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July 17, 2025 38 mins

Sixty-seven percent of founders freeze at the commitment cliff—that terrifying moment when your side hustle demands to become your main thing. When do customer demands become ultimatums? When does burnout force your hand? And how do you know when to quit the day job versus quitting the dream?

Join us for a brutally honest conversation with Seth Goldstein, former ink-stained journalist turned digital marketing strategist and host of Entrepreneur's Enigma podcast. We dive deep into the emotional and financial triggers that push founders over the edge, the reality of managing multiple ventures, and why calling it a "side hustle" might just be our way of avoiding commitment.

This isn't your typical "follow your passion" advice—it's real talk about opportunity costs, risk mitigation, and the moment when everything changes. Plus, we settle the age-old question: when do you put the lame horse down?

Keywords: side hustle, small business transition, commitment cliff, entrepreneurship, startup burnout, founder decisions, business strategy, Seth Goldstein

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