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Tech Career Insights: How I Transitioned from a Desk Job to Full-time Freelancing
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How I Transitioned from a Desk Job to Full-time Freelancing

24 April 2020, by Dominic Santo

Deciding to become a freelancer is a big decision, and, while some people are able to take to it like a duck to water, I felt like the change would be a bit of a shock to my system. To avoid this as much as possible, I decided to spend a few months preparing for my new venture before I left my full-time job. Here’s how I set myself up to win, as well as what I learned through the process.


Just over a year ago, I started feeling ‘stuck’ in my full-time job. I was stuck on the same project and working with the same people, and this lack of diversity led to me feeling complacent for most of the day.

I loved writing code, but being stuck in this negative mindset was really starting to affect me. I knew I needed something different – and not just a new project – but a whole new career path. I wanted to take charge of what I spent my days doing, so in my mind it made sense that I started working for myself as a freelancer.

Of course, making this decision was really scary. In particular, the idea of not having a consistent flow of income felt daunting.

To counteract this feeling, and be proactive about how I could get my new career path to work for me, I decided to do some proper planning for it before I left the security of my full-time job.

This planning took me almost a year, but I feel like it really paid off. To set myself up as well as possible, I started doing the following things before officially taking the leap:

  • Marketing myself
  • Attending meetups to build connections within the community
  • Taking on jobs for free to get more varied experience
  • Setting myself up with everything I needed to work remotely

Here’s how I did each of these things, and how they helped me win as a freelancer.

I started marketing myself

One of the first things I learned is that marketing yourself is tough. For one, you have to find your ‘voice’ – something that sets you apart – and that’s not easy.

In my experience, this took multiple iterations. One of the most effective approaches was to build up my LinkedIn profile to clearly show the work experience I had and the skills that past colleagues had endorsed. This meant that if someone landed on my profile, they could quickly and clearly see what I had to offer.

I also reached out to people directly on platforms like LinkedIn and Slack. Sure, sometimes this was a bit awkward, but, if there was any sort of lead I wanted to follow, or anyone in particular I wanted to hear my name, I kept trying, confident that at least one lead would get me somewhere.

I made attending meetups a regular part of my week

I found meetups to be another great way to network because there are so many different ones to choose from. Meeting people at these meetups was extremely valuable in showing me what was ‘trending’ in the tech space and what I should be looking into, beyond my bubble of expertise.

A practical tip that worked really well for me was mapping out a set of objectives before each meetup. As I started attending multiple meetups a week, I set the goal for myself that I would learn about a new tech, meet someone new, and schedule something with them in the future – be it a pairing session or just hacking away at something together at a coffee shop.

Eventually, I plucked up the courage to start hosting my own meetups. Being an organiser was another useful way to get myself top of mind when people wanted to reach out to someone with my skill set.

Being willing to put in this bit of effort helped me see that I could really help myself by opening up to what’s out there – it helped me realise not only what I knew and could contribute to the community, but also what experience I still had to gain and how much diversity exists in the engineering world.

I took on jobs for free to get more experience

It can be hard to wrap your head around the idea of working for free, especially when you’re adding extra pressure on top of your 9-5. However, I found that doing pro-bono work was a great way to get started on my journey into freelancing.

The first free work I ever did was for a digital marketing agency who needed some help with a little PHP scripting and a few Wordpress sites. While the tasks they gave me were nothing fancy, I had a lot of fun doing them because I got to see how a different company operated and what being a contractor would feel like. Getting a taste of having my own ‘clients’ was very useful down the line when being my own boss became my full-time reality.

Pro tip: I found a few of my initial freelance jobs through platforms like Nomad Now, Toptal and Upwork, so I’d recommend checking these out.

After a couple of months, having a full-time job and contract projects on the side, inevitably started taking a toll on me: I wasn’t sleeping well and the constant context switching was hard to keep up with. Luckily, because of the relationships I had built up with clients doing pro-bono work for them, I was able to set up some paid projects quickly, and this gave me the confidence to finally launch into my new career.

I set myself up with everything I’d need to work as a freelancer

Making the decision to plan for a freelancing career while I was still working a full-time job meant that I could afford to buy the things I would need to win while I still had a stable income stream.

Knowing that I’d no longer have access to a ‘traditional’ office, and would mostly be based in coffee shops and co-working spaces, I put together a list of ‘things needed in a freelancer’s backpack’. I took my time putting this list together because there are more things you need than you think, and these things are surprisingly easy to forget!

Beyond the obvious, like a laptop, these are the things I have on my list:

  • A spare charger that stays in the backpack: Because I alternate working from home and coffee shops, I find it annoying to have to plug and unplug my charger
  • Earphones or headphones to block out noise, which also stay in the bag
  • An extra plug point or double adapter
  • Stationery: I make sure I have at least one pen or pencil, because you never know when you’ll need to go back to the drawing board 😉
  • A notebook: I like to make notes and doodle sometimes to get the creative juices flowing
  • A spare modem/LTE option: I sometimes work off a virtual private server so I need a decent internet connection if the space I’m working from doesn’t have one
  • A power bank: Because Eskom…

Making the decision to thoroughly plan for my career in freelancing, and then launching into it, has taught me a lot about myself – both as an engineer and as a person.

For anyone who wants to stretch themselves and do more than just sit at a desk, I would recommend giving freelancing some thought. That said, it comes with many considerations, like admin work, context switching and mental discipline that people don’t always factor in. I’m certainly still getting used to these things – but I’m more energised than ever before and would do it all again.

Dominic Santo, is currently working as a freelance software engineer. He describes himself as an avid learner, inventor and hacker enthusiast.


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