Over 2,000 mentors available, including leaders at Amazon, Airbnb, Netflix, and more. Check it out

In 4 years I went from low paying job, no education, to a Software Engineer with Microsoft

I want to share my short 4 year journey of leaving a low paying IT job, to working for one of the most profitable companies in the world, with no formal education and how you can too!
Justin Middler

Software Engineer, Microsoft

My journey in IT begun as a 17 year old IT trainee while still studying towards my year 12 certificate here in Australia. As part of my IT traineeship, I provided hardware support to various Australian education institutions which involved repairing and working on faulty desktop computers, assisting teachers and other education staff with IT questions, and working on various networking appliances and rack-mounted computing equipment. This was great experience! but unfortunately like all good things this came to an end and I finished my schooling which meant I had to get a full-time job.

The same year I passed my year 12 exams and finished school, I started work in the Australian Federal Government as a Help Desk Analyst. This was awesome experience and I learned a lot from the people I assisted and my colleagues of course. 

After 2 or so years experience working on the help desk, I moved on to a regression testing role where I learned how to test software and how to check for bugs and errors prior to shipping software to our user base. This was my first glimpse into some of the lower level aspects of IT and large systems in general, as well as how software lifecycles worked, what code was and why people spent thousands of hours writing it, what a network was and how it worked etc.

Fast forward a year or so, my manual regression testing evolved into automation testing, using hacky pre-written scripts which I would execute, without knowing anything about them, how they worked, why they worked or what the benefit of using them was. After doing this for several months, I wanted to dig into the process more and understand what was happening under the covers, thus peaking my interest in software development and forcing me to learn to code. After about 6 months, I was now the person responsible for leading the testing automation effort in my team, and I was instructing and educating those around me on best practices and how to write Page Object Model based tests using C# and Selenium.

All of this experience and hands on work was invaluable and I continued to learn about large scale IT systems, networks, server management, DevOps, relational databases, CI/CD pipelines, cloud and more, however I was still stuck in the same role, despite my growing knowledge and willingness to go above and beyond to improve my knowledge and experience.

After two years in this role I decided to take the plunge one Monday morning, and walked into my managers office with my two weeks notice in my right hand. It was time to move on and challenge myself. Boy did I underestimate the wild ride I was about to embark on.

Prior to leaving my role, I accepted a position at a small boutique cyber security company in Australia, specialising in cyber security assessments, and cyber security governance pertaining to cyber security guidance in Australia. This was a massive learning curve for me, as like most other developers, over the years we hear the term security thrown around, and have some general idea on what is and isn’t ‘good practice’, but nothing could have prepared me to learn about everything from governance, risk and compliance, to conducting vulnerability assessments, to penetration testing, to security audits etc etc. All of this was completely foreign to me and to complicate matters even further, I had to almost overnight, become an expert in Cloud Computing, so I could assist our clients in understanding how they can secure their cloud workloads.

After a short period of time I left this company (less than a year) to have a go at running my own company specialising in software development. Did anyone ever tell you running a company was hard work? Well, if not I am here to tell you that without a doubt, this was the most demanding “job” I had ever held. I left my 9-5, Monday - Friday job so I could work for myself, what I hadn’t realised is I had signed myself up to work basically 18-20 hours a day. This wasn’t sustainable and while I learned a lot from doing this, I needed a stable source of income, and more importantly, I needed some bloody sleep!

At this stage, it had been two years since I left my first ever paid job in IT, and I had worked for a private Australian cyber security company and run my own company at this stage, but still wasn’t really sure what I wanted to do with my career and what direction I was destined to head in. I decided to return to my first place of employment, but this time round, as a contractor, so I could increase my income and move into a more cyber security focused role that allowed me to focus on my developed skillset that I had built over the last two years. Two years does not sound like a long time to learn anything, especially when the term cyber security is mentioned, and especially when it is such a broad term, but if you eat, live and breath something for two years, turns out you learn quite a bit about it.

Contracting was great money, and I was working on some meaningful projects, but I just wasn’t feeling fulfilled, and at heart I knew that I was a developer and that I loved writing code. So one day after work, I decided to apply to Microsoft, to my shock a few weeks later, I was invited to interview. The rest is history I guess, and now I work for (in my opinion) one of the coolest, most impactful and meaningful companies in the world, doing what I love and loving every minute of it.

So how can you kickstart your career and bootstrap into a high paying, impactful and meaningful job? Well, I think the following points are worth focusing on:

  • Find what you love to do, and go after it (no really, don’t waste your time for all the money in the world doing something you don’t enjoy, life is too short)

  • Hone your skills and know your worth, find something you are truly passionate about and become a master at it, truly obsess over it until you are an expert

  • Learn the fundamentals, you have to run before you can walk, this is especially true if you are for example, attempting to break into a technical cyber security position, but lack fundamental IT skills, because the reality is, you cannot protect assets if you do not understand how they work or what they do

In conclusion, do what you love, obsess over it until you’re an expert and master the fundamentals. This will ultimately force you to succeed in whatever you choose to do.

Unsure what you need to do to achieve the next step in your career? unsure how to even break into the field? Let’s have a chat - https://mentorcruise.com/mentor/justinmiddler/


Find an expert mentor

Get the career advice you need to succeed. Find a mentor who can help you with your career goals, on the leading mentorship marketplace.