The Hard Season

Matt Zilli, CEO of Planview, told me the hardest years of leading a company through billion-dollar growth (including restructures, tough people decisions, and uncertainty) became the most valuable leadership training of his career.

That really resonated for me. Some of the most uncomfortable stretches building my podcasts and business were the exact moments I wondered if I should pivot, slow down, or walk away. The audience wasn’t growing yet.

The results weren’t obvious. The path felt uncertain.

Ever had the "uncomfortable stretch"?

You know, those seasons forced me to get clearer, tougher, and more patient as a leader.

Matt called it in our conversation “SCAR TISSUE"...the kind you only earn by staying in the work when it’s not fun, not fast, and not guaranteed.

Wins build confidence. Hard seasons build leaders.

Looking back, the seasons I wanted to escape were often the ones doing the most to shape how I lead today.

Question: Do you think we leave the hard season too early or make a mistake by preventing it all together?

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