Reflecting on my thirties: My huge career change

On the verge of turning forty, I’ve taken a significant amount of time reflecting on my thirties in a number of different facets of my life. One massive change was in the area of my career where I have taken a lot of big risks and thankfully found a lot of success. The following post is the journey I’ve taken over the last ten years.

Just prior to my 30th birthday, I found The Four Hour Workweek by Tim Ferris while flying back from Thursday Island in the Torres Strait. My life changed on this flight as I suddenly realized in general terms what I wanted in my life.

While I found the idea of working only 4 hours a week a little boring and a lot of work to achieve, the concept of working fully remote in a location agnostic way became my absolute priority.

My early thirties were spent chasing that vision.

Two months before my 30th, I was working as a marketing coordinator, system analyst and occasional actor / model for a national carpet cleaning company headquartered in Newcastle Australia. The company still use a lot of footage of me cleaning things which means there is a chance you’ll see me when watching Australian TV.

In the years preceding I had worked my way up in the company, initially taking a part-time position as a telemarketer but quickly getting to a point where I was known in the company as the person who could ‘solve your problem’. I had a great working and personal relationship with the owners who in turn continued to give me further scope to improve the business, which I loved to be able to do.

After reading The Four Hour Workweek, inspired and filled with ambition, I told my boss that I wanted to work remotely or I’d leave the company. A massive gamble, but it paid off as he agreed, begrudgingly.

A few days after my 30th I started travelling up the Australian coast in my caravan carrying a constant feeling of being more alive than I ever had.

Within a month or so, I had managed to start getting more done per week than I ever was in the office, but it was only taking me the equivalent of three days work. At this stage I started working on an absolutely horrendous business plan which involved selling my own health products online. This business concept required a website and I started looking into how to build a website.

A week later I had built a hosted Joomla site on a VPS (remember those!?) and I was hooked. I first started programming in QBasic when I was 14 spending a few years building small games and experiments finishing up when I finished school (or actually, when I turned 18 and drinking seemed like a more social use of my time). I sadly never pursued it as a career but seeing the huge potential reach of building web sites, and my pursuit of location agnostic work, my interest once again exploded.

Needless to say, I spent months of time working on this business concept and it was a absolute FAIL. It is still good for a laugh with my mates even 10 years later though. I’m very open and share a lot about myself (not on socials but in a personal context) but the product video for this business still brings up strong feelings of embarrassment. I did learn a lot about putting together animated videos, doing voice-overs, writing copy, creating an alter-ego, and the background music is also done by me as well.

One of the secrets of success is to celebrate your failures so in keeping with this ideal, here is the video. Mock me as you will.

Oh geez…

I also happened to film myself for most of an entire week and create a time lapse which looks pretty interesting but is a great example of wasting time.

As many new web developers at that time, I fell into learning PHP which was the most popular web language due to a number of factors but notably the huge market share of Wordpress. I managed to secure my first ever PHP job in London in 2012 around the time of the Olympics at a fast growing startup which was very exciting and allowed me to see for the first time what working on a software team looked like. I was working this job for a number of months before one morning turning up to find that the UK tax department had seized all of the company’s computers and assets overnight and the company’s owners were all on flights out of the country. Job security when working for a early stage company is always questionable at best, but this finish definitely took the cake!

After returning to Australia from the UK, I started working as a junior developer for a fantastic and very talented agency called Newism and for a number of years refined my skills building web apps. To be able to work remotely as a web developer, I decided that I needed to spend the time learning and becoming proficient in the craft first in order to find remote opportunities.

During my time at Newism, I negotiated for reducing my 5 day week to 4 days in place of an increase to my initial, junior level wage. The owners where happy accept this.

I then moved into a tiny bedsitter apartment nearby work which used to be an old persons home, and as you can see here, it was very small. The building did contain a huge shared industrial kitchen with walk-in size cool-room and freezer for the 100 or so rooms in the building which I actually preferred as it was a great way of meeting the different people who lived there. As can be expected in such a place with good locality and cheap rent, it was an interesting mix of people on the way up, on the way down and some at the very rock bottom of life. I made some good friends here who I still keep in contact with today.

This apartment was within walking distance to work but also to the university campus and I started postgraduate study full time. My weeks at this point consisted of working Monday through Thursday at Newism, taking night classes at the university, and spending Friday through Sunday on campus studying. It sounds like a lot of work, but I loved every minute of it.

After a few years I completed a Master of Information Technology degree and followed it up with an MBA. I was so hooked on the study lifestyle that I decided to add the extra challenge in my last semester, also completing a Diploma of Project Management at TAFE (for those in the US, think Community College). At this point, my friends would often need to really push me hard to actually see me in a social situation.

Around the time I was finishing off my MBA and Diploma, I decided to go out on my own and start my own consultancy. A friend had an app that his company wanted built, their budget was about half a year of my salary at the time too giving me a decent path to standing the business up, so I decided to take the plunge. I resigned from Newism, rented a desk space at shared workspace (again, within walking distance of my tiny apartment), registered the business and got everything ready to go.

The day after my last day at Newism, my friend called and said that management at his company had shifted their plans and no longer wanted to proceed with building an app…


At the time it was still only a verbal agreement and so I didn’t have any legal recourse, and even if I did, I’m not the type of person to exercise those types of options. It may look bad quitting your job on a handshake, but I will say this, if I didn’t take this absolute leap of faith, I’d still likely be working at Newism today.

Having the expenses of a business and an office, but without any income, puts you in a very special position. It’s sobering and forces you to see things and think very clearly. I managed to use my network to get some contract work through a few agencies around town to keep my head financially above water for a number of months, but I started to wonder if consulting was really where I wanted to take my career.

Chasing work sucks. Having significant business acumen really helped me to get prospects over the line as I could align myself with a business well and allow them to trust me quickly, but it’s a time intensive, high risk activity with low future utility or value.

In light of this, I put together a startup idea named Utilitracker which pretty much consisted of only a low budget video introduction and a few technical concepts for power measurement that my brother and I had come up with. I completed half a degree in Electrical Engineer half a lifetime ago so I know just enough to ask some really bad, but sometimes innovative, questions. My brother Adam is a Mechatronic Engineer who could then push back on these ideas which created a great working dynamic for ideation. Some of the concepts we came up with I feel are still missing in the industry.

The video supposedly turned a number of heads and I was invited to pitch the idea in Sydney to a large panel.

This ended up as another FAIL and rightly so. The resources that we required to get this company to a point of an POC were quite staggering and would have required a significant amount of R&D. To productize the concept to an MVP level would have also taken a lot of resources on top of the initial POC requirement.

While Utilitracker didn’t have much of a real chance, I did get to meet a good number of people in the startup community in both Newcastle my home town and in Sydney. This paid off in two ways.

Firstly, one of the founders of Australia’s most successful accelerators approached me after the pitch session asking me to do relatively lucrative contracting work on a few personal startup projects that he was overseeing. It turns out that I apparently had come across as a quite the technical creative and these projects lasted for over two years and provided a small base income for me during that time.

At the same time, I also started working as CTO for Deckee. Mike, the initial founder and I met originally when Newism had built the original MVP of the site during a local accelerator. Jessica Watson also joined the team at the same time as I did and the three of us spent a few years working on the product.

Deckee found it difficult to get funding (doesn’t every business?) and so it was very much a case of living off credit cards and doing side-work for a number of years. Again, this sounds tough, but I actually loved every minute of it.

When you know there is no money coming in, you learn things much quicker than on a paid job. In the context of software you learn great skills in trading off code debt for delivery, testing what you delivered and if it’s good to keep, paying down that debt so that you can continue to work quickly with good modular infrastructure. You learn how to keep yourself in check and constantly creating business value as opposed to following personal interests or bike-shedding on decisions. You also learn to do things right the first time as opposed to just getting them done. I believe so often code debt is derived though engineers implementing the first option that they think of or what they’ve done before, when the process should be finding multiple approaches and trading them off against one another.

I feel what I learnt in the 2 years of working in this way was equivalent of what I would have learnt in 8 years doing normal salary work, changing jobs every two years. There was no back and forth between team members and sitting back, waiting for responses; no limits to technology choices apart from financial constraints; and no structured office times to hinder ‘when’ I was meant to doing my best work. I was in a state of pure creation and learning.

I was in the office many mornings when it was still dark allowing me to watch the sunrise as I worked. I would leave work at 7:00am most mornings to complete a 10km walk around the beautiful Newcastle beaches and then return to the office when everyone was arriving. Many of these days I’d still be in the office till after dinner. There where many consecutive 17 hour days during this time.

It got to the point one morning where the owners of the workspace sat me down for a meeting. The security company had called telling them that I had accessed the office at 3:30am in the morning and the person on security watch had thought this looked a little strange and the place might be being burgled. They asked me to refrain from coming into the office until later in the morning in future, not for any other reason apart from my own health as they where worried. They were probably right, I find for me, it’s after the 10th hour of work that my abilities start declining pretty rapidly.

Between 2015 and 2020, I continued working on Deckee taking on a few jobs from time to time to keep me financially viable, these included:

  • Locomote in Melbourne: during my time here I lived in an amazing hostel within walking distance to the office. My days where spent in a professional, financially lucrative office job environment, evenings was drinking and socializing with backpackers from all over the world. After leaving Melbourne and moving to the US, I took this job with me working remotely.
  • VoiceBase in San Francisco downtown: part of with a team of only about 8 engineers on systems that where processing at the time over 20 million minutes of audio per month.
  • Serena & Lily in the north SF bay area: leading a team of local and near shore (Costa Rica) engineers on an e-commerce site with around 1 million monthly users. This role started as co-located for the first few weeks but then went to a fully remote setup.

All up, when COVID-19 started, I had only worked in an office for a little over a year total out of the previous 5 years.

I found that portfolio videos are extremely beneficial in finding work. It is difficult as a software engineer to sell yourself due to the technical nature of what we do so in 2017 I decided to experiment with the idea of ‘show don’t tell’ and created my first portfolio video.

This was a good start but I followed in up in 2019 with what I believe to be a much better effort, giving better information about my technical abilities, more engaging and interesting product demos and actual video of me talking which allows the watcher (hopefully) to feel more rapport with who I am as a person. The last section which tries to give a better idea for who I am personally and what I do outside of software continues to get great feedback.

Not long after creating the second video, I was approached by a recruiter from Google and asked if I was interested in interviewing (silly question right?). I’m not sure that my portfolio video was what got me noticed, but I have a strong feeling that it was. This email arrived within a few days of my first child being born which had started me reassessing my goals of location agnostic work. Location agnosticism is great, but with a young family, I had started to think more about building the best working situation for the family, which led me to the idea that a higher paying, co-located role might be a better option than doing remote work.

The idea of working for Google honestly wasn’t even something that I had even contemplated though.

An immigrant, self taught developer who doesn’t even like calling himself an engineer because, I mean really, he just meddles with javascript? Engineers have learnt things properly and have a degree and a student debt to prove it. Google engineers are the people they write books and make movies about. My expectations of success where extremely low.

I originally interviewed midway though 2019 and while I wasn’t successful, the feedback was much better than I expected and the door was left open for me to take further interviews later.

After my interview experience, seeing only a glimpse of how Google works internally and the amazing characteristics of all the Googlers I met on the day, succeeding in the next round of interviews became my absolute priority.

I quit working in January 2020 to spend six months doing intensive study in proper computer science, mathematics and to practice designing and building complex algorithms. Not working for six months at that stage meant forgoing over 6 figures of income based on my current situation. Like I had done so previously in my career, I took another huge gamble. Tracy and I even decided to move to San Jose based on the idea that I was going to get the job.

It’s awfully funny how things work out when you do take these leaps in life. During these six months off I was also approached by a number of other companies and managed to get an offer from Amazon (and a few other non-FAANG companies) prior to doing the second round of interviews with Google. This took a lot of stress out of the situation for Tracy who was financially holding the family afloat, working while pregnant with twins, during COVID-19, while we got adjusted to a new house as well.

All up, my preparation consisted of over 100 hours of actual online interview practice with real people, 220 leetcode solutions and huge amount of reading and studying.

The work paid off and I managed to pass the interview process the second time round. After taking a gamble of this size, getting the Google job offer was a great experience and I started the role a few weeks prior to my 40th birthday. Internally as a new employee, or as a Noogler as I’m officially called, Google has absolutely exceeded my expectations which were very high to begin with.

While my career over the last ten years is quite storied, I truly believe that Google is my ‘forever’ job. Those who know me personally will think that it is crazy for me to say that I have a 20 year plan, even a 3 year plan would shock my Mum I think, but at this point with a young family, an amazing wife and doing a job that I love with the most talented and personable people available, I have trouble even thinking what my next career move would be? That is one of the best feelings ever.

It is also worth mentioning that I’m still the second largest shareholder in Deckee and have moved into a technical advisor role. We managed to build a great team while I was stepping back from the company so I’m not foreseeing much need to help there. The engineering team is currently only three people but have exceptional talent and experience and are starting to really drive up the level of output. It really feels that Deckee is starting to get some good acceleration and I’m looking forward to seeing where it ends up over the next 12 months.