BONUS: Why Creative Freedom Isn’t Enough (And What You Actually Need to Succeed)

In this bonus episode, Jenna flips to the other side of the mic, joining filmmaker and creative entrepreneur Caleb Coroneos for a candid conversation about what happens after you hit your goals.

You’ve built the business, bought your freedom, and proven to yourself that you can do hard things. Now what? This episode explores the quieter shift most founders don’t talk about—when the things that used to drive you no longer fit, and you’re ready to build from clarity, not chaos.

Whether you’re refining your business model, evolving your identity, or letting go of what no longer aligns, this one’s for you.

What you’ll take away

• Why creative freedom isn’t the finish line and what actually matters next
• The cost of staying in survival mode when your life’s moved on
• What it looks like to lead without chaos as your motivator
• How to let go of things that are working but no longer aligned
• Rebuilding your identity when your environment hasn’t caught up
• Jenna’s lessons from London, Cape Town, and startup life
• Five skills that actually move the needle as a modern founder

⏰ Key moments

00:00 Jenna joins Caleb as a guest on his podcast

03:30 Leaving corporate—and the fear under the leap

08:50 “Search for pride, not happiness”—the mindset shift that stuck

12:10 Letting go of what no longer aligns (even when it’s working)

17:30 Why freedom stopped feeling like the goal

21:00 Control, communication and leadership as identity shifts

26:40 When chaos no longer drives you—what comes next

30:10 Burnout, safety, and building from a different energy

36:50 Ambition, delusion, and taking the next big swing

41:00 What Jenna learned living overseas

47:20 You only get 8 big opportunities in life—here’s how to choose

50:30 5 essential skills for growth-stage founders

55:00 What Jenna wants to be remembered for

You can reach a point where the business you built no longer fits who you’re becoming. That doesn’t mean something’s wrong, it means it’s time to realign.

This episode is for the creator who’s built the thing, earned the freedom, and is now ready to create from clarity, not chaos. If you’re feeling that internal nudge to evolve, even when things look ‘fine’ from the outside, this conversation will make sense of what you’ve been feeling.

Send it to someone navigating the same shift. And let us know what it unlocked for you 🧠🚀

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