How I approach my core work
We cannot predict the future. We know that. And yet we don’t explore things we find interesting simply because we do not clearly see how they apply: how they connect to what we are working on now, how they will make money, or how they will advance our current work in the future. We artificially place hard limits on ourselves and our work because we don’t know how they will connect to interesting things in the future.
Of course we don’t know: we cannot predict the future.
So here’s the point: the dots connect later.
After dropping out of Reed College, thereby being freeing from the required courses, Steve Jobs took a calligraphy class. He loved the beautiful calligraphy that students had learned and used on every poster around campus. He was fascinated, learning about different typefaces, kerning, all of it… but it had no real application in his life.
Ten years later, as he was designing the first Macintosh, he says “it all came back to me. And we designed it all into the Mac. It was the first computer with beautiful typography. If I had never dropped in on that single course in college, the Mac would have never had multiple typefaces or proportionally spaced fonts. And since Windows just copied the Mac [to audience laughter], it’s likely that no personal computer would have them. If I had never dropped out, I would have never dropped in on this calligraphy class, and personal computers might not have the wonderful typography that they do.”
In his 2005 commencement address, he shares this story to make his first of three points about life.
“Of course it was impossible to connect the dots looking forward when I was in college. But it was very, very clear looking backward 10 years later. Again, you can’t connect the dots looking forward; you can only connect them looking backward. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”
Malcolm Gladwell is known for his writing, in which he explores unexpected phenomena found through his research. Probably intuitively, he does not come up with an idea for a book then research it. Instead, he is constantly exploring little insights and odd observations. Sometimes, he goes pretty deep on an area of research; once flying to another country for an interview, compiling lots of sources on the topic, then stuffing it in a drawer, not knowing how it would connect to anything he’s actively working on.
But years later, on a new project, an old interview springs to mind, interesting connections are made, and better insights come forward. That disconnected research has turned into highly praised articles and central stories that drive home his theses. In his MasterClass, he sums this lesson up, saying: if you don’t follow paths when you don’t know how they’ll connect later, you’ll never stumble into a lot of great stuff.
In my work I have found that this is the merit of ideas and ideation: to explore wildly, trusting that the dots will connect later.
We do not know how things connect looking forward, only looking backward. So create wildly, explore boundlessly. Don’t limit yourself to just what seems applicable; trust that everything will connect later.