The Curse of Knowledge

“Uh, it’s off Airport Road. You should be able to get there from Umstead. I think or, or maybe go up to Estes?”

I paused again. I was confusing the person asking me for directions more than I was confusing myself.

What was the matter with me?

I grew up in Chapel Hill and went to college there. I lived there for over a decade. I was a local.

And when a stranger asked me for directions, I couldn’t tell them.

I stammered over and over, and told them they might need to ask someone else or look at their phone.

Was something wrong with me?

One of the most rewarding, and challenging, things about working at Highrise is how fast the product changes.

Our team runs on a train schedule. This means every few weeks we announce an improvement or something new.

It could be a big feature like recurring tasks, or something small like a new rule for auto-forwarding emails.

The reward is we’re making the product more useful to ourselves because we use Highrise every day, and making it more handy to customers.

A big challenge is documenting these changes. It’s informing people that use Highrise with what has changed, why it changed, and how to make use of the changes.

The number one resource for this is our help site. It’s a living, breathing how-to guide or user manual.

It’s a beast of a resource to maintain. There are over 100 articles, countless screenshots, and videos.

And with frequent updates, this snapshot or how-to guide of Highrise can go out of date fast.

It came to our team’s realization when updating a screenshot. The settings menu now has a new option for all users (Referrals), and the old screenshot didn’t reflect that.

It was a tiny change. A person new to Highrise might not even notice it. Our team did, so we updated the screenshot.

This change sparked lots of others too. We began to notice videos were out of date by months. More screenshots too.

A pull request with one commit, a change to a screenshot, turned into a two-week project. 277 changes later, our team updated the entire help site to more accurately reflect the product.

What took us so long to realize things were out of date?

Nicholas Epley has a dynamite book on this topic. It’s called Mindwise: Why We Misunderstand What Others Think, Believe, Feel, and Want.

In the book, there is an eye-opening exercise.


Epley asks you to count how many fs are in this sentence. Start counting.

How many fs do you count?

Is it more than you can count on one hand?

If not, Epley has confirmed you’re a terrific reader, but a terrible counter.

Now count them again? Did you find all six fs?

Don’t forget that the word of has an f in it. See all six now?

Most people, including myself, only found three fs.

Why is that?

Epley explains it has everything to do with knowledge.

He continues, “Your expertise of English blinds you from seeing some letters. You know how to read so well that you can hear the sounds of some letters as you read over them.”

So, because of your expertise, every time you see the word of, you hear a v rather than a f, and you miss it.

Epley points out, “First graders are more likely to find all six in this task than fifth graders, and young children are likely to do better than this than you did as well.”

This is known as the curse of knowledge. Why is knowledge a curse?

Because once you have it, you can’t imagine what it’s not like to possess it.

Knowledge or a level of expertise gives you the lens of a microscope.

It means you notice subtle details a novice might not catch, and it also means your focus is so sharp, you might miss the big picture and you’ll struggle to understand a novice’s perspective.

Epley offers a slew of good examples in the book and elsewhere too.

One of my favorites is how Clorox bought Hidden Valley Ranch Dressing and spent a decade trying to make the original recipe so that it did not need to be refrigerated. All of their internal taste tests of the dressing came back as worse than the original. Or so they thought.

Hidden Valley finally sent a worse tasting version of the dressing to the market, and people loved it. Because not many people ever tasted the original dressing. The consumer’s perspective was way different than the company’s perspective.

Epley writes further, “The expert’s problem is assuming that what’s so clear in his or her own mind is more obvious to others.”

This is something our own team fell into at Highrise. We were spotting tiny changes like typos or a missing menu option in a screenshot, but missing the bigger picture that almost everything was out of date.

Our perspective was way different than someone who started using the product yesterday.

And it’s what happened to me when trying to give directions. I could probably get the stranger to the location if we rode in the same car.

I could tell her Airport Road is now named Martin Luther King Jr. Blvd. And there used to be tons of trees on Umstead Road that the city cutdown. I could point out all these tiny details.

But I couldn’t tell her how to get there on her own.

There was nothing wrong with me. I was cursed.

Cursed by knowledge.

If you enjoyed this post, please click the💚 and share it with others. If you enjoyed the ideas, I recommend reading Nicholas Epley’s book. It’s fascinating. And if you’re curious about what improvements we’re making to Highrise, catch up on our announcements.