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When Doing Everything Becomes Your Biggest Business Problem

When Doing Everything Becomes Your Biggest Business Problem

Update: 2025-08-19
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The hardest part about growing your business isn't hiring people or finding customers. It's letting go of being the person who does everything. In this anniversary episode, Gwen Bortner and Tonya Kubo revisit their second-most-downloaded episode: From Solo to CEO Part 1 - Pivotal Shifts To Become The Leader Your Business Needs.


Here's the uncomfortable truth: being good at your craft doesn't make you good at leading a business. Entrepreneurs excel at firefighting (and sometimes starting fires), but CEOs need to step back and let others hold the extinguisher. That transition requires both leadership skills and management skills — a combination that's harder than anyone talks about.


Gwen breaks down why this shift feels like fractioning your identity, why you can't just think your way into being a CEO (you have to act like one), and why true delegation is so much more complex than writing a checklist. Tonya explores the boundaries you'll need to set — with clients who want you personally, with team members who work differently than you do, and with yourself around protecting thinking time.


They dig into the identity crisis that comes when you're no longer the best at the thing you built your business on, why "I could have done this faster myself" will always be true (and why it doesn't matter), and how to own which problems are actually yours versus your team's. The reality: Growing from solo to CEO isn't about getting bigger. It's about getting comfortable with not being the one who knows all the details anymore.



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When Doing Everything Becomes Your Biggest Business Problem

When Doing Everything Becomes Your Biggest Business Problem