The $36 Decision That Changed My Life Forever
Sometimes the biggest breakthroughs happen when you have the least to lose.
I've made million-dollar decisions in boardrooms at Google, Oracle, and Microsoft. I've coached Fortune 100 executives through career-defining moments. I've spoken to thousands of leaders about courage and transformation.
But none of those decisions were as terrifying, or as life-changing, as the one I made with exactly $36 in my bank account.
The Moment Everything Shifted
Picture this: You're sitting in a parking lot, wearing a borrowed suit with the tags still on, about to walk into the most important interview of your life. Your bank account has two digits. You have no backup plan. And you're about to either change everything or lose what little you have left.
That was me, early in my career, sitting outside a Microsoft office in Illinois.
What happened in the next 90 minutes didn't just get me a job, it taught me the most important lesson I know about taking action when you're absolutely terrified.
The Question That Changes Everything
Here's what I learned that day (and what I now teach executives around the world): When you're stuck asking "How?" start asking "Who?"
Most people get paralyzed by the "how" of making big changes. How do I get that promotion? How do I make this career transition? How do I build the confidence to speak up in meetings?
But there's a different question that cuts through all the noise and opens doors you didn't even know existed.
Why Your Comfort Zone is Lying to You
The truth is, we're all sitting in our own version of that parking lot right now. Maybe you're not interviewing at Microsoft, but you're facing something that feels impossible:
The conversation you need to have with your boss
The business idea you've been sitting on for months
The leadership role that feels "too big" for you
The change that could transform your career (if you had the guts to make it)
You're probably telling yourself you need more experience, more money, more connections, or more time to prepare.
But what if the only thing you actually need is the courage to take the first step?
The Two-Word Strategy That Opened Every Door
In my newsletter this week, I'm sharing the exact strategy I used to go from $36 and a borrowed suit to landing my dream job at Microsoft—and how this same approach has helped hundreds of leaders I've coached breakthrough their biggest barriers.
It's not about networking (though that matters). It's not about luck (though timing helps).
It's about understanding that courage isn't the absence of fear, it's action despite fear.
What's Your $36 Moment?
Right now, there's something you want that feels out of reach. A promotion, a career change, a bold business move, or maybe just the confidence to speak up and be heard.
You're probably focused on all the reasons why it won't work, why you're not ready, why the timing isn't right.
But what if I told you that your biggest limitation might actually be your greatest opportunity?
Ready to Stop Waiting?
In this week's newsletter (#006), I break down:
The exact question that changed everything for me (hint: it's not "How?")
Why asking for help is actually the most courageous thing you can do
The mindset shift that turns fear into fuel for breakthrough results
My step-by-step process for taking action when you feel completely unprepared
Plus, I'll share what happened when I got that life-changing phone call, and why my response almost cost me everything.
Subscribe to The Activated Leader to get the full story and the framework that's helped thousands of professionals transform fear into their competitive advantage.
Because sometimes the scariest decision is the one that changes everything.
