There really is very little left to say about Steve Jobs (or Bob Dylan, for that matter). 

However at a pivotal point in both of their careers they were each presented with a similar problem, which not only questioned their ability at work but their judgment in life.

In 1997 Steve Jobs had returned to advise Apple, to take a place at the helm at the company he helped build.  Although later he would claim he was too busy with Pixar to take the permanent CEO post, Jobs was seen as some within (and without) the company as the only person that could save it from bankruptcy and make it great again.

In 1966, although not universally loved, Bob Dylan was a phenomenon in folk music. He was one of the most commercially successful musicians the genre had seen, bringing a spotlight and contemporary sensibility to a genre considered traditional, not pop.

In May 1997 Steve Jobs presented his vision for Apple to a packed auditorium of Apple developers and stakeholders in the San Jose Convention Center.

In May 1966 Dylan performed in the Manchester Free Trade Hall, to a room full of fans expecting the folk hero they had grown accustomed to. 

Steve Jobs’ key message that day was that ‘focus is about saying no’.  He went on to announce that Apple were killing off OpenDoc, a piece of software that was popular amongst developers in the crowd. In his words, they ‘put a bullet through its head’.

In Manchester, backed by The Band, Dylan used the second half of his set to showcase his new ‘electric’ sound to the room of appalled folk enthusiasts. 

From the Apple crowd in San Jose a software developer declared in front of the packed auditorium "it is clear on several counts you don’t know what you’re talking about." With his anger rising he asked Jobs’ to justify his actions before finally declaring "perhaps when you’re done with that you can tell us what you’ve been doing for the last seven years."

In Manchester the incensed crowd of folk-purists were disgusted at Dylan’s new sound. A solitary man, caught up in the fury shouted "Judas" at Bob Dylan.

For a brief moment, in Manchester and in San Jose, there was silence.

There is such a moment, in between action and reaction where all of the world’s permutations are presented to us. Depending on our knowledge, world-experience and discretion the choices available to us are considerable. It is the decision you make in that moment that separates you from others. In business, as well as in art your judgment is key. It is also something that comes to you after much failure. Lessons in humility and experiential insight are vital to becoming a great leader 

In San Jose, Steve Jobs took a moment before giving the most insightful, mindful and even-handed rebuttal. In Manchester, Dylan retorted ‘Play it fucking LOUD’ and the Band obliged.

Kipling said "trust yourself when all men doubt you, but make allowance for their doubting too." There is a time in most people’s lives where judgment and foresight are questioned, and our actions are called into account. Examples like these are fascinating in that they show a high stakes game being played out on a micro level, a company facing in a new direction, stakeholders that are resisting change, and the fundamental suitability of an individual to affect change.

Relatively trivial matters often have lessons to teach us. In this case, Steve Jobs trusted his judgment, put his ego to one side and maintained a course of action, the failure or a success of which he would own. It was his choice of direction. The questions asked of each man ran to the core of what they believed in, testing the limits of their ability to express themselves and required Bob Dylan and Steve Jobs to exercise judgment, improvise and stay true to their vision.

In case you had missed this: Bob Dylan remains one of the most influential musicians of the 20th century, and Steve Jobs vision for Apple became realized in the unprecedented success of the years that followed. 

Both Dylan and Jobs took stock of the situation and used all the tools at their disposal to present their vision, and at the end, the audience applauded.