Disproving your own ideas is one of the most valuable things you can do.
If you don't do this you'll lack clarity, take on too much risk, and spin your wheels on the wrong projects.
If you want to think clearly, reduce risk, and work on the right things, you'll need to derisk your work. That will mean proving yourself wrong over and over again.
Suppose you're going through a todolist for a critical project. Whether it's writing, marketing, or building a company, there's an omnipresent question: what do I do first?
One rule you can adopt is
do the hardest things first. The problem with this is that the hardest thing is not always the best thing to work on. Plus, there's the risk that you'll put hours into working on a hard problem -- with nothing to show for it a week later.
take on the easiest tasks first. This way you'll be sure to get things done. This strategy builds momentum as you create success spirals. However, the easiest things aren't necessarily the best things to work on. Plus, many worthwhile projects just aren't that easy. By focusing on what's easy you may miss neglected opportunities.
Yet another strategy is
do the most important things first. But how do you determine whether some task is more important than one another?
Think about this is in terms of
derisking your projects, and then executing. If you derisk something, you'll have high confidence that it will work. Suppose you're working on building a company whose core offering is relaxing audio poetry. Here's an important question that you'll want to look into upfront: will people pay to listen to poetry? Is poetry like meditations (that people will pay for) or would people prefer to read poetry? Another question: will people pay for this offering instead of paying for a poetry book over audio? A common failure of first time entrepreneurs is to build an elaborate app. And then find out that, once it's built, no one will actually pay for it. Derisk!
Another example, when I was teaching philosophy, occasionally students would write entire papers on a topic before checking in with me about whether the thesis was relevant and whether they understood the material. Before writing a paper, you'll want to ensure that you understand the research you are building on.
Whatever the cause, whether the task is too hard, the approach is wrong, or your thought is unclear, you don't want to work on what will fail. And if something is going to fail, you want to find out fast. Jacob Steinhardt formalizes this as a stochastic decision process. The key idea:
De-risk all components (to the extent feasible), then execute.
What does this have to do with disproving your own ideas?
Whether you're thinking about what to work on, constructing plans, or searching for intellectual insight, apply the framework of derisk and execute. In order to derisk well, you need to be good at disproving your own ideas.
Sometimes this looks like building an MVP or talking to potential customers. Sometimes it looks like setting a timer and writing all the reasons your thesis could be wrong. Sometimes it looks like the Stoic practice praemeditatio malorum: imagining all they ways your plan could go awry and realizing that you aren't prepared.
Evolution works by mutation, reproduction, and selection. By analogy, you need to select for the best ideas in your intellectual environment. To do that, ensure that the weak ideas don't survive. Disprove them. You can extend this analogy to idea generation, but let's save that for later.
That's the argument, here are three ways you can be better at disproving your own ideas.
First, be familiar with common techniques for disproving your ideas. If you're doing something where you can build a MVP, do that. Build the cheapest easiest version of the result and do that first. Sometimes this doesn't require building anything. If you're doing research, find a counter-example to your thesis. Refine it or move on. Try breaking down whatever you're working on to smaller pieces.
Second, become better at representing other points of view. In computer science there's this idea called the Turing Test. It's a test, originally constructed as a conversation, that an AI needs to pass by being indistinguishable from a human. An AI would pass a Turing Test if you couldn't tell whether you're talking to a computer or a human for example. Can you pass Idealogical Turing tests for opposing points of view? If not, that's a risk.
Third, create an environment where your ideas will be disproving. Consume different sources of information. More importantly, put yourself in the situation where people around you will tell you when you're wrong. Publish your thoughts. Share them with your friends. Chose friends who will tell you when you're wrong. Thank them when they do.
When something fails, you want to know why. Knowing why is crucial. You can't lose, Recalling Epictetus' maxim:
If you seek Truth, you will not seek to gain a victory by every possible means; and when you have found Truth, you need not fear being defeated.
After you've completed derisking, move on to execution. Some communities and people spend too much time arguing that such and such is false or won't work. At some point, you need to stop thinking and start doing. If you're thinking well and have clear goals, the value of action will outweigh the value of seeking new information.