I passed my Security+ almost 6 months ago. I did not and have not used my time wisely. That changes today, October 13, 2025. Today I start the 30 days of TryHackMe.
It has taken me some time to be clear on the path of study when it came to a career in tech. I also had to overcome some personal barriers and learn a few valuable life lessons along the way. Through mental overwhelming, divorce and navigating changes at my current job, I have given it all to God and he has answered my prayers. As much as I would like to beat myself up over the last 6 months, I must admit that clarity has finally come.
While studying for the Security+, I was met with doubt and uncertainty about choosing this career path. As I scrolled through social media, I was enamored by the lifestyles people in tech had. Because of the enamored feeling, I was tempted to explore every single path: Security Engineer, data analyst, software developer. You name it, I've researched it. This pattern kept me in limbo for the last 6 months, but it also taught me where I want to focus my energy. Enters pentesting/ethical hacking/red team!
I am excited to have clarity on the path I want to take, but as anyone who has ever been interested in this field knows, there are various ways to get into this industry. Now that I have clarity, I can make a roadmap for myself.
My Transferable Skills
Before beginning this roadmap, I created a list of transferable skills I've acquired through various employment. These are soft skills, not technical skills — and they remind me I'm not starting from scratch:
- Communication
- Attention to Detail
- Adaptability
- Problem Solving
- Collaboration & Teamwork
- Report Writing*
* Honorable mention to report writing — I am a good writer, and that matters in this field.
Where I'm Starting
I have very minimal experience in the tech industry. I did a summer internship back in 2015 at an advertising company in the IT department. Through research, I understand that the roles I desire are not entry-level roles; I will have to curate this roadmap to my experience. There will be pit stops along the way in the form of entry-level positions.
Although I know what I want to pursue, I know that I have much to learn. With that being said, I will skip over the qualifications for those positions and focus on studying and learning. As I study, document, and learn, the path will become clearer.
My Goals
My goal for getting a job in this industry is April 27, 2026. I also have a goal of attending Defcon in 2026 — more specifically, I would like to volunteer with a vendor. Thinking through these goals, the importance of not only learning but documenting is even clearer.
The Roadmap
Since I am Security+ certified, I can start with the hands-on technical skills. Security+ teaches theory. I have signed up for TryHackMe for the year. I am committing to 30 consecutive days — not only to learn these skills but also to create habits through consistency and discipline.
While working through TryHackMe, I have also found a YouTube course on learning Python by Dave Gray. It is a 9-hour course split between 25 videos. I am currently on video 3. My deadline is October 24, 2025.
I am also starting Hacking: the Art of Exploitation by Jon Erickson. This, like the Security+ exam, is theory. I am using this book as a refresher on what I have already learned, while also having a reference as I learn coding.
At the halfway mark of the 30-day commitment, I will create a LinkedIn. After my LinkedIn is set up, I will not begin looking for a job right away. I will take a few weeks to understand the layout and algorithm. I will create a content calendar and regularly post to the platform.
The year will only have about a month or a little less left at this point in my roadmap. This is where I will start focusing on the Network+ certification. I wanted to go straight into a pentesting certification, but I want to be well-rounded in this field.
Things are subject to change, as I went through this in real time. If anyone has any advice, suggestions, or wants to chat about this — leave a comment!
I am ready to change my life.
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