Love at first byte: find your dream cybersecurity role (with real stories)

The journey to a successful career in cybersecurity is as diverse as the threats we face as an industry. 

But according to Shakespeare himself: “the course of true love never did run smooth”. So, it takes a lot of trial and error before finding the right career match. 

Whether you're a college dropout, a veteran looking for a new flame, or simply someone with a passion for technology, the stories of those who have “been there and done it” can inject a much-needed dose of insight and inspiration to fuel your 2024 goals!

In this blog post, we dive into the career journeys of four remarkable individuals who found their perfect match in cybersecurity.

Olivier Laflamme: The college dropout who chartered his own course in cyber

Like all of our inspiring success stories, Olivier Laflamme's journey into the world of cybersecurity is a testament to the power of self-determination. 

Despite dropping out of college, Olivier didn't let traditional academic setbacks define his future. Driven by a passion for technology and an unyielding will to learn, he embarked on a self-taught path, diving deep into the intricacies of cybersecurity. 

His story is one of transformation, from uncertainty to becoming a skilled red team operator, showcasing that a formal degree isn't the only route to success in this field.

Today, Laflamme's a respected Red Team Operator. His journey highlights the importance of practical experience and self-education. He used online resources and hands-on practice to build his expertise, demonstrating that with the right resources and dedication, (almost) anyone can carve out a successful career in cybersecurity.

Not long after dropping out, I stumbled on PicoCTF by Carnegie Mellon and over the span of two months solved every challenge. I was hooked. During that time I met some great people and shortly after got hooked on RingZer0 CTF and Hack The Box. 

 

I dedicated thousands of hours to solving Boxes, Challenges, and Pro Labs. Those hours were undeniably well spent, in my opinion.

💡Read about Olivier’s journey here.

Gary Ruddel: A military operator’s transition into defensive security 

Gary Ruddell is now the Regional Head of Cyber Threat Intelligence at a global financial organization, but he didn’t always work in cybersecurity.

Starting off as a communications specialist in the UK’s Royal Navy who then progressed to military intelligence, Gary left the military in 2013 and has since worked as a Security Operations Center consultant, Senior Risk Analyst, and Threat Intelligence specialist. 

His military experience provided a unique perspective, particularly in structured and strategic thinking, which he effectively applied to cybersecurity. 

In cyber threat intelligence, Gary found a perfect blend of his military skills and his interest in digital security. 

His journey underscores the importance of finding a niche in cybersecurity that aligns with one’s skills and passions, demonstrating that the field offers diverse opportunities for everyone, irrespective of their background.

Having a military background helps because it cultivates qualities and attitudes that you need to succeed in cybersecurity: 

• Discipline

• Camaraderie 

• Continuous learning 

Everyone, regardless of whether they’re in cyber or not, would benefit greatly from internalizing and executing those three things. 

 

Discipline, for example, was critical during my early years of studying cybersecurity. I’d spend most evenings learning and practicing until 2 AM after a full day’s work. 

💡Learn more about Gary’s path to cyber threat intelligence here.

Jeremy Chisamore: Poker Player turned Pentester 

From stockbroker to professional poker player to high-end gaming PC salesperson (selling to celebs and professional athletes) and finally, Penetration Tester.

Reeling from layoffs and events outside his control, Jeremy adapted and diversified into multiple different career paths before diving head-first into cybersecurity. 

He was determined to succeed “without a plan B” and “even if it killed him.” 

Starting off as a self-taught junior security consultant (who admittedly forgot the OSI model acronym during earlier interviews) he’s now a Senior Penetration Tester at Oracle. 

The approach I took to progressing in poker is identical to the one responsible for launching my cybersecurity career: 

• Network with others who are ahead of you

• Learn hacking concepts from the best

• Invest in coaching and education

• Learn to coach yourself

• Analyze your weaknesses 

• Commit to the journey ahead

💡Delve deeper into Jeremy’s cybersecurity journey here.

Josiah Beverton: From physics student to Red Team Consultant

Josiah studied physics at university before moving on to Tesco as a Scrum Master and then, later, ATOS as a Security Analyst. 

His commitment to professional development and learning through Hack The Box helped him refine his offensive security abilities and land his first role as a Penetration Tester. He continues to develop his skills through the platform and is now part of the Red Team at Mandiant.

If you want to work as a penetration tester, you'll need to make a habit of closely checking the news for new vulnerabilities or exploits. 

 

For anyone thinking about a career in cybersecurity, it's important to obtain a solid grasp of the fundamentals and how things actually work. This will help you later on in your career and ensure that you aren't just reliant on tooling.

 

My biggest tip is to ensure that you are genuinely interested in the field you want to work in. Then share that passion with anyone you come into contact with.

💡Discover more about Josiah’s journey into pentesting here.

Cyber Cupid’s cybersecurity career quiz: Find the role that fits you

Ever wondered which role in cybersecurity would be your perfect match? 

Then let true love reveal itself with our Cyber Cupid Career Quiz!

Discover whether you’re destined to become one of the following:

• Penetration Tester.

• Security Architect.

• SOC Analyst.

• Purple Teamer.

• Bug Bounty Hunter.

Then, you can follow in the footsteps of some of our HTB community members and pave your own unique path to true cybersecurity commitment. 

Ready to uncover your career crush?

Author bio: Fiona Leake (fileake), Content Writer, Hack The Box Fiona Leake is a Content Writer at Hack The Box. Digging deep into how people think to create meaningful content that solves problems is what gets her out of bed in the morning. Fiona loves simplifying technical topics and enjoys occasionally trying her hand at only the most beginner-friendly HTB Machines. Feel free to connect with her on LinkedIn.