2018 has probably been the biggest year I've had in my adult life in terms of the volume and variety of changes that I have experienced in my work, family and personal life.

I started a new job right at the end of 2017 after working almost exclusively with the same company since the beginning of my career, which I was lucky enough to start when I was just 18 years old and freshly out of high-school. I managed to become completely debt-free after struggling with personal loans and credit cards for my entire adult life. I welcomed a second daughter, finally went on an overseas holiday to Fiji and after just shy of a decade of dating, living together and starting a family together, my wife and I finally got married. I even started experimenting with investing in stocks and taking on some freelance work to consume the 4 hour per day commute that I have to work and back every day.

Work: Agency to Start-Up


My career started at a small company originally called Creative Breeze, who needed a developer to take on the development of their Flash banner ads and small static websites for local businesses. I was able to get my foot in the door with a combination of luck and experience and skills that I developed during high-school working on my own website and Flash games.

The pay was not very good and the work wasn't particularly stimulating, but it gave me a good environment to learn how to work within a business, meet some people who helped me a lot in the following years and ultimately begin my career.

Creative Breeze was consumed by a global company, Mediabrands, approximately 18 months after I started work there. We rebranded to Airborne and had access to much more work opportunities than before, but the work I was doing remained largely the same for another 12-18 months (banner ads, small local business websites and promo sites).

Eventually we built the confidence to take on more complicated projects, notably a completely custom system for creating and managing promotions. This was probably the beginning of my journey in learning serious backend development skills, which from that point expanded rapidly by managing my own PHP framework, used for all of the work I did at Airborne going forward and regularly updated with new skills I'd learn over time.

I moved to a new position at an agency called XO Digital (now Enigma) based in Newcastle who were starting a Sydney-based office. This move was due mostly to pay disputes at Airborne, however after approximately 4 months I was re-hired at Airborne to continue my previous role.

Shortly after re-joining Airborne, we were merged with an activations company called Ensemble. This brought a significant shift in the work I was doing, for the better. I no longer worked on banner ads and rarely worked on smaller business or promotional websites. Instead, I spent the rest of my days at Ensemble working on some really interesting long-term projects for Nestlé, who needed software developed for their pop-up stores that the activations team were working on. During this period I invested a lot of time developing my frontend capabilities by learning Vue and stretched my backend skills pretty significantly as well. We created some work that I was really proud of - completely custom point of sale systems with customer-facing ordering software (similar to the McDonalds kiosks).

I was able to learn a lot during my time working in an agency-style business with the limited technical constraints and variety of work available. There were however some major drawbacks to working at an agency, which include:

  • Constant time pressure, which led to a lot of corner-cutting, stress and tension within the team. Losing clients because of faulty software that I produced was a real possibility. A lot of money could be lost by missing deadlines for advertising campaign launches, which fell on the shoulders of the company. Evenings, weekends and even holidays are up for grabs if deadlines are approaching and the work has not been done.
  • Repetitive short-term projects became tedious and did not allow you to properly develop your skills or experience with maintaining a long-term website or piece of software.
  • Dealing with a lot of people who understand absolutely nothing about what you do. The agency was large and facilitated a lot more than just software and digital advertisement production. A lot of time got wasted explaining sometimes trivial things your client services team time and time again, often in an attempt to convince them that something they've promised a client is either completely impossible or a much larger and more expensive venture than they assumed.

I don't regret my time at an agency because I learned all of the skills I have now, which allowed me to be successful in my move to a start up, however at the same time I will avoid working at an agency in the future at all costs; I don't believe there is anything there for me to gain anymore.


Just as Ensemble was starting to fall apart and I was actively looking for a new job, Simply Wall St reached out to me via my StackOverflow profile. I had applied for around 4 jobs and interviewed at one already, but I wasn't happy with the opportunities at the latter and rejected their offer. I was successful in the hiring process of Simply Wall St and started after my one month notice period at Ensemble.

I was hired as part of the growth team there, which gave me some of the technical responsibility of developing software that drove user growth in the main product. Fortunately the hard work on coming up with what this solution would be and validating that it was effective had already been done, so my job was simply to develop a new iteration of that system, which has been the best piece of work that I have done in my career. The entire time I have spent at the company so far has been about improving this software and its peripherals, which is exactly the long-term oriented work I was looking for and has massively increased my skills already. Other than the work itself, some other notable lifestyle improvements in working at a start-up instead of an agency include:

  • No time constraints. Of course there are expectations around when something will be delivered once it is defined and work has started, but these are realistic and based on great code and a working product being delivered, rather than a campaign start date being met. If the requirements change or there are hiccups along the way, the timeline can be adjusted to ensure the desired quality is met.
  • Proper planning and making things we actually care about. The work you do in an agency is handed to you in a briefing document and is typically non-malleable. You have to create something that exactly meets the brief in the shortest amount of time possible, and you are rarely if ever a part of the process of defining the brief meaning you're often spending your time developing things that make absolutely no sense in practise.
  • Working with smart people. A successful startup that makes its money from software obviously has intelligent people working on that software, versus the developers within an agency only needing to fulfil the role of building small websites with limited complexity for the lowest cost to the company possible. The entire team is focused on a single goal - the success of the product they are working on and the company, whereas every team in an agency basically has a narrower goal of pleasing the next layer of management rather than producing something they really believe in and care about.
  • Less technical constraints. Mediabrands was a global company with severe restrictions imposed on the equipment that was given to you. For example, you were not given basic privileges that allowed you to install your own software, which is extremely restrictive for a developer that constantly needs to expand and upgrade their toolset. You were not given the choice of operating system or hardware and getting software installed required approval from the global IT department which could take days to turn around. In Simply Wall St, everyone selects their preferred hardware and has no constraints on what software they decide to use, which makes sticking to best practises as they evolve many times easier.

This move was the best thing that has happened to my career because I can feel passionate about the work I am doing which I previously had to emulate by spending my own time creating libraries and frameworks of my own that would support the work I was doing for Mediabrands.

Debt Relief and Investing

During my transition from Mediabrands to Simply Wall St, I made an agreement to wrap up some outstanding projects that were coming to an end. I was able to set a very good hourly rate for the work and spent the next 5 or 6 weekends working full 12-18 hour Saturdays and Sundays, which quickly racked up significant value.

At the time I was over $25,000 in debt, whose repayments consumed over 35% of my monthly salary:

  • A completely maxed out $10,000 GO Mastercard that was costing me around $150/month in interest.
  • A car loan with a balance of around $15,000.
  • A ZipPay account with a balance of $2000 which was opened to buy a Thermomix.

I was able to completely pay all of this debt off by mid-January with a combination of the money I received from wrapping up these projects for Mediabrands, my new salary at Simply Wall St and some new ongoing freelance work that I managed to get my hands through a previous colleague.

The only debt I use now is a $1000 credit card with my bank, where all of my monthly recurring expenses are linked to, which include the typical things like:

  • Netflix & Spotify.
  • Hosting.
  • Gsuite.
  • Swimming lessons for my daughter.
  • Daycare.
  • Gas & Electricity.
  • Software subscriptions.
  • Gym.

This makes managing my budget trivial because I only need to pay 3 things each fortnight:

  • Rent.
  • The credit card, in full.
  • The family grocery account.

Finally being debt free and being exposed to stock market investing led me to start experimenting with investments myself. I spent the first half of the year investing primarily in US tech stocks, which were all climbing very rapidly over the time I held them. I sold all of my shares after the end of the financial year to pay for a holiday to Fiji, shortly after which all of the stocks I held fell quite significantly, which is extremely lucky for a first time investor.

Since my return from Fiji I've been investing mostly in ASX listed ETFs like ASX:VTS. I will probably continue to invest in ETFs and consider Superannuation contributions at least over the next year. I don't believe I have the motivation or interest required to learn to make investment decisions which would potentially yield more; the learning curve seems steep and mathematics was never a strong ability of mine.


The last 12 months have been the first time in my career that I was doing significant, recurring freelance work for clients who were paying real money. I netted a significant amount comparable with my actual salary, which allowed me to do a lot of things that I previously considered either impossible or not doable until post-retirement.

This all sounds great at first, but the number one things I ended up learning from the experience was that it wasn't worth the money. The money was quickly burned on big expenses like new furniture, hardware and a holiday, which are all wonderful things, but I don't believe they made up for:

  • The stress of frequent 12-14 hour working days.
  • Consumed weekends that could otherwise be spent with my wife and daughters.
  • Inability to properly invest my time on my work and relationships at Simply Wall St, which is where I am doing things I actually care about.
  • Reliving many of the bad parts of working in an agency as noted earlier in the article like deadlines and accountability, but with less layers of protection if something goes wrong.

My strategy in the new year is to try and dry out the extra work and get better with managing the money I do have so that things like overseas holidays every 3-5 years and good retirement savings are still possible. I'd like to properly commit my development energy to the work I am doing with Simply Wall St because I really believe the company has a strong future that I want to properly be a part of. Even more importantly I don't want to have to be working on weekends that I could be spending in front of a BBQ with my family.

Overall it has been a huge year and I'm hoping that my learnings set me up for a good 2019.