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Monday Motivation - Kaila Headley

Senior Legal Officer, Government of Barbados

Who is Kaila Headley?

I am a professional who has been in the legal field for almost a decade. I have a Master of Laws in International Business Law which I achieved in 2020. I am focused on my career development, education and fitness. I am a gym fanatic. Working out is my stress reliever and the gym is my place of peace, I go to the gym at least 5-6 days a week. I LOVE to travel and shop. I cherish my family and friends. My favourite downtime activity is catching up on my legal tv series, such as The Good Fight, Law and Order SVU and All Rise.

What does your day-to-day entail?

On a typical day, I wake up and check emails while drinking green tea. Turn on my laptop and begin organising my to-do list for the day. I usually have meetings daily so I work on my tasks between meetings. Legal work involves reading or reviewing copious documents so I am on my laptop at least twelve hours a day. My work as an in-house counsel for a statutory government authority is so diverse, I handle a wide range of matters including bankruptcy and insolvency, drafting legislative amendments, employment disputes, compliance, internal policy development, personal injury, data protection. I am constantly learning new things and new areas of law, so it is never boring.

Tell us your most memorable achievement to date.

My most memorable achievement was being chosen for the World Bank Youth Summit 2018 in Washington DC. It was an unforgettable experience, where I had the opportunity to network with young professionals from all over the globe working in different careers. What made an impact on me was how many of them came from developing countries like Barbados and overcame all kinds of odds to be successful in their respective careers and work with large conglomerates and multinational organisations which some of them founded themselves.

Any advice for our readers who are interested in working in your field?

You have to possess a love for reading because you will be doing a lot of it. Ensure that while you are studying, you secure some kind of internship in a legal office so that you can build your experience while figuring out if this profession really is for you. It can be a highly stressful yet thankless career because of some of the negative perspectives of lawyers from the general public. One of the misconceptions is that attorneys are all paid well but Barbados' job market is a little different so please do not pursue this career for the money. You have to love the law to enjoy it. One of your core responsibilities as an attorney will be to uphold ethical standards and always display professional behaviour to renew public confidence in the profession in Barbados. Finally, this practising in this profession requires a healthy work-life balance, maintaining mental health is crucial, so you need to find an outlet by doing other activities so that the career does not consume you.

Is there anything else you would like to share with us?

My career path was a little different. I began working for an insurance company as soon as I graduated from law school. It wasn't technically a legal position but legal work was involved. I then went on to the government in 2012 until the present, working in various government departments. So, my advice is that you should treat your career as a journey, you start at the bottom and gradually build your way up. No matter how daunting, it seems as long as you are dedicated and focused, you will reach your end goal.

I am always open to giving career advice in this field where needed, or for any collaborations. I may be contacted at


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