“You Caught Me In An Introspective Moment”

I recently was given a survey to fill out by an organization I do training for. I suppose it’s a pretty predictable set of questions about who I am and how I got into the industry, and advice I have for people who are just starting out. But it caught me at just the right moment and I ended up going into some depth. So if you’re looking for a bit more about me and my journey, and maybe a little bit of life advice, read on!

What is your Name and Title?

My name is Hal Pomeranz, and I’m a “lone eagle”– an independent consultant running my own business.

Titles are a little weird when you are a one-man shop like I am. Officially I’m “President”, “CEO”, and a host of other titles. But it seems a bit grandiose to claim to be CEO of just little old me. “Consultant” or “Principal Consultant” seems a bit closer to the truth.

Tell me about what you do in that occupation?

They always say that running your own business is like working two jobs. The boring part of my business is the “business stuff”—contracts, invoicing, collections, taxes, insurance, etc. Frankly I try to automate or outsource as much of that nonsense as possible.

As far as technical work, my current practice is centered around Digital Forensics and Incident response—helping companies that have had a security incident figure out what happened and get fully operational again. But there are many different aspects to that general description. For example, right now I’m helping one of my clients proactively improve their detection capability to help spot incidents as early as possible.

I also create and teach training courses to help people learn to do some of what I do.

I’ve been diversifying my practice by taking on occasional Expert Witness work, acting as a technical expert and weighing in with my opinion on various court matters. Many of these cases have centered around tech support scams that target unsophisticated computer users—particularly the elderly.

Do you have any certifications or degrees?

I have a Bachelors in Math with a minor in Computer Science. I tried going back to grad school for my Masters at one point, but working in the industry was so much more fun!

I earned a raft of SANS/GIAC certifications because they had a policy that you had to be certified in any class you taught for them—including incidentally the course that I authored.

How do certifications help you out in the industry?

I’ve been working in IT for almost forty years at this point, so for me personally my experience counts for much more than any certification. But when you are first starting out, I understand the feeling that having certifications can help you pass through HR filters and generally make you stand out from your peers.

If you will forgive a bit of editorializing, I generally consider certifications to be a tax on our industry. The difficulty is that many employers lack the in-house expertise to differentiate qualified from unqualified candidates. They fall back on certifications as a CYA maneuver, “Well it’s a shame that candidate didn’t work out, but we did our due diligence and made sure they had the correct certifications.” I don’t know how to solve this problem.

Why did you choose these certs and degrees?

I was interested in computers from a very young age, but when I went to college in the mid-1980s, Computer Science was still not widely available as a major outside of pure tech schools. I went to college fully intending to study Electrical Engineering, which was one path into Computer Science. Then I found out that EE was a five-year degree program with essentially no room for electives. I decided a Math degree would be easier. My first college math class was Discrete Mathematics and that experience made me realize that an Applied Math degree supplemented with as many CS classes as I could take was pretty much exactly what I wanted to do.

What got you interested in IT/Cybersecurity?

I was always fascinated by computers. When I was 11 years old, I bought a used TRS-80 from a friend of the family using my paper route money. Just before I started high school, I bought one of the original IBM PCs—again with money I’d saved up from delivering newspapers.

Where did that interest in computers start? I’m not sure, but I can remember a couple of formative episodes. In the 1970s, I can remember my dad bringing home a (briefcase-sized) portable terminal, complete with acoustic coupler modem. I remember being blown away by the idea that you could just plop down near a phone and interact with computers all over the world. I also had a friend with a much older sister who married a guy who did IT consulting for a living. This guy had all the cool toys and lived a very nice lifestyle. That seemed like a great deal to me.

What was your first IT job?

By the time I got to college, I had enough PC experience that I got a work-study job doing tech support for the administrative departments at our school. I guess this was the first in a long line of IT support jobs.

Just before I arrived at school, the nascent Computer Science Program (not its own Department yet!) had received a grant to purchase a network of engineering workstations. The head of the program, in a moment of pure inspiration, decided to go with Sun Microsystems computers. But he didn’t have time to manage the network in addition to his teaching responsibilities. He drafted interested students to be System and Network Admins for our small network.

I was a user on that network and fascinated with the computer games of the time—Rogue, Nethack, XConq, and so on. I regularly maxed my disk quota installing these games in my home directory. The student admins got frustrated with this behavior and told me, “Here’s the root password. Install those games where everybody can use them!” The rest, as they say, is history. I spent my last three years at a very theoretical liberal arts college getting a vocational education in Unix System and Network Administration.

Towards the end of my senior year in college I knew that I did not want to head directly to grad school. I had been sending out resumes to local organizations that were using Sun computers—which I figured out by looking at the UUCP maps of the time—but was not getting much response. Then one day the phone rang in the CS lab. It was a recruiter looking to fill a Sun Admin role at AT&T Bell Labs. I interviewed and got the job, which was something of a miracle when I think back on some of the cringeworthy answers I gave during the interview!

What was your first cybersecurity job?

I was hired at AT&T Bell Labs Holmdel as a junior Sun System Administrator. The Labs at the time were engaged in the process of moving from mainframe Unix systems to distributed networks of primarily Sun systems. But my boss was also a big wheel in the internal Bell Labs computer security team, having caught an attacker who was abusing the AT&T long distance networks for many months. She saw that I had an interest in computer security and became an important mentor. Through her I got to meet Bell Labs infosec luminaries like Bill Cheswick and Steve Bellovin. Though I’ve had lots of different job titles over the years, all of my work since then has had at least some infosec component.

What advice would you have for someone who is looking to start a career in Information Technology?

Start by recognizing that there is no “ideal path”. Some of the best people in our industry got here by very roundabout paths. And despite what you might hear, they weren’t always “passionate” about computers or information security.

Get as broad an education as possible—and not just in STEM! I deliberately chose to go to a liberal arts school because I wanted to study many things besides science and engineering. And the perspectives I gained through that broad education have very much informed my technical career. And just maybe helped me avoid some of the burnout that is so prevalent in our industry.

Recognize that the technology you are training on today will not be around for your entire career. When I was going through school, CS classes were taught in the Pascal programming language! Learn fundamental concepts that you can apply to any technology—networking, routing, algorithms, data structures, cryptography, the “CIA triad” and so on. A long career in infosec is based on a broad knowledge of technology.

What might be some challenges or obstacles someone might face as they look at starting their career?

Standing out from the crowd seems to be the biggest problem for people starting out these days. There are a lot of folks who heard they can make a good living at computers and information security and there seem to be too many candidates vying for too few junior positions.

Research and blogging seem to me the best path for getting noticed. While your peers are flogging their guts out for the latest certifications, maybe you could be spending your time doing original research and documenting your findings. The availability of free virtualization means it’s never been easier to create your own personal lab environment.

A well-written blog shows interest and passion for the subject. It demonstrates your technical capabilities. And it also demonstrates your communication skills, which are becoming only more valuable in our industry.

What challenges have you faced in your career?

Simply having a career through multiple decades has been a challenge in and of itself. I’ve persevered through multiple recessions and various industry catastrophes. My key there has been diversification. I’ve been a system admin, a network admin, a security admin, a DBA, a network architect, a developer, a forensic analyst, an incident responder, an expert witness, a trainer and course author, a technical editor and author, and who knows what else. The best piece of advice I ever got was, “Learn one big new thing every year.” If you can do that, you will always find a way to be in demand.

On a personal level, many of the challenges have been learning to get out of my own way. Being open to learning and understanding that I was not always the smartest person in the room. Understanding the perspectives of my customers and putting their needs ahead of what I thought was “right” from my narrow perspective. Realizing that process and documentation (if done properly!) actually make things better rather than just being a drag. And frankly just trying to be less of an asshole to everybody I interact with.

What do you think are the most important non-technical skills for a student to learn?

Communication skills are number one. Pick a subject that you know very well. Can you succinctly document your knowledge so that somebody new to the subject can understand at least the basic concepts? Now can you explain that subject 1-on-1 with another person? Can you explain it to a room full of people?

How do you “think like a hacker?”

From my perspective, this mindset is all about anticipating failure. When you’re a system and network admin, you begin to learn what architectures work and which ones don’t work. You learn where the points of failure tend to occur. Eventually this becomes a bit of a “sixth sense” that you internalize without even thinking about it.

The hacker mindset is the same. What if this were to fail catastrophically? What could cause that to happen? Could I cause that to happen? How could I leverage that?

What advice do you have to avoid burnout?

I do believe in the usual advice. Have interests outside of computers and technology. Remember that you work so that you can live, not the other way around. Never be afraid to say, “No.” Take time off—and by that I mean real time off where you are not worrying about your job and day-to-day responsibilities.

But this advice comes from a place of extreme privilege. Many of you are out there struggling to afford your lives, working in a corrosive job environment, and fighting battles that may be hard for others to understand. I see you.

It is the responsibility for all of us with privilege to address some of the fundamental inequities in our society. Do whatever you can to make the world better for everybody. And I find that helping others works to combat burnout as well!

What advice do you have about imposter syndrome?

Every day in real life and on social media you are confronted with people who seem to be so much more confident and knowledgeable than you. But remember that you are only seeing at most 10% of who that person really is. Sure, if you compare 100% of you to the best 10% of every person you meet, you’re going to end up feeling not so good about yourself. But once you get to know these people, you realize that they have their own insecurities and “blind spots” just like you.

Get comfortable with the idea that while you can never know everything, you do know something and that something has value. And you can share that thing you know with other people. And they can share what they know with you and others. And we can all get better.

Why did you become a teacher?

I grew up in a very welcoming technical community and was fortunate to be mentored by a great number of people—some well-known, some not. There was an understanding that when I reached a level of expertise that I would “pay it forward” by teaching the next generation. I take that very seriously.

I was also fortunate to come of age in a time when large IT staffs were common. You would start work as a junior member of the team and receive on the job training from the senior admins. These days it seems like very small or even one person IT shops are the norm. You can’t learn everything from Google and Stack Overflow! Teaching and writing are my way of trying to provide that mentorship that I received in the early stages of my career.

Is there a moment in your career that shaped your approach to teaching?

I can remember watching Bill Cheswick present at one of the first USENIX conferences I attended. Bill was commanding the room with his knowledge while decked out in an Aloha shirt, cargo shorts, and Birkenstocks. And I realized that training didn’t have to be stuffy and academic. That was a powerful moment that’s stuck with me as I train others.

Do you feel that teaching has made you more knowledgeable?

You never learn a subject so thoroughly as when you need to teach it to somebody else. Creating course material and teaching have increased my understanding of technology in ways I never expected. And I learn things from my students every time I teach!

I hear people saying, “But I’m not an expert! Nobody wants to listen to me teach!” Nonsense! Expertise is a subjective marker and many people underrate their abilities. Start teaching even before you think you’re ready. Watch how your understanding grows rapidly.