Aug 31, 2026 · 56 min · 15 segments
In Episode 52 of the DTF Cyber Podcast, Damian, Troy, and Fern debate the ultimate cybersecurity career question: should you build your path as a deep specialist or a broad generalist? The hosts…
There's a lot of places people can go these days.
And it depends on where you go.
People have choices.
You ask 100 different people what to do.
You get 200 different answers.
And what I think of is when most people are looking to get into security, they have a plethora of options.
And none of those are pen testing.
I think we just need to call it out right now.
If you're new to security, do not expect to be a pen tester on day one.
Yeah, but everybody coming out of school, that's what they want to do, right? That's a cool and sexy thing.
I want to be a pen tester.
I want to hack.
I want to break into stuff.
Yeah, but that's the worst path to go down because what ends up happening is you go up against these juggernauts who've been doing it for 20 years that'll smoke you like, I don't know, like a Friday night.
What's easy to smoke? A cigar.
Brisket.
Yeah.
Because at the end of the day, if you're not able to compete at the highest level in these fields, you're going against people that have been in the industry for, you know, decades, right? Yeah,
but I think, Fern, I think it's like the same motivating factors that get people to want to go into cybersecurity, like TV shows and movies, also propel them into those, yeah, I want to be like the guy I saw on Hackers, you know.
And so everybody thinks they're going to come out of college as a pen tester or a red teamer.
Those jobs are fewer and far between.
And so what happens is people have this really rude awakening when they get to the job market looking for those roles.
Like, wow, either the role's not there, or as you said, Fern, somebody's already in that role with much more experience.
So back to Damien's point, do I go specialist route or do I go general? I think it's a great discussion.
There's a lot of places people can go these days.
And it depends on where you go.
People have choices.
You ask 100 different people what to do.
You get 200 different answers.
And what I think of is when most people are looking to get into security, they have a plethora of options.
And none of those are pen testing.
I think we just need to call it out right now.
If you're new to security, do not expect to be a pen tester on day one.
Yeah, but everybody coming out of school, that's what they want to do, right? That's a cool and sexy thing.
I want to be a pen tester.
I want to hack.
I want to break into stuff.
Yeah, but that's the worst path to go down because what ends up happening is you go up against these juggernauts who've been doing it for 20 years that'll smoke you like, I don't know, like a Friday night.
What's easy to smoke? A cigar.
Brisket.
Yeah.
Because at the end of the day, if you're not able to compete at the highest level in these fields, you're going against people that have been in the industry for, you know, decades, right? Yeah,
but I think, Fern, I think it's like the same motivating factors that get people to want to go into cybersecurity, like TV shows and movies, also propel them into those, yeah, I want to be like the guy I saw on Hackers, you know.
And so everybody thinks they're going to come out of college as a pen tester or a red teamer.
Those jobs are fewer and far between.
And so what happens is people have this really rude awakening when they get to the job market looking for those roles.
Like, wow, either the role's not there, or as you said, Fern, somebody's already in that role with much more experience.
So back to Damien's point, do I go specialist route or do I go general? I think it's a great discussion.
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