After Nearly 30 Years in CyberSecurity, I Still Learn Something Every Day

Cybersecurity Playtime Today:

Today, while searching through some web logs and reviewing some of the data from our HoneyPoint deployments, I found an interesting scan. The payload was pretty common, something we see, nearly every day – but the source, a pretty mature organization with a reputation for being tightly managed and capable, was what caught my eye. The scans went on for several days across a couple of weeks – sourced from a web server that clearly was not as securely managed as their reputation might insist. So, I notified them, of course, and played in the data a while, fascinated by some of the nuances of it. 

Good Days Versus Bad Days:

This is pretty much a daily occurrence for me – on the good days, at least. I get to play with data, learn something new, experiment, hypothesize and test myself. Those are the good days of being an infosec entrepreneur, CEO and researcher. The bad days are the ones when I have to struggle with sales efforts, manage difficult resources/projects or solve the same security problems as I tackled in the 90s. Those are the days when I am less happy about what I do. But, fortunately, those days are pretty few and far between. 

Fighting the Cybersecurity Good Fight:

After 30+ years in technology and “cybersecurity”, I still find a wealth of things to learn and play with. I never seem to get to the point where I feel like I know stuff. I try and remain intellectually curious and mentally humble at all times. I also try to believe in the magic of technology and fight the cynicism of doing infosec for 30 years. That keeps me making new things, and investing in new solutions, like our new ClawBack data leak detection tool

I try to keep fighting the good fight, so to speak. I’ve spent a lot of time learning about attackers – what motivates them, how they operate and how tools evolve. I’ve learned a lot about the economics of cyber-crime and the information security industry, as well. I’ve grown my understanding and world view around the day to day of infosec. I try to add value to someone every single day. Those things keep me going and keep me engaged. They help minimize the burnout and maximize my patience with the often challenging task of being an infosec person and an entrepreneur. Sometimes, living to fight another day is all you can ask for, and some days it seems like you can’t wait to jump back into the fray. Such is the infosec (“cybersecurity”) life.

Advice for New Cybersecurity Practitioners:

If you’re new to cybersecurity or considering joining us, my advice to you is simple and a gut check. Be sure that you are ready for a career that requires life long learning and life long change. If you want to have a repeatable, 9-5 job that you can master and forget when you walk out the door, this probably isn’t for you. Attackers are amazingly dynamic, and thus, infosec must be just as dynamic as well. This isn’t an industry built for mastery – it’s an industry built for being a life long student. While that’s not always easy, it can be fun and rewarding. Got what it takes? I sure hope so – because we need help and we need it for today and the years to come…

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