More than anything else, I suffered from taking on too many projects in my earliest days as a freelance professional designer. I was unsure of the quantity or consistency of work I’d get. To deal with that, my natural reaction was to say ‘yes’ to everything. That has many negative side effects. Some examples are: more deadlines to hit and possibly miss, more people to communicate with (takes time away from designing), mediocre design because I didn’t have the time to communicate well about the design work or do good work on it. I learned to work fast, but that initial body of work wasn’t work I was proud of.

Arrogance is the biggest turn off. I expect the quality of a designer’s work to always be higher than their ego. If there is an imbalance in the opposite direction, that’s a big red flag. When a designer behaves like they have it all figured out, that doesn’t make me feel good about them. It makes me think they’re naive, unrealistic, and dishonest (either with me, themselves, or both). I want to work with people who are comfortable not knowing. Not knowing and deciding anyway, is a big part of getting good design work done. Also, don’t take credit for work that isn’t yours. We all understand that design is a collaborative process most of the time. Acknowledging that and then being open, specific, and confident about what your contributions were and what others’ contributions were helps people understand your experience and trust you.

Everything! Seriously, though: no one really knows what they’re doing. Everyone I admire is figuring out the next thing as they go. I think that’s one of the reasons I’m attracted to them. They don’t rest on their laurels. They’re moving forward, challenging themselves, and mustering up just enough confidence to do crazy things that might fail. Also, it helps to not take things too seriously.

— I learned when and how I work best, and organize my time around having solo time when I’m best at it and collaborative time when I’m best at it. I tend to tune this every three months or so. I love consistency, but contextual things change and a tune-up is necessary.
— When faced with anything new: don’t react, listen.
— Being the best version of myself usually results in me doing my best work too. I work hard to put myself in a good state-of-mind.
— And recently, I’ve been loving this way of thinking about things: fall in love with problems, not solutions. (Hat tip to Dane Howard at Ebay for planing that seed.)

The Brand Gap — Marty Neumeier’s book is the best articulation of what ‘brand’ and ‘branding’ are. Crazy-fun and quick read too.
Massive Change — This book which accompanied an exhibition, radio program, and other media of the same name talks about — and shows examples of — the power of design to shape the future. Design is this context is very broadly cast, which is part of what makes it so exciting.
The Timeless Way of Building — By architect Christopher Alexander, this is probably my favorite design book of all time.
Designing Programmes — This Karl Gerstner classic is both eye-candy for any person who prefers less over more and has a modernist sensibility. It’s also a great look at system-design in graphic forms. Sadly, it’s out of print, but that’s what libraries are for.
And finally, I’d suggest my book — Product Design for the Web — for anyone interested in building web products and apps.