ISSUE 88
17 JUNE 2026 | READ ONLINE
Hi Reader,
Earlier this week, I was in Anaheim, CA. And while I was there, I sat down for a bowl of poke across from someone who reminded me of something I’ve forgotten.
She is a founder. A Yale graduate. Probably half my age. She ordered her bowl like she had nowhere else to be and nothing to prove, and then she started talking about the company she is building.
I had come straight from running the first session of a four-part career masterclass. Still in conference mode. Lanyard buried somewhere in my bag, six open loops running in the back of my head, that low hum of being “on” that you carry through a multi-day event.
And she just went. About the thing she is making. About the people she is pulling toward it. About the doors she is knocking on without apology, the asks she is making, the help she is gathering.
At one point, I put my fork down. Not for anything dramatic. Just because I realized I was watching something I used to have more of.
Let me back up.
I call myself an entrepreneur. I am one. I have built two companies, written a book, and put my name on the line more times than I can count. But somewhere between the first leap and the hundredth, I had started to protect things. The reputation. The brand. The careful version of the message. I had picked up caution the way you pick up frequent flyer status, slowly, without noticing, until it was just how I traveled.
She had none of that yet. Just nerve, the real kind.
What strikes me about that is how easily we lose it without ever deciding to. We do not wake up one morning and choose to play smaller. We just accumulate things worth protecting, and protection has a way of hardening into hesitation.
Here is what makes her so rare, and I can put a number on it.
The Global Entrepreneurship Monitor’s 2024/2025 report found that 49% of people worldwide would not start a business for fear it might fail, up from 44% in 2019. Almost half of us see the opportunity and walk away from it. And there’s more. A 2025 study in Business Strategy and the Environment, drawing on Global Entrepreneurship Monitor data, found women are roughly 30% more likely than men to report that fear in the first place.
So when a young woman talks about her company like the worst case is just a no, she is not simply being young. She is doing the thing that almost half the world, and most of the women in it, talk themselves out of.
Here is the part I want you to think about.
What she has is not a trait you are either born with or stuck without. In one of the most-shared Harvard Business Review pieces of the past year, “Now Is the Time for Courage,” Harvard Business School professor Ranjay Gulati argues that courage can be learned, just like any other skill. He defines it plainly: a willingness to take bold, risky action in service of a purpose you believe is worthy, usually in the face of a real and abiding fear.
Now, I know I talk about this in my own book, Clarity in Chaos: Lead with Purpose in Disruptive Times.
But one of the five things that Ranjay Gulati found that brave people actually do is exactly what my dinner friend is doing (and doing it well). They enlist allies. They find connection. They build the network and intentionally lean on it.
The risk-taking is only half of what I saw. She also refuses to do any of it alone. She asks. She gathers people.
I flew home from Anaheim genuinely energized. After a multi-day conference, I’m usually feeling tired. This time, I came back wanting to shed a little caution. To go for the bigger thing. To ask out loud instead of working it out alone in a corner.
You do not have to be twenty-five to do this. You do not have to start a company. The question is smaller and more useful than that: what would you do this week if a no were just information, and if you let yourself actually ask your people for help?
Two Options for This Week
Option A: Make the bold ask. Pick one thing you keep circling around and haven’t let yourself do. The pitch. The introduction. The idea you keep editing instead of sending. Do the version that slightly scares you, and treat any “no” as data.
Option B: Lean on your people on purpose. Tell one person in your community what you are actually building, and ask them for something specific. Skip the vague “let me know if you think of anything.” Make a real ask. Courage is not a solo sport, and the bravest people in the room are usually the ones with the most hands on their back.
So, with this newfound courage, I’m going to make the bold ask and talk to some more people in my community about an idea I have.
Tell me – will you do the same?
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