Every leadership milestone — the promotion, the launch, the breakthrough — is also a starting gun for the next struggle. The leaders who thrive aren’t the ones who avoid this cycle. They’re the ones who recognize it.
Drawing on his career across music, public service, and executive coaching, Chris Leonard maps the inflection points that define every success journey — and shows leaders how to lean into the next climb before it becomes a crisis.
A note on Seth Godin’s The Dip
This talk builds on and extends ideas explored in Seth Godin’s The Dip. Where The Dip asks “should you push through or quit?” this keynote asks a different question: what happens when you do push through — and win — and the cycle begins again? Leaders who have read The Dip will find this talk a natural, challenging next chapter.


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