Man. Sometimes, you just can never predict how an illustration is going to go. After reading
Malcolm Gladwell's latest book, "What the Dog Saw" - I was inspired to create a Gladwell portrait promo piece (as I'm currently overdue). Given his signature hairdo and striking features, I thought Gladwell would be a snap to portray.
After looking through dozens of photographs, I marveled at how much Gladwell's appearance changes... he never looks the same twice! I now knew his likeness would be a challenge to capture. I mean seriously, do any of these guys look alike to you???



This last one looks like he's had an MJ nose job! But anyway...
My initial idea/sketch was to portray Gladwell alongside some of the memorable people/concepts from the book.

Kinda dull, not very dynamic. I soon got carried away on a redo. I stopped once I realize it was taking a direction in style that was all wrong.


Obviously the likeness was hurting, too - but I was still just playing around here.
I went back to the drawing board on the concept sketch - shooting for more dynamics. I intended to include Ron Popeil, George Soros and Cesar Millan, the Dog Whisperer -- people profiled in the book. The plane is an allusion to the JFK Jr. story (
"The Art of Failure -Why some people choke and others panic" - probably my favourite essay), as is the ketchup bottle an allusion to
"The Ketchup Conundrum".

Once this sketch was done, I started working his head... exploring various ways to render it:


Done! No, not really. I was kinda digging this, but not entirely. I felt like the style wasn't there yet. I decided to push it another way, and got here:

I was happy with this likeness. Which led me to putting him in a setting...

.. and eventually reworking the colours and composition to this:

At this point, I considered the illustration done, project complete - although I did end up tweaking it a bit further thanks to the input of some valued friends and colleagues (shout outs to
Matt Howe,
Kagan McLeod,
Michael Cho and Ian Rapsey). In spite of the rework, I wasn't satisfied. The sticking point for me (raised by Matt) was that it lacked a true concept. Which set me thinking all over again... what did I want to
say about the man?
I had this brilliant idea of having a group of people waiting at a bus stop (or airport gate - hadn't decided yet) reading Gladwell's books. They would represent various age and social groups, but would all be sporting Gladwell's signature hairdo and spectacles -- having been "infected" by the Gladwell thought process. Gladwell himself would be walking by, amused. It didn't work. I sketched it several times and eventually decided the concept wasn't quite so brilliant after all. The focus on Gladwell himself was lost. His presence was all but meaningless - just a casual observer.
Finally, today I suddenly had the idea of portraying Gladwell as a guru, implying that he has revealed, through his books, a form of intelligence enlightenment. I thought this idea would be clear, and that the guru connection would resonate well.
In this first version, I created a background intended to resemble eastern motifs:

This palette wasn't yet right, but I abandoned it because I decided the eastern motif itself wasn't fitting. I also realized his legs needed serious medical attention. Below is the final (final?) illustration:

I thought it would be appropriate to put Gladwell in front of a backdrop of NYC buildings - since NY is his home, and he writes for
the New Yorker. I also found appeal in the representation that he is a shaman amidst the city's chaos. I added the 3rd eye to drive home the concept of him being an enlightened guru. I felt it was an appropriate symbol since he famously makes observations and sees patterns where others do not.
In summary, I think it can truly be said that a piece of art is never really finished. It's perhaps magnified where illustration is concerned: Under the constraint of deadlines, it's always a matter of setting priorities and making sacrifices.