[Joyful] tradeoffs of freelancing

Working as a freelancer, most Australians conceptualise it like a sole trader eg self employed craftsman with a high degree of autonomy and skill. Typically you would get to this professional state after a 4-6 year apprenticeship… in the medieval craft guilds system this was known as a “journeyman” before you reached the rank of “master”.

Freelancers, especially with shorter contracts, have a beautiful balance of freedom and flexibility. We can directly scale down our work (and thus our income) in order to scale up other activities like hobbies, families, activism, community service, travel (thus implying a rise in expenses). But one dynamic which gets lost here is the professional development aspect. As a craftsman your skill and experience develops steadily over your working life and you perfect your skills at 55 for the tasks you were stumbling over at 16.

Software engineering has a different paradigm. Technological change has been a steady drumbeat, but in the past three decades it has steadily accelerated. Circa 2010 with the web 2.0 era, it stepped up again with the constant refresh of web stacks, front end libraries, deployment methodologies, the radical change in organisational theory brought about by devops etc. It’s a tenet of the field that you have to be constantly learning and upskilling/crossskilling just to keep up with the field. 30 year programmers in obscure, legacy technology are increasingly a thing of the distant past of the 2000s. This is simply a professional requirement of SWE: a mindset of being able to constantly adapt and learn new tech.

So in the context of freelancing, I have a secret third option alongside the work/spend dichotomy. I can work on personal/PD type projects to directly increase my earning potential (or stop it from decaying). I’m especially lucky when I get a contract that lets me develop my skills in the process, particularly if it gives me access to a particularly complicated stack or expensive API tooling.

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