Ben Barry
What difficulties did you face at the beginning of your career?
The application process for the design program at my university was very competitive — approximately 300 students apply and 60 are accepted. You can only apply after having completed several core art classes — drawing, and basic design. I thought, because I was really good with computers and photoshop, that I was already a good designer, and didn’t take the application process as seriously as I should have. I failed. It was devastating at the time, but it turns out it was the best possible thing that could have happened to me. It forced me to reaffirm that design was truly what I wanted to do with my life, taught me humility, and strengthened my work ethic. I waited another year and applied again, this time with a lot more preparation. I was accepted. There have been many challenges in my career since then, but I’ve been incredibly fortunate to have worked with incredible people and had incredible opportunities.
What should a young designer do in order not to get hired by anybody?
Apart from the obvious things like being rude, self centered, cynical, etc... I’d say that lack of passion and curiosity are the biggest red flags for me. Having a ‘portfolio’ that consists only of a dribbble account is also an immediate no-hire, presenting work with context is important.
Are there any things you wish you knew at the beginning of your career?
One of the first realizations I had a few months after starting my first job was that to be successful, not only did I have to design beautiful, well crafted, thoughtful solutions, but I also had to convince someone else that it was the right solution, and often times to spend more money to produce it. I now think that 60–70% of the design process is talking and listening to the client, pitching work, figuring out how to produce it, and then getting it produced. Designing something in school meant hours concepting, drawing, designing, and then maybe producing one physical comp to present. Designing something in the real world means all of that, and then having to convince numerous other people it’s the right thing, and then how to produce and distribute the idea.
Are there any rules or habits that help you do your job more efficiently?
One thing, which is less relevant now that I’m freelancing, but was very important when I was at Facebook was managing my time. Being a maker, I had to block off, and be very protective, of time to actually work and make things without distractions. I kept a schedule where Monday and Friday I was available for meetings, and Friday morning I had open office hours. Tuesday and Thursday I was in the office, but my calendar was blocked off so I could work on whatever I needed to, and Wednesdays I worked from my desk at home so I could be in a distraction free environment. There is a great article by Paul Graham that inspired this change.
Would you recommend some books that young designers might find useful?
Whatever You Think, Think the Opposite  by Paul Arden, Understanding Comics  by Scott McCloud, How to See  by George Nelson, Start With Why  by Simon Sinek (actually, you can just watch his TED Talk and get basically the same content in under 20 min).
Ben answered the questions on June 24, 2014.
The answers were published on June 25, 2014.