Back in my day
Technology has come a long way in such a short time. Many years ago, in a previous life, I was really into computer (in)security. A friend of mine helped me with my first Slackware install and despite that I still enjoyed it. I got into going to 2600 meetings, regularly went to DEFCON and was totally hooked. This is it for me, this is what I want to be when I grow up.
As time went on I found myself with a sysadmin gig where working in security seemed like it would be pretty boring. This was at a time where companies were just understanding the web wasn't a safe and trusting place. Ideas like risk management and acceptable use policies were what people worked on. Many companies didn't appreciate they would need pen testers to help protect them.
Fast forward to the year 2020. People now get paid insane amounts of money for "hacking". There are people that look for vulnerabilities in code and/or networks and even certifications to show one has the ability to do it (or at least took a class on it). Not only can you get paid to be a hacker, but also many of those jobs let you work from anywhere on the planet. What I've found most surprising is all of the tools and the resources that are just a few keystrokes away.
A family friend turned me on to the OverTheWire site that gives you challenges that call for various computer skills. From the site, you start out with a basic login for a host that contains the puzzles. Moving forward, you get the account for the next level by solving the puzzle on the current level. Each puzzle gets increasingly more difficult starting with just being able to log in and higher levels include things like setting up public/private keys for ssh finding local exploits and privilege escalation.
Later, I came across Hack The Box that was even more advanced. Once you manage to get an invite (by solving a short challenge) they provide you with VPN access to their entire network that contains a number of vulnerable hosts for you to hone your pentesting skills. It's extremely organized and well designed with a leaderboard. Best of all, it's free!
Both sites are completely free. I couldn't imagine having these resources when I was growing up. What a difference it would have made if I had the chance to hack into other computers with no risk of trouble from the law or anyone else! We've come a long way from hanging out on the BBS on our 2400 baud modems screaming, "Don't pick up the phone!! I'm on the internet!"
Now get off my lawn!