The Power of Unexpected Connections & The One Who Changed My Trajectory

I recently listened to a Mel Robbins podcast about the power of unexpected connections—how chance encounters can change the trajectory of your life. 

She started off with this:

“It’s the idea that there’s a stranger out there that you’re meant to meet who could become one of your closest friends. When you stop and truly think about it, everyone that you love now in your life was once a stranger.”

Katia Walsh is the definition of this type of unexpected connection for me.

She and I met back in 1999 when we were both research analysts at Forrester. 

Something clicked. 

We became fast friends. Both young moms, we raised our children together. And, well before social media made it easy to do so, we stayed in touch as we made career moves that took us to opposite ends of the country and overseas. We cheered each other through every personal and professional milestone.

Nearly a year ago, we reconnected in Boston. I was at Harvard Business School for a reunion, and she was its newly minted Chief Digital Officer, fresh off a successful run as one of the world’s first Chief AI Officers. (Not too shabby, huh?)

While we were catching up, I mentioned that I was just beginning to work on my next book, all about generative AI.

Her eyes widened.

Without hesitation, she asked: “Can I write it with you?”

The book isn’t even out yet, and I know I struck gold with Katia. 

For one thing, we trust each other innately.

For another, neither Katia nor I have strong egos that get in the way of our work. We have the utmost respect for one another, allowing us to deliver—and hear!—feedback without it being clouded in defensiveness or resistance. 

And, frankly, she’s the ultimate fact-checker. 

Katia has been on the ground, in the generative trenches for the past two decades.

I’ve never deployed an AI model, but she has multiple times. So, I’ll write a chapter, and she’ll verify what works and what doesn’t:

  • “That’s not important. Instead, put more emphasis on this.”

  • “Don’t promise that. It’s too risky. Take that out.”

  • “You may think that’s really cool, but trust me: It’s not.”

She’s the perfect reality check. 

And we are the perfect book writing combo—one I never could have predicted.

That’s why this concept of unexpected connections continues to pop into my mind: I truly struck gold back in 1999.

Your turn: Who do you count as your most monumental unexpected connection? Better yet, could you co-author a book or start a company with them? 

— Charlene

What I Can’t Stop Talking About: 

  • How to stick to habits. I hate calorie tracking. I never finish my to-do list. I’m terrible at going through emails. The logical conclusion I’ve told myself: I must be really bad at developing and sticking to habits. Then, David Allen gave me advice that was a true Big Gulp moment for me. Here’s what it was.

  • Confucius’s guide to gaining wisdom. He says we gain it in three ways: reflection, imitation, and experience. My two cents? We often mistake wisdom for age

  • Technology: a creator or destroyer of jobs? A study found that 60 percent of today’s workers are employed in occupations that didn’t exist in 1940. A sign that tech—and AI—creates more jobs than it erases? Here’s my take.

  • Knowing, doing, or leading. Where do you stand as a leader on the “Knowing-Doing-Leading Gap " when it comes to AI adoption? I’d love for you to take my poll—but please be honest!

My Latest: 

  • Catch up on my latest 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. 

  • My upcoming book. If you’re reading this, you are the target audience for my new book, Winning with Generative AI. Sign up for updates and early access and join my exclusive LinkedIn launch community.

  • Communication is the key. Effective strategy begins and ends with good communication. If you can’t communicate your generative AI plans—internally or externally—with clarity, you can’t expect those plans to get very far. In Leading Disruption, I share the importance of communication—and how to get it right! 

  • How AI can (and should!) inform OKRs. Objectives and key results are vital benchmarks for nearly all organizations, but what are they at their core? And how should we consider adjusting them in the age of AI? I’ll be sitting down with Jeff Gothelf and Josh Seiden, authors of “Who Does What By How Much?: A Practical Guide to Customer-Centric OKRs” in my next livestream. Join me on Tuesday, July 10 at 9 a.m. PT / 12 p.m. ET on LinkedIn and Facebook Live for more! 

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]

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. 

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

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Charlene Li

If you found this note helpful, please forward and share it with someone who needs the inspiration today. If you were forwarded this, please consider subscribing.