In this article, I want to talk about a subject that makes people uncomfortable – failure. I’m going to share with you some of my own personal failings. I will explain why I believe failure is so important. I will also explain why you should not let failure stop you from trying to achieve your hopes and dreams. Sometimes, you have to fail to succeed. Mostly on Twitter I try to share positive affirmations and encouragement. Some of you might be surprised to learn that I am not always so positive a person in real life. There have been tweets I’ve deleted because I felt that they were too negative. I am going to do my best in this post about failure to keep it positive. I believe that I had to fail to succeed with my exploits later on.
I enjoy writing
Often times, pentesters and red teamers lament writing the report at the end. That is part of the process where I feel very comfortable. I’ve written about this previously on peerlyst.com, and I believe that there is value in liberal arts degrees in infosec. However, I think that there is such a need for people in infosec period that we should help anyone who wants to come in. That is one reason I volunteered to write this article, because people like InfoSecJon are advancing the community by helping recruit new members and helping them build their skills.
I first tasted failure at a young age
Failure has been with me from an early age. I was always interested in sports, but I was never very good at them. During my childhood I played PeeWee football, baseball, and basketball. For a year or two I tried to play roller hockey before getting discouraged and giving up. When I was twelve I took up golf and still play today, despite it being a deeply frustrating sport. During junior high school I tried out for wrestling (quit when I realized I had to wear a singlet), tried out for the basketball team (got cut pretty quickly), but successfully played football and track and field. When I got to high school, things changed. I never grew taller than about 5’7” and as a lineman squaring off against dudes who were over six feet and close to 300 pounds, I decided that quitting was my best option. I tried out for and made the golf team two of my three years of high school, which greatly improved my game. However, I failed to make the team my senior year. This failure taught me more than any of the successes the previous two years. Which brings me to the first point of this article – you often learn more by failing than by succeeding.
My experience with failure carried into my collegiate life
After high school I failed out of college at least twice before going back for real in my late twenties. Having burned out of an IT job, I went to college to earn a liberal arts degree. With an undergraduate degree in history, pretty much all you can do is go to graduate school. That is what I ended up doing. My master’s thesis won a faculty award not given out every year, and I presented at multiple academic symposia. I was also awarded a graduate assistantship for my second year of grad school, meaning I was a teacher’s assistant for a few classes each quarter (my alma matter is on the quarter system). This afforded me the opportunity to sit in on undergraduate classes outside my particular historical focus area as well as earn a second bachelor’s degree in philosophy (it was my undergraduate minor and I was only two classes away).
Failure continued to follow me after grad school
All this hard work in graduate school did not materialize into any success. I was rejected from both doctoral programs I applied to – I could not afford to spend more than the $800 I already spent applying to those two programs. Despite my success, I was not offered an opportunity to be an adjunct professor at my university. Nor was I even able to secure an interview for an adjunct position at any college or university. All of these combined failures taught me a valuable lesson – academia is not a place for me. However, that time improved my skill as a writer, which is crucially important in information security.
First crack at InfoSec
So with a master’s degree in history and totally frustrated by the prospects of remaining in academia, I started a web comic. Living in the small town I was in, with very few bills to pay, I was able to survive for six months with a small loan from my family. I failed a lot with the web comic for months, and turned to facebook to vent my frustrations. One day, I got a message from an old friend. He asked me what I thought about starting an information security consultancy and performing offensive security engagements. I told him I didn’t know anything about that, and I had not worked in IT in about five years. He was my mentor, pointing me in the right direction or how to get started learning and on May 1, 2017 my wife and I started JSP InfoSec. We were failing left and right, but I was learning as well. After a few months I decided to look for temporary work, but I was instead offered a full time position as an information security consultant. While that firm ultimately did not work out, I learned a ton about infosec while conducting engagements for clients across the country.
Found my success
We failed for a few more months at JSP InfoSec before I started looking for a full-time gig. What followed was nearly four months of failing, applying to hundreds of jobs and finally getting four interviews. Three of them were pretty big-time fails. The last firm said yes, and all it takes is one. I’ve been there for over a month and I am really enjoying my time there. I’ve been learning a ton about desktop support, building computers, and setting up windoze servers. All of this is valuable information to have when performing offensive security engagements.
So hopefully this article has shown you that just because you fail once (or many times) that does not mean you should give up. I have provided example after example of how I have failed but that these failures have taught valuable life lessons. My boy often likes to say, “we don’t give up in this family” and I like to think of that as our motto. There were times in my life where I did not follow this advice. However, all the times I did ultimately paid off. From sports I learned that sometimes you just need to walk away from some things to focus on others. When you are thinking about throwing in the towel and giving up for good, just remember these stories. Remember that just because you have failed 99 times, that doesn’t mean on number 100 you won’t finally achieve success. Colonel Sanders famously failed to sell his chicken recipe hundreds of times before he finally achieved success. Each of my failures has been more educational than any of my successes have. Which isn’t to say that you shouldn’t try. Rather just keep that in mind that sometimes you have to first fail to succeed later.
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Check out Medjay’s story of his experience with the 3 common struggles starting an infosec career