The Courage to Change
Overcoming Fear in Your 30s, 40s, 50s, 60s, and Beyond
It’s 10:40 AM on July 3, 2025, and I’m watching the Bitcoin markets, thinking about change. Fireworks are just a day away, and it’s the perfect time to blow up the old you and build something new. Whether you’re in your 30s, 40s, 50s, or like me, in your 60s, fear of change can lock you in a cage— but I’ve got the key! I’ve pivoted from near bankruptcy to a Yahoo! seven-figure deal, to the dot-com crashes to best-selling author, and then to a bookstore gig. Talk about change!
Here’s the thing. Change CAN be scary, but it doesn’t HAVE to be. It can be your ticket to a fun, fulfilling life. Let’s dive into why courage beats fear at any age—and how to make the leap.
Back in my 30s, the dot-com bubble burst, and my affiliate income vanished. Panic set in—should I crawl back to a “safe” job? Instead, I teamed up with a coder friend, Eron, to build a multiplayer game site. We had no clue it’d become Yahoo! Games, but that pivot saved me. Later, in my 40s, after years of online hustle, I took a wild left turn—a minimum-wage bookstore job. People thought I’d lost it, but that gig sparked ideas for my speaking career. In my 50s, I started co-hosting The Bad Crypto Podcast, raving about blockchain. Each shift led to uncertainty, but each one lit me up. Change is my superpower, and it can be yours too.
Why Fear Holds Us Back (and How to Break Free)
Fear of change is like a bad habit—it won’t let go without a fight. In your 30s, you might worry about starting over when peers are climbing ladders. In your 40s, it’s the “I’m too old” lie creeping in. By your 50s or beyond, you might think the ship’s sailed. I felt that when my first site crashed—I was 30, broke, and terrified. But here’s the kicker: change isn’t age-restricted. A 2019 study from the American Psychological Association found that adaptability peaks when we embrace new challenges, no matter the decade.
My bookstore pivot proved it. At 40-something, I swapped my entrepreneur hat for a cashier slot at a Barnes & Noble shop, chatting with customers about books. I wanted to know what it was like to be on the other side of the author world. Those conversations fueled my next book idea. Fear whispers, “You’ll flop,” but courage shouts, “What if you soar?” The older you get, the more you realize change isn’t a threat—it’s a playground.
How to Summon the Courage to Change
Ready to ditch the fear and dance with change? Here’s how to do it with pizzazz:
Face the Fear Head-On
Name it. When I started this Substack, I considered my fears—no one would care, it wouldn’t make money, etc. Then I asked, “What’s the worst that happens?” The jury is still out but I don’t care. I’m doing it because I have things I want to say. Consider your fears, then challenge them. Spoiler alert: they’re weaker than you think.Start with a Baby Step
You don’t need a grand leap. After the dot-com bust, I started with a small game prototype with Eron—no big risks, just play. Try a side hustle, a course, or a new skill. My podcast began with one shaky episode; now it’s been a weekly thing for almost nine years. Small moves build courage.Lean on Your Tribe
Surround yourself with cheerleaders. When I pivoted to speaking, a mentor from a conference hyped me up, sharing tips for being a more effective speaker. My Bad Crypto co-host keeps me bold in what we share on our share. Find friends or online communities who say, “Go for it!”—they’ll catch you if you stumble.Embrace the Unknown with Play
Treat change like a game. My attempt to produce the world’s first cometitive Internet reality show was a gamble, but we had fun making it. Take a class, join a meetup, or test a crazy idea. I once tried stand-up comedy in my 50s. I flopped, as one does their first time out, but it sharpened my stage skills. Play turns fear into fuel.Celebrate Every Win (Big or Small)
Toast your progress. When iFart hit #1 in the appstore, we celebrated with a nice dinner out. After my first bookstore shift, I treated myself to ice cream—small win, big boost. When Bad Crypto hit 10,000 downloads, we popped virtual champagne. Celebrate pivots, even if they’re messy. It rewires your brain to love change.Learn from the Legends
Look at icons. Colonel Sanders pitched KFC at 65 after years of flops. Vera Wang designed her first dress at 40. I started a new podcast in my 50s—proof age is just a number. Study their stories; they’ll inspire your next move.
The Thrill of a New Chapter
Here’s where it gets wild: change unlocks surprises. A random crypto tweet connected me to a sponsor. A 40-year-old friend ditched law for his passion for DisneyWorld, now raking in revenue. A 50-something coder rebooted after a startup fail, launching a hit app. The older you are, the richer your experience—use it to reinvent.
Take the Leap Today
Picture this: at 35, you start a podcast that explodes. At 45, you open a café that becomes a local gem. At 55, you write a book that inspires thousands. That’s change’s power. I’ve turned pivots into profits—Yahoo! after a bust, podcasting after a shift—and the fun never fades.
Right now, it’s your moment. Pick one fear, take one baby step—sign up for that class, pitch that idea, call that mentor. Share it in the comments—I’ll cheer you on! Blast past fear and build a life that rocks. 🎉