Every year, I try to find something new that I have no idea how to do, and then I try to get good at it. Not expert-level good—I'm not aiming for a YouTube channel or professional status. Just competent. Good enough to understand it, to appreciate it, to have actually done the thing rather than just read about it.
What I've discovered is that the part I enjoy most isn't the mastery. It's the first part—the wildly awkward beginning. The first time you do something and have absolutely no idea what you're supposed to do, and there are people around who clearly know what they're doing. You have that profoundly uncomfortable feeling of being the only person in the room who's lost. I genuinely enjoy that feeling, and I'd encourage other people to enjoy it too.
The Questions You're Not Supposed to Ask
I ask my CFO questions sometimes, and I always preface them the same way: "Hey, Liz, I'm going to ask you a question. Don't tell anybody I'm asking you this because it's probably something I should know as a CEO." She laughs and says she won't. Then I'll ask about some acronym someone used or some calculation we're required to use, and I'll admit I simply don't know what it is.
I think that feeling of not knowing—the thing people actively avoid—is actually something you should seek out. My sons and I learned to hunt this year. Everything about it was uncomfortable. As we learned more, there was this unexpected moment of just sitting together quietly, possibly not seeing anything for hours. The experience turned out to be completely different than anything I'd expected at the beginning.
My youngest son is learning guitar, and teaching him different songs and techniques has been wonderful. Not because I'm some virtuoso, but because we're navigating that space between not knowing and beginning to understanding together. People who sit around wanting to be comfortable, wanting to be great at one or two things, are missing out on this experience of discomfort and discovery.
Grabbing Things With Your Hands
When we started our journey with AI, I didn't know much about it. I'd read some books, listened to talks about blockchain, and tried to get educated. But until you grab something with your hands and start actually doing it, you have no idea how it really works. And that first experience of genuine engagement—not reading about it, not theorizing about it, but doing it—is such a compelling moment.
My son said to me the other day, "Dad, I want to build a trailer to put on the back of the go-kart." I said, "Yeah, sounds great. Let's build a trailer." It's genuinely fun. You go to the hardware store trying to picture how an axle might work, examining different components, and the first time you build it, it goes so poorly. It falls apart. It's bouncing down the road, disintegrating into pieces.
And if you're not laughing about that, you're missing the point entirely. It's not failure. You've just learned at least one way that it doesn't work. Thomas Edison reportedly said he knew 10,000 ways not to make a light bulb. That's the mindset—each attempt that doesn't work is information, not defeat.
The Companies That Support Discomfort
Here's something important: if you work at a company that doesn't support you in that uncomfortable moment, find a new company. You don't know how many laps around the track you're going to get in life. You don't know how long those laps will last. Fill them with incredible things. Fill them with experiences, challenges, and struggles. Fill them so that it's not boring.
C.S. Lewis once wrote that, "Indeed, the safest road to Hell is the gradual one—the gentle slope, soft underfoot, without sudden turnings, without milestones, without signposts." It's boring. You don't want that. That's not something you're going to look back on and think, "I lived this wonderfully comfortable, predictable life." The highs and the lows are what make it worth it.
The Speed of Learning
One thing that surprises people: that super awkward Bambi-on-ice moment when you don't quite know what you're doing? It ends remarkably fast. You figure it out quickly, and then it becomes old hat, and then you need to find something new to feel awkward about again.
This past year, we learned several things as a company. We sought out experts and asked them questions that revealed our ignorance, and here's what I've found: experts love answering questions. The people who are genuinely good at things—I've yet to meet many who are arrogant about it and unwilling to help. I find that deeply reassuring. Most people, when asked, will help. And I think that's a valuable lesson for all of us in building community.
Fill Your Laps With Struggle
This isn't about my favorite music or what I'm currently reading. It's about something more fundamental: look for opportunities to feel awkward and uncomfortable. Innovation happens when you get profoundly uncomfortable. I find it genuinely enjoyable—learning new things and seeking out that discomfort.
Obviously, you need some people in a company who want to stabilize systems, and you need others who want to innovate constantly. You need that tension. But I think you move significantly faster when you get excited about discomfort rather than avoiding it.
This year, I'd encourage everyone: if you've never built something, go build it. If you've never learned something completely outside your expertise, go learn it. Find that moment where you're the least knowledgeable person in the room and lean into it. That's not a bug in your professional development—it's the entire point.