Dean: Innovation and the Art of Failing Up


Above: Steve Jobs (Photo: Apple)

By Royann Dean

The death of Steve Jobs struck a nerve in the global community. In my lifetime, I cannot recall anyone who has been showered with such praise from so many different parts of the world. He’s been called an innovator, a genius, a visionary and one of the best CEOs of the modern age. The products that he created have not only revamped entire industries but changed the way we interact with technology and with each other. In the early 1980s, who would have thought that one day non- techies would swoon over electronic devices, wait in line for new products they didn’t need and become fiercely loyal to a technology brand? There is no doubt; Steve Jobs was a game-changer.

When Jobs was a young man, he once said that all he wanted to do was “put a ding in the universe.” What he had was a passion for what he did. He was not a designer or an engineer but he had an eye for how things should look and a feel for how things should work. He was also a relentless marketer, building the Apple brand into one which has come to represent the best in strategic design implementation.

In the 1990s, Jobs was fired from Apple. When he found himself back at the company, he had a strong vision of what it needed to do to differentiate itself and to grow. He engaged multiple design disciplines to ensure that the products worked in ways that people could not previously imagine. And he also wanted them to look sleek. In short, he used design to make Apple’s products easy to integrate into our lives with minimal effort and more importantly, they made us look and feel, well, cool. Make no mistake, Jobs was by no means perfect. His employees and co-workers readily admit that he was not the easiest person with whom to work. A perfectionist, he was a micromanager who could be rude, arrogant and think nothing of belittling his staff in meetings. His management style can be debated but undoubtedly, he was passionate about his work and had a strong, clear vision of what he wanted.

What Steve Jobs accomplished in his field is remarkable, but one could argue that he would have been successful in any area. Why? He was the quintessential entrepreneur. He wasn’t afraid to fail. Each time something didn’t work, he learned from the experience and made the necessary adjustments. Radio and broadcast journalist Tavis Smiley describes this as ‘failing up’. It’s likely that the culture in which Jobs grew up played a role his success. He grew up in California during the 1950s and 1960s, immersed in a culture that encouraged liberal thinking, innovation and creativity. It opened up his thinking about what was possible and taught him that it was okay to change things.

Too often, we do not embrace innovation and lack passion about what we’re doing because we are afraid of failure. The Caribbean has its fair share of talented people, but sometimes we do not have leaders or policies in our respective communities that empower us, encourage innovation and entrepreneurship and embrace change. There is an institutionalised discouragement from challenging the norm and we are told to just fall in line. Admittedly, it can be rather difficult in some countries to be innovative, in practice, because of limited resources with regards to funding, advice and assistance. The old guard will frequently hoard power and discourage ideas that disrupt the status quo if they think that they may become displaced.

In a recent article, designer Bruce Nussbaum said that young creative types and new capitalists will drive change in business. Smarter technology and higher degrees of global connectivity as well as the development of creative industries make this a very realistic endeavour.

The next Steve Jobs may not come from the Caribbean. That’s not necessarily the goal. The point is that we learn from his life and realise why he impacted us so greatly. The point is to be passionate, smart, brave; to fail up and, to quote from that pivotal Apple campaign, “Think Different.”

Royann Dean is a branding specialist and the principal of tmg*, a strategy and design firm in Nassau, Bahamas. She can be contacted at

Note: the opinions expressed in Caribbean Journal Op-Eds are those of the author and do not necessarily reflect the views of the Caribbean Journal.