My Pivot Journal is a Ventures Africa weekly series documenting people’s career transitions from one industry to another, especially to tech.
Throughout her life, Olufela Osideko had various aspirations. While working as a sales assistant in a supermarket’s pharmacy section, she dreamed of becoming a pharmacist due to the job security it promised after graduation. The pandemic’s arrival also sparked an interest in music, but unfortunately, these dreams never fully materialized. But everything changed during the lockdown when she was introduced to the world of cybersecurity. Amidst uncertainty, Olufela seized the opportunity and embarked on a new path. Here is her pivot journal.
How it started
As a child, I had many interests, including playing video games, but unfortunately, it wasn’t considered acceptable by others around me. I have a vivid memory of the day I joined a friend at school to play games, and upon returning home, my cousin reprimanded me for engaging in what they perceived as a male activity.
Growing up, I had limited access to a computer. It wasn’t until I was preparing for the JAMB exam that I had my first direct encounter with a computer. It was also during this time that I delved into the world of graphics design, further expanding my experience with computers.
After completing high school, I pursued a science-focused path. At the time, the prevailing options seemed to be either studying medicine to become a doctor or pursuing a career as a pharmacist. My interest was drawn to the latter, especially because I was working at a supermarket with a pharmacy section, and I aspired to be like the professionals there. Despite my efforts taking the JAMB exam three times, things didn’t work out as planned.
Then came the year 2020, along with the global outbreak of Covid-19. Prior to the pandemic, from January to February 2020, I diligently attended tutorials to prepare for the exam. Although I achieved a score of 265, which was decent, I had hoped for a higher result around 300. Unfortunately, with the onset of Covid-19, everyone had to stay at home, disrupting plans and routines.
I discovered my talent for music during this time, and it occurred to me that attending a music school could be a great opportunity to develop my skills further. With each passing day, my freestyling skills improved, and I began to entertain the idea of forgoing traditional university education to attend a music school. I wanted to enhance my voice, master the guitar, and aspire to become a global singer. However, I knew my parents may not view this career path favourably, especially for a young woman. This internal conflict left me feeling uncertain and confused about which direction to take.
A friend of mine noticed I was down and sent me a link to check out CyberGirls Fellowship, a free 1-year program that equips girls and women aged 18–28 with globally sought-after cybersecurity skills, getting them certification-ready and positioning them to start a career in cybersecurity. Given that I wasn’t very tech-savvy and didn’t have a background in computers, I registered more out of curiosity and a desire to follow her advice than any real expectations. During the registration process, I came across a commitment requirement of seven months for the fellowship, and I couldn’t help but laugh at the idea. I was unsure if I could dedicate such a substantial amount of time to this unknown “thing” that I had just gotten myself into.
After a few months, I received a call from someone who informed me I was chosen but would I be willing to commit seven months to the learning process? It was a significant decision to make, considering that I had no prior knowledge of tech or cybersecurity. However, the idea of leaving my house every morning and feeling like I was actively engaged in something motivated me. So, despite my lack of expertise in the field, I agreed to it.
Starting out in the tech field can be overwhelming for many, as there is an abundance of resources available. Even now, I still face the challenge of information overload and come across numerous courses. However, Cybergirls played a crucial role in shaping my focus and guiding me toward what truly mattered. As someone with a non-tech background, the learning process was like navigating through the unknown since I lacked familiarity with how things worked in this domain. Nevertheless, the program laid a solid foundation for my journey.
Cybersecurity is a diverse field with various niches, and as beginners, we were advised to choose a specific area to avoid feeling overwhelmed. As we advanced, the time came to select a specialization. After thoughtful consideration and self-reflection on my interests, I made the decision to pursue Penetration Testing and Vulnerability Assessment. And this is because I loved the offensive side of cyber security. I love breaking into systems, exploiting bugs in software, and finding vulnerabilities that give them access.
I pursued my learning journey through TryHackme, a comprehensive platform offering cybersecurity education. Additionally, I explored Hack The Box, another platform in the cybersecurity domain. The platform’s main offering might not be beginner-friendly, but they do have an alternative – Hack The Box Academy, which caters more to beginners, making it accessible and accommodating for learners at various skill levels.
I also followed a few selected individuals, such as Hacker’s Plot videos, and David Bumbal, who conducts interviews with industry experts, among others. Keeping my list concise, I tried to avoid feeling overwhelmed while still gaining valuable insights from these sources.
One particular book I found fascinating was Tribe of Hackers by Marcus J. Carey which delves into the experiences of various cybersecurity professionals, detailing their journeys from the beginning, their career paths, and the factors that contributed to their success. It’s been incredibly insightful to learn from their stories. Additionally, Portswigger web academy has been an invaluable resource for me. The academy covers a wide range of topics related to web applications and web hacking, offering various modules that have played a crucial role in enhancing my learning experience.
By February 2022, we were all sitting in our hub, attending our graduation party, it was really amazing, and guess what? I was the overall best-graduating fellow for Cybergirls cohort 1.0, it was a dream come true.
Upon graduation, the next step was to pursue an internship. Initially, I was scheduled for a virtual internship with a company in Botswana, which I preferred over a physical one because I had plans to return to school. However, things took a different turn when an Information Security company called Digital Encode reached out to the founder of Cybersafe Foundation, Confidence Staveley. They expressed their interest in having me join their team. This unexpected offer opened up exciting opportunities, and it presented an appealing prospect that I couldn’t resist. I resumed work officially as a Junior Penetration Tester.
How it’s going
From the outset, I believed my internship at Digital Encode would last for six months, after which I would figure out the next steps in my life. Surprisingly, after six months, I received a promotion and was offered a full-time position. Being a high school graduate, I never imagined being in such a significant role at that point in my life.
I began my career as a junior penetration tester and gradually progressed to become an Information Security Analyst. Eventually, I moved up to the position of Associate Consultant at Digital Encode. With this advancement, my responsibilities have significantly increased. I now have a team under my guidance, and part of my role involves sharing my knowledge and expertise with others.
Here at Digital Encode, I’ve been fortunate to work on numerous projects alongside an incredible team. Additionally, I had the rewarding experience of discovering a critical bug in a popular payment gateway. After reporting it, I was even awarded a bounty for my efforts. When I think of Bug bounty, I always think it is for the elite, until I discovered a valid bug myself.
While my journey has had its share of challenges, I remain optimistic about the future. I am unsure of what lies ahead, but I firmly believe that with dedication, hard work, and proper planning, I will accomplish remarkable things.
First, you need to know why you want to pursue a career in cybersecurity. While financial aspirations drive many individuals, it’s essential to recognize that money doesn’t always come quickly. In the cybersecurity field, some professionals have gained expertise through years of experience and hard work that you might not possess yet.
Sharing my learning process on social media platforms, such as LinkedIn, has proven to be advantageous. When it comes to job hunting, documenting the learning journey can have a considerable impact and make a positive difference in the eyes of potential employers. As you progress and mature in your career, having this record to look back on proves invaluable. It not only helps you track and measure your growth but also serves as a tangible representation of your accomplishments.