The 19th Annual Sistahs-in-Law Retreat

By: Crystal-Claire Simmonds

The 19th Annual Sistahs-in-Law Retreat coincided with the first major snowfall of Toronto’s 2025 winter season. Although I braved the weather to make my way to the Queen’s Quay district downtown, I fully expected the event to be sparsely attended – perhaps just myself and the organizers. Instead, I was shocked to see hundreds of BIPOC guests and speakers, dressed in business-casual attire, pouring into the beautifully decorated venue despite the snow and frigid temperatures.

As soon as the elevator doors opened, the delicious aroma of Caribbean cuisine filled the air. Guests helped themselves to chia–coconut and berry parfaits, Jerk chicken, Escovitch fish, assorted salads, and breakfast sandwiches. While enjoying their meals, they could also browse a vibrant array of Black-owned business booths set up just outside the main hall. Vendors showcased jewellery, makeup, natural and organic body products, and even a hireable photo booth, among others.

Following breakfast, the president of the Black Female Lawyers Network, Rebecca Scantlebury, and a distinguished group of panelists – each with unique legal backgrounds – shared impactful personal stories about their professional journeys. They spoke candidly about overcoming adversity as they pursued their legal qualifications, as well as the grit and determination required to excel in their respective fields.

A recurring theme throughout their stories was the power of community. In such a supportive space, attendees were able to reflect on whether their own experiences were “normal” or if they needed to advocate for change. Many expressed that hearing directly from those who had already achieved key milestones made their own professional goals seem more attainable – just as track and field star Roger Bannister transformed the “impossible” into reality by breaking the four-minute mile, his breakthrough made it possible for many others to follow.

After the main talks, breakout sessions began. Some involved physical activities, while others focused on the development of legal skills. One of the latter was the OJEN interactive panel discussion, where high school students who are aspiring legal professionals “L’il Sistahs” received guidance from the “Big Sistahs” – lawyers and law school students who offered insights on applying to law school, avoiding burnout, and preparing for career challenges. The panelists included lawyers, Esinam Ayesu-Attah andChioma Oriwu, and law students, Maureen Coulibaly, and Macaila Russell. It was moderated by OJEN’s Kassandra Thompson.

The Big Sistahs emphasized their desire to be the mentors they themselves wished they had earlier in their journeys, and they generously answered every question. A lunch break followed, after which the L’il Sistahs were guided by the Big Sistahs on how to form sound legal arguments for the mock debate which covered a discrimination-related case using both statute and case law to structure their arguments. Once presentations were delivered and feedback was shared, the event gradually drew to a close. Finally, attendees collected their gift bags, exchanged contact information, and thanked the panelists for paying it forward on such a cold winter day – before saying goodbye until next year.