A walk with Kevin Kelly can unsettle something you thought you knew. I once mentioned that artificial intelligence was going to take people’s jobs. Kevin wanted to examine that assumption. Which jobs? What new work might appear? Had I thought it through, or simply heard it often enough to believe it? Within minutes, my confident prediction had become a much more interesting conversation.

Kevin is one of my dearest friends. We have known each other for more than twenty years, through hikes along the Pacifica cliffs and wanderings through San Francisco. No one does amused better than Kevin. His whole face joins in. He takes such pleasure in an unfamiliar idea that you want to bring him something he hasn’t encountered before.

I made this portrait in 2017 at The Interval, the Long Now Foundation’s gathering place at Fort Mason. Its library and exhibits encourage people to think beyond their own lifetimes. Kevin, a founding board member of Long Now, has spent much of his life doing just that.

His education took an unconventional course. After leaving college, he traveled through Asia in the 1970s with a camera. Photography became a lifelong undertaking. Vanishing Asia, his collection of roughly 9,000 photographs in three volumes, grew out of fifty years of travel across thirty five countries. The accumulated detail is astonishing: elaborate clothing, handmade buildings, the particular ways people have found to live. He kept returning, recording traditions that were changing or disappearing.

I find that especially interesting in someone so closely associated with the future. Kevin has devoted an enormous part of his life to preserving a record of what we are leaving behind.

As editor and publisher of Whole Earth Review, he helped people discover useful knowledge and put it to work. He then helped launch Wired in 1993 as its founding executive editor. The magazine took seriously the possibility that digital technology would change the way people lived together. Kevin was interested in what people would do with these new capabilities, and what those choices would do to us.

His books gave him room to pursue these questions. Out of Control examines how complicated systems can organize themselves without a central director. In What Technology Wants, he proposes that technology has tendencies resembling those of biological evolution, growing more diverse and interconnected. It is a provocative way of looking at our inventions, and at how much influence we retain over what we create.

Kevin calls his view of progress protopia. Life can improve by small degrees even as each advance introduces problems of its own. His optimism allows for this untidiness. There will be things to repair, consequences to reckon with, and reasons to keep trying.

I know that optimism best through our friendship. Kevin makes it enjoyable to reconsider something, to admit that you haven’t looked closely enough or that another possibility deserves a hearing. After more than twenty years, I still look forward to our walks. There is always something I want to ask him, something I want to tell him. And there is the pleasure of knowing that whatever I bring, Kevin will have another question.