Luck, Failure & Curiosity - Insights From a Motivational Speaker

What Amazon’s CEO gets right about careers, and how it aligns with the mindset that helps anyone thrive through change.

 

“An embarrassing amount of how well you do in your twenties comes down to attitude.”
— Andy Jassy, CEO of Amazon

I just read Andy Jassy’s thoughts on career growth, and I felt like I’d time-traveled back to my days as a documentary cameraman—hearing yet another wise person say what so many before him had echoed in different words:

• Be curious.

• Be willing to fail.

• Don’t overthink it.

Let’s break it down.

🚀 Curiosity Is the Curriculum

Jassy talks about having a high “WhyQ”—that’s your Why Quotient, and at Amazon, it’s practically a superpower.

“We ask why, and why not, constantly... It helps us deconstruct problems, get to root causes, and unlock doors that might have seemed impenetrable.”

Curiosity is no longer a “nice to have.” It’s your compass in the chaos. In a world where AI is rewriting job descriptions in real-time, the ability to ask better questions beats knowing the ‘right’ answers every time.

💥 Failure Is Feedback in Disguise

Jassy’s career path included sportscasting, soccer coaching, and selling golf gear. Not exactly a straight line to CEO.

“I tried a lot of things... early on, it’s just as important to learn what you don’t want to do.”

Failure isn’t the opposite of success—it’s how you build a map to it. Your twenties (and let’s be honest, your thirties, forties, fifties...) are for making bets, not having blueprints.

🍀 Luck Favors the Flexible

Jassy even admits luck played a big part in his journey.

“One of the things I did best was not overthink it.”

That’s not just humility—it’s wisdom. When you stay curious, keep showing up, and learn from the detours, the luck often finds you.

It’s no surprise these three ideas—luck, failure, and curiosity—show up in my Changeability framework too.

🧠 OWN UP

• Choose optimism—loudly.

• Watch your words.

• Get off the unhappiness machine.

🎓 WISE UP

• Learn like your future depends on it.

• Wear your L-plates proudly.

• Make curiosity your curriculum.

💪 STEP UP

• Make failure part of the plan.

• Stop waiting to feel ready.

• Ask for help—it’s strategy, not surrender.

There are over a million words in the English language.
But when we talk about success, the same few rise to the top:

Disciplined. Gritty. Curious. Focused.
Notice what’s missing?

Secrets. Hacks. Shortcuts.
You can’t microwave mastery.

So if you’re wandering, experimenting, questioning?
You’re not behind.
You’re just building Changeability.

—

💬 Who’s someone you know who’s embracing the squiggly path and making it work? Tag them. Tell them. They may not know it yet.