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When dreams change, it’s not failure — it’s a way forward

Steve Jobs, Oprah Winfrey, and Vera Wang all had dreams that were very different from the areas where they found success and happiness. Photo sources below.

It’s easy to get excited when our kid declares they want to be a doctor. We start planning a future filled with white coats, diplomas, and medical conferences.

Or when they fall in love with playing guitar, and suddenly we’re imagining their Grammy acceptance speech.

But kids change.

Dreams evolve.

And that’s not a sign of failure — it’s a sign of growth.

There’s this cultural pressure to find a “calling” early and stick to it. 

But the reality is, most of us don’t follow a single, unbroken path, and kids are no different. 

Their passions will shift, and when they do, it’s not time to panic or feel like they’re giving up. It’s time to celebrate their evolution.

Steve Jobs — the spiritual guru? 🧘

As a teenager, Steve Jobs was obsessed with spirituality and Zen Buddhism — not technology. 

Source: Pinterest 

He spent time in India searching for enlightenment, only to come back and co-found Apple. His journey wasn’t linear, but every experience, even the detours, informed the visionary he became. 

Would his parents have been thrilled about his spiritual pilgrimage if they had expected him to take a more traditional path?

Probably not. 🤷 

But Steve’s search for meaning was vital to shaping the person who would forever change how the world interacts with technology.

In fact, Steve felt that his experience in India was so transformative that he encouraged Mark Zuckerberg to visit the same Ashram he lived at in the early days of Facebook.

Oprah Winfrey — the teacher? 🧑‍🏫

As a young girl, Oprah Winfrey was deeply inspired by her grandmother, who was her first teacher and instilled a love for learning. 

Source: Pinterest

Oprah dreamed of becoming a classroom teacher, even practicing with a makeshift classroom of dolls in her grandmother's yard. She took early steps toward this goal by excelling academically, and winning a full scholarship to Tennessee State University

While she initially saw teaching as her future, her path shifted when she got an opportunity to work in radio — and then television. 

Oprah may not have become a teacher, but she held on to those values. Through her talk show, she educated millions, using her platform to teach the world about empathy, resilience, and storytelling. 

Her dream of teaching evolved into something even greater, but at its heart, her core desire to connect and uplift others simply looked a little different than she originally planned.

Vera Wang — the figure skater? ⛸️

As a teenager, Vera Wang’s dreams looked a lot like mine — she wanted to be an Olympic figure skater.

She trained her butt off and competed at the national level, hoping to represent the U.S. at the 1968 Grenoble Olympic Games. 

When she didn’t make the team, Vera was forced to rethink her future. She shifted her focus to fashion, landing a job at Vogue, and working her way up to senior editor. 

She eventually became one of the most recognized names in fashion.

Vera’s passion for beauty and precision carried over from skating to fashion, proving that even when failure occurs, skills live on, taking on new and extraordinary forms.

So — when your kid’s dream morphs into something new, don’t view it as a failure. 

In fact, don’t even look at it like they’re starting over.

Support their pivots, because every new passion they pursue rounds out their character and teaches them refreshingly new lessons.

Dreams are not static — they’re a process of discovery.