Many Heads, Not Many Hats: The Founder's Identity Crisis

"Not just the cover of the head - the head itself. A new brain that thinks different, speaks different, prioritizes different. And somehow, these heads are all attached to the same body. It's less of a mad hatter situation and more of a Medusa situation. Multiple perspectives, multiple personalities, all trying to navigate a world that treats each one differently."

"I was on a consulting call recently, and we got into this topic of focus shifting and dealing with multiple projects. The founder I was talking to was struggling with something I see all the time: they were migrating from a successful consulting practice into building a software business, and nothing was working the way they expected. Their focus was off. Their priorities felt wrong. And despite having years of professional success behind them, they felt like they were starting from scratch - except worse, because their instincts kept leading them astray."

"You're coming from a salaried position, or from freelance work, or maybe you've been running a small agency with a low headcount - something personal, something you've built relationships around. And now you're trying to build a software business. A completely different animal."

Founders shifting from consulting or small-service businesses into software often face a radical identity change requiring fundamentally different thinking, priorities, and behaviors. Previous instincts and relationship-based approaches can become liabilities when productization demands scalable processes, different metrics, and distinct customer dynamics. Multiple internal roles emerge simultaneously, causing conflicting perspectives and attention fragmentation. Failure often stems from encumbrance of legacy practices, misaligned focus, and expecting prior tactics to work unchanged. Effective transition requires deliberate shedding of old habits, creating clear priority frameworks, and adopting product-centered strategies that support scalable growth rather than personalized service delivery.

Read at The Bootstrapped Founder