You can always pivot when you’ve reached a point where you’re feeling stuck or like you’re not learning as much. It just takes time, patience, and process.

Cherita Ousley’s story is a powerful reminder that your career path doesn’t have to be linear to be successful.

She started off her career aiming to become a physiotherapist, earning both her Bachelor’s and Master’s degrees in Kinesiology. Her studies focused on body movement in the context of physiotherapy, occupational therapy, and sports medicine. During grad school, she even pursued research, working closely with a professor on she even pursued research, working closely with a professor on preventing falls in persons with multiple sclerosis (research and thesis).

Today, Cherita is a Product Manager at Microsoft, shaping the help and assist features for Microsoft 365 Copilot on the Data Platform team. Before that, she was a Software Engineer—and before that, an Exercise Specialist and Personal Trainer.

Exploring new career paths

With a keen interest in physiotherapy, Cherita worked as an Exercise Specialist to see what the day-in-the-life was like. After 8 months, she realized that she did not want to commit to another 3 years of school. She pivoted into personal training across different fitness studios. It was fun, but unstable and she had to constantly put herself out there.

Then a couple of friends in tech suggested she try coding because “tech isn’t going anywhere.” Intrigued, she enrolled in a full-time 3-month Coding Dojo bootcamp. It meant quitting her job as a personal trainer, but she was all in. There, she learned multiple coding languages and stacks—advancing only by passing each rigorous test.

Turning classroom knowledge to real world experience

After her bootcamp, Cherita worked on side projects to showcase her application of skills. She googled different projects and followed YouTube tutorials to gain experience. She networked and found ways to gain exposure and experience. Eventually, she became a Teaching Assistant for another coding bootcamp. That experience led to her first developer job as a Junior Application Developer at the same company where she once worked as an Exercise Specialist!

As she continued to build up her skills through side projects, Cherita continued to stay involved and volunteer with tech communities like Black Girls Code. At one event, she was really inspired by a Microsoft panelist and connected with her. That’s how she found out about the Microsoft LEAP program which recruits, develops, and upskills people with non-traditional backgrounds. She applied for this competitive program and eventually landed her first role at Microsoft as a Software Engineer!

How to build a strong network

• Don’t go into an event or conversation expecting anything or thinking something will come out of it.
• Introduce yourself and share what your goals are and where you’re currently at.
• Be curious about how people are doing what they are working on and offer to support (don’t be transactional).
• Use LinkedIn to build up your presence and stay connected. Don’t be afraid to ask people for tips, advice or profile endorsements/recommendations.
• Get involved with different tech communities (e.g. Black Girls Code, Digigirlz, Girls Who Code).
• Talk to lots of people who are already in the space you want to be in and ask them what they do.
• Follow people who work in your dream companies to understand what they’re doing.

Breaking into tech from a non-traditional background

1. Define what you mean when you say you want to be a part of “Big Tech” and be clear about it.
2. Familiarize yourself with the space you’re interested in. If you want to become a Software Engineer, then look for SWE resources to learn about languages, data structures, and algorithms.
3. Work on side projects to develop exposure, skills and experience.
4. If you enjoy it, then invest your time in taking more advanced courses and joining different programs.
5. Find mentors and peers who are already in the space you want to be in. Share your progress and ask for feedback.
6. Be open to smaller opportunities that will help you eventually get into big tech companies.

Cherita’s final words of advice

• You need to do the work while developing yourself everyday.
• Be patient because everything is a process.
• Building relationships never stops.

Thanks for reading 🌻

Thank you so much to Cherita for taking the time to share her unique career journey with us! I hope this inspires you if you are interested in joining big tech but have no idea where to start. There’s definitely a path forward and there are so many resources that you can leverage (like Microsoft Learn where I got my technical certifications).

Explore Cherita’s story in her own words: Kinesiology to Technology and find more inspiring stories in my #MakingTheMove series!