Chesaree Rollins of Chicago: Balancing Motherhood, Business, and Culinary Excellence

This Mother’s Day weekend, the Chicago Defender celebrates dynamic Black women excelling in their careers while guiding and nurturing their families.

With Mother’s Day around the corner, heartwarming tales of mother-daughter bonds take center stage. These stories embrace the beautiful whirlwind of motherhood and endure its ups and downs with love, patience, and unwavering commitment.

Hailing from Chicago, Chesaree Rollins (Chef CheSa) is the creative force behind CheSa’s Bistro & Bar in Chicago’s Avondale neighborhood. Building upon her success with CheSa’s Gluten Tootin Free Food Trucks, she sought to expand her culinary horizons beyond mobile dining and event catering. 

Her culinary passion thrives on captivating palates with a fusion of Creole and contemporary American flavors. Within the welcoming confines of the 1800-square-foot bar and restaurant, patrons can anticipate an artfully curated meal crafted from scratch with thorough care.

Balancing Motherhood, Business and Self-Care

Balancing a career with the responsibilities of motherhood is a journey marked by evolving strategies and heartfelt priorities. Rollins’s urgency to provide for her family often overshadowed the need for personal time. However, over time, she devised a plan where her family stepped in to offer support, enabling her to manage business and motherhood more effectively. 

“Recently, I decided to close the restaurant on Mondays and Tuesdays, dedicating those days solely to spending quality time with my daughter. Whether it’s a trip to the park, a movie night or simply cooking dinner together, these moments are essential for ensuring she feels cherished amidst my busy schedule,” said Rollins.

Despite managing her maternal responsibilities alongside her business endeavors, she radiates nurturing energy towards her staff.

“As a mother and a leader, I’ve found parallels between nurturing my daughter and guiding my team. I still have a maternal role in the workplace, and providing support and guidance to my employees has become integral to my leadership style. Instead of merely delegating tasks, I aim to offer a nurturing environment where individuals feel valued and supported. Whether it’s offering advice on handling challenges or providing resources for personal needs, I strive to be more than just a boss.” 

Rollins explained how she also pays it forward to her team by celebrating life milestones and organizing events to celebrate and reinforce the importance of compassion and empathy in leadership.

She recognizes the paramount importance of self-care in shifting between her responsibilities as a mother and a business owner. Whether she indulges in a peaceful massage or another restorative activity, Rollins understands that replenishing her energy benefits her health and happiness and enables her to show up as her best self for her family, team, and business.

“Prioritizing self-care remains an ongoing journey for me. Following a near-fatal stroke in 2023, I’ve been challenged to shift my focus from work to personal well-being. Finding a balance between caring for myself and fulfilling my responsibilities is a constant struggle,” Rollins said.

“Even simple acts like getting a massage seem elusive amidst the demands of daily life. However, I’m determined to prioritize self-care, recognizing its importance in maintaining my physical and mental health.”

Rollins says that establishing routines, like signing up for a massage membership, provides her a glimmer of hope in “reclaiming moments of tranquility amidst life’s chaos.”

How This Mother-Daughter Duo Shines

Chesaree Rollins and her daughter Chloe.

Mother-daughter partnerships in business can be compelling and rewarding. They often bring a unique dynamic to the workplace, combining the mother’s wisdom and experience with the daughter’s fresh perspectives and innovative ideas. 

Additionally, mother-daughter partnerships can serve as inspiring examples of female entrepreneurship and leadership, breaking down stereotypes and paving the way for future generations of women in business.

“Whenever I introduce a new dish or menu item at the restaurant, she becomes my trusted taste tester. Her feedback, as a young and honest critic, helps me gauge the appeal and quality of the food. I value her opinion on taste and visual presentation, as she provides a fresh perspective. She serves as my “director of taste,” guiding me in crafting dishes that resonate with our customers,” said Rollins of her 10-year-old daughter Chloe. 

Rollins notices that her daughter’s traits often reveal similarities. She possesses natural charm and social adeptness, and despite her young age, she demonstrates remarkable problem-solving skills and adaptability. This is especially evident during the challenges of the pandemic when she effortlessly navigated technology to stay connected with her friends. 

“Her innovative thinking and compassionate nature mirror qualities I strive to embody personally and professionally,” Rollins said. 

When contemplating the legacy,  Rollins stated, “I hope to leave for my daughter; I emphasize the importance of purpose, passion and longevity. While I encourage her to forge her path, I stress the significance of investing in oneself and creating generational wealth.” 

“Growing up with limited discussions about legacy and generational wealth, I aim to instill in her the value of building a lasting legacy beyond material wealth. My businesses are tangible examples of this legacy, showcasing the potential for future prosperity and stability,” she said. 

How She Built Her Business

The inside of Chesaree Rollins' restaurant CheSa's Bistro & Bar.

Learning to cook was a journey of self-discovery for Rollins. Her mother was often busy with work, so she took it upon herself to explore the kitchen and experiment with cooking. 

“I vividly remember thawing out chicken breasts and preparing simple meals while she was away, mimicking the steps I had observed her take. Despite my young age, I immersed myself in cookbooks, eager to learn and replicate the dishes I read about. While my grandmother was also a skilled cook, I didn’t have the opportunity to witness her culinary process firsthand. Instead, I relied on trial and error, gradually honing my skills through practice and perseverance.”

Her journey into entrepreneurship began during a corporate career, working as an executive for a food supplier company. However, a pivotal moment occurred when she was diagnosed with celiac disease while pregnant with her daughter Chloe. 

Faced with limited options for gluten-free food, she saw an opportunity to fill a gap in the market by starting a gluten-free food truck, purchasing an abandoned food truck in Chinatown, and embarking on a new chapter in her professional life.

“The evolution of my business saw various phases, from partnering with restaurants for catering to ultimately establishing a brick-and-mortar restaurant. The journey was challenging, including navigating a $2.5 million audit at my corporate job and being laid off. Determined never to be at the mercy of others again, I embraced entrepreneurship wholeheartedly.”

During the onset of the COVID-19 pandemic, Rollins pivoted her business model, transitioning from food truck operations to operating out of a ghost kitchen for pickup and delivery services. 

Despite facing setbacks and downsizing her team, Rollins remained resilient and focused on providing quality gluten-free cuisine to my customers. 

The success of the pickup and delivery services laid the foundation for the full-service restaurant that exists today at CheSa’s Bistro & Bar.

For more information on CheSa’s Bistro & Bar, visit


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