Hi. I’m Jill.
I grew up around people who were told, regularly and by experts, that what they were building wouldn’t fly.
Some of it didn’t. Voyager did: around the world, nonstop, on one load of fuel. My father flew it. My uncle designed it.
So I learned two things early. Experts are usually right. And “usually” is doing a lot of work in that sentence.
I’ve founded three companies: Looking Skyward, a nonprofit; Path 2 Flight, a marketplace platform that used technology to remove the three biggest barriers to flight; and Hello Jill Hoffman, the one you’re reading right now. I’ve written three books, stood on stages, failed at things in public, and changed direction more than once. Freakonomics found the failing interesting enough for a three-part series.
I also invest in frontier technology. So I’m not only watching those rooms. I’m placing bets in them, with real money and real consequences when I’m wrong.
Along the way, I noticed something.
Every room has an opinion.
About Jill Hoffman
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A meeting, a group chat, a comment section, a dinner table, an entire industry. The room forms its view, and then it goes to work on yours.
I’m not against the room. Other people know things I don’t. Consensus is often right. Changing your mind is usually a sign you’re thinking.
What interests me is the moment just before you agree. The small tap on the shoulder that says wait, something’s off. Most of us feel it. Most of us override it, politely, because the room sounds so sure.
Following the crowd and automatically resisting it have something in common: either way, the crowd is still choosing your direction.
So the work is simpler, and harder. What do I actually think? And, more to the point, why do I think it?
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Every other week I write In Her Orbit: one room I’m actually in, written down while I’m still in it.
I speak to leadership teams about the same thing, where the stakes are higher and the catering is better.
The goal isn’t to become immune to influence. It’s to know when you’re being influenced, and still hear yourself think.
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The room isn’t the enemy. Speed is.
Most bad decisions aren’t made in ignorance. They’re made by people who agreed before they finished thinking.
The objective isn’t certainty. It’s judgment.
Listen to the room. Question the room. Question yourself. Then decide.
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One essay every other week, free. No hot takes, no productivity hacks, no daily anything.
Jill is the author of three books, including How to Build an Airplane in Your Living Room: A Guide to Living an Unconventional Life. Her fourth is forthcoming from Greenleaf Book Group in 2027. She has spoken at conferences, corporate events, and leadership gatherings across the country. She was featured on Freakonomics in a three-part series on failure, grit, and reinvention. She splits her time between Washington, D.C. and Wyoming with her husband. She has two lovely adult daughters, and yes, she sometimes golfs.
“I grew up thinking everyone had an airplane in the garage. Turns out, we were the weird ones. I’ve been interested in people who think differently ever since.”
— Jill Hoffman