April 21, 2021

Career Path Assistance

I’m 38yrs and I want to start a career in Cybersecurity. I am retired military unfortunately I didn’t do this there but I been working with IT for over 20yrs. Where should I start, I have a homelab that I’m currently deploying pfSense, Kali, Windows Server, Ubuntu, Windows 10, Metasploitable and other varied testing machines for hacking and networking. The biggest issue is not knowing how to step back out there in the civilian work sector. Please give me advice and thoughts. I appreciate it in advance. Oh and should I be using VMWare or Proxmox?



When you say you’ve worked with IT for over 20 years, is that 20 years of work experience or free-time experience?

Best place to start is always going to be the Security+ offered by CompTia, as that is a certification that basically every employer wants to see for entry level and even some mid/high level. It’s a pretty generic foundational cert geared towards beginners.

Beyond that, experience is key. People want people who have administered networks/systems in the past when hiring them to secure those same systems. You’ll typically see recommendation here for newbies to start off in helpdesk and try to work their way into networking/sysadmin. Your prior military experience may be relevant even if you don’t think it is. Job interviews in CyberSecurity are one part technical knowledge and one part character assessments; prior military is usually a bonus point in the latter.

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