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Jesse Bennett-Chamberlain

February 28, 2011

Tell us about your background. How did you get started? Have you always worked for yourself at 31Three? Was it always your plan to provide help to the design-challenged developer?

When I was in my early 20’s I spent a lot of my spare time helping out at my church as a youth leader. We would have different youth events at the church every few weeks, and one of the things I really enjoyed doing was creating posters to advertise them. A designer in the church eventually took notice of them, and asked me if I wanted to apply for a job at a newspaper he worked at. I somehow managed to land the job, and worked there for the next five years. That job was really my only training. I had no clue what I was doing as a designer (my previous job was building and fixing bicycles at a hardware store) so I just watched the good designers around me, and tried to emulate what they did.

During the last year of working at the paper, I started taking on a lot of side projects. It got to the point where I had to make a decision which one to pick, as I couldn’t do both of them. In August 2002 I gave my 2 weeks notice, and registered the name 31Three.

Focusing my business on providing help to the design-challenged developer was never my plan out of the gate. I had no plan. I think it took me around 6 or 7 years to realize that from all the different jobs I had taken, the best ones were when I worked with developers.

So how do you typically collaborate with developers? Is there a particular work-flow you prefer, or is it all improv. Do you prefer developers come to you with prototypes in place, or do you like to be involved from the beginning?

Improv is a good word for how I operate. I guess that doesn’t sound too professional, but because it’s just me at 31Three, I do my best to fit into the environment of the developers that I’m working with rather then forcing them to fit into mine. I often tell my clients to just treat me like another member of their team.

I rarely enjoy starting a project with a completely blank slate. I generally tend to feel a lot more creative when I’m redesigning something that already exists. Not entirely sure why that is. It actually frustrated for a long time, and in the back of my head I’d have this nagging feeling that I wasn’t truly creative because I had a hard time building stuff from scratch.

In the effort to make yourself a member of your client's team, do you maintain a set process or adjust it to fit? What's your favorite part of the design process?

I probably do have a process... but I’ve never put it in writing or formalized it to any degree. I’m not even sure I know what it is myself. So much of how I work varies from client to client and what I think will work best for them.

The best part of the design process for me is those early stages when I’m coming up with different aesthetic ideas. That seems to be the most unstructured and free flowing part of my job... and the portion where I actually feel creative. It wasn’t until I discovered a post by Wilson Minor called “The Optimizer” that I learned to take the pressure off of myself.

How do those early stages look? Do you jump directly into Photoshop, or is it more of a sketching & mood boarding type of thing?

It depends on what type of site it is. If it’s a high-content, “newsy” type of site, I’ll usually start in InDesign and work out a basic grid and layout... and then build on top of that. If it’s a site that requires a bit more visual “flair” I’ll start by looking through what images I have to work with (if the client has provided any) or through a stock image site to see if anything sparks an idea. I think this is one of the main reasons I loved working on the Steinway project so much. Rather than using screenshots as my main image, I got to use beautiful images of pianos. It’s a nice change when given the opportunity to work on sites that are selling physical objects over virtual.

As for sketching, I’ve never been much into it. At least not for web design. If I have a logo that I’m working on (which is fairly rare these days) I’ll break out the sketchbook. Otherwise I usually find that when I try to sketch things out, it never ends up working out in real life.

Describe your work day (hours & rituals you keep) and your work environment (how your workstation is set up & what your office is like).

I get into work at 9am and start off by clearing out the inbox and getting the little things off of my plate. That normally takes until 10:30am or so. Next I’ll figure out what I’m going to tackle for that day, and get a small start on it before lunch. After lunch is when I really dig in and get into my best working zone. At 5pm I wrap things up and call it a day.

My office is a small space above a local dry cleaner. It’s not glamorous by any means, but I’m very thankful for it. It’s got a window, some old trim and a bit of character. Most importantly, it’s cheap. I’m thinking about building on an addition to the house sometime down the road to add an office, but it will have to wait until both of my girls are in school.

For the last 3 years I’ve been using a 24” iMac. I was planning on getting a new machine this year, but Dave Ruiz convinced me to upgrade it with an SSD drive. Very glad I did. I can probably stretch another year or two out of this one now. I don’t even think about the computer anymore. I never notice any system hangs, or lag when switching between open apps. Best upgrade I’ve ever done. I also have a secondary LG 23” monitor that just keeps my skype, ichat, itunes, twitter, etc window off of my main monitor. Besides that, I have a 1TB FW800 drive that I use as my main storage, as the SSD drive is only 120GB and another 1TB drive that for Time Machine. I just started using BackBlaze as well for offsite backups. Can’t be too careful.

This has been great Jesse, thank you for taking the time.

My pleasure.

Jesse Bennett-Chamberlain's Work
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