The Road Not Taken: If I'd Stayed at Apple, I'd Never Be an Entrepreneur

In this series of posts, Influencers explain how their career paths might have changed. Read all the stories here and write your own (please include the hashtag #RoadNotTaken in the body of your post).

"Could have," "would have," and "should have" are all statements of regret, and not ones that I tend to use. I "should have" practiced more yoga and I "could have" started when I was younger, so I rarely look back. So when I was asked to write this, it gave me time to reflect and dream about what life might have been like if I had not left my job at Apple.

I was a marketing manager at Apple Australia in the early 1990s (yep, last century!). I remember celebrating Apple's 10-year anniversary at the Sydney Opera House with my colleagues. In fact, I still have the 10-year celebration coffee table book, which documented the timeline and significant moments of the first 10 years.

John Sculley was the CEO when I joined Apple but he left during the time that I worked there. He was famous for his publicized "biggest" corporate salary ever and his showdown in the boardroom with Steve Jobs during his tenure (which caused Steve to leave the company he founded). Mike Spindler had taken the helm of the global operation.

Apple was at an interesting moment in history — it had started to license its operating system to hardware suppliers, it had shipped a handheld device called Newton (which touted handwriting recognition), and for all intents and purposes the business model and range looked very similar to those of its competitors. Market share was dropping, margins were shrinking, and the marketing had become uninspiring.

Apple had completely strayed from the original vision created by Steve. In 1987 (two years after Steve was ousted by the board), John Sculley set aside a $60K (a lot of money then) budget to produce the video Knowledge Navigator. Those at Apple at the time told me it was his way of trying to align the team to the last of Steve’s vision. Maybe someone can clarify that for me. If you take a few minutes to look at this video you will see that everything in this futuristic video has now come to reality.

The bigger and clearer your dream, the bigger and clearer other people understand it and are likely to support it.

I left Apple when I wondered where it was going and what its purpose was. I didn't think it had a future as what the organisation was doing was so far from this vision. There are a few of my colleagues still at Apple, and how different it is now! Steve Jobs returned to the helm in 1997, after spending 12 years growing, learning, creating and discovering... what a difference his return made.

If I had have stayed at Apple, I would be working for the top-ranking market capitalization company, according the 2014 Financial Times Global 500, which now has technology that has changed the way the world lives. There are many others now in the space doing amazing things that we could not have even dreamed up back in the '90s.

(Financially if I had kept the Apple stock options I was issued as an employee, my finances would be slightly different too.)

If I had stayed at Apple, I never would have done my own thing – I wouldn't have created an organisation that supports thousands of small businesses across Australia and New Zealand. RedBalloon wouldn't be a best employer, a leading Australian brand or a great tech success story. I’m grateful for my Apple experience. I learned about brands and distribution; I learned about customer experience and employee engagement; and I learned to dream.

I left Apple because I didn’t see a career for myself there. And despite everything Apple has achieved since I left, I am still glad for the choice I made and for the road I chose to travel.

Naomi Simson is the founding director of Australian online tech success story RedBalloon - she has written more than 800 blog posts at NaomiSimson.com, is a professional speaker, author of Live what you Love (order now) and now TV personality on Channel 10s Shark Tank (airing January 2015). Get to know her further at Instagram, Twitter or FaceBook.

Photo: Author's Own