Taking a risk: putting defeat aside to claim her win

Jameela Roland embarked on a path of growth and learning that led to an unexpected, exciting career

Editor’s note: We caught up with Jameela Roland to hear the epic tale of her journey from homelessness to Microsoft. Here, she tells our writer her story in her own words.

I never expected to find myself homeless at 24.

In high school, I was that student who could give my work only 60 percent of my effort yet still get an A. It just came easy to me. And I had a plan: I’ve always loved Japan and wanted to attend university there once I graduated.

But by my senior year, I was struggling with depression. I started missing classes and watched my grades suffer. Things fell apart, and I didn’t get into the school I wanted. So, I made a new plan: I would attend a local college, improve my grades, and then reapply.

I ended up starting and restarting college at three different schools, but none panned out due to unexpected circumstances. My depression resurfaced. At one school, I learned I wouldn’t be able to transfer the earned credits that I needed to go to the school I wanted. It felt like every time I took a risk, it didn’t pay off the way I wanted it to.

I felt defeated. But I kept trying.

I got a job at a hotel chain before I eventually ended up working as a production assistant on the set of an indie film in Los Angeles. It was a great opportunity, and I learned a lot, including what it was like to live independently in a different state. When we wrapped filming, I realized I missed the cold, the rain, and my mom, and I headed back to Seattle to live with her.

Nowhere to go

Beyond occasional babysitting gigs, there were no “bites” during my job search. To help deal with my depression, I decided to get a dog who I could love and who would love me unconditionally.

I adopted Starship Trooper—a Labrador retriever, American Staffordshire terrier, and Rottweiler mix. I wasn’t making much money, and I realized that I should be feeding him better than bulk dog food. That food was trash. I thought, “I can’t keep doing this. What if he gets sick? I can’t even afford a vet.”

I reached out to a company that had contacted me earlier and started a new retail job in June.

But by August, our landlord had decided to sell his home. Because we were on Section 8 (a housing subsidy program), we couldn’t find a new place to live before we had to vacate. Unfortunately, most landlords wouldn’t consider us as tenants because the program carries a stigma.

We were homeless.

My mom and I went from spending the first, terrifying night in our car to “couch surfing” at the homes of family members and then to motels. Unfortunately, I had to leave Trooper at boarding facilities. I finally had the dog I had always wanted, but I couldn’t even see him. It wasn’t cheap, either.

Through this challenge, my mom and I stuck together. I was working to support us, with one goal: to survive. She took care of home base, and we searched for a new place to live. It was nerve-wracking and stressful, but we managed to find a townhouse by October.

Now or never

At my job, I learned that my manager had worked there for 20 years and still had to work weekends to make ends meet. I refused to accept that for myself. I didn’t want to just survive; I wanted to thrive.

My younger sister reintroduced me to the Year Up program, which paid a stipend and provided six months of career training along with a six-month internship with a Seattle company. You had to be no older than 24 at the start of the program, and I was weeks away from turning 25.

I thought, “If I’m going to do this, I have to do this now.”

Jameela Roland
Jameela Roland and her dog, Trooper

After six months of professional and technical training courses, Year Up assigned me to an internship. I was shocked to see that I was assigned to Microsoft, which I envisioned was more for coders. The internship was for a studio technician working with video content.

Within the first week, I was asked to slice video footage. By week two, I was able to go on location for a video shoot, which was so cool!

I had a great time in the role and learned so much, but I didn’t expect a job offer from Microsoft. But, at the end of my internship, I was the first person to be hired by Microsoft directly after my Year Up graduation. I had already been looking for my next job in that space, which felt daunting because I didn’t have a formal education and it was outside of the purview of Year Up’s support system. I was excited to have found a role on a team dedicated to helping me achieve my goals and grow my professional presence.

At my Year Up graduation, I served as the keynote student speaker. This led to me being invited to speak at a Congressional hearing with the Year Up founder about opportunities for youth to break the cycle of poverty. It was all so unexpected and exciting.

Jameela Roland and her mom
Jameela Roland and her mom

Seeding a future

I’m currently a business operations associate managing workload and video post-production work, plus I coordinate video shoots, deadlines, and more. I’m loving what I do, and I’m learning every day.

Life is so much better. I’ve since moved out on my own, and I appreciate that I have the security to take care of things when the unexpected arises, for Trooper and myself. I’m happy that my mom doesn’t have to be concerned about me and can now focus on herself. Because of my new career, our relationship has evolved from a caretaker relationship to a friendship. We still partner up, but now it’s when we want to, not because we have to.

College didn’t pan out, but I realize now that I didn’t properly assess risk when making my early choices. I didn’t realize all I could lose until I became homeless. When it’s time to do something different, I’ve learned to ask, “What can I lose? What can I gain?” I’m grateful that I took a risk and participated in the Year Up program.

Now I feel like a sprout on the ground. I’m ready to grow, and I’m getting the sunlight I need to do so. At Microsoft, I’m not just in the system, subject to movements beyond my control; I’m part of the system, contributing to the greater environment of change.