Hello guys and gals of EH!

I've noticed that for some reason it is the younger folks and folks in the middle of their careers that are asking questions over here; why is that? Just kidding

I've recently taken a medical retirement and have been searching for the meaning of life. Ok, ok, I've been looking for something meaningful--and challenging--to do, which would, ideally, also supplement my disability income. And here I am.

There are a few questions that I'd like to ask, but most of them are conditional on the one that I'm going to start with. But first, let me give you some relevant background.

After having completed my degree in electrical engineering in the early 80s, I worked as an engineer for about eight years, then changed careers and did a couple of advanced degrees in totally unrelated fields. Yet, I had to move in 1999 and changed track again: in 2000, I completed a two year diploma in programming (C, C++, VB, HTML, Hardware, Networking) and worked for a year as a programmer analyst. Had to move again and returned to my old, unrelated, career until retirement. I'm 55, and here's my question.

Assuming I did a lot of reading etc., did a few levels at the Hacking Dojo, took an online course from Offensive Security, and eventually took and passed a certification exam, such as OSCP, do you think it would be possible at all for someone like me, who didn't really have any meaningful career in the industry, to find a part-time freelance job in penetration testing?

Many thanks.

P.S. I'm located in Canada

Having always been a workaholic and having studied a lot in my life, I'm not afraid of sacrifice if by that you mean the time and energy. Pentesting seems like an exciting and challenging work, and that's what looks attractive to me.

Thanks for the encouraging post, Grendel.

<what he said ^ >

Yes I cant agree with jjwinter more its all about how skilled you are and how you come across.

That'll all give you a solid foundation. The Dojo is probably a good place for you to start. It can be beneficial to have someone to ask questions to when you're just getting started. There's several other high-quality training providers out there, but the majority are self-study. While they often have forums and/or IRC channels available, you're usually left to your own devices and told to try harder. That's great if you're trying to take your skills to the next left, but it can be discouraging for novices who are just starting out.