Helping ambitious leaders avoid the Career Expiration Trap.

I'm Ollie Henderson. I've spent 15+ years founding businesses and I'm still experimenting today. I've learned what keeps leaders ahead. Entrepreneurial skills that create momentum regardless of what shifts.

Real conversations with business and thought leaders like Daniel Pink, Rory Sutherland, and Lynda Gratton about leading multigenerational teams, implementing AI strategy, and building what comes next as the rules of work change.

No generic future-of-work trends. Just practical insights for leaders who refuse to expire.

You can also read more about these themes in the Ollie on Work newsletter.

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