When You Don't Know What You Don't Know: Embracing The Big Gulp

Author

Charlene Li
March 10, 2025

When you look back over your life so far, which big gulp moments most stand out to you?

Those moments—the ones where you realize you don't know something important, or you're thrust into a situation you're not prepared for—can feel terrifying in the moment. But leaned into (instead of steered clear of), they can become meaningful inflection points in our lives.

When I think about it this way, I go back to Amsterdam—in my mind, at least.

When I was 23, I was working at a consulting firm there. I shared an office with one of my first bosses, Ian Smith—a kind, thoughtful, and direct leader who wasn't afraid to do things differently. From that desk, I absorbed so much just by watching how he worked with clients and built relationships with the team.

I'll never forget the day he had to step out during a client presentation. The client was waiting. So was I. Finally, I just stood up and started presenting. 

(I had built the deck, after all).

When Ian returned, he simply said, "You're running the case now." When I protested that I wasn't ready, his response was straightforward: "There's no one else. You've got this."

I was WAY over the tips of my skis. As a young Asian-American in Amsterdam, nobody quite knew what to make of me. I'd return home each day thinking, "What just happened in that meeting? What do I do next?"

Then came the moment that crystallized everything. A few days later, a client said, "I think we should do a free cash flow analysis of this." I nodded and said, "Great."

I left the meeting thinking, "What's a free cash flow analysis?"

The next day found me frantically putting it together. I showed my work to colleagues who said, "No, that's completely wrong." So I learned how to do it on the spot. 

That moment of being completely out of my depth made me realize I needed a stronger foundation. I wanted to be able to walk into any situation and have a framework to build something on. So I applied to Harvard Business School, got in, packed every piece of warm clothing I had, and went.

I needed that MBA—the discipline of formulating my thoughts on the fly, raising my hand, and creating a cogent argument gave me confidence. It wasn't easy—I had to take on debt, and it took me five years to pay it off. But it was an investment I wanted to make in myself, and I'm so glad I did.

Business school certainly isn’t for everyone! If anything, there are so many more resources available now—freely—than there were back in the 90s. YouTube tutorials, online courses, and professional communities can provide targeted knowledge without the same financial burden. But my point is that when faced with that big gulp moment, you need to choose your path forward, rather than passively retreating from the challenge.

Tracing all of this back to those moments in Amsterdam reminds me that those "I don't know" experiences are instructive. They're signposts pointing toward new paths of growth. But how you respond to them makes all the difference.

You can meet these moments with fear and anxiety—or with curiosity and excitement. The problem exists either way. How you respond to it is what you have control over.

Where in your life or career are you facing a big gulp moment? And how will you choose to respond?

- Charlene

What I Can’t Stop Talking About: 

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My Latest: 

  • Catch up on my webinars! You can still review the slides and recordings of my two new webinars. In “Unlocking The Power of Generative AI,” I explain how to set up a generative AI “playground,” three ways to elevate your leadership with step-by-step instructions, and the broad outlines of creating a strategy. In “Developing a Winning Generative AI Strategy for Competitive Advantage,” I walk through the steps needed to create a cohesive AI strategy. 

  • "I don't want to mess with it." A CEO's candid confession about AI adoption resonates with many leaders hesitant to disrupt their well-oiled operations. But you don't have to choose between operational excellence and innovation. In Leading Disruption, I’m sharing four key dimensions for seamlessly integrating AI, plus real-world success stories from organizations getting it right. Here’s to NOT choosing between operational excellence and innovation. 

  • Separating AI agent reality from hype. AI agents are dominating headlines—but what's substance versus noise? Join me Tuesday, March 11 at 9am PT/12pm ET for fresh insights from my upcoming book with Katia Walsh. I’ll explore how leadership changes when your workforce includes both humans AND digital workers. Whether you're AI-curious or AI-anxious, this is one livestream you won't want to miss.

My Upcoming Appearances:

If you want me to speak at an upcoming event or conduct a workshop with your executive team, please drop me a note at [email protected]. 

If this information was helpful, there’s plenty more!

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Thank you for subscribing to The Big Gulp Newsletter, which goes out to thousands of disruptors every other week to help you on your disruption journey—plus a curated recommendation list of the things I can’t stop talking about. 

Charlene Li

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