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Challenges Of Being Your True Self In Cybersecurity

Becky Pinkard

Becky Pinkard is a well-known information security executive, speaker, and published author. Originally from the US, Becky now lives in London with her wife and three kids. She is VP of IT and Intelligence at Digital Shadows, a company that protects organisations against digital risks across the open, deep and dark web.

I met Becky at spacious Digital Shadows offices in Canary Wharf, London, where we discussed challenges around diversity and being true to yourself, Becky’s story getting into cybersecurity and dug into advice for those who want a career in the industry.

From a travel agency to technology

Becky’s career started with a degree in psychology and a big dream to travel. “I couldn’t afford to travel, so I got a job at a travel agency in a little town in Texas. I was 23 and my youngest colleague was probably 65. I was the only person in the office that could find Solitaire on the computer, and this made me the resident computer genius while knowing nothing about computers,” laughs Becky.

As Pinkard didn’t see herself working at a travel agency much longer, she spent her free time learning about operating systems and computers. “In 1995 I started a Master’s program in Management of Information Systems. I enrolled in three courses: accounting, cobalt, and C++. The three courses were designed to make sure I hated what I was doing. So I dropped out of the Master's degree, moved in with my parents, and got my first tech job working on a help desk. On my first day I asked my manager about his job and pointed out that I wanted it, he suggested learning my job first. Now when people talk to me about millennials and say that they want everything so fast, I think it sounds just like me a long time ago,” says Pinkard.

Getting into security

A year later Becky started interviewing for the Network Operations Center job. “It was an overnight job and my supervisor carefully asked me if I was OK to work with ‘only men’. His question surprised me and I asked him if men would be OK to work with me! Since then I got interested in security and started to learn everything about it. There was no Google, so I had many conversations with people and looked for resources about computer security. I wanted to get a job in security, but I didn't know what options were there: whether it’s app security, mobile testing, penetration testing, forensics, threat and vulnerability management, security awareness training, compliance, or privacy - I didn't know any of that. When I got my first job in security, it just all accelerated from there,” says Becky.

Security is like a puzzle

Throughout our conversation, it was clear that Becky is fascinated by the complex problems in cybersecurity. “There's a certain psychological mindset that you need to have: experimentation, adjustment, and change. If you don’t know where to start, approach a problem like a giant puzzle, find something that looks like a border or something you recognise, pick it and start from there. Figure it out. That's where the psychology mindset helped me because I realised that there is emotional context to it,” says Becky.

Reasons to get into security

“First, understand the reasons why want to get into security. If money is the only reason, maybe you shouldn’t do it. Find a specific security sector and talk to people about it. I think the most important thing is to have passion, excitement, and curiosity for what you do. If I didn't have those things I wouldn’t enjoy my career. There are many days when I don't want to go to work. But I do and usually nine times out of ten, I end up having an awesome day and I still learn something new,” says Pinkard.

Challenges in the industry

The biggest challenge was just being myself as a lesbian in the industry. I grew up in a very conservative family surrounded by the church, and later on, in life I had a hard time to believe in myself. When I worked with people who weren’t fair to me I believed that it was my fault. I thought I wasn’t good enough for the job. When you don’t feel worth it someone can knock you out with a feather. When you build up a belief that you’re growing, learning and giving back - and someone just breaks those beliefs you begin to doubt yourself. Now I believe it’s proof of a bad relationship or bad management. If you’re ever in a situation like this - don't be afraid to raise your hand up and express your concerns and disagreement,” shares Becky.

Emotional intelligence and business

Is emotional intelligence necessary in business? Becky learned it the hard way. “Once I was told that there are no emotions in business. I took that to heart for a very long time. When I felt upset or frustrated I repeated to myself that there are no emotions in business. But recently, as I was walking to the train station, I remembered this phrase I was told years ago and realised that actually no, there is emotion in business. There is emotional intelligence that teaches you how to process emotions in business and how to be your authentic self in a professional environment. I wish someone had told me this long time ago,” adds Becky.

Becky says that now the industry accepts more authenticity. Throughout her career, Pinkard gave many presentations about security but only in the last couple of years, she started talking about diversity, women in security and her own personal story. “It’s been tough and I have felt uncomfortable. For a very long time, I felt that the knowledge I had to share wasn't valuable enough. I think it all goes back to childhood. When I was a kid, my grandmother told me that women were born to serve men. I grew up with that idea and I didn't know anything different until I was 14 and started questioning it. It took many years to evolve these thoughts. Eventually, you have to leave things that shaped you or learn how to incorporate all of it,” says Pinkard.

Becky's advice if you're just starting out...

Find a mentor. Find someone that you trust, can talk to and bounce ideas off. Don’t leave it all in your head, talk to someone and get help.

It's OK to be wrong and it’s OK to fail. If you are driven and want to do a lot of things, don’t be afraid to take a magic leap forward. The worst feeling is to regret something you haven’t done but could have.

Don’t feel the pressure to have a total career mapped out too soon. Give yourself time to enjoy the space and find out what really interests you. “When I started my career, my goals were very short-sighted. Only when I was in my career for 11 years, I started thinking about whom I wanted to be at a later stage in my career. Everyone has a different appetite and awareness, so embrace your authentic ways of looking into your life and understand your needs,” says Becky.

If you have some uncertainties, just pick up a book and learn more about it. “When I got into security, I ended up reading mostly technical books. As I got busier and busier, I didn't have time to read about other topics. Read books about different subjects to accelerate your learning”.