Hey friends, Chase here. Today, I want to talk about something we all face at some point—the moment when what once felt like a dream becomes a trap. It’s a tough place to be, but if we can recognize it early, we can turn it into an opportunity for growth and reinvention.

When Success Becomes Stifling

Back in 2010, I co-founded CreativeLive with a simple but ambitious idea: to give the world access to free, world-class creative education. We started small, but over time, we grew to serve tens of millions of people and raised more than $60 million from top-tier investors like Richard Branson, Reid Hoffman, and Google Ventures.

At first, my unconventional background as a creator—not an MBA—was celebrated. I brought a personal brand and a community along for the ride, and it seemed like a competitive advantage. But eventually, the pressure to conform crept in. The same people who once admired my unique approach began questioning it.

The Subtle Drift Away from Purpose

What started as small adjustments in how I operated became a slow drift off course. It wasn’t dramatic at first—just a few degrees off. But after walking that path for long enough, I found myself far from where I wanted to be. The very thing I had built to inspire creativity felt stifling and uncreative.

And here’s the thing—this story isn’t unique to me. It happens to many of us. The artist who becomes a manager. The entrepreneur buried in spreadsheets. The corporate climber who wakes up one day and wonders how they got there.

If you’ve ever felt that way—or if you do in the future—this is for you.

Signs It’s Time for a Change

Listen to Your Gut When something feels off for too long, it’s your gut telling you it’s time to move. Ignoring that voice comes with real consequences—stress, poor health, and a fog that clouds your creativity and joy.
Nothing Lasts Forever Even the most exciting roles can run their course. Dreams change, and that’s okay. Letting go of a title or identity that no longer serves you is hard, but it’s often necessary for growth.
Build Your Escape Pod Early Don’t wait for a crisis to figure out your next move. Start building skills, connections, and momentum now. When it’s time to make a change, you’ll be ready to transition on your terms—not out of desperation.

Embrace Change as a Constant

Change is inevitable. It’s uncomfortable, but it’s almost always a catalyst for something better. When you start hearing that little voice whispering about a new chapter, don’t ignore it. Trust it. Your future self will thank you.

Until next time, take care and keep pushing toward what feels true and right for you.

Enjoy!

"Sandra Bullock"

SmartLess

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