Why subscribe?

I don't just teach about avoiding the Career Expiration Trap - I've lived it.

I've spent 15+ years founding businesses and continue to experiment today. After thousands of conversations with leaders, I've learned what actually helps people stay ahead when existing skills aren't enough.

Now I help leaders develop these skills and build what comes next.

Through 250+ podcast conversations with operators like Daniel Pink, Lynda Gratton, and Rory Sutherland, plus years of advisory work with founder-led teams, I explore how ambitious leaders navigate major transitions as the rules of work change.

The Ollie on Work community includes people like you who are interested in building entrepreneurial skills that create momentum - whether that's redesigning how teams collaborate across generations, implementing AI strategy, or building culture that unlocks performance.

You can also hear me interview interesting people about all things work and leadership on the Ollie on Work podcast.

I'm also the author of the career and entrepreneurship bestseller Work/Life Flywheel. Here's what Daniel Pink said about it:

"Creating new opportunities requires fresh thinking. With the Work/Life Flywheel model, Ollie Henderson gives you the system you need to make bold changes in your career and the motivation to share your ideas with the world."

Cheers!

Ollie