Today we’d like to introduce you to Keyana Darling.
Hi Keyana, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
My story begins on the southeast side of Houston, in a community where opportunities often felt out of reach. I was a high school teacher, showing up every day for my students while quietly carrying the weight of financial stress at home. As a single mom, I was doing everything I could to keep us afloat—teaching by day, parenting by night, and budgeting down to the last dollar in between.
There were moments I questioned whether I’d ever be able to break out of the cycle. I was passionate about education, but I was also burnt out and underpaid, making around $45,000 a year and living paycheck to paycheck. I wanted more for myself and for my children—more stability, more freedom, and more purpose. But like so many others in my position, I didn’t know how to take that first step.
Then one day, I decided to share my story publicly. I wrote a heartfelt LinkedIn post thanking someone who had taken a chance on me—not because I lacked the qualifications, but because they saw my value. I had the degree, the experience, and a wealth of transferable skills. I just needed someone to open a door. In that post, I was honest and vulnerable about my journey: from the classroom to the dream of breaking into tech, and my deep desire to grow if given the opportunity. I didn’t expect much—just hoped that maybe someone would listen.
And then something incredible happened. The post took off. It resonated. Thousands of people read it, shared it, and commented. And among them was someone who looked beyond my résumé and saw me—my story, my passion, and my potential. That single post opened the door to a life-changing opportunity: I was offered a role as an Onboarding Community Manager at Microsoft.
It was my very first role in tech. I had no prior corporate experience, but I brought with me the same heart and hustle I had in the classroom. I fully leaned into that role—welcoming new employees, creating a sense of connection, and building community within one of the largest organizations in the world. It was the role that changed the entire trajectory of my life.
But my journey didn’t stop there. I’ve always been a storyteller. Long before this career shift, I was creating content, working with brands, and building online communities on my own. So, when the opportunity came to step into a role as Social Media Strategist for the Microsoft Learn handles, I knew it was exactly where I belonged.
Now, I am on a team where we lead social strategy focused on educating and inspiring both business professionals and future learners—especially around Copilot. When I joined, our Instagram had just over 2,000 followers. A few months later, we’re closing in on 32,000. But what matters more than the numbers is the impact—the messages we get from people who say our content helped them understand, feel seen, or take the next step in their learning journey.
What sets me apart is that this isn’t just a job for me—it’s personal. I’ve lived this. I’ve marketed myself when no one else would. I’ve told my own story before I had a title. I know what it means to create content that connects, because that connection is what changed everything for me.
I went from a classroom in Houston to one of the most recognized tech companies in the world—all because I took one brave step and told my story. That single act of courage opened doors I never knew existed. And now, I walk through them not just for me, but for everyone watching—especially my children.
I’m living proof that you don’t need a perfect résumé to enter the room.
You just need your story, the courage to share it, and the grit to keep going.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
When I first started my job search. I’d submit applications and get rejected almost immediately—often without a second glance. It was discouraging to know I had the skills, the degree, and the drive, but still be overlooked because my résumé didn’t fit the mold.
Balancing job hunting with parenting was its own challenge. I was teaching full-time, raising my children alone, and trying to stay hopeful while facing constant rejection. There were nights I questioned if I’d ever get a shot—if anyone would ever see past the lack of “tech experience” and recognize the value I brought from the classroom.
But I kept going. I shared my story. I leaned into my strengths. And eventually, someone saw me—not just my résumé, but my potential. That moment changed everything.
So no, it hasn’t been smooth. But every obstacle made me more resilient, more resourceful, and more determined to open doors for others like me.
As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
We’d love to learn more about your work. What do you do, what do you specialize in, what are you known for, etc.? What are you most proud of? What sets you apart from others?
I’m a Social Media Strategist at Microsoft, where I lead content for our Microsoft Learn channels—and I’m also a lifestyle content creator who’s passionate about storytelling that feels real, relatable, and human.
By day, I help shape how we educate and inspire learners around the world, especially in the AI and digital skills space. By night, I create content that reflects the life I’ve lived: one full of resilience, humor, and heart. I specialize in content that connects—whether it’s helping someone understand a new tech concept or reminding them they’re not alone in their struggles.
What I’m most proud of isn’t a title or a follower count—it’s the messages I get every day from people who say, “You made me feel seen,” or “You gave me the courage to try.” That’s the impact I care about.
What sets me apart is that I show up as myself—always. Whether I’m on a corporate call or posting a reel, you’re getting the same Keyana: funny, transparent, a little goofy, deeply empathetic, and always real. I’ve built a brand on authenticity because I know what it’s like to feel invisible. I’ve been the single mom submitting résumés and getting rejected before anyone even read my name. I’ve been the woman with no corporate experience, just heart and hustle, hoping someone would take a chance.
Now, I use my platform to open doors for others—to show that you don’t need a perfect résumé to belong in the room. You just need your story, your voice, and the courage to use both.
Is there a quality that you most attribute to your success?
For me, it’s the courage to be open and speak up—especially in rooms where I may not feel like I belong. That willingness to use my voice, even when it’s uncomfortable, has been a defining part of my journey. I’ve learned that representation doesn’t just happen—it’s created when people like us show up, speak up, and stay true to who we are.
Being open means I’m always learning, always listening, and always willing to grow. But it also means I’m not afraid to challenge the moment when something needs to be said. I carry that mindset into every space I enter, whether I’m leading a conversation on social platforms or collaborating behind the scenes. It’s not always easy, but it’s always worth it—because every time I speak up, I’m not just advocating for myself, I’m creating space for others to do the same.
Contact Info:
- Instagram: https://www.instagram.com/therealmsdarling/
- Facebook: https://www.facebook.com/keyana.darling
- LinkedIn: https://www.linkedin.com/in/keyanajdarling/
Image Credits
Patricia Berry for the brown photo
