I had a very interesting discussion with my brother earlier today about reason versus intuition – when each can be used when evaluating a business decision, and how useful they are.

His position is that reason is very useful, but that it's dangerous to succumb to the allure of believing that reason can be applied to reach good decisions in every case, because reality is far more complex than we are capable of grasping, and often our logic is gravely flawed or missing critical information.

This was in response to one of my earlier posts, where I mentioned that I'd like to build a mental model that maps closely to reality in order to make better business (and life) decisions.

His position is supported by this Tweet from Daniel Vassallo, which I've shared before:

It's also supported by a book called Thinking, Fast And Slow, I believe. The book's main point is that our statistical intuition is very bad. Humans just aren't built to appreciate and model the complexity of the real world in our minds.

It says that any data that we think we can integrate into our mental model of the world is likely not very useful, given the number of other variables that are missing. And that means any data which gives us confidence is actually probably misleading us and giving us false confidence.

That said, reason must clearly play a role in decision making – without it, we relinquish control of success entirely.

But perhaps it's something which we should recognize as a signal pointing to some possible truth, rather than the ultimate arbiter of all truth. And we should incorporate many signals into our decision making process.

My conclusion is that our intuition is not entirely accurate, nor is it entirely wrong. Our reason is not entirely accurate, nor is it entirely wrong. And the advice of other people, drawn from their experience, is not entirely accurate (their context isn't our context, after all, and never will be, and we can never know truly what the differences between their context and our context is, which means we can't account for it) but probably isn't entirely wrong.

The point I'm making here is that there are many different inputs we can choose to accept, and no one of them tells the full story. We should learn to integrate many sources of information that may be painting many different pictures into our decisions.

We are operating in a world of limited information, and we'll never be able to make totally sound, completely safe decisions.

This is why it's important to treat decisions probabilistically, assigning a percentage of success and a percentage of failure to each, and only making decisions in which the reward, adjusted for probability of success, positively offsets the failure, adjusted for probability of failure.

Seth Godin talks about making decisions probabilistically in his post "A simple 2 x 2 for choices":

...consider a portfolio of projects. Some of them have a very high likelihood of working out, and each one of these outcomes is pleasant, if not game-changing. Play often enough, though, and your persistent generosity will pay off.

And then, mix into that some of the moonshot projects that most people are afraid to take on. They’re afraid because they have equated “low chance of success” with “risky.” They’re not the same. Risky implies that failure will cost a lot. It won’t. You can thrive with this strategy because you have a portfolio, and because you realize that “unlikely” is not the same as “not worth trying.”

That we must think probabalistically, integrating many sources of information into our decision-making process, is a conclusion I've come to via reason.

This shows that not only can reason be useful in a direct, decision making-capacity, it's also (and possibly more) useful in a meta role: perhaps it should direct the way we make our decisions more than the actual decisions themselves.

And why all this focus on decisions, anyway? Well, if I can make sound decisions, I will eventually succeed in business, if I stick around long enough. And if I can't, I'll eventually fail, no matter how long I stick around.

On this note, one thing that bothers me is when I see people who are obviously producing poorer content than I am.[1]

It's concerning, because from my perspective there are many issues with the content they're putting out, yet they're truly doing the best they can, according to their reason and abilities and context.

It makes me wonder how lacking my content (by which I mean writing, thinking, and decisions) is to somebody who knows more and has more experience than I do.

Yet there's nothing I can do to correct this except continue producing content, hoping that eventually it will improve enough that I'll begin to succeed.

It's true that I don't know where other people are in their own journeys, and also the ability to produce quality content is reliant on the ability to judge quality content, and the ability to judge quality content comes from consuming quality content. But how does one consume quality content without knowing what quality content is?

My only answer is that one must consume lots of content and then apply reason, logic, and intuition to that content to over time construct a mental model which assigns a percentage or degree of trust to the quality of each piece of content consumed.

One can then use the "Quality Content Model" so constructed as a measuring stick against which to judge the quality of one's own content.

The drawback here is that failing to consume a lot of content will result in a poor Quality Content Model, which will result in poor-quality content. So the only solution is to consume lots of content, and then produce lots of content of my own so as to improve its quality according to that arbitrary metric.

The interesting thing is that the construction of this Quality Content Model is a thing which almost completely falls into the domain of the intuition. We don't necessarily use reason to determine why we like something; it is occasionally applied after we realize it's great, in order to figure out what makes it great.

In a way, our intuition is a bit like a machine learning model; we have to feed it stimuli, and a lot of it, in order to produce a model against which to judge other content, and then we also have to train it to produce content which meets that standard.

So the first step is obtaining an understanding of the standard; the second is learning to produce content to that standard. And that's a whole other challenge.

Ira Glass puts it really well:

Nobody tells this to people who are beginners, and I really wish somebody had told this to me.

All of us who do creative work, we get into it because we have good taste. But it's like there is this gap. For the first couple years that you're making stuff, what you're making isn't so good. It’s not that great. It’s trying to be good, it has ambition to be good, but it’s not that good.

But your taste, the thing that got you into the game, is still killer. And your taste is good enough that you can tell that what you're making is kind of a disappointment to you. A lot of people never get past that phase. They quit.

Everybody I know who does interesting, creative work they went through years where they had really good taste and they could tell that what they were making wasn't as good as they wanted it to be. They knew it fell short. Everybody goes through that.

And if you are just starting out or if you are still in this phase, you gotta know its normal and the most important thing you can do is do a lot of work. Do a huge volume of work. Put yourself on a deadline so that every week or every month you know you're going to finish one story. It is only by going through a volume of work that you're going to catch up and close that gap. And the work you're making will be as good as your ambitions.

I took longer to figure out how to do this than anyone I’ve ever met. It takes awhile. It’s gonna take you a while. It’s normal to take a while. You just have to fight your way through that.

– Ira Glass

While Ira Glass is talking about the creative pursuits in this quote, the beautiful thing is that this applies to business as well. Building a business is creative work, even if it might not seem like it.

Although it's not as aesthetic and compelling as a Robert Frost poem or a Vivaldi concerto, we are nonetheless creating, forming something into existence from the void of our imaginations via our wills.

And so we just have to keep trying.

I'll close with a great quote from Justin Jackson's 2020 year in review:

Business is like surfing. Surfing is mostly about being in the water, paddling, and waiting for the right wave. The same is true for entrepreneurs.

Ultimately, whether or not we get super good at producing the content that fires the engines of business, as long as we continue to try, we're expanding our luck surface area, building compounding results, and we'll most likely succeed eventually.

That's what I must believe in order to motivate myself to continue, anyway. It's also the only thing that makes sense; how else could so many succeed, if it was so hopeless?


[1] It's a little bit of a fallacy to assume that I can linearly judge the quality of content – I can never know its true purpose or the context in which it was conceived, so I can't genuinely judge whether or not it is poorer than the content I can produce, although I can perhaps assign a degree of probability to whether or not it is