Entrepreneurship is often romanticized as a journey of freedom and self-determination, but beneath the surface lies a complex reality that many founders face alone. In a recent conversation with Hersh Rephun, a personal brand strategist and former publicist with decades of experience, we explored the phenomenon known as “CEO disease” or “founder syndrome” – a collection of symptoms that can significantly impact entrepreneurs on their journey.

But this is you. If you’re founding something, if you’re starting something, this is you, and no one’s going to save you, no one’s going to tell you what to do, because no one has as much invested in it as you. So in this instance, for some reason, it really started to feel a little lonely. That was something I noticed.

The most striking symptom that emerged from our discussion was the profound sense of isolation that comes with leadership. As Hersh poignantly observed, “This is you. If you’re founding something, if you’re starting something, this is you, and no one’s going to save you, no one’s going to tell you what to do, because no one has as much invested in it as you.” This fundamental truth creates a unique psychological challenge that many entrepreneurs are unprepared for when they begin their journey.

The isolation of entrepreneurship requires a mental shift that doesn’t come naturally to most people. Hersh described his evolution from feeling lonely to taking a more holistic view of his business. “What I need is to step into this and take a holistic view of the business and just do all the things that don’t appeal to me, that are important to get done,” he explained. This shift from seeing yourself as “a piece of the puzzle” to recognizing that you are “the puzzle” itself represents a crucial transformation in how entrepreneurs must view their role.

What makes this transition particularly challenging is the lack of external validation or guidance. When working within established organizations, there are frameworks, mentors, and colleagues to provide direction. In contrast, the entrepreneurial path demands that you create your own map while simultaneously following it. This dual role can create cognitive dissonance that manifests as doubt, micromanagement, or resistance to change – all hallmarks of founder syndrome.

One of the most insightful aspects of our conversation centred around the relationship between entrepreneurship and failure. Contrary to popular motivational mantras like “failure is not an option,” both Hersh and I agreed that not only is failure an option, but it’s also an inevitable and valuable part of the entrepreneurial journey. As Hersh reflected on his own experiences, he noted that failure is relative and often represents a pivot point rather than an endpoint.

The COVID-19 pandemic provided a dramatic illustration of this principle for Hersh. When all his agency’s projects were suddenly cancelled, rather than desperately trying to salvage his existing business model, he chose to pivot entirely. This willingness to let go of a path that no longer served him allowed him to discover new opportunities in podcasting and personal brand strategy. The ability to recognize when to persist versus when to pivot represents a critical entrepreneurial skill that often develops through experience rather than training.

Perhaps the most profound insight from our conversation was Hersh’s advice about the importance of listening to ourselves. In a world filled with constant input and information, entrepreneurs often look outward for answers rather than trusting their own instincts. “We don’t spend enough time listening to ourselves,” Hersh observed, suggesting that making space for our unconscious mind to speak to us represents an act of self-confidence that many entrepreneurs lack.

His parting wisdom was both simple and profound: “When you’re alone, you’re the smartest person in the room.” While this might seem obvious, it speaks to a deeper truth about entrepreneurship. The most valuable insights often come not from external sources but from processing information through our unique personal filter. It’s this filtering process, done in moments of solitude and reflection, that allows entrepreneurs to develop the distinctive perspectives that ultimately lead to innovation.

Understanding and navigating founder syndrome isn’t about eliminating struggle from the entrepreneurial journey. Rather, it’s about recognizing these challenges as integral parts of the process and developing strategies to work through them. By embracing isolation as an opportunity for clarity, viewing failure as a pivot point, and trusting our own unique insights, entrepreneurs can transform the symptoms of founder syndrome from obstacles into stepping stones on the path to fulfilment and success.

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