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My Blog

Maps & Milestones

Welcome to Maps and Milestones, where we navigate the twists and turns of career growth, leadership, and personal transformation. Join me as we explore actionable insights, inspiring stories, and bold steps to help you map out your next big move.

Personal Growth, Leadership Lessons Lilah Jones Personal Growth, Leadership Lessons Lilah Jones

From "Too Ambitious" to Google's Public Stage: The Barrel Strategy That Changed Everything

I was told I was “too ambitious” and rated “Needs Improvement.” Six months later, I was speaking on Google’s public stage. My Barrel Strategy turned rejection into recognition and changed everything. Here’s how I built visibility, found advocates, and led with courage when doors closed.

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Personal Growth, Leadership Lessons Lilah Jones Personal Growth, Leadership Lessons Lilah Jones

From Google to Freedom: Why I Documented My 9-Year Exit

After nine years at Google, I did something few leaders dare to do: I filmed my resignation. From Google to Freedom isn’t about drama or a viral moment. It’s about documenting the calm that comes when you’ve built your exit with intention. In this story, I share what my resignation footage really captured: the strategy behind my transition, the lessons from one difficult meeting that changed everything, and the freedom that comes from long-term, courageous planning. I call it strategic activation, the difference between running from something and running toward something. Through this journey, I learned how to build authority while employed, create options before I needed them, and lead with purpose. If you’ve ever felt ready for more but unsure where to start, my story will show you how to build your bridge to freedom, one intentional step at a time.

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Career Advancement Strategy: Why Smart Executives Never Put All Their Leadership Eggs in One Basket

Rejection can feel like the end of the road, but for smart executives it is often the turning point. In this post, I share the painful promotion I did not get (and why it was the best thing that ever happened to my career). The truth is, most high-performers make the same mistake: they put all their leadership eggs in one basket. The most successful leaders do not wait for validation from a single decision-maker. They build diversified career portfolios that make them rejection proof. Learn how to shift from hoping to be chosen to creating your own strategic choices.

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The Identity Trap That's Sabotaging Your Leadership Potential

Success can be deceiving. You’ve earned the title, built the reputation, and mastered the role; yet somehow, it feels like you’re running in place. The truth is, many leaders don’t get stuck because of a lack of skill or ambition. They get stuck because they’re clinging to an outdated version of themselves.

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The Hidden Reason High-Performing Teams Make Faster Decisions (It's Not What You Think)

High-performing teams don’t move faster because they have more confidence—they move faster because they’ve learned to trust something deeper. After working with hundreds of leadership teams, I’ve seen that the real differentiator between teams stuck in analysis paralysis and those making bold, timely moves isn’t data, certainty, or buy-in. It comes down to asking a single question that unlocks momentum almost instantly—a question I reveal (along with the full framework) in this week’s issue of The Activated Leader newsletter.

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The Meeting That Almost Ended My Career

I walked into what I thought was a routine team meeting at Oracle—twenty minutes later, I was questioning everything I thought I knew about leadership. Picture this: you’re presenting your carefully planned Q3 strategy to your global sales team, and your most experienced rep interrupts: “Lilah, can I be honest? This isn’t working.” The room goes silent. In that moment, you have two choices: defend your position or do something that feels completely counterintuitive. I closed my laptop, and what happened in the next hour taught me more about leadership than any MBA course ever could.

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The $36 Decision That Changed My Life Forever

I was sitting in a parking lot in a borrowed suit with just $36 in my bank account, about to walk into the most important interview of my life. No degree. No connections. No backup plan.
What happened next didn’t just land me a job at Microsoft, it rewired the way I make decisions, coach leaders, and take action when the stakes are high.

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