The Universal Art of Developing Skills

Step inside my home, and you may mistake it for an art gallery. I fill my walls with framed prints, canvases, and works of art that I’ve collected through my travels. But here’s the thing: I never set out to be an art “collector.” 

Wherever I go, I make a point to visit a gallery or market with local art to pick up a souvenir. From Morocco to Cuba to Amsterdam, I return home with a new piece to hang up.

These days, my favorite masterpieces, however, come from an artist friend of mine. I love abstract art with loads of color and plenty of movement, and if you’ve watched any of my LinkedIn livestreams or had a virtual advising session with me, you’ve likely seen one of his works directly behind me: 

Beautiful, right? He made this one using a blue-streaked rag and painted the dots using a hole-punched Zip-loc bag!

As you might be able to tell, it’s probably not surprising for a disruption leader who thrives on transformation to prefer this art style. Every time I look at these paintings, I see something new. I discover something different. 

But like all of my passions, how I’ve come to appreciate art has taken time, effort, and a fair share of self-confidence. The same can be said for how I’ve grown into my role as a disruptive leader. The parallels between art collecting and disruptive leadership are surprisingly similar. Here’s what I’ve learned about both along the way:

You have to get out of your comfort zone. 

🖼️ When my kids were young, I’d take them into galleries and encourage them to look around. It was worthwhile, even if they could only handle it for 10 minutes. We’d walk around, and I’d ask questions—to them but also myself. “What do you like?” “Why do you like it?” 

📈To push yourself to your next level of disruption, you also have to force yourself to get comfortable with the unfamiliar—and the best way to do that is to immerse yourself. If you want to take more risks as a leader, you’ll never get there unless you spend time in risky scenarios, asking yourself what you like and why.

You can’t let fear stop you. 

🖼️ It can be intimidating to buy art, and it can feel strange to consider yourself a collector. I’ve been collecting art my whole life, and it doesn’t matter that I didn’t get it right every time. I bought a lot of art that I don’t like. But those duds served a purpose in helping me to hone my evolving tastes. 

📈You will never get disruption right the first time or even the 20th. If you wish you had a better AI sensibility, you can’t wait for every scenario to be ideal before you dig in.

You have to practice the skill.

🖼️ People often say, “Oh, you must just have an eye for art.” Not the case for me. I’ve had to work at it. What is now a gut instinct—to determine what art I consider good versus bad—doesn’t happen overnight. Like any other skill, it requires practice and takes time. 

📈Sure, some natural-born leaders might be out there, but don’t let most of them fool you. Some of the best leaders—and bravest disruptors—have gotten to their level through a mix of dedicated, long-term commitment and effort. As much as there’s artful leadership, it’s a skill. And skills take practice and persistence.

When I traveled to Morocco, I visited several galleries and must have flipped through thousands of paintings. When I saw this piece, it took my breath away, and I couldn’t stop thinking about it: 

Your turn: If you too enjoy art, how have you developed your sensibilities around it? And I’d love it if you’d share your favorite piece with me and why it speaks to you. 

— Charlene

What I Can’t Stop Talking About: 

  • The importance of sleep. I attended a wellness conference last week, and all the speakers agreed on sleep’s impact on health and performance. “The Sleep Doctor” Michael Breus emphasized understanding your chronotype—the natural circadian rhythm you inherit. You can’t change it, but if you know how it works, you can plan your day around your peaks. To figure out your chronotype, go to

  • The joy of being a “happy B.” I once worked for a company that implemented a grading system for its employees, but I wasn’t about to play this game that fed on the insecurity of overachievers. Sometimes straight As just aren’t worth it, and here’s how I was able to succeed on a B average.

  • My 14-minute-mile disruption. I don’t love running. I barely even like it! It’s a big gulp moment for me every time I put on my running shoes in the morning, but I’m determined to sustainably get in the best shape of my life with little gulps. What gulps are you taking to disrupt yourself?

  • The five most obnoxious things male colleagues have said to me. I’m sure every woman working today has their list, but my list of phrases likely has some crossover. If you are an unaware (or, worse, intentional) user of one of these phrases, consider this your reminder to “know better, do better.”

  • Your most-requested speaking topics. I’ve delivered keynote speeches to rooms of 10,000 leaders and run intimate workshops for less than a handful of execs. Although my empathy and optimism are constant, what I’m asked to discuss is ever-changing. I asked my followers what topics most entice them, and the results surprised me!

My Latest: 

  • Join an upcoming webinar! I’ll be hosting two webinars over the next few weeks. The first, on Wed. April 24 at 10 a.m. PST / 1 p.m. EST, is “Unlocking the Power of Generative AI: A Leader's Guide to Getting Started.” It provides a hands-on tutorial on how leaders can use generative AI. The second, on Wed. May 8, “Developing a Winning Generative AI Strategy for Competitive Advantage,” focuses on the steps needed to create a cohesive strategy. I hope you can attend one or both of them!

  • The final step in your AI prep. The last thing you must do to prepare your organization for generative AI feels like show-and-tell. You need to share learnings—on Slack, for instance—and treat prompts as the valuable assets they are. Watch my latest livestream or read my LinkedIn newsletter to find out how.

  • A playground for AI leaders. Do you worry it’s too much work to build a successful AI strategy? Then it’s time you play. You’ll need a secure playground—with some guardrails, of course—so you can explore, and in Leading Disruption, I walk you through how to set one up. 

  • AI team, assemble! If only disruptive leaders had access to the AI version of Avengers, right? Short of that, I’ve learned how to construct a small-yet-impactful team to get the job done. Tune in to my livestream tomorrow, April 16, at 9 a.m. PT / 12 p.m. ET on LinkedIn and Facebook Live if you are eager to form your team of AI superheroes.

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.

Charlene Li

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