Lessons from Steve Jobs
Looking back to an article I first shared in 2023
Gary Bloomer | SHAKING THE TREE # 330
The Steve Jobs paradox: Visionary, showman, and the art of the “unconventional”
Within the past 50 years, few figures in the tech industry have garnered as much attention as Steve Jobs. As the co-founder of Apple Inc., his life and work have been the subject of countless articles, yet the sheer volume of coverage often masks the more nuanced lessons he left behind.
While many analysts focus on his perfectionism, a “Shaking the Tree” perspective asks us to look deeper. To truly understand Jobs, we must stop viewing him through the stale lens of a corporate deity and instead examine him as an unconventional disruptor who succeeded precisely because he refused to accept that things had to be “done the way they’ve always been done”.
Jobs’s famous “reality distortion field” and his legendary keynote presentations were not just theatrical performances; they were master classes in unconventional marketing.
He understood that a brand is not a hollow promise or a corporate slogan—that instead, it is the consistent, memorable delivery of value. He didn’t just sell technology; he sold a departure from the “same-old” status quo.
Why Jobs remains the ultimate case study
If we focus on the idea of meaningful leadership and innovation in relation to the Jobs legend, his legacy becomes clearer:
Visionary innovation as disruption: Jobs didn’t just iterate; he “shook the tree” of established industries. He proved that the most “life-changing” content and products come from focusing on what makes people feel something worthwhile, rather than just filling a market gap.
Leadership through empathy and expectation: Like the best modern leaders who prioritize the “soft skills” of empathy and connection, Jobs demanded excellence not just because he was a perfectionist, but because he was deeply connected to the user experience.
The courage to reframe: Jobs excelled at “reframing and retooling” what the market thought it knew. He taught us that to stand out, one must be willing to abandon “stale” traditional approaches in favor of a fresh, bold perspective.
Simplicity as strategy: His “less is more” approach wasn’t just aesthetic; it was a strategic rejection of the unnecessary clutter that plagues most businesses.
Perseverance over perfection: Perhaps his greatest lesson for today’s creators is that trust is built on accountability and delivery, not on the impossible goal of absolute perfection. His return to Apple proves that even the most visionary leaders must be willing to own their failures and “fix them memorably”.
What I’ve Learned
“When I first wrote about these icons, I was captivated by the ‘what’—the products, the keynote stage, the sheer scale of the results. But the more I’ve written over the last few years, the more I’ve realized that it’s the ‘how’ that actually matters.
What I’ve learned is that we often pedestalize figures like Jobs to the point of irrelevance. We treat them as if they had a ‘magic’ we can’t touch. In reality, the lesson isn’t to be Steve Jobs; it’s to cultivate the courage to be unconventional.
Today, I am less interested in how many iPhones were sold and more interested in the guts, commitment, and vision it takes for a creator or leader to stop asking ‘What is everyone else doing?’ and start asking ‘What does this world actually need?’.
True innovation happens the moment you stop repeating the saddest phrase in the business lexicon: ‘...we’ve always done it this way’.”
As always, thanks for reading.
—Gary
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Next time on Shaking the Tree: Content lessons from Stephen Colbert
ABOUT THE AUTHOR: Originally from the U.K., Gary Bloomer is a writer, branding advocate, marketing specialist, and an award-winning graphic designer.
His design work has been included in Creative Review (one of the UK’s largest design magazines). Since 2009, he has answered over 5,000 marketing and business questions in the Know-How Exchange of MarketingProfs.com, placing him among the top 3% of contributors. He lives in Wilmington, Delaware, USA.