The Lessons That Come From Failure - Reflections Of A Drop Out

First of all I don’t recommend dropping out of high school to anyone, but given I did it anyway, I am in a good position now to reflect on what it had taught me and how it has shaped me today.

I won’t go too much into detail; I guess I was like most 15 year olds; out of control hormones and a crazy bitch attitude on high alert.

It would be important to mention that I was never an ‘academic’. I didn’t absorb knowledge through having someone speaking at me; I needed context and interaction. After an incident at school, I started getting bullied and I simply decided ‘screw this!’.


My biggest ambition at that age was to be a hairdresser. I had been working casual jobs since I was 13 and I enjoyed work a hell of a lot more than school. I didn’t need school to be a hairdresser, or work in a restaurant, which was my resume highlight at that point.

For the next few years, I bounced around doing many different jobs. When I say many, please believe me, I mean many! With every new job, I was super engaged and enthusiastic. Then a few months later, never longer than a year, I was bored and onto the next one. Nothing kept my attention. I liked the conquering; mastering something new. I hated the monotony of repeating that for the next year.

As a high school dropout in a small town, you get a reputation. I can’t hold a grudge for the views that people had, I actually have to be grateful for their attitude. That feeling of exile was the catalyst that pushed me to move to the city shortly after I turned 18.

My first job trial upon arriving to the ‘big smoke’ was going door to door, to businesses, trying to sell them children’s books and steak knives. About 10 minutes into this and about 7 minutes after I had decided I sure AF was not going to take this job, I knocked on the door of who was to be my new employer. He told me “If you can do this shit, you can definitely work for us!”.

That was my first role in Business Development. The job was to go door to door speaking to businesses about their telecommunications provider, trying to sign them over or upgrade them. It was a good job and I did quite well. I was promoted into a new role after 12 months where we were to launch a new technology. By this point, I was in the peak of my partying stage and I had dropped the ball. I was offered commission only or to leave. I chose to leave and hung my head as a failure.


I was still only 19 at this time. I had moved to the city as soon as I turned 18. I was incredibly ambitious but I was still a normal 19 year old who loved to party. I didn’t know where I fit in the world and was still breaking free of the shackles of my past. A very big one of those being the fact that I was ‘uneducated’.

After the next company went into receivership, I was 22 and had started to pull myself together. I pulled up my socks, implemented all of my great new sales skills and scored a job with one of the worlds biggest recruitment firms.

They didn’t ask about my education nor did I tell them. The only conversation we had was about me not going to University. I saw no need to tell them it went beyond that. I was hired and thrown into the fiery depths of corporate life.

That was the moment I felt out of my depth. They were all so polished; pocket squares matching their underwear, posh accents and neat hair. I felt like a bogan! After all of those years building myself up and away from my past, I was back to feeling inferior! My accent was rough, my style was ‘edgy’, I was good at my job but I was unbelievably insecure about myself when I was around these people.

I was petrified that someone would find out that I was a fraud. This felt like the biggest opportunity I would ever have in my life. It was my ticket to working overseas, to money, to status, to ridding myself once and for all of the reputation that I had back home.

Because I hadn’t finished school, I assumed that everything I didn’t know was something that everyone else learnt in school. I didn’t want to admit that I wasn’t on par with these people so I would frantically work to learn it all.

Enter Google… Every conversation, I would write down words that I didn’t know and Google them. I second guessed every word I spoke, every punctuation I punched into my keyboard — almost as though I went back and decided that I actually knew nothing — from that point on everything was cross checked.

To my surprise, I managed to survive and even learnt that corporate life, with all of its bells and whistles, does not really make you any better than you were. Yet it taught me some incredibly valuable lessons and was an amazing training ground.


Skipping forward many years now, more experience gained, two international opportunities and many countries visited. It is easy now to reflect on that experience and take away the valuable lessons I had gained by not completing school.

  1. It is now second nature to research. I never assume that I am right, I am always open to being wrong in order to learn.
  2. I LOVE learning! It became addictive. It was so exciting to drop a new word into an email or (when I had developed some serious bravery) into a conversation! I would watch people open up as they realised that I could handle conversations on just about anything, usually only ever knowing enough to know which questions to ask in order to have them teach me the rest.
  3. It taught me to be humble — we all have to start somewhere, don’t kick the person who hasn’t had the opportunity to learn yet — take the opportunity to be the teacher.

These days, I think I now work for myself and it amazes me how just often I feel grateful for these lessons. It is humbling to think of where we start and how much we can transform if we have a curiosity and willingness to put our ego aside and take education from wherever we can get it.

Author; Stephanie O'Brien