“I have a fax from Sam for you.”

Those words struck fear into my heart. Sam was supposed to be on a plane halfway around the world. He wasn’t supposed to be sending me new things to do. Plus I was pretty sure that he didn’t even know how to work a fax machine. With him it’s iPhone or nothing. Here is what he sent me. It’s a little blurry but trust me, you wouldn’t be able to make it out even if it weren’t.

A bit later he attempted to explain his latest wild idea. The Enterprise Octopus had reared it’s head once again. It has done so several times. This time a new illustration was needed.

“I need you to draw the anatomy of the enterprise octopus with a bunch of people inside and you are on top with Doppler for a head. The tentacles are grabbing all this stuff. Then I need you to draw the octopus as bowl, upside down, with a man drowning in paperwork.”

Did I mention he was insane?

Fortunately at the time I had David Carroll working for me and he took the first stab at it. That’s what a good minion is for after all. David’s idea was to make Octi into a sort of enterprise machine, with its eyeballs and mouths on hinges with people popping out to say hi. It was a very creative idea and I really think he did a great job on it. I added a little cherry on top, translating Doppler into Radar and making it a man’s head. as well as a few touches like the rubber grommets. I also really dug all the rivets David added and how precise the seams were.

David also drew the safe and the screen by hand. The truck comes from a Yellow Icon icon pack.

Of course Sam had asked for two drawings, so I took a stab at the back. The idea was an enterprise that had collapsed under its own weight. The standard array of office apps aren’t getting the job done and pure chaos reins supreme. I went with the idea that the tentacles were literally crushing people, perhaps having been chopped off in places. People are trying to work with files but have no idea what to do or can’t work with them. Others have given up. Oh and Sam wanted a man with a bag over his head representing the employee, lost in a sea of files and confusion.

Here are the steps I took in creating it. If you’d like to see these in full res you can check out my Skitch account. I worked in chunks, sending progressive updates to Sam to be sure I was on the right path. That way if something was wrong he could stop me early and set me back on the right direction. Sam and I work best like this, especially for complex designs or illustrations and allows for a lot of feedback throughout the entire process.

As you can see, the first stab at the piles of paper looked a bit like rice. I ended up biting the bullet and drawing 10-15 unique pieces of paper and then cloning them all over the pile. I then unified them by giving them a universal light sorce.

You can also see where our styles diverge a bit. I used a more traditional illustration method, painting the scene with a Wacom pen and tablet. David used vectors and a much more controlled and precise style. His people are a bit stiffer, like what you’d see on a bathroom door. Mine are pudgier, luke plastic bags filled with blue jello. Neither way is right or wrong and I really liked seeing our different interpretations of the same subject.

David had given us a great start but Sam was a bit concerned that the Enterprise Octopus was looking too machine like. He wanted something a bit more organic. I went back and retouched it, removing many of the machine bits. To give the COLORS acronym a bit more contrast I added a wavy blue banner. This helped the words stand out a bit more.

To see them at full size and to get a bit more context check out Sam’s blog post explaining this madness. It goes into a lot of depth explaining what each represents and is a fascinating analysis of how enterprises work.