From people Pleaser to CEO: My Journey of Leadership

Growing up, I was always driven by a desire to please those around me. I worked hard to meet the expectations of others, often putting my own needs aside. It was a pattern that followed me well into adulthood. Raised by two incredibly strong and resilient parents, I inherited my father’s entrepreneurial mindset and my mother’s nurturing heart. My father, an Italian immigrant, juggled several jobs to provide for our family, teaching me the importance of hard work and perseverance. My mother, one of twelve siblings, filled our home with love and care, showing me the power of kindness and compassion. Their values shaped who I became, both as a woman and as a leader.

At just eight years old, I began working in my parents’ canteen, learning the ropes of customer service and responsibility, while most kids my age were enjoying carefree childhoods. By the age of ten, I was helping my father on building sites, surrounded by the sounds of hammers and the hum of construction, while learning about grit, teamwork, and the satisfaction of a job well done. I loved these experiences, not only because they allowed me to spend time with my dad but because I felt a deep desire to make him proud. Little did I know, those early lessons were planting the seeds for a career built on leadership, hard work, and perseverance.

It wasn’t until I got my first job at Just Jeans at 16 that I truly discovered my passion for retail. That part-time job was far more than a paycheck; it was the beginning of a 30-year love affair with the retail fashion industry. I thrived in the fast-paced environment, from interacting with customers to understanding how a store really functioned. Every sale felt like a personal achievement, and I was hooked on the energy of the business.

It didn’t take long before my dedication was recognised, and I was offered a full-time role at Just Jeans. Accepting that role meant making a difficult decision – leaving school earlier than expected, a path that didn’t quite align with my parents’ vision for my future. Although they supported me, I knew they had hoped for a more traditional path. For a long time, I wrestled with the weight of their expectations, but deep down, I knew that retail was where I belonged. That decision marked the first of many pivotal moments in my leadership journey.

As I climbed the corporate ladder, moving from sales assistant to CEO, each new role brought its own set of challenges. I approached each challenge with determination and a belief in leading authentically. One of the most important lessons I learned is that true leadership has little to do with titles or authority. Real leadership is about staying grounded, being kind, and leading with purpose. It’s about lifting others up, fostering meaningful relationships, and creating environments where people feel valued.

But, like many people-pleasers, my journey wasn’t without its struggles. I often found myself overcommitting, trying to meet everyone’s expectations, while neglecting my own wellbeing. It took time – and a few tough lessons- to realise that I didn’t have to please everyone to be a successful leader. Some of the most defining moments in my career came when I was willing to take bold risks and trust my instincts, even when it meant standing alone. I learned that leadership requires courage – courage to be yourself, make tough decisions, and embrace the unknown.

Looking back, I’m proud of the young girl who spent her weekends learning the value of hard work on building sites, and I’m even prouder of the woman I’ve become – a leader who now mentors’ other women to lead with confidence. My story is a testament to the fact that you don’t need a perfect path to become a great leader. What you need is the courage to pursue your passion, embrace your uniqueness, and believe in your potential.

Throughout my career, from my early days at Just Jeans to leading some of Australia’s most iconic retail brands, I’ve come to understand that leadership is not about status or power – it’s about impact. It’s about empowering others to believe in themselves, just as I’ve learned to believe in me.

So, as you reflect on your own journey, ask yourself: What small step can you take today to start believing in your potential? And how might that change the course of your future?

Written by Colleen Callander.

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