Jolene Jacoby: The Courage to Begin, the Confidence to Grow, and the Importance of Putting Yourself First 

How often do people postpone their own happiness while trying to become everything everyone else expects them to be? In the pursuit of career growth, financial success and personal responsibilities, many learn to keep going even when they feel exhausted, question their abilities or forget what brings them joy.  

For women especially, the pressure to prove themselves can make them wait for confidence before taking a chance and put their own wellbeing last.  

Jolene Jacoby, a South African living in Dubai, has spent more than two decades discovering that growth often begins with a step taken before feeling ready. From building a career in procurement and supply chain to finding an unexpected passion for public speaking, her journey demonstrates the courage to explore unfamiliar paths. A personal turning point in 2024 also led her to reconsider success, reminding her that pursuing a fulfilling life must include caring for the person living it. 

Jolene grew up in a single-parent household, where money was not always in abundance. However, she and her sister never allowed their circumstances to limit their dreams or determine what they believed they could achieve. Their upbringing taught them that while they could not always control their starting point, they could choose how they approached the future. 

For Jolene, this remains one of life’s most important lessons. Not everyone begins with the same opportunities or resources, and life will inevitably present challenges. But where you come from does not have to dictate where you are going. What matters is the determination to keep moving forward, the courage to pursue opportunities and the willingness to believe in what is possible, even when the journey is difficult. Your past is part of your story, but it does not have to define the person you become. 

None of it started with a plan. It started with an admin job and a head full of questions. 

A Career Which Began with Curiosity 

Jolene’s career did not begin with a carefully mapped-out plan. Starting in administrative roles, she was curious about how businesses operated and eager to learn. Rather than limiting herself to the responsibilities of a single position, she explored different functions, took on new challenges and gradually built a diverse skill set. Each experience opened another door, teaching her that growth often comes from being willing to try something unfamiliar. 

“I have always believed that your starting point does not determine your destination. You don’t need to have everything figured out from the beginning. Sometimes, you simply need to be curious, ask questions and have the courage to take the next step.” 

That mindset ultimately led Jolene into procurement and supply chain, where she developed extensive experience managing strategic sourcing initiatives, supplier relationships and commercial negotiations across multiple high growth markets for some of the biggest multinationals in the World. Her career has been marked by tangible results, including delivering significant savings through supplier negotiations, driving sustainability initiatives and delivering long-term value add results for the business. 

These accomplishments reflect more than commercial expertise. They demonstrate her ability to identify opportunities, navigate complexity, build relationships and turn challenges into measurable outcomes. Yet Jolene believes that the most valuable lesson from her professional journey is not a particular saving, contract or achievement. It is the mindset that made those achievements possible. 

She has learned that success rarely comes from knowing everything. It comes from being willing to learn, asking the right questions, listening to different perspectives and having the confidence to make decisions even when the path ahead is not entirely clear. 

This is a lesson she believes is particularly important for women in the workplace. 

Learning to Move Beyond Self-Doubt 

Too often, women can feel they need to meet every requirement, have every answer and be completely confident before putting themselves forward for an opportunity. They over analyse decisions, question their capabilities and worry about how they will be perceived. 

Jolene believes this can become one of the biggest barriers to progress. 

Imposter syndrome does not necessarily disappear as experience grows. Even accomplished professionals can find themselves questioning whether they are good enough or whether they truly deserve their success. The difference lies in learning not to let those thoughts dictate what you do next. 

“Don’t wait until you feel completely ready. Ask questions, learn from the people around you and do your best. You don’t have to know everything, and you certainly don’t have to be perfect. There is a difference between recognizing that you have something to learn and convincing yourself that you are not capable.” 

Lessons From Different Cultures and Markets 

Jolene’s years working across diverse cultures and markets have taught her the importance of remaining open-minded. There is rarely a single formula for success, whether in business or in life. Understanding people, appreciating different perspectives and building genuine relationships can make all the difference. 

Her experience has reinforced the importance of looking beyond individual responsibilities and understanding the people involved in a situation. Different cultures and professional environments bring different expectations, experiences and ways of approaching challenges. Listening carefully and recognising these differences can help people work together more effectively. 

As Jolene puts it, when you over-index on the relationship, the rest often follows. 

For her, relationships are central to successful collaboration. Commercial knowledge and professional skills matter, but so does the ability to understand people, build trust and communicate with consideration. Strong relationships can make difficult conversations easier, encourage the exchange of ideas and create a foundation for working towards shared goals. 

These lessons have also influenced her approach to personal development. Remaining curious means accepting that there is always something new to learn from others, regardless of their background, experience or professional position. 

Rather than treating success as a fixed destination with a single route, Jolene sees value in staying open to different experiences and allowing them to expand her understanding of people and the world around her. 

Discovering an Unexpected Passion for Public Speaking 

For Jolene, stepping outside her comfort zone has never been limited to her corporate career. One of the most unexpected discoveries along her journey has been her passion for public speaking. 

It was not something she had necessarily imagined herself pursuing, yet by giving it a chance, she discovered an entirely new avenue for personal expression and connection. Public speaking became more than standing in front of an audience. It became an opportunity to share experiences, tell stories, challenge perspectives and create conversations that resonate with people. 

That discovery reinforced something she now encourages others to embrace: you cannot always know what you are passionate about until you try it. 

We often place ourselves in boxes based on our professional titles, existing skills or the roles we play in our personal lives. We become comfortable with what we know and sometimes convince ourselves that certain opportunities are simply not for us. But our current abilities do not define our future potential. 

By trying something new, we give ourselves the opportunity to discover strengths and interests we might never otherwise have uncovered. 

Jolene’s advice is to remain curious throughout life. Learn a new skill, explore an unfamiliar subject, accept an opportunity that challenges you or simply put yourself in a situation where you have something to learn. Not every experience will lead to a new passion, but every experience has the potential to teach you something about yourself. 

A Personal Turning Point in 2024 

Alongside her professional achievements, however, Jolene’s journey has prompted a deeper reflection on what success actually means. 

In 2024, a personal experience forced her to turn her attention inward and reassess her own wellbeing. Like many people, she had spent years balancing responsibilities, meeting expectations and showing up for others. It became a turning point in recognising how, when you’re in the challenging phases of life, your wellness becomes even more important. 

That experience strengthened her interest in holistic wellness and the connection between physical, mental and emotional health (Regulate, Fuel, Perform). It also reinforced her belief that success should not be measured solely by professional accomplishments or how much we manage to achieve. It should also be measured by how we feel, how we live and whether we have the capacity to enjoy the life we are building. 

“We spend so much time trying to be the best at everything we do, but we sometimes forget to look after the person who is doing it all.” 

Understanding What Wellness Really Means 

For Jolene, wellness is not about perfection or following a rigid set of rules. It is about self-awareness, understanding what you need and making conscious choices that allow you to function at your best. It means recognising when you need to slow down, establishing boundaries, making time for recovery and understanding that asking for help is not a sign of weakness. 

It also means accepting that wellbeing is personal. There is no universal formula that works for everyone. The important thing is to develop habits and practices that support you physically, mentally and emotionally, allowing you to navigate life’s demands with greater resilience. 

She is especially passionate about encouraging people to stop waiting for the perfect moment to invest in themselves. We often tell ourselves that we will rest when work becomes less demanding, pursue a passion when life becomes less busy or prioritise our wellbeing when everyone else’s needs have been met. 

But life rarely becomes perfectly convenient. 

Why Putting Yourself First Matters 

In Jolene’s view, putting yourself first does not mean putting others last. It means understanding that your wellbeing influences how you show up in every area of your life. Whether you are a professional, a leader, a partner, a parent, a friend or someone pursuing a completely different path, your physical and emotional capacity matters. 

Being at your best does not mean being available to everyone all the time or never struggling. It means investing in yourself so that you can approach your responsibilities with greater energy, perspective and self-awareness. 

Whether you want to be an outstanding procurement professional, a better leader, a supportive partner, a present parent, a confident public speaker or a successful wellness coach, the principle remains the same. You cannot continually give to everyone else while neglecting yourself and expect to operate at your best indefinitely. 

Exploring New Possibilities 

Projecting forward, Jolene is continuing to explore opportunities that bring together her interests in storytelling, personal development and holistic wellbeing. Rather than defining her future by a single professional title, she is interested in building on her experiences and using what she has learned to encourage and support others. 

Her journey has taught her that growth is not a destination. It is an ongoing process of questioning, learning, adapting and discovering new possibilities. There will always be something more to understand, another challenge to embrace and another opportunity to become a little more confident in who you are. 

The Courage to Begin, the Confidence to Grow 

In due course, Jolene’s message is simple: do not allow fear, self-doubt or the need to be perfect to determine the limits of your life. 

Step outside your comfort zone. Ask the questions. Learn something new. Give yourself permission to be a beginner. Do not let imposter syndrome convince you that you are incapable of achieving something simply because you have not done it before. 

You might discover a passion you never expected, develop a skill you never knew you possessed or realise that you are capable of far more than you had imagined. 

And while you pursue those possibilities, remember to look after yourself. Your ambition matters, your relationships matter and your responsibilities matter, but so do you. 

Because the starting point for becoming the best version of yourself, in any role or area of life, is recognising that you are worth the investment. 

Your potential is not defined by where you begin. Your future is shaped by your willingness to grow. And the more you invest in yourself, the more you have to give to the world around you.