Turning Life into Leadership: How Personal Experiences Shape Corporate Success

In the hustle and bustle of the corporate world, leadership often seems like a numbers game – balancing KPIs, meeting financial targets, and optimizing metrics. But true leadership requires more than just hitting targets; it demands empathy, adaptability, and courage.

That's where our personal experiences come in. In my book, “Freefall: Leadership Lessons from the Skies”, available at www.freefallleadership.com, I explore how my journey into skydiving offered profound insights that I applied to the world of business. From overcoming fear to trusting in the team, the lessons from those jumps echo the same principles we need in the workplace.

Yet, I've found that skydiving isn't the only arena where life's experiences translate into leadership skills. Sports, hobbies, and even moments spent with family can be a rich source of wisdom that we often overlook. Here, I'll share some of those transferable lessons – insights that encourage leaders to lean into their personal journeys and bring those lessons into the boardroom.

After all, leadership isn't just about managing tasks; it's about guiding people, embracing change, and making decisions that align with values, even when other objectives try to pull us in different directions.

Skydiving: Embracing Fear and Taking the Leap

Skydiving taught me a lot about fear – how it feels, how to confront it, and how to act despite it. Looking out from the edge of a plane, I learned that fear is not a barrier but a gateway. In those moments, I had to trust my training, my equipment, and my instructors. In the corporate world, leaders face similar leaps of faith. When launching a new initiative or navigating a major shift, fear of failure or the unknown can hold us back.

But leadership is about courage, and courage isn't the absence of fear – it's the ability to move forward in spite of it. It’s about making bold decisions, even when financial targets and market pressures create a sense of urgency and risk. Being able to pause, assess the situation, and take the leap is a skill that pays off, both in the skies and in the boardroom.

American Football in Ireland: The Importance of Roles and Trust

Playing American football in Ireland was a unique experience – one that taught me the value of roles, strategy, and trust. The game is a blend of physicality and tactical precision, where every player has a specific role, and even a small lapse in execution can change the course of a play. As a running back, I quickly realised that my success was directly tied to my ability to trust my teammates, especially the offensive line protecting me whilst making the hole in the line for me to run through.

The key lesson? You can’t win alone. No matter how skilled you are, the team’s success depends on each player understanding their role and delivering their best. It’s about trusting your teammates to do their part, even when the pressure is on, and the stakes are high.

In the corporate world, the same principles apply. Strong leaders know that success comes from empowering their teams, not from micromanaging every detail. They focus on building trust, understanding the strengths of each team member, and allowing them to excel in their roles.

But in the face of quarterly targets and metrics, it can be tempting to revert to a command-and-control approach. True leadership courage means stepping back, trusting your team, and focusing on the bigger picture – just like trusting your team mate to make that crucial block.

Stand-Up Comedy: Resilience and Thinking on Your Feet

After 20 years in stand-up comedy, I’ve learned that performing in front of a live audience is an exercise in resilience and quick thinking. Comedy is about connecting with people in real-time, reading the room, and adjusting to reactions on the fly. Sometimes a joke doesn't land, and you have to pivot quickly without letting it shake your confidence.

In leadership, especially in times of change or crisis, this ability to adapt on the spot is invaluable. Leaders often find themselves facing unexpected challenges, needing to adjust their strategies in real time. It’s about being able to respond with confidence when the plan doesn’t go as expected. Resilience is key – not letting a setback define you, but learning, adapting, and delivering again.

Just like on stage, in business, it’s not about avoiding mistakes but about how you recover and keep the momentum. Planning to make mistakes is a crucial part of the process – this is how we learn.

Cooking with Family: Creativity and Nurturing Connections

Cooking, especially when done with family, has become a favourite ways to unwind. But it’s also taught me a lot about creativity and nurturing connections. When you’re in the kitchen, sometimes you follow a recipe, but other times, you make do with whatever ingredients you have and create something unique. My wife can create something special from anything. Her name is Michelle, and I call her creations, the ‘Shelly Specials’.

The real joy comes from sharing that creation with others and watching how it brings people together.

In leadership, creativity is about finding new solutions when the usual ways don’t work. It’s about turning challenges into opportunities, like making a meal out of limited resources. And just as cooking can bring people closer, leadership is about building strong relationships, fostering a sense of community within your team, and celebrating the moments of success – big and small.

Leaders who focus on connection and creativity can often find innovative ways to solve problems, even when the pressures of performance loom large. It’s about blending the ingredients of your team's strengths and making sure that everyone feels like they have a seat at the table.

Navigating Conflicting Objectives with Courage

Leadership in the corporate world often involves balancing multiple, sometimes conflicting objectives – hitting revenue targets, maintaining customer satisfaction, and keeping the team motivated. It’s a complex juggling act, and the pressure to prioritize numbers can sometimes overpower other considerations like team well-being or long-term vision.

This is where courage as a leader becomes essential. It takes courage to make decisions that might not immediately align with financial targets but are better for the team in the long run. It takes courage to prioritize people, to invest in relationships, and to trust that those decisions will pay off down the line. This balance between immediate results and enduring values is what separates good managers from great leaders.

Conclusion: Leaning Into Your Story

Your personal experiences are not just stories to tell; they are tools you can use to become a better leader. Whether it’s facing the fear of a jump, thinking on your feet during a tough crowd, or creating something new with loved ones, these experiences shape the way we lead. The courage to lean into these lessons, especially when other objectives conflict, is what defines us as leaders.

In the end, leadership isn’t just about hitting targets – it’s about guiding people through change, even when the path is uncertain. It’s about knowing when to take the leap, when to support others, and when to adapt. When we draw on our personal experiences, we bring a unique perspective that can inspire others and create a more resilient, courageous, and human-centered approach to leadership.

So, next time you find yourself on the edge of a challenge, think back to those moments in your own life where you faced uncertainty. Bring those lessons with you and use them to lead with courage.

I hope this newsletter inspires you to see the connections between your personal experiences and your professional life. Let’s continue to learn, grow, and lead – both inside and outside the boardroom.

Please share any personal experiences which have helped you in your professional life.