How Risk-Taking Leads To Career Wins

The Oscars – Hollywood’s biggest night – isn’t just about glitz, glamor and golden statues. They’re a case study in risk-taking, reinvention and betting on bold ideas.

Year after year, the films that dominate the Academy Awards aren’t the ones that played it safe. They’re the ones that took big swings—defying expectations, breaking storytelling conventions, and proving that the biggest rewards go to those willing to take the risk.

This year was no different. From Dune: Part Two’s sweeping sci-fi spectacle to Emilia Pérez’s genre-blending audacity, the biggest winners of the night weren’t the films that followed a formula—they were the ones that rewrote it.

And there are plenty of lessons in here for all of us.

Success — whether in Hollywood, business, or your own career — isn’t found in following the blueprint of what’s worked before. It’s found in daring to create something new, something uncertain — something that might fail, but also might change the game.

This year’s Oscar winners proved, once again, that taking big risks isn’t just the secret to winning in Hollywood. It’s the secret to winning in life and your career — however you define it.

The Risk Of Thinking Bigger Than Anyone Believes You Should

What Denis Villeneuve’s Dune Gamble Teaches Us About Leadership and Risk-Taking

When Denis Villeneuve set out to adapt Dune, the odds were stacked against him.

Frank Herbert’s novel had long been considered unfilmable. David Lynch’s 1984 attempt was a box office disappointment. Alejandro Jodorowsky’s ambitious vision never even made it to the screen. The book’s sprawling narrative, dense political intrigue, and existential philosophy made it a nightmare for traditional Hollywood storytelling.

Villeneuve didn’t just attempt the impossible—he doubled down on it.

Rather than condensing Dune into one digestible blockbuster, he convinced Warner Bros. to take an unprecedented risk: let him film only half of the story, with no guarantee that he’d ever get to finish it. If Dune: Part One flopped, there would be no sequel. No closure. Just an unfinished vision, left in the sands of Arrakis.

It was an audacious gamble. But that’s what true leadership looks like — betting on a vision so compelling that others have to follow.

And it worked.

Dune: Part Two won Best Sound and Best Visual Effects at the 2025 Oscars — a testament to Villeneuve’s world-building mastery. While it didn’t win Best Production Design, the film’s success proved that taking creative and financial risks can pay off massively when paired with a clear vision and execution.

The key lessons from Villeneuve’s Dune bet teach us about making bold career moves, leading with vision, and taking risks that redefine industries.

Lesson For You:

If your vision doesn’t scare people a little, it’s probably not big enough. The biggest ideas — the ones that change industries, careers and lives — often sound impossible at first.

Ask Yourself: What would it look like if this actually worked? What needs to be true if it had a shot?

The only way you’ll find out is by taking the risk.

The Risk Of Reinventing A Beloved Classic

What Wicked’s Film Adaptation Teaches Us About Bold Leadership And Reinventing Success

For nearly two decades, Wicked has been more than just a Broadway hit — it’s been a cultural phenomenon.

Fans didn’t just love it; they claimed it. The show became a rite of passage for theatergoers, a defining soundtrack for a generation, and a near-sacred experience for those who had witnessed its magic live.

So, when Universal finally decided to adapt it for the screen, the stakes were impossibly high.

Would the movie work? Could it capture the electricity of live theater? Or would it flatten Wicked into just another formulaic Hollywood adaptation—technically competent but missing its heart?

The easy, conventional choice would have been to compress the entire story into one film, slap on some CGI, and call it a day. Universal didn’t do that.

Instead, it made a bold, unprecedented move: It split Wicked into two films. A musical film franchise — a rarity in Hollywood.

At first glance, this decision seemed like a massive gamble. Musicals are already a tough sell at the box office. Splitting Wicked into two meant doubling the budget, doubling the risk, and asking audiences to invest in a story that wouldn’t be complete until a second installment.

Here’s why it was a stroke of genius. Rather than cramming Wicked into a condensed, oversimplified adaptation, this move allowed the filmmakers to:

1. Deepen the storytelling – giving pivotal moments the space to breathe rather than rushing through them.
2. Expand the world of Oz – creating something truly cinematic, not just a stage-to-screen translation.
3. Take creative risks – positioning Wicked as a cultural event, rather than just another movie release.

This wasn’t just about making a musical — it was about reimagining how a Broadway hit could be adapted for modern audiences.

And that’s where the real leadership lesson lies. Because too often in careers, leadership, and business, we default to the safest option — the proven formula, the conventional wisdom, the way things have always been done. But true visionaries? They know when a bold move is necessary.

Universal’s decision with Wicked offers a masterclass in strategic risk-taking, long-term thinking, and the courage to defy expectations.

On Oscar night, Wicked: Part One won Best Costume Design and Best Production Design — a clear win for big, ambitious storytelling.

But the wins weren’t the whole story.

The nominations alone spoke volumes — a testament to the film’s impact:

1. Best Picture – Recognizing Wicked as more than just a blockbuster musical, but a cinematic achievement.
2. Best Actress – Cynthia Erivo’s powerhouse performance as Elphaba earned her a well-deserved nod.
3. Best Supporting Actress – Ariana Grande’s take on Glinda proved she was more than ready for the big screen.

This wasn’t just another Broadway-to-Hollywood adaptation. It was a statement. A big, green, defying-gravity kind of statement.

Audiences are hungry for stories that take risks. They want spectacle, yes — but they also want depth, world-building and a reason to care. Wicked delivered all that and more, proving that when you commit to a vision, bet big, and refuse to cut corners, the results can be nothing short of magical.

And the same holds true for careers. Playing it safe might keep you comfortable, but true impact comes from daring to do something different — whether that’s taking on a bold new role, championing an idea no one else believes in, or stepping into uncharted territory.

The biggest rewards? They go to those willing to take the risk.

Lesson For You:

Sometimes, the riskiest thing you can do isn’t changing something — it’s changing how it’s done. Innovation isn’t always about creating something brand new. It’s about seeing an opportunity to make something better, bigger and more impactful than it’s ever been before.

Ask Yourself: Where in your work or career are you playing it safe because you’re afraid of upsetting the status quo? What if the boldest move you could make isn’t reinventing the what, but the how?

The Risk Of Blending The Unthinkable

What Emilia Pérez Teaches Us About Risk, Reinvention And Career Boldness

Some movies succeed because they perfect a formula. Emilia Pérez won because it shattered the formula entirely.

A legal drama-musical hybrid? A film that seamlessly jumps between high-stakes courtroom battles and full-blown operatic numbers? On paper, that sounds like an identity crisis — something that should never work.

But Jacques Audiard wasn’t interested in playing it safe. He didn’t care about what Hollywood said was “supposed” to work. He cared about making something that hadn’t been done before.

And it paid off.

Emilia Pérez led the Oscars with 13 nominations and won Best Supporting Actress for Zoe Saldaña and Best Original Song for “El Mal”. The film forced audiences and critics to rethink what’s possible in storytelling, blending legal drama with musical elements in a way that defied convention.

And that’s a lesson far beyond Hollywood.

In careers, leadership, and business, we often get stuck in what’s tried and true. We follow conventional wisdom because it feels safe. But real innovation—the kind that changes industries, opens doors, and creates new opportunities—comes from those willing to break the mold.

Audiard took a bet on Emilia Pérez and won. The question is: What’s the risk you need to take to break your own formula?

Lesson For You

Disruptors don’t wait for permission. They don’t ask if audiences are “ready.” They create what doesn’t exist yet, and in doing so, they force the world to catch up.

Ask Yourself: Where in your career are you avoiding a bold move because it hasn’t been done before? What if that’s exactly why you need to do it?

The Risk Of Owning Your Perspective, Even When It’s Unconventional

Why The Brutalist’s Bold Vision Proves That Standing Out Is the Only Way To Win

Some films are designed for mass appeal. The Brutalist was not.

Brady Corbet’s striking and uncompromising film isn’t an easy watch. It’s visually stark, emotionally intense and artistically daring. It doesn’t cater to audiences—it asks them to meet it where it is.

And yet, it won big.

At the 2025 Oscars, The Brutalist took home Best Cinematography, a testament to its haunting visual storytelling. And Adrien Brody? He walked away with Best Actor, proving that performances and stories that demand something from their audience can leave the deepest impact.

Corbet didn’t water down his vision. He didn’t aim for safe, digestible storytelling. Instead, he leaned into what made The Brutalist unique — and in doing so, he created something unforgettable.

Lesson For You:

Your unique perspective is your greatest advantage. Trying to fit into expectations won’t make you stand out—it’ll just make you blend in.

Ask Yourself: Where are you playing it safe, watering down your ideas, or softening your voice to be more palatable?

What if leaning harder into what makes your perspective unique is exactly what will set you apart?

Because in the end, no one remembers the people—or the films—that played it safe.

The Career Risk That Never Pays Off? Playing It Safe.

Every single film that won big at this year’s Oscars had one thing in common: it took a risk. They gambled on themselves when there were no guarantees. They bet that audiences would follow them into the unknown. They didn’t play by Hollywood’s rules—they rewrote them, and they won.

Every film that triumphed at this year’s Oscars shared a common thread: they took bold risks, venturing into uncharted creative territories without any guarantees. They defied Hollywood norms and, in doing so, redefined them.​

This fearless approach isn’t confined to the silver screen; it resonates deeply within our professional lives. Research underscores the value of embracing risk: a study revealed that over half of the women surveyed believe that taking more risks in their careers leads to quicker advancement.

Moreover, another study found that individuals who exhibit risk-taking behaviors tend to experience higher job satisfaction. ​

These insights highlight a compelling narrative: while playing it safe may offer comfort, it’s the calculated risks that often pave the way for significant career growth and fulfillment.​

So, the next time you’re at a crossroads—debating whether that bold idea, unconventional move, or innovative project is too audacious—remember: no one ever won an Oscar by playing it safe.

Similarly, legendary careers aren’t built on complacency. They’re forged through daring decisions, resilience, and the courage to venture beyond the familiar.​

Embrace the unknown. Take that leap. Your next big win might just be on the other side of that risk — and the award for Best Career Move will go to you.