A few years ago, I was thinking about joining an ed-tech startup, and I was talking with the main product guy, Frank. We were in a conference room, talking about education in general; as we transitioned to talk about the startup, Frank got up and drew three circles on the whiteboard.

The first circle was labeled Academic. Frank described how the startup had student tools like a scheduling planner and a degree planner—various free tools that students could use to help them with college. We talked through these tools, and why they were valuable. Hundreds of thousands of students were using these tools every day to help them with their academic journey.

The second circle was labeled Employer. It represented the startup's tools for recruiters, who could sift through students to find the specific ones they wanted to hire. That was to be the business model of the company—to help students get jobs.

Frank drew a third circle connecting the other two, and wrote a big question mark in the middle. He explained that they were missing a way to help a student persuade an employer to hire them, and that was the next step in the evolution of the company.

Eventually, the question mark became our "rich profile"—a LinkedIn for college students. Students didn't need to do anything to build out their profile because the system would build it for them. The more they used our academic tools, the richer their profile would become, and the more enticing the student would appear to recruiters. It's a compelling model. Ultimately, it was the model that led us to be acquired by the massive educational software company Blackboard. But at the time, it was just a sketch of an incomplete story, poorly drawn, on a whiteboard. It was what you might call a "stupid-simple" sketch.


Frank later taught me a basic principle that I remember and reteach to my students. He called it "simplicity on the other side of complexity." Here's how he explained it.

Draw a basic bellcurve. From left to right is understanding, and up and down is complexity. At the left of the diagram, and at the beginning of taking on a new complex problem, you are blissfully naïve. Your descriptions of a topic are overly simplistic and reductive. They are based on assumptions, stacked on top of guesses, and are likely wrong and incomplete. You don't know what you don't know, and so when you talk about things with other people, you aren't able to fully engage.

To move to the right on the diagram, you start to experience things and learn. Your knowledge and insight grows as you become more and more of an expert. You see things from different perspectives, and you start to form an integrative whole. As you peak in the middle of the curve, you see the meaning in the data, and you've formed your own opinion about it. This means that, to some extent, you own the information—it's meaningful to you and so you can act on it.

But you can't necessarily communicate that information. You've integrated it for you, but that doesn't mean you've distilled it down to a meaningful, concise story for someone else, someone still at the left side of the curve. And as Frank described, the top of the curve is the unfortunate place where people typically try to explain complex ideas. Because they have all of the data, they think other people need all of the data, and so they drop a massive document or spreadsheet on everyone else. Maybe they orate an endless meeting. Often, the audience leaves more confused than when they started.

But keep moving to the right on the simplicity curve. Continue to experience things, to find that meaning in the data, and to revise and recast your opinion. Because at the right of the curve is simplicity, again. This is simplicity on the other side of complexity. It's where you've not only been able to synthesize the content into your own worldview, but you've discerned the essence of the idea in such a simple, direct way that you can communicate it to other people. And you can communicate it in a way that people with little or no knowledge of the subject matter can then themselves move along their curve, moving to the right.

The place you land on the right—the simplicity on the other side of complexity—is often super obvious in retrospect. That's sort of the point: it's made obvious to others because you did the heavy lifting of getting through the mess.


Frank borrowed the idea from Oliver Wendell Holmes, a Supreme Court justice who said "For the simplicity that lies this side of complexity, I would not give a fig, but for the simplicity that lies on the other side of complexity, I would give my life." Frank was on his way towards that simplicity. He had been living with an academic suite of products for close to a year. He had no business model. He had experimented with selling ads, and partnering to charge for the academic planner, and selling books, and none of these ideas had legs. But in trying these ideas over the course of the year, through trial, error, conversation, and meaningful reflection, Frank had worked his way towards simplicity.

Here's how naïve I was: I left the interview thinking his diagram was dumb.

That's all they had? Three circles on a whiteboard? From the diagram, I quickly decided that there wasn't a huge amount of insight in this company, and I didn't really want to join a startup with no real visionary leading the charge. I wrote off simple as thoughtless.

But later, as I talked over the meeting with my wife. I found myself redrawing the diagram to explain the business to her. And I realized that in its simplicity was power. Frank had transferred complex ideas to me, in such a simple container. As I drew the diagram, I gained ownership over the knowledge and the problem itself. I started to realize that I actually had a pretty good understanding of their business, and I could start to imagine the product suite that would get them there. More importantly, I saw the opportunity that Frank saw, and as I described it out loud, I started to realize that it was a really good idea. Jess heard me saying things like "it was really stupid." She asked me how I could be so animated about explaining something really stupid, and that really made me think.

His diagram provoked meaning for me, because its simplicity was a placeholder for a large, important, and well-considered vision. I don't mean Frank had solved the problem; I mean he had synthesized the problem.


I scheduled another meeting with Frank, and we re-drew the diagram and used it, yet again, as a backdrop for a conversation; we spent three more hours talking about the business. And we redrew it again and again over the next two years, with more detail, with nuance and specificity. We filled in the third circle—and actually built and shipped that part of the product—and that simple little diagram became the north star of the company's product strategy. It was easy to learn, easy to talk about, and easy to understand. It was simplicity, on the other side of complexity.