We caught up with the brilliant and insightful Nilaja Montgomery a few weeks ago and have shared our conversation below.
Nilaja, thanks for taking the time to share your stories with us today What was the most important lesson/experience you had in a job that has helped you as a business owner?
While in a previous role within a tech giant company, I got the best advice I had ever been given about promotions and climbing the corporate ladder. It was this…there are no ladders, only maps. At first, I couldn’t believe my ears as I had come to my boss’s boss to ask how do I hone my skills for the next position within the company. She told me to hone the skills that I enjoyed honing the most. And actually, as I type this, I am realizing that talk is what really made me realize that I wasn’t happy in the corporate sector. I wasn’t happy doing the same types of things every day. I wasn’t happy having the same conversations, albeit with different clients, but the monotony made me numb. I wasn’t excited to go to work. When I was excited to log into my computer, it was to see my coworkers and find out how they were. It was to do everything but the business I was paid to do. So, I had to make a change. Now, I am back in school and getting my second master’s. This one is for Clinical Mental Health Counseling. My prior degree is an MBA. It’s funny; I pivoted to the MBA from a Doctorate in Physical Therapy when I couldn’t find childcare for my then 2-year-old while my husband was deployed. But that’s a story for another day. The point is, the days of corporate ladders are over, in my opinion. This same boss prompted me to read “Lean In” by Sheryl Sanberg. It was so eye-opening. In that book, she compares her career to that of a jungle gym. That stuck with me forever and is a visual I come back to often. I remember the days of navigating the jungle gym during recess in school back in Gary, IN. It was complex and took skill to ensure you didn’t fall flat on your face in the dirt. I loved it, and it was fun and challenging. The goal was always to be the one standing on top. When I did stand on top, the accomplishment was grand. I am back on the jungle gym of life!
Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
Hello, Folx + Friends. My name is Nilaja (knee-lah-jah), Jendayi (gin-dah-yee). I am an Amazon Best-selling Author + currently utilizing my project management skills as the Director of Operations for a boutique tech company, Veterans’ Digital Ally. I am also a Counselor in Training at Adler University, focusing on Social Justice issues and starting my practice in 2026! I have been speaking and sharing my story of leaving the Corporate Arena and creating my own arena. I am a veteran of the Iraqi War, where I helped to save lives as the Brigade Medical Supply Officer and the Evacuation Platoon Leader, assisting soldiers who were injured to safety and medical help in Landstuhl, Germany. I have been married to my veteran for over 17 years, and we have one kid who’s pretty amazing, in my biased opinion. We run Veterans’ Digital Ally and work with as many social impact groups in Colorado as possible to level up and scale their businesses. We are passionate about closing the digital equity and accessibility divide. We are currently working with Comcast and Mt. Carmel Veteran’s Resource Center to pilot the need for our program to help with the Digital Accessibility Plan for the State of Colorado! Wish us luck!
What’s a lesson you had to unlearn and what’s the backstory?
A major lesson I have had to unlearn, and in many ways, I am still unlearning, is that my value lies in my productivity. Rest is a revolution. I used to work myself until I was so tired I couldn’t function. It began when I was a child in the Gifted and Talented Program at the now boarded-up Benjamin Banneker Elementary School in Gary, IN. I had recently moved to Gary from New Orleans, LA, and was picked out by teachers as a gifted student. The pressure began. I was constantly told through actions and culture within the school that it wasn’t okay to be average; we had to be the best. We had spelling competitions and science olympiad.
I participated in the City-wide Science Fair, where we were interviewed for the city paper and asked what we wanted to be when we grew up. I, of course, wanted to be a doctor. It wasn’t enough to want to help people. I had to know how and have a plan to get there. I would eventually attend college at Indiana University. I wanted to apply to the music school because my passion was and still is music. However, I was told by the adults in my life that music was a hobby and that becoming a doctor was what I should be using my scholarships for. So that’s what I tried to do. I pulled all-nighters often, running off of very little sleep. I also participated in sports and nearly lost my mind. I didn’t become a doctor but graduated with a bachelor’s in Kinesiology. I was and still am fascinated by the human body. But it’s no secret that I don’t always value Western medicine’s approach to healing or treating symptoms. I am learning to listen to my body and rest when necessary. I have unlearned the idea of perfectionism and pushing past limits to recognize my limits and treat them with the respect they deserve. This is when my best work has been accomplished. Thanks to my therapist for helping me reassess and reorganize my values. I value myself in a way that I am unsure I had ever valued myself before.
Have you ever had to pivot?
While I was still chasing my childhood dream of doctorhood, I applied to twelve Physical Therapy Programs. I fully expected to get into a program near family or even within Colorado. That did not happen. I got into the one program that I had only applied to because my best friend from Basic Training at Fort Jackson had applied to the same program. I didn’t expect to get into that program and hadn’t even considered it a reality. That was the only program I was accepted to. When I got the acceptance letter, my husband was deployed. I sent him an email, hoping he could help me figure out how to make this work. We had a 2-year-old and no childcare. I tried to figure it out, but all the plans kept falling through. Defeated, with my 2-year-old in the backseat strapped into his car seat, sleeping, I sat in a Starbucks parking lot. I was crying like a 2-year-old toddler myself when I got a phone call from my husband from overseas. I answered in the most cheerful voice I could, Hi! He immediately asked, what’s wrong? I told him I couldn’t figure this one out. He suggested that I inquire about MBA programs. I was primed for Graduate School and shouldn’t waste my GRE scores and pre-requisites. So, I drove over to Colorado Technical University and enrolled that day. I completed my MBA in less than the two years afforded me and began working in the corporate world, making more money than ever. I think I needed that boost of confidence to realize that anything is possible. During my time in Business School, I was tested in more ways than one, but I succeeded, graduated, and landed the job I intended to land. When you can pivot once and find success, pivoting becomes easier each and every time.
Contact Info:
- Website: https://www.nilajajendayi.com/
- Instagram: https://www.instagram.com/nilaja.jendayi
- Facebook: https://www.facebook.com/NilajaJendayi
- Linkedin: https://www.linkedin.com/in/nmonty/
- Twitter: DNA
- Youtube: https://www.youtube.com/@nilaja
- Yelp: DNA
- Soundcloud: DNA
Image Credits
Larissa Johnson Photography,