This is How It Happens, Or What I Learned from Steve Jobs


When Steve Jobs was seventeen, he dropped out of Reed College after just six months. The tuition was too expensive and he wasn’t sure where it was leading. But he stuck around the campus, sleeping on floors in friends’ dorms and started dropping in on classes that looked interesting. At that time, Reed had amazing calligraphy instruction. Jobs, struck by the beautiful, calligraphed campus posters, decided to take a class. Jobs had no practical application in mind at the time, but as he described it in his 2005 commencement address at Stanford, he was fascinated learning about “serif and san serif typefaces, about varying the amount of space between different letter combinations, about what makes great typography great.”

It was a full ten years later before any of this knowledge came to practical use.

When Jobs was designing the first Macintosh computer, he remembered that calligraphy class, and incorporated it in the Mac. In his words, the Mac “was the first computer with beautiful typography.” When he decided to learn calligraphy, Jobs had no idea that it would ever be useful; he did it because he found it compelling.  He describes, “Of course it was impossible to connect the dots looking forward when I was in college. But it was very, very clear looking backwards ten years later.”

This is how Small Answers started too, with some random events that connect only with hindsight.

Several years ago, I was working for myself and not finding much satisfaction with it. Motivated by a desire to create a professional community for myself despite the absence of an office job, I had the idea of starting a career group, and Leda was my first member. When we reached out to friends about joining, I was shocked that so many people were eager for such a group. There was obviously an unmet need there, a desire for people, at least women our age, to work through our career and life questions with the help of peers.

A few months after starting our career group, I started dating someone new. In that early honeymoon phase of the relationship, there was a lot of silliness that lead to the creation of fanciful characters and stories. A grapefruit with an upturned ladle for a helmet became Captain Paloma. Two pears, Bartlett and Bosc, could not agree on chocolate versus lemon flavored desserts. In moments of boredom at work, I would write up rhyming stories about these new friends (including a couple that couldn’t agree on a rhyme scheme). I had fun writing these stories and on a whim, I signed up for a class on creating children’s books at San Francisco City College.

You may have noticed that Small Answers is not a children’s book. The class I signed up for was held in an art room at Fort Mason that smelled pleasantly of paint and rubber erasers. Almost instantly upon walking into the classroom, I realized that I didn’t want to create a children’s book. I sat, looking at the syllabus and thinking about what I wanted to write about. I wanted to write about the things we were talking about in career group. I wanted to write a book for adults looking to shape their careers.

I immediately sought out Leda as a co-author. We schemed about a book, outlining ideas and researching ones that had already been published, but quickly decided just to start writing. Why not start with a blog to have a place to put what we write? We had no idea what it would become, we started because it seemed like a fun adventure. We called it Small Answers.

Those are the disparate dots that lead to Small Answers: some silly rhymes, a career group, a children’s book class, and (on Leda’s part) a long history of writing and blogging. Certainly if you had told me that a rhyme about a grapefruit-headed pirate would lead to a blog of truthful stories and me spending much of my free time writing, I wouldn’t have believed it. It is impossible to connect these dots in any way other than with hindsight, with which we can look back to see the pattern they created.

Since we don’t know how the dots will connect later on, we are left to create each one because it makes sense somehow in the moment. Steve Jobs said, “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.”

I try to trust my gut to tell me if a certain decision or activity feels good and makes sense. I hope that if I do something because I want to and it feels right, that it will, eventually, make sense. At the very least, if a dot is stranded and doesn’t later connect, I will have enjoyed creating it.

I have to remind myself of this frequently. While I aim to do the things that come naturally and honestly, the “shoulds” crowd in. My desire to plan, to predict and control the future overwhelms the messages that my gut is sending and discourages any faith that the dots will connect in another ten or fifteen years.

We never know what is coming, and are bad indeed at predicting. But if we simply move towards those things that draw us in, we each become a collector of dots. Our collection is a curation of the experiences and knowledge that make us each unique. It’s what made Steve Jobs different than Bill Gates, Apple different than Microsoft, and certainly makes me quite different than both of them.

Jobs again: “This approach has never let me down, and it has made all the difference in my life.”


Image: Untitled (Solar Set) by Joseph Cornell, 1958