Lead Out Loud: An accidental entrepreneur's journey to leadership

The path to leadership can be an unexpected journey, especially in creative industries, where passion drives individuals rather than a strategic pursuit of leadership roles. Many leaders find themselves in these positions by accident rather than design. Taylor James is one such leader—an entrepreneur who launched a No. 1 podcast and built Coventry’s first purpose-built podcast studio.

In a recent episode of Warwick Business School’s ‘Lead Out Loud’ podcast, Taylor joined Rachel Dickinson to share his journey from passionate creative to ‘accidental entrepreneur’—highlighting the role of resilience, adaptability, and self-belief in leadership.

Following Passion and Taking Risks

After launching the Waffleshop podcast in 2020, Taylor realised his desire to help others share their voices, which led him to create TwentyTwo Digital. His path was unconventional—leaving school before completing his A-levels, he followed his passion rather than traditional career expectations. Taylor refused to be discouraged by the stereotypical, Dragon’s Den-style image of entrepreneurship. Instead, he carved his own path and now inspires others to do the same.

Dr Rachel Dickinson, an expert in creativity and leadership, echoes the importance of embracing unconventional routes to leadership. With a background in theatre and education, she brings a unique perspective to business leadership, aiming to infuse lecture theatres with the creative energy of a rehearsal room—where individuals feel free to experiment, learn, and grow.

The Power of Self-Knowledge

Understanding different types of knowledge and building a strong sense of self is crucial for entrepreneurship, according to Dr Dickinson. “So much of our formative education is focused on external knowledge—consuming, memorising, and proving worth through exams,” she says. “But we don’t focus enough on self-knowledge. What kind of space are we creating for people to pause, reflect, and see the value in their own lived experiences?”

For Taylor, self-reflection was a game-changer. “One of the biggest lessons I’ve learned is that it’s okay to change the labels people put on you. Just because you’ve had a negative thought doesn’t mean it’s true,” he shares. “Sitting here now as an entrepreneur blows my mind because I always thought, ‘I can’t do that.’ But I’ve learned that resilience is key—every successful leader has learned from their failures.”

 

Confidence and Overcoming Imposter Syndrome

Many leaders struggle with imposter syndrome, questioning whether they deserve their success. Taylor has faced this first-hand. “Imposter syndrome tells you that you don’t deserve something. But now, when those thoughts creep in, I challenge them. If I wasn’t capable, I wouldn’t be here. I remind myself of my achievements—charting podcasts, awards, big guests—I have the proof that I belong.”

Dr Dickinson agrees, noting that imposter syndrome often stems from deep-seated doubts. “We’ve all had moments where our skills or talents are questioned. The key is to ask: Who is making you feel this way? Is it society, past experiences, or your own expectations? The sense of self-doubt can be crippling, but it’s essential to talk about it, challenge it, and ultimately use it to grow.”

Building Environments for Growth

Leadership isn’t just about individual confidence—it’s about creating environments where others can thrive. Dr Dickinson emphasises the importance of fostering spaces where people feel safe to take risks. “In a university classroom, I see my role as creating an environment where students can push themselves outside of their comfort zones—not because someone is forcing them, but because they feel safe enough to take the first steps. Leadership is about fostering that sense of trust and belonging.”

Taylor shares that his biggest fear wasn’t failure—it was not trying. “The fear of not doing it was worse than the fear of taking the first step,” he says. “I didn’t want to be stuck in an unfulfilling job, so I took the leap.”

The Bottom Line: What Great Leaders Do Differently

• Follow the unconventional paths: Leadership isn’t always a straight road—it often comes from following passion.
• Challenge self-doubt: Recognize imposter syndrome and actively push back against it.
• Create safe environments: Leadership is about fostering trust so others can take risks.
• Lead with resilience: Every great leader learns from setbacks and keeps moving forward.
• Trust the journey: Confidence comes from reflection, self-knowledge, and acknowledging personal growth.

Leadership isn’t just about experience or hierarchy—it’s about mindset, adaptability, and creating spaces where innovation and self-belief can flourish.
 

Further reading:

Involving marginalised communities in sustainability initiatives

Does evolution explain impatience in business?

How middle managers help companies to change strategy

The new AI 'prediction products' and the risks they present

What can entrepreneurs learn from Moby Dick?

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