Courage Over Confidence: - Insights From a Motivational Speaker

Courage Before Confidence: Designing a Life That Matters
Insights from Debbie Millman on The James Altucher Show, Ep. 218

We like to think we’re rational creatures. But as Debbie Millman reminds us in her conversation with James Altucher, the ancient part of our brain—the reptilian bit that regulates blinking, heartbeats, and digestion—is not easily reasoned with. And when uncertainty knocks, it’s that part of our brain that answers the door... usually with a scream.

Uncertainty, Millman says, is automatically perceived as negative. That’s not weakness; that’s wiring. So if you’re waiting to feel perfectly safe before you make a leap, you might want to grab a seat—you're going to be waiting a while.

But here’s the good news: feelings are fleeting. Whether it’s the temporary thrill of a new TV or the pang of rejection, these emotions are chemical blips, not life sentences. As Millman puts it, “They won’t kill us. Any more than a flatscreen TV is going to delight us for the rest of our lives.”

The Hedonic Treadmill and the Fool’s Game

Millman unpacks the endless chase for external validation. That serotonin rush you get when you finally buy the thing you’ve dreamed of? It disappears fast. And so, you chase the next thing, and the next. A bigger TV. A better gadget. More followers.

Generation Z—dubbed by some as Generation D, for “depressed”—is now measuring self-worth in likes and follows. “It’s never enough,” she warns. “Because human beings aren’t wired that way. We always want more.”

This chase is what psychologists call the “hedonic treadmill.” It’s the illusion that happiness is just one purchase or achievement away. But as Millman points out, anytime you search outside yourself for something lasting, you’re playing a fool’s game.

What Do You Really Want?

So what’s the antidote to this treadmill of disappointment? Clarity. Intention. Vision.

One of Millman’s most profound exercises is the Ten-Year Plan for a Remarkable Life. Picture this: It’s winter 2027. Where do you live? What’s on your bookshelf? Who do you wake up next to? What kind of dog is snoring at your feet? Map out one single day in full, vivid detail—right down to your sheets and your coffee cup.

It’s not about fantasy. It’s about focus. “Put your whole heart into it,” she urges. “Write like your life depends on it—because it does.”

Once you know what you want, the next step is sacrifice. What are you willing to give up to get it?

Buffett’s famous 5/25 Rule echoes this idea. List the 25 things you want most. Circle your top five. The rest? “Avoid at all costs.” Why? Because distractions love to dress up as opportunities. And the most dangerous ones are the ones you love—just not enough.

Courage First, Confidence Later

People often say, “I’ll start when I feel confident.” But confidence doesn’t come first. Courage does.

Millman flips the script: “Confidence comes from repetitive success. Courage is what gets you started.” That first step? It’s never backed by certainty. It’s backed by boldness.

And if you’re worried about what others will think? Don’t. “Nobody really cares,” she shrugs. Most people are too busy worrying about their thing to obsess over yours.

The New Reality of Work and Identity

Altucher and Millman also reflect on the breakdown of corporate loyalty. In a post-automation, post-outsourcing world, the old path of security is gone. But this collapse also brings opportunity—the chance to rewrite your script.

Millman challenges us to stop editing out possibilities before they’re even on the table. “I won’t apply for that job—they wouldn’t pick me.” “I’m not good enough.” That’s fear, masquerading as practicality. And it's robbing you of your future.

A Life By Your Design

In a world that encourages comparison, consumption, and playing it safe, Millman offers a refreshing path forward: dream big, act small, and move with courage. Don’t wait for confidence. Don’t chase happiness at the mall. Don’t trust your lizard brain to guide your life.

Instead, write it. Design it. Build it—one courageous step at a time.

Because the most remarkable lives aren’t stumbled into. They’re designed—by people who dare to imagine, and then do.