You know you need a big vision. You’ve heard it a thousand times.
And you know you need to do the work. That’s not news either.
But sometimes the vision gets so big, so personal, so loaded with consequence, that you can’t look at it directly anymore.
You freeze.
Not dramatically. Not obviously. You just... get busy. You tinker around the edges. You call it progress. You avoid the thing you actually want because wanting it that much feels dangerous.
I’ve learned to hold big visions without freezing—it took years of practice. But this week, three conversations gave me clearer language for how it actually works. Language I wish I’d had sooner.
A vision that scares you is doing its job
My goal is to terrify [my technical colleagues] at least once a month. That means I’ve come to them with some proposal or an idea that is out there, but not so out there that we can just write it off right away. They have to be like, “Oh my gosh, what is he talking about? Yes, that’s probably possible. That sounds super hard. And it would be amazing.” So, my own desire to terrify people around me is actually a forcing function that makes me sit down and think about: Where are we going? What do we want to do? And what’s possible?
- Kareem Choudhry, “chief innovation instigator” at Xbox
Remember that quote from Kareem in the book? It’s one of our favorites. This week, Michael Gervais, high-performance psychologist and host of Finding Mastery, talked about vision in the same way: if it doesn’t scare you a little, it’s probably not worth chasing.
You have to know where you’re going. And that destination has to be compelling enough that when things get hard—and they will—you keep moving anyway.
The flip side of that, though, is that a truly big vision can be overwhelming. The thing you’re aiming for can be so large that staring at it every day doesn’t motivate you. It paralyzes you.
That’s not weakness. That’s human.
So what do you do?
Stop staring at the vision—instrument it
This is where Rita McGrath’s work on early warning signals clicked for me in a completely new way.
Rita’s method allows you to stop trying to hold it in your head all the time.
How? By translating the vision into signals you can track. Then building systems—processes, data, teams—that monitor those signals for you. Signals that tell you when you’re drifting and when the ground is shifting beneath you.
Then let go.
Externalizing the monitoring gives you permission to put your head down and work without the constant anxiety of “am I drifting?” You don’t need to white-knuckle the future. You need to know when you’re off course and trust that your signals will tell you.
Look up occasionally. Check alignment. Adjust. Then get back to work.
No drama. No daily existential crisis. No freezing.
I’ve thought about vision and execution for years, but I’d never seen this piece so clearly before. The early warning signals aren’t just strategic tools—they’re psychological relief. They let you hold a vision that’s big enough to scare you without being crushed by it.
Innovation is practice, not perfection
Dean Carignan brought this home during our Innovating Out Loud session this week.
The conversation was framed around AI, but the insight cuts across every domain. From The Insider’s Guide to Innovation at Microsoft, one pattern shows up again and again: the teams that succeed aren’t the ones obsessing over the future every day. They’re the ones building repeatable practices that move them toward it.
Dean’s point was grounded and practical: pick a problem that’s painful enough that solving it is worth the learning.
That’s the behavioral key. If the problem doesn’t hurt, the friction of change won’t feel justified. If the problem does hurt, the learning suddenly becomes worth it. That’s when new practices stick—not because someone mandated them, but because the pain made them necessary.
Especially with AI, resistance shows up fast: fear of getting it wrong, anxiety about designing yourself out, frustration with ambiguity. The antidote isn’t more inspiration. It’s finding a problem painful enough to make the discomfort worthwhile.
Bringing it all together
You don’t need to stare down your biggest ambition every morning.
You need three things:
A vision big enough to scare you.
Signals that tell you when you’re drifting.
Practices that let you focus on execution instead of anxiety.
That’s it.
What to do with this
If you’re leading through uncertainty—AI, transformation, reinvention—here’s where I’d start. As usual, with questions.
Is your vision exciting enough to pull you forward and valuable enough to sustain you?
Do you have early warning signals that tell you when you’re drifting—or the environment has changed—so you don’t have to hold the whole thing in your head?
Are you building practices that let you and your team focus on doing the work instead of fearing the future?
If not, don’t overthink it.
Say it ugly. Do the work. Let the systems help you carry the weight.
Resources
🎥 Michael Gervais webcast — Vision that’s big enough to scare you
🧭 Rita McGrath — Early warning signals & strategic inflection points
🎥 Innovating Out Loud with Dean Carignan — Navigating AI with practice, not panic
📘 The Insider’s Guide to Innovation at Microsoft — Patterns that make innovation repeatable, scalable, and sustainable.
Question for you:
What’s the vision you’ve been avoiding looking at—and what signal would tell you if you’re still on course?
Read by AI-JoAnn
