, so it better be worth it. No point in spending time on something that you're not gonna stick to anyway. And if you do stick to it but it's leaving you drained... well, that's suboptimal (though at times necessary). One thing that can help with this is learning about your natural energy cycles, then planning your work around those – experiment with scheduling different kinds of work for different parts of the day and see what works best. Even better is when you become able to notice your energy levels in the moment and choose work dynamically – labeling in advance the tasks to be done with the amount of energy they require can help here.

Octopodes (I couldn't resist) vs. Elephants

Over time, you'll figure out the right balance. But beware! It's tempting to get settled in your routines (after all that's what routines are for), so you need to remember that different routines work in different contexts. This means that the right balance is dynamic, constantly shifting along with the shifts in your environment and the nature of your current projects. You're not just looking for a person-structure fit, but also for structure-context fit. That's why I like to think in terms of modes.

When there's a lot of different deadlines to keep track of, more structure is the right play, because the primary demand is for control. Too much spontaneity would likely lead to constant firefighting (because intuition is not great at tracking deadlines) and procrastination (because having to determine the most urgent task every time you sit down to work is overwhelming). I like to call this the octopus mode, with the mental image of juggling all your priorities so well it almost seems you have multiple arms.

But when your goals flip to more distant goals, keeping you commitments under control is relatively easy – as long as you're able to maintain the standards you have for your output, you're good. The amount of structure you used in the octopus mode would become stifling and the effort that goes into it would feel like a pointless overhead, so you want to relax into a more spontaneous, intuitive approach. This is the elephant mode, when you're able to deploy a lot of power to a few goals that you pursue with determination... but you can't be bothered when you don't feel like it.

For me, the octopus mode means that during my weekly review, I'll go through all my projects one by one, checking that the work for all the upcoming deadlines is on track (ideally with enough buffer time), and scheduling each task for a specific day when I want to get it done. As I'm ramping amp my thesis writing though, my weekly goals are becoming much more similar and I'm turning into an elephant – primarily just getting as much writing done as possible. There are not that many looming deadlines, so I can monitor them all simultaneously (instead of project-by-project) and instead of scheduling single tasks, I tilt toward scheduling areas – most days are for the thesis, fewer for writing the newsletter, digital networking, or just learning about whatever I feel like. There are still tasks of course, but I treat them more like suggestions. This also lends itself to more flow, since I can focus on one area for entire days.

For you, this might look different, but as long as you're mindful of both the person-structure fit and the structure-context fit, you'll find the right mode variations and learn to switch them as needed.

Last week’s dig-ups

Personal metawork

• I started playing around with ChatGPT 4 and BingAI. A lot of learning is still ahead of me (e.g. how best to use them for research and learning, or about the stuff that I need to be able to use the code they write for me), but getting feedback on my writing seems like a great use-case (I fed it my essay from last week). I wonder how it benchmarked the ratings though, I need to test this with the writings of some of the writers I admire

• Did you know you can use OpenAI's WhisperAI for audio transcripts for free? Here is a great guide on how to do that, I tested it with one of my thesis interviews and it works like a charm!

• Andrew Huberman talks about the need to internally reward yourself for achieving small milestones to help you get more energy. Nothing new, but hearing it gave me an idea to create a “streak tracker” in Notion to help me avoid some bad habits, and so far this simple trick is working great!
  I used different ways of tracking habits before, but for these “focus commitments”, having the default be a continuation of the streak (I only change the date when I fail), automatically counting the length of the streak, and seeing the tracker right on my master dashboard somehow works the best, making it much easier for me to stick to the commitments.

Collective metawork

• Bureaucracies and central planning don’t work – however, in this pod, they come to the conclusion that the free market is ideal. While I agree with many of their points, they seem to be oblivious to the alternative to both hierarchies and markets – collaborative communities.

• This is such a fantastic episode of the Leaderhmorphosis podcast that I’ll need to relisten to it and take notes. Miki Kashtan talks about the difference between “Power over” and “Power with”, the importance of having a Conflict-engagement system and much more.

Entrepreneurship

• Alex Hormozi reminds everyone that success requires massive effort, and people tend to underestimate what “massive” means.

Philosophy & Sense-making

• After this interview with Sam Altman, I think I’ll be able to put my worries about AI-driven existential risk to rest for some time. Not that it can’t happen, but it seems that the people at OpenAI are approaching the challenge very responsibly. I might listen again with video to see how credible Altman seems, but he at least sounds convincing.

• With the “banks melting” as Elon says, Balaji Srinivasan and others think that Bitcoin might soon replace the dollar as the reserve currency. I hope hyperinflation is not in the cards, because that would get ugly but it’s true that going off the gold standard correlates with a lot of bad trends. And if the world was going to change to a new reserve currency, things would certainly get worse before they got better… so maybe we’re headed for that now?

Reflection

• Well, most of the reflection is once again above already, but one fresh insight is that writing the essay wasn’t as fun as other times. This is what I meant last time when I said writing about productivity tips feels boring. The problem is that I’m largely writing about things I already know when I do that (instead of using writing to think), and I haven’t yet discovered how to make that feel more fun. I hope over time I’ll learn how to weave more philosophy into it. Or perhaps I could shoot a video when I want to talk about personal metawork.

And that’s it for today! Let me know what you think and until next time, may the grammar be with you.

Octopod Chris