Say Yes When You’re Young (and Old)

Lessons from Derek Sivers and the power of openness.

When you’re young, the world is full of possibilities. But here’s the thing: most of those possibilities won’t come knocking on your door. You have to open the door yourself—and sometimes, that means saying “yes” to opportunities that might seem random, scary, and even a lousy deal—if not a ripoff.

By the way! My newest book, Wiser Guy is available for preorder. That’s something you can say YES to!

Derek Sivers, the founder of CD Baby and one of the most unconventional entrepreneurs I know, is a perfect example of this. He didn’t start CD Baby with a grand vision to revolutionize independent music. He just said “yes” when a friend asked him to sell a CD online. That one “yes” turned into a $100 million business that changed the music industry forever.

Embrace the Science of Luck

Saying “yes” isn’t just about being agreeable—it’s about creating opportunities for serendipity. Derek often talks about the “science of luck,” which shows that lucky people aren’t just born that way. They’re curious, open, and willing to engage with the world. They talk to strangers, try new things, and take chances.

When you’re young, you have the freedom to experiment. You don’t have a mortgage, kids, or a reputation to protect. This is the time to lean into curiosity and let luck find you. Say yes to the weird internship, the side hustle, or the random coffee meeting. You never know where it might lead.

Build a Portfolio of Experiences

Think of your early years as a time to build a portfolio—not just of skills, but of experiences. Every “yes” adds a new piece to that portfolio. Some will be duds, sure, but others will be game-changers.

Derek Sivers didn’t just say yes to selling CDs. He said yes to being a circus ringleader, a musician, and a programmer. Each of those experiences added depth to his portfolio and prepared him for opportunities he couldn’t have predicted.

When you’re young, don’t worry about having a linear career path. Focus on collecting experiences that make you interesting, adaptable, and resilient.

Derek Sivers during his days in the circus.

Learn When to Say No (Eventually)

I’m not saying you should say yes to everything forever. As you gain experience, you’ll need to get better at saying no to protect your time and energy. But when you’re starting out, defaulting to yes is a great way to discover what you love—and what you don’t.

Even Derek Sivers, the king of saying yes, eventually learned to say no. But he only got there after years of experimenting and exploring. So, don’t rush to close doors before you’ve had a chance to peek inside.

Take the Leap

Here’s the bottom line: when you’re young, saying yes is your superpower. It’s how you build momentum, create connections, and discover your path. So, the next time an opportunity comes your way—even if it feels a little outside your comfort zone—just say yes.

You might not end up with a $100 million business like Derek Sivers, but you’ll end up with something even more valuable: a life full of stories, lessons, and possibilities. And who knows? One of those yeses might just change your life.

And then, bizarrely, you may discover what I have: that at the end of your career, you start saying yes again to stuff you would not have considered in the middle of your career.

I do this all the time now. Sometimes for the simple pleasure of helping a product or company that I like. Sometimes out of a feeling of social responsibility. And sometimes to just make the world a better place.

So, go ahead. Say yes. The world is waiting.

Mahalo,

Guy