Very few people do not allow fear to prevent them from taking leaps of faith in their careers and make transitions to leave comfortable and secure jobs to go into new waters.

Attorney-at-law, Tricia-Gaye O’Connor is among the few. She left, what she calls, a comfortable role and has taken on a new and challenging, but rewarding one. Though she admits being scared, her excitement and drive to achieve success motivates her.

She recently resigned from her role as an in-house counsel for, National Commercial Bank, Jamaica Limited (NCB). She is now the managing partner and lead partner of Caribbean-wide corporate practice for international law firm, Dentons at their Jamaica office.

“After being called to the Bar in November 2002, I started practising commercial law at Myers, Fletcher, and Gordon (MFG) and stayed there until 2011. I transitioned from private practice to being one of the in-house commercial lawyers at NCB. I was in that position until the end of February 2023 and started my new role at Dentons at the beginning of March,” she told Our Today in an interview.

O’Connor said she went back into private practice because, though she was very good at her job at NCB, she was too comfortable and wanted to spread her wings to do more activities that would challenge her beyond her imagination.

“Everybody speaks about change and doing the things that frighten them. I was at a stage where I said ‘it’s time to do something that really scares me’ and that was leaving the safety and security of what I knew. I worked with a very good team and was leaving a good organisation to go into the unknown,” she said.

“In the context of having a mortgage and children, that was a huge, bold step, but I had to do it. The opportunity to work at Dentons presented itself and it was quite exceptional. To be the managing partner and helping to build out the office in Jamaica is a big deal for me. I think that if I had stayed in my nice, secure, and comfortable environment, I would have always wondered ‘what if’. I didn’t want to do that,” she continued.

As her profile states, O’Connor specialises in banking and finance advisory and transactional work. Her experience as counsel includes providing legal support to management and operational teams in banking, credit finance, private placements, life insurance, information technology, and fintech start-ups.

As a lawyer for 21 years, O’Connor said that she does not regret her decision to become an attorney-at-law. “I have not once regretted it. I didn’t know what to expect and it turned out to be so much better than what I could have imagined,” she highlighted.

She shared how grateful she is for the experience of being in-house counsel for NCB as it exposed her to the business of the financial sector.

“Being in-house, you know what your clients think when they receive advice, you know what they’re looking for and its usefulness, you know exactly how to craft responses. Going from in-house to private practice makes lawyers unique in the sense that we have experience from both sides. In private practice, there is one perspective, but in-house means that you’re a part of the business of your client. So, their success is your success. Being able to take that kind of knowledge and experience elsewhere and apply it makes for a very interesting perspective,” she said, adding that she missed handling different types of matters in private practice because of the businesses that clients engage in.

For any other attorney-at-law who may be considering the switch back into private practice, O’Connor said, “you will have to test yourself and stretch yourself, but it’s very exciting,” explaining that though tests will come, making such a change will give them upper hand where experience is concerned.

FROM MANAGEMENT STUDIES TO LAW

Her original plan was to study business and focus on various aspects in the business world. It was almost second nature as her parents had their own business in the auto parts industry. However, she did not get excited about her studies.

“Initially, I thought it was best to do business. When I started, the theories never excited me. I remember in my first year as a student of Management Studies at the University of the West Indies (UWI), Mona, my friend, Damien Stewart, said that I should do law. I was not interested and I let him know. I didn’t know the depths of what law was about and there were no lawyers in my family. So, I had no one to give me perspective on what it would be about,’ O’Connor said.

“He said that I should do it to keep my options open. I acknowledged him and then brushed him off. On the very last day of inter-faculty transfers, Damien found me in the library and annoyed me into submitting an application. I still was not interested. We went back and forth until I caved and said, ‘you know what, fine. Let me just do it so that I can get you off my back, ’ she continued.

O’Connor said she remembers filling out the forms in triplicate originals. “I said to myself, ‘I can’t believe I’m doing this just to get somebody off my case’. I completed the application a couple minutes before the deadline and submitted the paper work. I then forgot about it.” 

To her surprise, O’Connor was accepted into the Faculty of Law. She got the news after attempting to collect her grades when the staff in her faculty office said, “congratulations, you’re in Law.”

She has not looked back since.

LIFE LESSONS LEARNED WITH TRANSITION FROM IN-HOUSE TO DENTONS

As a mother of two boys, O’Connor said that it is important to teach her children that they should not box themselves in to any particular space throughout their lives.

“I’m feeling proud of myself for making this change at this stage of my life. It is never too late to try something new. That’s something I’m trying to teach my sons from now. You don’t need to pigeon hole yourself into any particular space. I’ve learned about the principle of being comfortable with being uncomfortable and this is what this transition is for me,” she shared.

“I understand that I will be uncomfortable for a while but it will be okay because after some time, I’ll get the hang of it. I know there is a learning curve and that there are going to be challenges but it’s okay because this is how I will achieve growth. I have to do this and be stretched,” she continued and added that she looks forward to some really fabulous things happening in her capacity at Dentons.

In a moment of wisdom sharing, O’Connor said that being in the comfort of her previous job prepared her for the place that she is currently in.

The “business acumen that I’ve been exposed to became part of me as I was acclimatised to the ins and outs and principles of the job. I did not realise how natural it was for me to execute job tasks until I was put in a new space and seamlessly applied the knowledge,” she said.

Send feedback to [email protected]