Dealing with Imposter Syndrome

David Fraley (@Maekshyft)
5 min readDec 22, 2020

So in this blog post, I wanted to talk about something that I’ve been dealing with a lot lately. I have been seriously dealing with imposter syndrome. For those of you that don’t know what imposter syndrome is, it’s Wikipedia definition is

Impostor syndrome (also known as impostor phenomenon, impostorism, fraud syndrome or the impostor experience) is a psychological pattern in which an individual doubts their skills, talents or accomplishments and has a persistent internalized fear of being exposed as a “fraud”.

Before I go any further with this, I want to preface this all by saying that I am not boasting about my accomplishments. I am not bragging about what has been done or given to me and I am extremely grateful for those that have gotten me to where I am currently. What I hope to express by talking about this is how real imposter syndrome is. I want to express how this can happen to anyone and things you can do to over come this psychological mishap.

Back at the start of April, I got laid off from work and would be laid off for the next 3 months. I started the first 2 weeks just playing games left and right and just kinda enjoying the time off from work. However, that gaming stint did not last long before I got extremely bored and was looking for something to do to better occupy my time. I decided to take my Information Assurance and Security degree I had spent almost 10 year acquiring and build on it. I went to Udemy and bought The Cyber Mentor’s Practical Ethical Hacking class and start working towards that. I wasn’t going at it full steam ahead, but I was consistently working towards it. For the next few months, I would continue to work on those classes and then eventually taper off due to getting called back to work. It wasn’t until about 3–4 months ago I decided to start diving heavily into the infosec world again. I started a mentorship with Phillip Wylie, who is quite well known for his pentesting career and skills as an ethical hacker, as well as a mentor and teacher.

It was doing stuff on my own and participating in Phil’s class each week where I soon felt a passion start to blossom for this industry. I wanted to learn absolutely everything I could from anyone I could find. So I started to network and connect with others in the industry on Twitter. That is when everything skyrocketed for me. I went from roughly 400 followers to 1,317 followers as of writing this post. That was the also the first time I really experienced imposter syndrome. I was unsure of why these people wanted to follow me. I was nothing special. I have no REAL certifications for infosec. I am not currently working in the infosec industry, I am just a help desk analyst for a medical billing company. Hell, up until recently, I didn’t even consider myself a hacker because, while I was studying to become a hacker, I had barely cracked shell (admin access) on a handful of machines. Yet, for all that I knowingly lacked, people kept following me. I didn’t let it stop me, so I kept interacting with more and more people.

Then before too long, I got the invite to be on my first ever security podcast, Security Happy Hour, on Cyber Warrior Studios (@CyberWarriorSt1 on twitter) channel. I was blown away. I even told him “I don’t think I know enough to be on your podcast man”. He responded with “That’s what this podcast is made for. I bring people, small and big, on my channel and we just talk about cyber security”. I was baffled and got stunned with imposter syndrome yet again. I don’t know nearly enough to be on this podcast! I’ll never get to talk because I won’t know where to jump in. What if I say something dumb or untrue? I decided “Screw it, I’m doing it!” I went on this podcast and had an absolute blast! It was then that fellow person on the podcast reached out to me and said “send me your resume”. I was like “you say what!?” He said “send me your resume and we’ll go over it and tailor it for a security position and help you get your foot in the door.” I emailed him, we updated the resume and then a couple days later, he asked me if I would be willing to co-present with him at BSides Dublin next year. Again, I said yes, wondering what the hell I was going to talk about at a security conference.

Few days ago I was gifted a fantastic opportunity to participate in a workshop hosted by Cover 6 Solutions (@Cover6Solutions on Twitter) at the recommendation of my buddy from the podcast. I was shaking from sheer excitement from this. I was blown away yet again, wondering “what makes me so special to receive this? Shouldn’t someone that’s more deserving get this?” I actually almost thought of gifting it back to someone else who I thought was more deserving of it than me. I sat back and thought about it for a minute. “These people really believe in me and my abilities…otherwise they wouldn’t have been so willing to put me to the test on this.” So I accepted it.

Now again, I am not listing this stuff to boast about anything or show off what I’ve done or had given to me. I am eternally grateful for everything that has come my way and I know I’ve been working hard. But it’s hard not to feel like I’m not deserving of this stuff. It’s hard not to feel like I don’t know enough to be considered for such things. It’s hard not to let imposter syndrome creep in and have me question why I’m at where I’m at…

I’m here to tell you that dealing with imposter syndrome doesn’t get better and it doesn’t go away. I still get it from time to time and I’m sure I’ll get more of it as I stumble down this career path. But if there’s one thing I keep telling myself, it’s that I’m worth it. I am getting these wonderful opportunities presented to me because of the hard work and dedication I am putting towards my passion of cybersecurity. If I didn’t bust my ass to study, network, and learn anything from anyone, I would not have these opportunities. I would still be back at 400 followers, playing video games all the time, not going anywhere.

The point of all of this, and I know its a long one, is that while there is no cure for imposter syndrome, there are ways to deal with it. Tell yourself that you got where you are because you put in the time and effort to get there. You are succeeding because you are putting in the grind hours to better yourself. You are more deserving of the things that come to you than you realize and if you don’t take those opportunities someone is offering to you, you are letting them down and halting your own progress. Believe in yourself, your abilities, your talents, your skills, and your hard work, dedication, and passion will carry you to endless bounds. Do not be afraid to reach out to someone if you are experiencing this. I always tell people to reach out to me if you need. I will ALWAYS help out in any way I can. You. Are. Worth. It.

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David Fraley (@Maekshyft)

Ethical Hacker in the making. Love learning about it as much as I can and I've made it my mission to bring as much of Infosec together as I can!