Some Life (And Leadership) Lessons

Author

Charlene Li
December 09, 2024

Confucius identified three ways we gain wisdom: 

"First, by reflection, which is noblest. 

Second, by imitation, which is easiest. 

Third, by experience, which is the bitterest."

He's right about all of them, of course, but that third method rings particularly true across today's organizations. We often mistake experience for age, assuming wisdom comes automatically with time. But you can be old and not be wise. You can accumulate thousands of experiences and not have wisdom.

The opposite is also true: You can be young and, through a few intense experiences, become incredibly wise for your age. It's all about integrating those experiences and their learnings into what you do next. That's the bitterest part, but it's what leads to wisdom.

As I reflect on my own journey, I'm particularly grateful for the wisdom I've gathered—often from unexpected places and, sometimes, through those "bitter" experiences Confucius mentioned. 

What's fascinating is how often the most valuable lessons came from learning when to challenge conventional wisdom—and find my own path. 

Here are some of the life and leadership lessons I’m thinking about as we wrap up 2024. 

Experience is what you get when you don't get what you want. 

I was 27 when I learned this piece of wisdom at the San Jose Mercury News. One of the biggest reasons I joined was because of Kathy Yates. As president of the paper, she was something rare—a woman with a Stanford MBA leading a major institution.

The first time she shared this saying with me, I had to take a beat. Then it clicked: This wasn't about failure or shame. It was about reframing every "no" and misstep as stepping stones to wisdom. This mindset shift is crucial for leaders, as it transforms setbacks from failures into opportunities for growth.

Consider context when taking advice—even from trusted mentors. 

Earlier in my career, I sought counsel from friends serving on large corporate boards. Their advice? "Don't do boards—they're a nightmare. So many conflicts. You'll get stuck and accomplish nothing."

It was probably the worst advice I could have gotten. As a woman of color and CEO in the hot space of digital transformation, getting that first board seat would have opened crucial doors, many of which—for women and people of color—are still closed (despite what people say about diversity being in demand). I ended up landing a board seat a few years later, and my experience ran entirely counter to that early advice. I loved every minute I served on that board.

This experience taught me a crucial leadership lesson: While mentorship is invaluable, effective leaders must evaluate advice through the lens of their unique context and challenges.

Don't work the third shift. 

I learned this one before I even got married. If the first shift is your job, and the second shift is your family, then the third shift is the guilt that comes from feeling like you didn't do enough in the other two shifts.

I remember tucking my son into bed one night and telling him I wouldn't see him in the morning because I had a red-eye flight. He looked at me and asked, "Mommy, do you love your clients more than you love me?"

"I love you and your sister more than anything," I told him. "And? I also love my work. I wouldn't be the mom and person I am without my work."

There's no such thing as perfect balance—only a series of less-than-optimal compromises that we need to own and be comfortable with. I learned early on that I would need to sacrifice some time with family, friends, and myself for my work because I'm driven by and passionate about it. And it's all okay, as long as my choices live in harmony with each other.

Embrace vulnerability and your authentic story. 

If you’ve ever booked me for a speaking engagement, you’ll know that when I go on stage, I do so filled with joy and excitement. But there was a time when I used to dread speaking on stage. The way I'd been instructed to speak—with authority and self-importance—made me feel small because it wasn’t me.

It was only when a coach encouraged me to get personal and speak with my voice and my experience that it all started to click. One of the things I did was to talk about what it's like being the only "only" in the room—the only woman, the only person of color—andI started to feel even more comfortable. I remember the first time I shared my story of growing up Asian-American in Detroit. It was incredibly hard. I felt vulnerable. But that vulnerability broke something open for me, and that something now grooves along with me, every time I step on stage.

Through reflection, imitation, and yes, some bitter experiences, these lessons have shaped not only how I lead, but how I live. They remind me that wisdom isn't just about what happens to us—it's about how we integrate those experiences into who we become, and how we find the courage to chart our own course.

What piece of wisdom are you grateful for gathering along your path? Hit reply and let me know!

-Charlene

What I Can’t Stop Talking About: 

  • The Architecture of AI Trust. Building trust in AI requires the same careful scaffolding as teaching a new concept. Here's how our AI Pyramid of Trust helps organizations move from basic safety to true transformation. No crossed fingers required. 🤞

  • What's the difference between anxiety and excitement? A friend once told me it comes down to confidence. After falling off a stage (yes, literally), I learned that it's not about avoiding mishaps—it's about knowing you can handle whatever comes your way. Bookmark this—and go get excited about your next big thing. 

  • Why I run to keep up with AI. Spoiler alert: I'll never catch up. 🏃🏻‍♀️🏃🏻‍♀️🏃🏻‍♀️For me, the joy is in the journey of discovery and learning, even when it's uncomfortable. Here’s why growth requires embracing the chase. 

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. It’s a great primer for executives looking for a quick intro to generative AI. In “Developing a Winning Generative AI Strategy for Competitive Advantage,” I walk through the steps needed to create a cohesive AI strategy. 

  • Is your AI strategy getting lost in translation? If no one knows about the value you’re creating, it may as well not exist. In Leading Disruption, I reveal five critical steps to bridge the AI communication gap and build true organizational alignment. Head over to my newsletter if you’re ready to amplify your AI impact.

  • Are AI process changes keeping you up at night? Contrary to popular belief, updating your processes for AI doesn't have to be chaotic. Join me on Tuesday, December 10 at 9am PT/12pm ET for my next livestream, where I’ll share a systematic (and surprisingly smooth) approach to evolving your processes for the AI era. 

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!

📌 Sign up for updates and early access to my upcoming book, co-authored by Katia Walsh, which is all about creating a winning generative AI strategy.

📌 Want more? Check out my weekly publication, Leading Disruption, on LinkedIn.

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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