My Journey into Cyber Security: eJPT to eCPPT to OSCP (Part I)

Way back in November 2019 I was playing professional ice hockey and needed to transition into a real job that would pay the bills. I thought to myself:

“How am I going to get a job in cyber security?”

Why cyber security? Because I like computers, I like solving problems, and it pays well. Naturally what ensured was a plethora of YouTube videos, podcasts, and blog posts from middle-aged white men who were usually bold with a beard (classic computer dudes). After looking at my screen for an unhealthy amount of time, and hearing the same things repeated over and over again, I decided to go down the root of getting a Master’s degree and picking up certifications as I went.

The common entry-level debate in cyber security (and IT in general) is whether or not to get a degree or certifications to get a job. I was in the fortunate position where I could say “screw it I’ll do both” and opted for what I dubbed the Hannah Montana approach (the best of both worlds). What ensured was a very busy 12 months from October 2020–21 where I completed my Master’s degree and obtained the eJPT, eCPPT, and OSCP (the title may have spoiled this). That 12-month period gave me the opportunity to assess, for myself, the best approach to take when trying to get an entry-level job in cyber security, along with the quality of entry-level penetration testing certifications on the market.