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The People Side of Business

[S5, Ep38] The Messy Middle: The Stage No One Warned You About

The People Side of Business · 2026-03-05 · 18 min

Episode notes

Send us Fan Mail Let me paint you a picture. Your revenue is solid, your calendar is full, your inbox is buzzing, and even your accountant is happy. And yet you're lying awake at 3am thinking - how does this feel successful and like it's flying apart at the same time? My friend, welcome to the messy middle. And if that question feels uncomfortably familiar, this episode was made for you. Episode Highlights: What the messy middle actually is, and the five questions that will tell you whether you're in it right now Why you cannot hustle, market, or mindset your way out of this stage - and what actually moves you forward The story of the "everything is fine" founder, and what was really happening behind the scenes ️ The leadership identity evolution from expert to architect Most scaling advice was built for someone who looks nothing like you. You have decades of experience, a team you genuinely care about, clients you're deeply committed to, and a business you poured your life into. The messy middle is what happens when all of that growth starts to expose every crack and crevice, and the way you've always shown up stops being enough to hold it together. The good news?

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