🌪️ My new book is available for pre-order! Reserve your copy.

Dan Wakefield, at 88, taught me how to be a better website designer

Indianapolis native and author Dan Wakefield died last Friday at the age of 91 in Miami. I worked for Dan for many years in the autumn of his life before selling my business. When I met Dan he was already in his 80s and I was genuinely impressed by his desire to at least know about new technology.

Many people, including Dan himself, would say technology was his nemesis. But I think nothing could be further from the truth. Some people actively avoid technology. Dan wanted to know about it and could instinctively understand how it related to what he knew (like a podcast and radio) and how he could potentially use it. At best Dan took a “Know thy enemy” approach to technology.

Still, Dan was cantanerkous at times. A word that seems harsh but feels apt. My long-time colleague Alex Felder and I struggled often with what to do with his requests. Perhaps the most obvious are the colors of his website (green and orange), the background of his website (green stripes), and the (tiny) photo he liked best of himself positioned squarely at the top. Alex did much more of the design work on that site than I ever did, but that site reflects a lot of Dan’s requests and Alex deserves much of the credit for working through them.

Dan made me a better website designer and, I think, a better writer in a roundabout way. This despite being around 88 at the time. When an eye-related procedure failed to improve his vision as expected he called me and asked if I might be able to help him figure out a way to use his iPhone and computer.

I instinctively knew we’d need some kind of screen reader technology, but the best-in-class versions of these services are pricey. At the time we were operating on the assumption his inability to read text was temporary. So, we tried using the built-in Windows and iOS screen readers, which proved a nightmare. Not because the features were bad (though at the time they were not great. I understand they have improved a lot in just the last few years), but because everything they had to contend with was objectively terrible.

His email was festooned with spam, junk, banner ads, and all manner of cruft. It was horrifying to listen to the screen reader muddle through line after line of the worst, most offensive spam subject lines in his inbox and get hung up on ads for car dealers or whatever. This experience taught me a lot, though he probably didn’t know it at the time. There wasn’t much I could do for what was intended to be a short-term disability. But over time he adapted because Dan always adapted.

Five men in white shirts and slacks stand in a hot courtroom during the Emmett Till murder trial, 1955.
Dan Wakefield (far right) reporting for The Nation magazine during the sham Emmett Till murder trial.

I’ve been able to take that experience with me into the classroom recently. On Tuesday of this week in both of my classes at IU, I introduced my students to Emmett Till. There’s an excellent photo of Dan in the courtroom as the proceedings are underway. I think Dan would be a little happy to know I could put this photo up on the screen, and despite the heavy backstory of the trial — something that commanded a level of attention I have never seen and likely never will again from everyone in the classroom — I could point to the young man on the wall and say, “I’m telling you all of this because of this man, Dan Wakefield.”

He was 23 at the time of the photo, almost the same age as my students. And I could tell them about my experience working with Dan, the accessibility issues we encountered together, and how to make better websites. I tell them often to have empathy for the viewers — something that gets lost among most large companies and brands.

And I’d close my introduction with what Dan decided was “probably the best line I ever wrote.” It was the opening line to his Nation piece about the trial:

The crowds are gone and this Delta town is back to its silent, solid life that is based on cotton and the proposition that a whole race of men was created to pick it.

Dan Wakefield reporting for The Nation

“AI could never write that. Have empathy for your readers. Be humane and recognize the best you can do comes from being there, being on the ground, living the experience, and fully understanding everything that is happening around you. He did not write this piece from 1,000 miles away, with a chatbot, by Googling, or with Grammarly. He showed up and thought deeply about the work.

The Internet has no shortage of well-deserved, honorable, and true accounts of his work, including his obituaries in The New York Times and The Washington Post. Dan was proud of his work and knew what he liked both in prose and style. I can’t help but think he’d hate the photo both the Times and Post used in their obituary of him.

Dan Wakefield cuts the ribbon at an Indianapolis park named in his honor.

Dan is far too unknown in Indianapolis. A small park not far from his house bears his name. A rare honor for someone to receive while alive. I was there when he cut the ribbon to snap photos. So was Dick Lugar, who came into town just to honor his good friend.

Perhaps someday the Indianapolis Public Library will chisel “WAKEFIELD” on the upper reaches of its limestone walls not far from “VONNEGUT”. My students had never heard of him, but they know his name now. They know Emmett Till. And, I think, they are recognizing the limits of technology. Something Dan was quick to notice.

His website at danwakefield.com was largely untouched after I sold my business. That irritates me for many reasons, but my login there still worked. So this morning I quietly updated his homepage to include a note of his passing not far from his preferred photo of himself. I also submitted a request for archival at the Internet Archive, because the loss of this website, like others, is a loss of his work and unique personality.

Onward and upward, Dan.

Want to know when stuff like this is published?
Sign up for my email list.

Photo of Justin Harter


Justin has been around the Internet long enough to remember when people started saying “content is king”.

He has worked for some of Indiana’s largest companies, state government, taught college-level courses, and about 1.1M people see his work every year.

You’ll probably see him around Indianapolis on a bicycle.

Leave a Comment