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Raised within his father’s advertising agency, Stephen Gates’ future as a brilliant design leader seems almost predetermined. Here, he reflects on his journey—and the methods behind his creative madness. 

“Here’s to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in the square holes. The ones who see things differently. They’re not fond of rules. And they have no respect for the status quo. You can quote them, disagree with them, glorify or vilify them. About the only thing you can’t do is ignore them. Because they change things. … The people who are crazy enough to think they can change the world, are the ones who do.”

This text comes from Apple’s 1997 landmark commercial for its “Think Different” campaign. And that famous first line—“Here’s to the crazy ones”—can today be found tattooed on Stephen Gates’ arm. He has said that some days it’s an affirmation. Other days it’s a reminder. Regardless, it’s right where it should be

Born and bred in the Pittsburgh area, Gates’ mother was an artist and his father worked in advertising. As a kid he would write and illustrate his own books, which he printed with his dad on the 700-pound letterpress in the basement. (When he got to Kindergarten, he was surprised to discover that his classmates read books written by authors other than themselves.) After an Apple IIGS changed his life, he grew up and found his way to Vertis Communications, where he worked as interactive creative director with some of the world’s top companies; as creative director and designer at TM Advertising; and then as VP of Global Brand Design and Innovation at Starwood Hotels and Resorts Worldwide, where he pioneered apps for the Apple Watch that wound up in one of Tim Cook’s mainstage keynotes. Following a gig at Citi, he now works as head design evangelist at InVision—and in addition to his brilliant speaking engagements around the globe and his podcast series, he’s known for his writings on leadership, design, craft and career.

The following text comes from an article that is a veritable highlight reel of Gates’ wisdoms; he was kind enough to allow us to republish it here to ring in the latest episode of Design Matters.

Here’s to the crazy ones.


Success is a Choice (and Everything Else I’ve Learned So Far)

As I’ve been searching for the next chapter in my career over the past few weeks, I’ve found myself reflecting on the course my career has taken and thinking a lot about what I did right and what I did wrong. It has been an amazing journey that has let me work on things I never dreamed would be possible, and I want to share some of the things that I’ve learned and have been successful at in the hopes that they might help other people. I think that I’ve been building toward writing this article since I started this blog 12+ years ago, as this piece weaves together a lot of the best articles I have written into one cohesive narrative. My blog has been a critical part of my process in forcing me to constantly evolve as a designer, thinker and leader; since I was sharing the insights I’ve learned along the way, it kept me from resting on past successes. I have broken the article down into the six areas that I think are critical for a successful creative career, and each of those have specifics on how to do them well.

1. Success is a Lot of Hard Work
Over the years the No. 1 question I get from pretty much everyone is, “What’s the secret to your success?” My answer is short, sweet and always the same: “Have great ideas and work your ass off.” I then watch the hopeful, bright-eyed enthusiasm melt off their face as they realize that the secret they are seeking seems to be the two things they apparently want to avoid: time and hard work. The reality is that to be successful takes a lot of time, a lot of hard work and there is just no getting around it. You are going to have to evolve from a designer or copywriter to an associate creative director to a creative director and on and on. Each of those stages will require you to learn new skills and constantly evolve. Here are the two key insights I have learned that have helped me turn all that hard work into success.

One of the most common career mistakes I see are creatives who think that pouring all their hard work into learning how to use applications will make them successful. Don’t misunderstand me, knowing applications is a critical part of any career, but those applications are nothing more than an electronic pencil. Just like a pencil, if you don’t have any ideas to draw, write or communicate, then even the best tool is useless. You need to learn applications to the point where you no longer have to think about how to create your ideas and are just able to let your creativity flow. But it’s that focus on learning applications so they are tools to express your ideas that is critical, because if you only focus on your ability to use the tools, then you will hit a ceiling because agencies and businesses value the ability to create ideas over the ability to just create executions.

As I put together this article I wanted to pass on tangible advice, but I will admit that there is also an element of luck in being successful. It happens when you get one of those rare and magical moments where everything you need lines up and the universe gives you an amazing opportunity. The problem is that most people are completely unprepared to act on those opportunities and they either don’t have the skills, knowledge or insight to take advantage of them. I have found that to be successful you have to be willing to constantly work and prepare for these future opportunities even when you don’t know when or if they are going to arrive. It is a hard thing to do because it requires a lot of discipline, self-motivation and belief that the work will pay off at some unknown point in the future. I have always tried to approach my career like it is a blue-collar profession; I work to evolve the skills I think are strong and work to learn and improve the skills I think are weak. For me it has paid off because when those rare moments come around I have been ready to take advantage of them, which has made all the difference.

2. Success is an Idea-Led Career
I’ve always focused on making the foundation of my career the ability to deliver great ideas over the ability to just hit a deadline, know a new technology or use an application. I think this has worked because those applications, technologies, design aesthetics and even the needs of society have changed, but the need for great ideas will never change. Here are the three key insights I have learned that have help those ideas get stronger and work better within a team.

In my article “Jiro dreams of sushi. You need to dream of design,” I wrote about master sushi chef Jiro Ono, who teaches his chefs that to be a great chef you need to have tasted great food so you have a palette and can tell when you cook great food. It’s a critical concept as a creative as well because to be successful you have to be in a constant two-part cycle of experiencing the best of your chosen creative profession and then using that knowledge as a measuring stick to judge your work. This means that to be a great designer you have to constantly experience great design, or to be a great writer you have to constantly read great copy and then you use that taste level and insight to drive your work forward. You also have to understand that this cycle of consumption never stops, no matter how long you have been in the industry. It has to constantly evolve to keep up with changes in society, psychology, technology, creativity and design. I have seen many great creatives who think that they know it all, or that they don’t need to keep up this constant evolution—and they are the ones who quickly find their work becoming increasingly less effective, until their career fades away.

I have always coached my teams on the importance of being able to externalize and share your creative process with the rest of the team, which is a concept that runs counter to what is often encouraged by a lot of companies where individual achievement and ownership is valued over the work of the team. I think it’s important to not only share your process and ideas with the team, but to develop a culture where the team will constantly try to pressure-test and find weak spots in those ideas to make them stronger. It’s something that requires strong leadership to work so that everyone doesn’t feel like they are being attacked or their ideas are being put down, but instead allows everyone to contribute and take ownership in creating the best ideas. I have seen this concept work as the core of a lot of groups at companies like Apple and Google, where they are relentless in seeking out the best ideas by sharing their work, knowing it can always be better and using that process to continue to refine it until it is something great.

Also in “Jiro dreams of sushi. You need to dream of design” is another theme in which Jiro talks about his lifelong dedication to sushi and his constant work to improve his craft. This is a trait that I’ve come to embrace over the course of my career, and it’s a trait that I see shared by every great creative mind I’ve ever known. I think it’s a byproduct of the fact that they constantly work to develop their palette and they constantly want to make everything they do better. I’ve come to embrace the fact that there is no time when design is completely out of my mind, because I am constantly looking for new inspiration, tormented by the flaws in my old work and looking for that next great idea. When a project is finished I allow myself 15 minutes to enjoy the work that was done, and then I am onto the next project. I have little use for nostalgia because when I look back I see only the mistakes and things that I could have done better. Nostalgia is for people whose best days are behind them and for people who look to the past for answers. That eternal dissatisfaction can be a strong motivating force to keep your work moving forward, but it is also something that needs to be kept in perspective because if it gets out of balance, you can become a naysayer who lets that dissatisfaction take over their process and blind them to new ideas.

For Lessons 3, 4, 5 and 6, click here.


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