Creating Your Own Luck & Preparing Early For A Cyber Career

Creating Your Own Luck & Preparing Early For A Cyber Career

Meredyth Grant

Following his unexpected medical discharge, ex-Royal Marine Chester Pitts showed how making smart career decisions early on led to a cybersecurity role at Salus Cyber.

Chester’s motivation to upskill himself, military-bred confidence and tenacity positioned him well for training and employment opportunities. His story shows that while many resources exist for military leavers finding jobs, it’s individual efforts and advance planning that really count. Know your options and be prepared.

Choosing cybersecurity after leaving the military

Chester’s cyber journey hasn’t been easy after 10 “less technical” years as a military mechanic. He undertook additional study and training off his own back, learning and upskilling every evening after active duty. “It has been a tough journey.”

Suffering a back injury in 2019, Chester was medically discharged by September 2022. With a young family to consider, he’d already been considering his next steps and steadily building his cybersecurity skills. During a 2020 deployment in Norway he was introduced to offensive cybersecurity after watching a colleague developing his cybersecurity skills.

Quickly developing a keen interest, Chester resolved to develop his career plans: dischargement was the final push he needed. His focus and curiosity are an example to other military leavers. “I’d not considered many options,” he stated.

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Chester Pitts cyber security

Discipline is key

Discussing career planning, “Set goals you can achieve,” Chester advised. “Creating a timeline and ticking off milestones really helped me – I could visualise my progress.”

Chester faced tough moments during studying and training that threatened to derail his progress. “A lot of things didn’t make sense,” he explained. However, leveraging his military-honed perseverance, “the penny dropped and things clicked into place.”

A key transferable skill military leavers can offer in the cyber and corporate worlds, resilience like this can’t be taught by doing a course. “I kept pushing. It’s all starting to pay off.”

Choosing the right cyber training

Challenging yourself by undertaking extra training and building your qualifications will make you more employable and help you succeed in a post-military career. Chester demonstrated how achievable this is – studying formally and informally during his downtime, he used learning credits on a PYTHON training course, developing his IT skills.

Independently broadening his frame of reference by consulting hackthebox.com and tryhackme.com‘s unique cyber learning paths, Chester then undertook his first formal qualification – the eJPT (eLearnSecurity Junior Penetration Tester): “I really got a taste for it after that,” he enthused.

Having earned his eJPT, Chester completed his CCNA (Cisco Certified Network Associate) course through the CTP (Careers Transition Partnership) by the time he left the Marines.

Too often, military leavers enter the job market without a plan, wasting time, money and motivation on ill-suited training. However, Chester quickly identified the resources that would be most useful in achieving his goals.

Discovering TechVets via a military colleague in cybersecurity, he used their services to obtain extra qualifications that augmented his career transition and personal development. “For me, TechVets came into its own with their career and training advice,” he stated.

TryHackMe is a TechVets partner – join us to access their premium training and kickstart your cybersecurity journey.

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Entering the cyber workplace

While many veterans search and apply for jobs in the conventional ground-up way, a word that occurs repeatedly in advice sessions on building new careers is ‘networking’. Opportunity comes knocking when you least expect it – so interacting with more people increases your chances of finding work. The wider your network, the greater your chances.

Based on Chester’s efforts and his testimonial about choosing cybersecurity as a career, TechVets had specifically selected him for a SANS Work Study programme worth £2,000. He attended the SANS 560 Enterprise Penetration Testing Course, experiencing practical ethical hacking tasks covering diverse contexts from network security to Azure AD.

Showing initiative, Chester also worked as a SANS representative assisting attendees, and thus couldn’t attend every class. SANS supported him with an online training package accessible on-demand for up to six months. This knowledge now deeply informs how his current role progresses.

Meeting a lot of like-minded people on the SANS course, Chester grew his network and frame of reference – a testimonial for in-person courses over online learning. Advising those nearing the end of their military service, “My travel and accommodation during the course were covered by the military as I was still within my resettlement period.”

To help military leavers begin a cyber career, TechVets can provide their members with access to free training via the Cisco Digital Academy. 

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Knowing or connecting with veterans working in your field of interest can open doors. People who directly relate to your experience are always going to be an asset in the often-daunting process of finding work post-military.

While Chester was lucky enough to find a military colleague at Salus, he still believes it’s been a case of “right time, right place.” However, you don’t need a SensorPODS camera to see how reaching out to people could lead to your first role.

The TechVets Discord server was also a great networking resource to him, offering interactions with veterans working in cybersecurity and employers offering advice. It helped him and other members to navigate the overwhelming array of learning pathways and resources available to veterans.

Standing out to employers

Chester simply describes his good employment fortune as “plans coming together” – but he’s positioned himself to take advantage of that luck through preparedness, diligence and putting himself forward. These combined qualities are what employers look for and will help you stand out if nurtured.

After leaving the Marines, Chester planned time off devoted to family and studying toward his eCPPT (eLearnSecurity Certified Professional Penetration Tester) qualification. However, just before this exam, a LinkedIn connection offered an interview with Cheltenham-based Salus Cyber for a junior cyber role – where he still works.

Describing his profile being selected as “potluck,” Chester was actually very active on LinkedIn, putting him top of mind with cyber-connected friends. He showed that confidence, visibility and preparation increase your chances with job opportunities: despite not having undergone an interview in 12 years, Chester was immediately offered the job.

Currently working through his two CREST PEN-testing certifications, Chester realises that it’s essential to have accredited qualifications to get noticed and progress in the cyber industry. They’re a minimum required in his current role – Salus is providing his training and using it to gauge his performance and progress.

Strong values equal strong business, especially in tech and cyber. It’s why a lot of companies actively seek military leavers and veterans, who have the confidence to handle different situations with their deeply-ingrained soft skills. “We’re able to communicate well within teams, which is key in cyber,” Chester confirms.

Embrace failure

Failing is par for the course during retraining. Chester recently passed his CREST theory exam, but failed the practical component. He must now wait eight weeks to re-sit. “It’s a tough exam even if it’s conceptually simple: time is the challenge. Not too many people pass first time,” Chester admitted.

The process helped him identify knowledge gaps and refine his learning strategy toward becoming an established Salus team member: “Helpfully, feedback is provided for those who fail the exam.”

Reflecting on whether he’d still be in the Marines had he not injured his back, Chester reflects, “Probably. I’d always told myself when I wanted to leave – though I’d like to have gone into a job knowing how to do it already.”

Chester’s self-motivated success reiterates the importance of planning and studying in advance. He shows that it’s life’s trials that make us – and what we make of them.

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