Kendra Cowart on Why Life’s Rejections Are a Blessing

The Chicagoan

Kendra Cowart’s story is one of those rare, layered tales that invites you to question what you think you know about the so-called “right path” in life. Kendra’s journey began in the western suburbs of Chicago, where, despite an upbringing she describes as privileged, she never quite felt like she fit in. Struggling to connect with the people around her, she constantly felt a need to explore life beyond the surface-level ambitions that others seemed content with. For Kendra, life’s rejections and obstacles weren’t just hurdles to overcome—they were turning points that ultimately led her to a more fulfilling life.

At 21, Kendra met a mentor who changed her perspective on what life could be. This mentor didn’t just provide career advice or life tips; she asked Kendra a fundamental question, one that would shape her entire approach to life: “How are people experiencing you?” This question opened up an avenue of self-reflection that many of us don’t explore until much later in life, if at all. Kendra realized she was seeking validation in the wrong places and needed to understand herself first to make meaningful connections with others. This wasn’t about changing her personality but about recognizing her strengths and focusing on where she could grow.

Despite her eventual focus on coaching, Kendra’s path was anything but linear. She enrolled at the University of Missouri (Mizzou), hoping to find her “tribe,” but her expectations were met with more isolation. Mizzou, she found, wasn’t the dream college experience she’d hoped for. But this setback only fueled her to look inward. Watching others seemingly glide through life while she struggled, Kendra yearned for a community that shared her drive and curiosity. Her search would eventually lead her to the world of network marketing, a turning point that shifted her focus to personal development.

Network marketing introduced Kendra to a world of personal growth seminars and self-help books, a journey that would expose her to people living the life she envisioned. She credits this period as a “blessing in disguise”—one that equipped her with tools to face life’s challenges head-on. Through workshops, seminars, and a budding interest in personal development, Kendra began to see the true value of self-improvement. For her, these experiences highlighted the importance of mindset, a perspective she now brings into her own coaching.

Today, Kendra is a full-time coach, working with the Life Score Foundation on the South Side of Chicago, a wellness resource center focused on social and emotional learning, workforce development, and financial literacy. She describes her role not just as a job but as a calling. Working with Life Score allows her to bring the same transformative tools that shaped her life to others in her community. In Kendra’s words, she’s there to be “the spark plug,” igniting potential in people who may not yet see it in themselves.

Kendra’s story is also one of resilience in the face of societal expectations. As a Black woman, she’s seen how people often view her through a specific lens, one that doesn’t always align with her experiences or ambitions. She’s driven by a desire to dismantle stereotypes and build bridges between communities, bringing a holistic wellness approach to spaces that might otherwise focus only on the bottom line.

Through her coaching, Kendra helps clients recognize that setbacks and rejections aren’t just unfortunate events to get over. “It’s all protection,” she says, emphasizing that everything that happens—whether it’s people walking away or situations not working out—is ultimately for your highest good. She believes this mindset has allowed her to navigate life’s challenges with a sense of peace, knowing that every rejection has, in fact, redirected her toward something better.

For those struggling to find their footing, Kendra’s approach is refreshing. She encourages you to embrace the unknown and to trust that the life you envision is possible, but only if you’re willing to grow and adapt. Her message isn’t just motivational—it’s practical, reminding us that personal growth is a lifelong commitment. Kendra’s journey isn’t about arriving at a destination but about learning to see each stage of life as a stepping stone.

The true lesson from Kendra’s story is one of self-awareness and resilience. Life’s detours, she believes, are not roadblocks; they’re necessary steps toward becoming who we’re meant to be. Her life is a testament to this, and through her work, she hopes to inspire others to find peace in the process, knowing that what’s meant for them will always find its way.