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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.

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 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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