Blueprints of Ambition
Finding myself through founders.
It hit me recently.
I was at the Soho Apple Store for a trade-in and was helped by an amazing sales associate.
I forget her name, but she was a Cancer and, like me, a fellow Steve Jobs enthusiast.
She mentioned that one of her friends was working on a movie about him. I couldn’t contain my excitement.
"Tell me more!" I exclaimed. "Is it a biopic? When does it come out? Who’s playing him?"
We look it up, it’s called The Book of Jobs. The plot summary immediately resonates with me. Finding heroes as a young woman is challenging, especially when success is often tied to masculine traits. As I skim through the IMDb profile on her phone, thoughts rush in. The excitement of a movie about my greatest source of inspiration, the fate of meeting this specific associate, and the enduring legacy of Steve Jobs. The iPhone 16 had come out earlier that morning, and the store was packed. It’s inspiring to see one man’s vision still feel so fresh and relevant. Though Apple is now run by many people with different approaches than Steve, his legacy lives on in the rounded corner of every product. As I waited upstairs for my new phone to update, I soaked it all in - the excitement the brand continues to generate. The Book of Jobs stayed on my mind, but so did the idea of founders and CEOs. I think of my own. Two names stand out, and if you know me, this will come as no surprise: Steve Jobs and Yvon Chouinard. They are contrasting figures, yet their impact in their respective fields is comparable.
This fascination with founders has been with me for years.
Let me take you back to February 2021.
At 18, I dropped out of the first college I attended. Months of feeling unfulfilled, restless, and craving more had led to this decision. At the height of COVID, when people were taking time to follow their passions, I couldn’t bear to sit, dying inside, in Zoom breakout rooms. Digital media was booming, and I was constantly seeing people building their dream lives or sharing their journeys. I couldn’t stand wasting my time and energy on something that wasn’t giving me anything back. Five months into college, I walked away. A month later, I broke the news to my parents. Their reaction was as bad as it could get, but I had never felt more certain about a choice in my life. That’s when I learned my first major lesson: the more you love your decisions, the less you need others to. It’s a mindset I carry with me every day.
Despite my disdain for academic learning, my thirst for knowledge never wavered. Determined to prove my decision wasn’t foolish, I dove headfirst into absorbing as much as possible. With nothing but time on my hands and endless resources at my disposal (gotta love living in the 21st century), I spent these months of freestyling life building an army of ideas, people, concepts, brands, and art - everything that would shape me.
Fast forward to now: college is behind me (to avoid being disowned so early in life, I did end up going back), I work a corporate job, and I spend my free time doing what I love. I’m exactly where I’ve always wanted to be.
As I sat on a deeply uncomfortable wooden stool on Prince Street, I thought about what The Book of Jobs might be like. I hope they do him justice. My thoughts, once again, drift to my heroes - Steve being the first. So few people have left such an impact. I think about Emily Weiss, having just finished reading Glossy, which left me uneasy about the harsh realities of being a female founder. It’s tough for women to find figures to look up to. Not that women should look up to women or guys to guys, but the business world often feels like an uphill battle for anyone trying to make a name for themselves.
My love for Apple has been a constant throughout my life, deepening as I witnessed the brand evolve. My admiration for Steve Jobs, however, is newer but has completely taken over many aspects of my life. I remember reading Walter Isaacson’s biography of him almost overnight. The sleek cover, with Steve’s face staring at me, was like a mirror. When I read about his spiritual pursuits, his distaste for authority, his obsession with design, and his reality distortion field, I was hooked. Where had this guy been my whole life? I don’t condone how he treated others, but credit where credit’s due - he knew how to get shit done. That book was instrumental in reinforcing my desire to follow my passions. It also taught me that charisma and great social skills will get you far. Yes, Jobs was a mastermind, but he had an incredible team turning his visions into reality. Reading that book showed me the power of collaboration and the combination of diverse skills. One of my favorite quotes from him speaks volumes about leadership: “The greatest people are self-managing—they don't need to be managed. Once they know what to do, they'll figure out how to do it. What they need is a common vision. And that's what leadership is. Leadership is having a vision, articulating it so that others can understand it, and getting consensus on a common vision.”
Last year, I took a business management course (for credits, don’t be fooled), and in my final reflective essay, wrote: “One theme that particularly stuck was leadership, especially as related to Apple. At the start of 2023, I read Steve Jobs by Walter Isaacson and After Steve by Tripp Mickle. Both books deepened my admiration for Apple and broadened my understanding of effective leadership and innovation. Steve Jobs’ relentless pursuit of perfection, his unique product designs, and his leadership style propelled Apple to unprecedented success. On the other hand, After Steve shed light on how Apple navigated the post-Jobs era, showing how the company adapted to new leadership while staying true to its core values. (…) While visionary leadership such as Steve Jobs is essential to a company’s success, its sustenance also depends on adapting well to change and transitions in leadership. With this insight came a more holistic view of business management: one which stressed balancing innovation with continuity; visionary leadership with effective succession planning; individual brilliance with collaborative teamwork.”
Now, as I sit here reflecting, I’ve never thought more about founders and CEOs than I do today, surrounded by people either making a name for themselves or just beginning their journey - myself included. The power of founders lies not just in the companies they build, but in the stories they leave behind. Steve Jobs, Yvon Chouinard, and Emily Weiss may seem like larger-than-life figures, but they were once just navigating the uncertainty of their 20s, trying to find their footing in the world. That’s why it’s so important to seek out the stories of those who resonate with you, whose journeys may offer guidance or spark something within you. We live in a time where the resources to learn from these visionaries are at our fingertips. If there’s someone who’s inspired you, take the time to dig into their story. You might just discover something that propels you forward on your journey. The path isn’t always linear, and often it’s in the moments of doubt that we uncover what truly drives us - that’s the beauty of it all.
As Steve Jobs quoted in his famous commencement speech, borrowing from the Whole Earth Catalog, "Stay Hungry. Stay Foolish."
That’s what we owe ourselves: to chase what brings us fulfillment, to stay curious, and to embrace the uncertainty along the way.
(I do not own the rights to the images, but the curation and layout of this mood board are my original work.)