‘He not busy being born is busy dying’
— Bob Dylan

In this fast paced world, one could be forgiven for thinking that the earth's RPM increased annually. For the entrepreneur, this statement is most poignant, as in the modern world of business, to stay stagnant is to die a slow death.

Bob Dylan, was an ardent supporter of this viewpoint throughout his music career, heralding similar philosophies since the release of his 1960’s classic; “The Times They are A-Changin’’. Indeed the times are changing unequivocally fast, as the information generation consumes more in a day then previous generations did in a month.

Remaining true to his own philosophies, Dylan's recording career, spanning fifty years, has been through numerous re-births, exploring many of the traditions in American music—from folk, blues, and country to gospel, rock and roll, and rockabilly to English, Scottish, and Irish folk music, embracing even jazz and swing.  

In recent years, Dylan has gone through another surprising personal career reinvention. He now channels his seemingly boundless creative energy as a wrought-iron gate sculptor with his work presently on display on New Bond Street, London.


Most people I come across follow the conventional logic that annual personal plans like New Year Resolutions pave the way to success.  At the pace that the business world (and the entrepreneur) evolves in 2014, goal setting on an annual basis is no longer viable. Resolutions should be an on-going process ingrained in your daily routine: a never-ending operation that constantly evolves, refines, restructures, and disrupts your own personal status quo.  

Below I have listed two examples of people who have reinvented themselves throughout their careers. These "step changes" and re-births are only possible when one moves with fluidity and yearns to constantly evolve their skills , interests and image on a journey towards personal fulfilment:

Jay Z - Rapper to Business Mogul


Rising from humble beginnings, the Brooklyn, NYC native, who refused to sign a record-deal, went from selling albums from the boot of his car to being one of America’s most recognisable stars and the owner of an NBA basketball franchise (the New Jersey Nets).

His entrepreneurial nature was evident at an early stage as the rapper refused to split the profits from his music with record-company executives. Instead he decided to found his own label; Rocafella Records. He distributed his own albums and marketed his own music, ensuring that he received all the profits from the money he made.

His business ventures include the 40/40 Club, a chain of sports-themed restaurants, a Greenwich Village bistro, a multi-million pound clothing range (which he sold in 2007 for £124 million); a line of beauty products known as Carol’s Daughter, a NY Times best-selling book, video-game production credits and a cigar company, all while working as sports agent. As if this wasn’t enough, his wife, RnB singer Beyoncé has also earned £212 million in her own career.

Insight: While it may not seem so, there is a common thread in Jay Z's ventures: a consumer focus leveraging his personal brand.  He has built, through music, an image that defines modern day consumerism and pop culture and has exploited the value of this brand through consumer products that represent the "good life" that his brand symbolizes.  Like Jay Z, entrepreneurs looking to build a portfolio of businesses need to think limitlessly and be sector agnostic. They need to constantly re-invent themselves and break into new sectors they are passionate about, by partnering with specialists and leveraging a common theme that sews the portfolio together.   

Steve Jobs - Hippie to CEO


Steve Jobs is most famous for founding a company which has been ever-present for the last 30 years, but in Apple’s foundation years he was known for quite a different reason.

During the late 70’s Job’s refused to wash for weeks on end as he was wrongly convinced that his strict vegan diet ensured his body didn’t omit bad odours.

There are stories of Jobs being physically removed from his own office and forced to go home to shower during this time as his work colleagues could no longer stand the smell. He would also frequently promote the use of LSD claiming that it allowed him to imagine the future directions in which technology was heading. He once chastised Bill Gates for being “unimaginative” telling a journalist that the Microsoft founder would "be a broader guy if he had dropped acid once or gone off to an ashram."

Slowly, as the company grew and Jobs realised the importance of making a good impression and upholding a reputable public image, he cleaned up his act, made himself more presentable and stopped making such shocking comments. In private, Job’s maintained his Zenist philosophies and maverick business style; both of which went on to be a huge part of Apple’s success.

Insight: Your early experiences and relationships will play a part in your future career journey, but you don't yet know how the puzzle pieces will fit together.  Jobs' classes in calligraphy at Reed College in the 70s  went on to define the shape of the fonts that we are all used to on our personal computers.  The art is in connecting the dots of seemingly unrelated events and experiences in one's life.  Jobs was a master in this art, repeatedly connecting - at various stages of his life journey - the people, ideas, and products he came across from different industries and different parts of the world.

The difficult question, of course, is: as we go down our journey of re-invention, how do we know which of our everyday experiences will be the pivotal ones, as Jobs's calligraphy classes turned out to be for him 10 years later?  As Dylan once sang, the answer, my friend, is blowin' in the wind.