Dark Reading’s Becky Bracken: Hello and welcome to Dark Reading Confidential. It’s a podcast from the editors of Dark Reading, bringing you real-world stories straight from the cyber trenches. I’m Becky Bracken, senior editor and your host. Today, I have taken a little editorial liberty and invited somebody I very much wanted to hear from right now: Hal Pomeranz. Hello, Hal.
Hal Pomeranz: Hey, Becky, how are you?
DR’s Becky Bracken: I’m OK. I’m hanging in, I think like a lot of people.
Hal, you’re a longtime expert — your resume is distinguished. You’ve been at the SANS Institute, and you are now an independent consultant. I think most people who know the field already know who you are, but give us a little bit of background and let us know what you’ve done.
Hal Pomeranz: I’ve just been around a really long time; I started this whole adventure when I was young. Professionally, I started as a Unix systems administrator and had some early mentors who got me into information security.
In my years in the industry, I did operational IT through the whole dot-com era. When that imploded, I switched over to being an educational software developer for a good chunk of time. Then Rob Lee dragged me into the digital forensics and incident response (DFIR) space, which became a full-time avocation. That’s really what my consulting practice is about these days: full-time incident response, digital forensics, and expert witness work.
DR’s Becky Bracken: What you’re too humble to say is you are an expert’s expert. We first met when you gave us your expert opinions for Dark Reading webinars, where you were deep in the technical weeds. Since we’ve become acquainted, I have been struck by your wildly encouraging LinkedIn and message board posts — especially right now, at a time when so many in cybersecurity are being laid off.
Navigating Historically Brutal Tech Downturns
Hal Pomeranz: It is an unprecedentedly bad job market right now.
DR’s Becky Bracken: It’s terrible. You scroll through LinkedIn, and it’s heartbreaking. As a journalist, I have lived through job uncertainty throughout my career. Cybersecurity folks haven’t — this is new territory for a lot of people whose jobs are closely tied to their identities.
Hal Pomeranz: I have wandered those fields myself. I’ve lived through several major economic downturns professionally. The dot-com bubble bursting was a massacre. Six or seven years later, we had the real estate bubble burst, which impacted spending across all industries.
There were times when work was very hard to come by. I felt that feeling of being at a loose end and depressed because you’re not getting to do that thing you’re passionate about — the thing that gets you out of bed in the morning. And, of course, you’re worried about all the financial aspects on top of it.
DR’s Becky Bracken: I discovered that 13 years ago, you gave a talk at the SANS 360 DFIR Summit titled “Fighting Your Dragons,” where you spoke about facing your fears and overcoming them. Most people aren’t as generous with their failures as they are with their successes. You shared a Mark Twain quote: “Do the thing you fear most and the death of fear is certain.” That seems to matter almost more today than it did then.
Hal Pomeranz: That talk was a real departure for me. It was very scary to give because it was the first time I’d spoken publicly on a non-technical, deeply personal subject. Right before I was about to deliver the opening remarks, I had a moment of panic where I couldn’t catch my breath.
It’s a subject I believe in philosophically: You have to get outside your comfort zone because outside of your comfort zone is where the learning and growth happen.
Afterward, I got more positive feedback from that talk than any technical presentation I’d ever given. It was an eye-opening experience. I realized people are hungry for authentic, personal communication. We spend so much of our lives connected through channels where we don’t always express who we truly are.
Overcoming Imposter Syndrome and the ‘Noob’ Mindset
DR’s Becky Bracken: I want to run through some of your greatest hits. A few months ago, you wrote about the tough job market, praising those who prioritize mentorship and support colleagues in need. How did that perspective develop?
Hal Pomeranz: I came of age in a much simpler time when there were fewer of us doing high-level technology. I was fortunate to work in large IT organizations — like Bell Laboratories — where senior engineers took the time to mentor me without expecting any immediate payback.
The implicit deal was that when I became a senior person, I would pay it forward and mentor the next generation. We don’t have as many of those massive IT shops today where you can serve an informal apprenticeship, so making courseware available, writing blog posts, and releasing free information is my way of continuing that legacy.
“Learn one big new thing every year. Doesn’t matter what it is — that diversity is what carries you through difficult moments.” —Hal Pomeranz
DR’s Becky Bracken: In another post on InfoSec Exchange, you mentioned that despite working with computers for five decades, when learning a new technology, you still feel like “the dumbest noob on the planet” and face self-doubt. Naming that feels incredibly important.
Hal Pomeranz: I had been seeing a lot of posts from people saying, “This is too hard, I feel stupid, I want to give up.”
At the time, I was struggling with a new architecture setup in the ELK stack, bashing my head against OpenSearch and Lucene, feeling like I would never figure it out. But self-doubt is natural. Experts struggle to learn new concepts just like beginners do.
The key is allowing yourself to be a beginner over and over. The more challenges you work through, the more confidence you gain that you will eventually find a solution.
DR’s Becky Bracken: Looking at current market dynamics, you recently drew parallels between today’s AI-driven hype cycle and the dot-com bubble. What lessons can the industry take from past contractions?
Hal Pomeranz: When the dot-com bubble burst, people left offices carrying chairs and laptops because they knew final paychecks weren’t coming. Data centers became ghost towns, and people had to transition into entirely different industries because the jobs evaporated.
Hal’s Survival Playbook for Tech Contractions
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Diversify skills: Acquire one major non-adjacent technical skill annually.
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Build networks early: Establish relationships before you urgently need them.
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Engage locally: Prioritize local user groups and alumni networks over mega-events.
To survive these cycles, you have to build your network and diversify your skill set before things get difficult. When operational IT work dried up after 2000, I was able to switch to educational software development because I had already cultivated those skills and maintained connections outside my immediate niche.
DR’s Becky Bracken: For professionals feeling sidelined or overwhelmed by social media highlights during major events like Black Hat, what is your advice?
Hal Pomeranz: Social media shows everyone’s curated 10% peak experiences — it doesn’t reflect the 90% that is everyday work, tedium, or struggle.
Focusing on local user groups, local meetups, or online alumni networks is often far more valuable than large national conferences. The cybersecurity community is fundamentally tight-knit and willing to help.
Don’t be afraid to reach out or ask questions. People in this field are passionate about what they do, and asking for help is often the first step toward finding your next opportunity.
