The Complexity Trap: Why You Overcomplicate Everything and How to Stop

You make things more complex than they need to be so that you can avoid doing the simple things that matter.

Doing is better than theorizing

If you’re someone who likes to think and research and plan and get deep into the complexities of things—that’s your comfort zone. And because it’s your comfort zone you have a tendency to view this type of “work” as more important and useful than it is.

Wanting to stay in this comfort zone, you delay action by convincing yourself that you’re not quite ready. You don’t have enough certainty or clarity. There’s missing information. 

Doing this, you fail to realize that useful information and knowledge you want and need can often only be gained by courageously taking simple but uncomfortable action. As Nassim Taleb writes in Skin In The Game: 

“The knowledge we get by tinkering, via trial and error, experience, and the workings of time, in other words, contact with the earth, is vastly superior to that obtained through reasoning…”

Here’s the hard part: you must take action without certainty and full confidence. Complexity addicts crave certainty and think they need it before they can take action, and so they never make progress. Those who understand the virtue of simplicity take action before they feel ready or certain—because they know that confidence and clarity exist on the other side of taking such action. 

You must leave your comfort zone—the world of theory, complexity, endless planning and thinking—and do something tangible and real. You must take imperfect action. And the longer you’ve spent swimming in the sea of complexity, the more uncomfortable it will feel. But once you experience the rewards that can only be found in simple action, you’ll want to do it more and more. 

Start as simple as possible and grow outwards towards complexity

When you’re inside the complexity trap, you try to plan everything top-down. You try to find or build a complex solution from the start. This almost never works because you’re dealing with so many unknowns. 

For example, perhaps you want to grow a YouTube channel and you’re spending weeks planning your strategy, reading up on everything, learning all the tactics and tips. Well, you don’t really know anything. It’s not until you publish your first ten videos or so and see what happens that you get the data that matters. For all you know, one video of yours might go viral and completely change your plan. 

As a principle, it’s much easier to build a simple system and grow it into a complex system (if complexity is needed) than to build a complex system from scratch. As written in The Systemantics Bible:

“A COMPLEX SYSTEM THAT WORKS IS INVARIABLY FOUND TO HAVE EVOLVED FROM A SIMPLE SYSTEM THAT WORKED The parallel proposition also appears to be true:[g. ] A COMPLEX SYSTEM DESIGNED FROM SCRATCH NEVER WORKS AND CANNOT BE MADE TO WORK.”

If you want to grow the YouTube channel, what’s the most simple approach you can start with? It’s publishing videos consistently. Get that nailed and then add in some complexity. Instead of a complex plan with dozens of variables and tasks and tactics, you trim it down to “I’m going to publish 10 videos over the next 4 weeks and then figure it out from there.” And then you just act.

As Paul Graham writes in How to Do Great Work, “Begin by trying the simplest thing that could possibly work. Surprisingly often, it does. If it doesn’t, this will at least get you started.” 

A good question to ask yourself when you start falling into the complexity trap: “What would it look like if it were simple?”

Side note: the simpler you make it, the harder it is to pretend you’re not procrastinating. When you’re in the weeds of complexity, it can feel productive. You feel smart. But you’re just in motion, spinning your wheels. Except you can kinda “hide” in it. But when you make the path extremely simple, like “I need to publish a video tomorrow.” Then any procrastination you engage in is obvious. You can’t hide. 

Another way to put it is that you want to…

Plan less, iterate more.

It’s hard to understate how limited complex planning is. It works much less than people think it does. Even in the big leagues, how often do 30+ page business plans work? Almost never. 

This especially applies to you and your work or your career. You don’t know what you don’t know. You don’t know what’s going to happen over the next 5 years (or even 5 weeks). You don’t know if your project will work, what the market will do, and so on. As such, one of the best things you can do is just execute and take action with a focus on iteration and growth. 

Peter Kaufman puts it perfectly:

The most powerful force that could be potentially harnessed is dogged incremental constant progress over a very long time frame. This is above genius. It’s absolutely above genius because you can understand it.”

Separate the truly essential from the non-essential

You must learn what to ignore so that you can focus on the essential things that truly lead to progress. 

Let’s revisit the business example. What do a lot of people do when they want to start a business? They spend a huge amount of time working on things like branding, getting business cards, building a nice-looking website, getting all the documents sorted, and dreaming about what the future will be like. 

That is non-essential work, at least on day one. It will become essential, sure. But at this given point in time, it’s not. The essential task is to validate the business idea: get a customer. Figure out how to do that and execute towards it with intensity and speed. Everything else can wait and be ignored until that’s done. 

You have to constantly ask yourself, “What’s not important right now?” And start by removing things so that only the simple and essential is left behind. 

Another way to view this is peripheral action vs generative action.

Planning is peripheral action. Cold calling is generative action.

Researching is peripheral action. Writing is generative action. 

Designing a nutritional plan is peripheral action. Choosing not to eat the donut is generative action.

Peripheral action has the potential to be useful. That potential is fulfilled by generative action. A nutrition plan has no power if it’s not used. A plan is useless if it’s not put into action. 

If you’re like me, your tendency is to engage in peripheral actions instead of the simple, generative actions that move the needle. 

The obvious solution is often the right one

Not getting enough sales in your business? Make more cold calls. 

Not doing well at school? Spend more focused hours studying. 

Not losing weight? Eat less. 

Complexity lies to you by saying “there’s no way it can be this simple. There must be another way. Keep thinking and strategizing.” 

Increase the speed

Complexity grows when there’s room for it to grow. If you lack intensity, have no deadlines for yourself, or zero pressure, then it’s very hard to fight this tendency to make things more complex than they need to be. It’s a manifestation of a deep desire to stay in homeostasis and avoid action. 

The inverse of that is that when you are under pressure and you must operate with speed, you’re forced to simplify things because you know that action must be taken. And so you reduce complexity into simplicity. You might not have 100% certainty or confidence, and simplicity doesn’t completely map on to reality, but you need to act and so you find a “good enough” map of reality and then move forward. 

Even the complex benefits from the simple

You might say, “Yeah, well some things simply are complex. I’m trying to build a business, and that’s no simple thing.”

In one sense you’d be right. Building a business is complex. There are many variables, from the wider market conditions, to the customer, to the people you hire, to processes in the company. It’s not an isolated and controlled domain. 

But even given that complexity, the best course of action is to find the simple actions that lead to progress. Sure, you don’t know what the market is going to do over the long term. It’s complex. But you can’t predict it, so you’re better off just focusing on a simple idea, like making something that people want. You can’t control or predict everything, but you can control the actions you take today. 

Complex systems vs simple systems

One consequence of the complexity trap is that we build convoluted systems for doing things. The perfectly optimized morning routine. The productivity tech stack with 5 different tools linked together. If that’s your system, then as soon as one of those things breaks (like one of your 5 productivity apps glitches out and won’t open, or your ice bath is too warm), then you’re weakened and thrown off your game. Meanwhile the person who has a simple system: pen, paper, sit down and do the work—is less likely to have something break. 

You should make the system as simple as it can possibly be, and no simpler. In other words: there’s a space for project management apps and second-brain note-taking tools, of course, and trying to use pen and paper or too simplistic of a tool to replace them might only reduce your effectiveness. But you have to be honest with yourself and reject the tendency to move towards complexifying. 

When I committed to my goal of making 100 YouTube videos, I thought I needed a better system to manage everything. I started creating a complex task management system in ClickUp. I spent hours on it until I realized I didn’t need such a complex system at all. All I really needed to do was open a new document, outline the video, write it, record, and edit it. I know the workflow in my head, so I don’t need to map it out or use a Kanban board. It’s not that complex; it’s just about getting the work done. I know where things are at without needing a digital tool or complex system to remind me of where a video stands in progress. The complex system in this case didn’t add any value. It had negative impact, actually, because it made my workflow more complex than it needed to be,. 

So I reverted back to the very simple system I had, using the same note-taking app for all the work, recording, simple editing, and publishing it.

Heuristics, principles and mental models over frameworks

What we’ve just looked at are a bunch of simple heuristics, principles and mental models. You’ll notice these are not complex frameworks or step-by-step systems, for obvious reasons. Heuristics and mental models are simple filters that make decision making fluid. They are encoded wisdom. You need to deeply embed them into your mind by acting upon them again and again and realizing how potent they are. 

This is how you reduce complexity. A simple heuristic like “doing is better than theorizing” or “knowledge gained through action superior to that gained elsewhere”—when deeply embedded in your psyche can change the way you think, act and make decisions, for the better. You rely less on complex frameworks and more on automatic decision-making. 

Let’s quickly recap all the heuristics and principles we just looked at so we can further embed them in our minds: 

  • Doing is better than theorizing. Knowledge gained through action and experience is superior to most other forms.
  • Start as simple as possible and grow outwards towards complexity
  • Plan less, iterate more. 
  • Separate the essential from the non-essential. Understand the difference between peripheral and generative action. 
  • The obvious solution is often the right one.
  • Increase the speed.
  • Even the complex benefits from the simple.
  • Complex systems are fragile, simple systems are robust. 

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