OwnTrail | Blog

Storytelling, mentorship and weathering the highs and lows with Aleenah Ansari

We chatted with Aleenah Ansari about her journey as a writer in and out of tech, journalist at heart, mentor, and more.


Storytelling is a strong throughline in your trail, appearing in both personal and professional milestones. Where did this love of story come from, and looking back, did you expect it to lead you to where you are today?

As a queer Pakistani woman, storytelling has always been the heart soul of who I am and how I talk about myself. I grew up sitting at the foot of my grandma’s bed as she weaved stories of picking mangos from her neighbor’s trees or pulling pranks on her siblings.

I never thought that storytelling would become a part of my career until I started college. During my freshman year, I accidentally filled out the application to be a writer at my college’s newspaper, The Daily of the University of Washington. I traded in Chemistry study groups and Biology office hours for interviews with artists, changemakers, and educators of color who were dedicated to lifting as they climb. Somewhere in between early morning interviews and late-night transcription sessions, I began to see myself as a writer who wanted to empower communities that weren’t always represented in the media. I found that interviews were a sacred space – people would share not only what they did, but who they were. We discussed questions like “what gets you out of bed in the morning? When do you feel the most connected to your work?” These are the questions that I continue to ask colleagues, collaborators, clients, and folks that I meet.

“Somewhere in between early morning interviews and late-night transcription sessions, I began to see myself as a writer who wanted to empower communities that weren’t always represented in the media.”

Storytelling has continued to be a core part of my work, title or not. I’ve done everything from telling the stories of engineers behind Microsoft’s underwater datacenter and Yammer community for visa-dependent employees to highlighting authors and entrepreneurs of color who share their own non-linear journeys. My work has been featured in Microsoft Inside Track, The Seattle Times, Center for Neurotechnology, GLAAD, Kulfi, CNBC Grow, and more.

While you’re building an impressive career at Microsoft, you’ve actively sought out and worked with organizations of all sizes including the locally-focused vending machine pop-up Gender Vender. How have your experiences at larger companies helped your work with smaller orgs and vice versa.

One of the greatest privileges of working at a large tech company like Microsoft is that I have virtually limitless resources to tell stories and try out new initiatives. Plus, how often do you get to work on stories and products that could reach hundreds of thousands of users? Working at Microsoft has taught me how to intentionally create inclusive experiences for everyone, and the importance of asking for feedback whenever possible.

In every organization, I focus on authentic community-building. I want to be a connector, someone who makes people feel a little less alone, especially when they’re paving their own way.

Since college, you’ve been active on both sides of the mentorship table. What are some of the most powerful lessons you’ve learned through these experiences over the years.

As a queer Pakistani woman in tech, I didn’t see people like me in tech. I also believe that you can’t be what you can’t see, which is why mentorship has been such an integral part of my life. I wouldn’t be where I am if I didn’t have mentors who advocated for me when I wasn’t in the room, and mentees who gave me more perspective on my own work.

One of the powerful things I’ve learned is that mentorship is a two-way street. Although you can count on me to give feedback on portfolios or share strategies about how to sell the impact of your work, I learn just as much from my mentees. In our conversations, we mutually share stories and advice, and it makes both of us much less alone. They also invite me to reflect more deeply on what gets me out of bed in the morning and when I feel the most connected to my work.

Mentorship has also taught me that you can learn from anyone. I believe in creating space for people to show up authentically, which is why I ask people about their dreams and the moments they felt the most proud of themselves.

P.S. If you’re trying to find a mentor that aligns with your values and goals, check out this article I wrote with tips on how to get started!

You wrote some beautiful and vulnerable words about imposter syndrome and identity. Why did you choose to share this on your trail? Who do you hope to reach by sharing your experience?

I always want to show up authentically, which includes sharing both the highs and the lows. The last few years have brought the highest highs: buying a condo, becoming a speaker and mentor, writing stories about representation in media for The Seattle Times, Grow, Kulfi, and more. These are things I could have only dreamed of when I was younger, and I know my 8-year-old self would be incredibly proud of the woman I’ve become.

“These are things I could have only dreamed of when I was younger, and I know my 8-year-old self would be incredibly proud of the woman I’ve become.”

In between, there were moments of self-doubt and questioning if I really could succeed. The narrative I frequently told myself wasn’t one where I honored everything I’ve accomplished. It was one where I call myself words like “inadequate” or “lucky” rather than “hardworking” and “empowered.” As I’ve gotten further in my career, I’ve focused on celebrating my accomplishments while committing to continuous self-improvement – I can continue to work on my craft as a writer, and I’m proud of how far I’ve come.

I take great comfort in knowing that rejection is redirection, a mantra that has kept me going when I get yet another rejection email in my inbox (something that happens at least twice a week). I hope that sharing my journey in its entirety makes people feel a little less alone, while also making the statement that your career isn’t meant to be linear! Your career goals will change and shift with you, and that’s a good thing.

You’ve put your career aspirations out there, including an aspirational milestone to work at Spotify. What did it feel like to name this and other aspirations in a personal yet public way?

“I’m a firm believer that the more people know about your career aspirations, the more they can advocate for you when you’re not in the room when the right opportunity arises.”

I’m a firm believer that the more people know about your career aspirations, the more they can advocate for you when you’re not in the room when the right opportunity arises. By telling every mentor, colleague, and manager about my dream of working as a creative director at Spotify, I hope that this helps me manifest my goals into existence. So if you’re a Spotify recruiter (or a company that’s telling multimedia stories about the people behind products and initiatives), my DMs are always open!

I’m also a big believer in having dreams and aspirations that scare you a little – it’s a sign that you’re on the brink of something great. As my dreams and goals shift, I know I’ll continue to use OwnTrail as a platform to share my wins and my ever-changing career aspirations.


Learn more about Aleenah’s non-linear journey as a creative in tech, speaker, and mentor, and follow her on Instagram (@AleenahAnsari) and LinkedIn for updates on upcoming talks, career tips, and updates on my latest travel adventures.

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