Two weeks ago i quit! — my technical freelancing thoughts so far

Adrian Cantrill
7 min readNov 2, 2016


Just over a month ago I wrote on medium about quitting my full-time job. four weeks later I finished up and for the last two-weeks or so I’ve been a tech freelancer. I’m not sure how I view it yet — do I have a real job? do I run my own business? is it real?

Labelling things is hard, and I’m not sure anything really fits at the moment.

TL;dr as background for those who didn’t read my previous posts — I’m 37 and a huge tech enthusiast. I’ve worked in IT for 17 years, 10 of them in the cloud space (AWS, Azure, Google). I love learning, getting certified and mentoring others. I write courses for a cloud guru — until recently part-time, but as-above, it’s now full time.

I’m two-weeks in; and I promised to share my experiences and feelings during the transition— my hope is that it helps others looking at a similar endeavour. I’m not here to influence, only to inform — but if anyone wants to chat — give me a yell and we can talk/type.

General State of mind

This is an interesting one, as on the surface nothing much has changed. Until I quit, I’d been working full time at home, doing a job that I found relatively easy. I’ve swapped it for another work from home, or anywhere job. On the surface it doesn't look any different — you wouldn't know from looking at me that anything has changed. But thats where the similarities end.

Lets talk employers first — while I’m officially freelancing, I do consider a cloud guru (ACG) to be my employer, or maybe primary client? — how does this freelancing thing work anyway.

They are a great bunch of people — all amazingly talented and fun to work with, and be around. In the space of 6-weeks, I’ll have travelled internationally twice with them, one to the UK to help run a conference, the other to Las Vegas for an industry event. I’m also co-organising a Brisbane tech meet-up which will run monthly. I did have a comfort zone, it’s over there next to my old job.

In summary, this is a win — I love the change and the challenges.

Next up is how much difference it makes working for myself. There is a raw link, a direct feedback between the effort I invest and the financial reward. This combined with the fact that I’m doing something I love — teaching others, it makes it SO easy to get out of bed in the morning.

There is a flip-side, it’s easy to work too much, but I’ll talk more on that later. I’ve no complaints here — if I want more success, I improve, and I do more of what I’m doing; the money adjusts accordingly.

It also hit me that I don’t have a schedule — or if I do its entirely self-managed. Working from home before freelancing was middle-of-the-road flexitime; this is something else. The freedom of being able to work when I want, have time off when I want and being able to invest in improving my own efficiency is a surreal experience. I love it — and I’m not sure I can ever go back to a role where time is linked to money, rather than delivery — it seems so backwards.

I was concerned the financial uncertainty would bother me — that the lack of a consistent paycheck would be an issue; it isn't.

I think it isn’t for a number of reasons 1) I have a financial buffer, 2) this whole endeavour is planned, with financial checkpoints and reviews and 3) I have a very understanding partner who is supporting me all the way (Love ya Nat).

When I quit, I knew to expect variation in incoming funds — that i’d have some good months, and bad. Even on a daily basis its variable — I get paid when students buy, so there it is again, the raw relationship. I deal with this in two ways — I personally work a month ahead, living of last months income. This way, there are no surprises, I already know the income for a specific month.

I’m also working on multiple courses, each providing independent income — the idea being diversification. This is win as well — if i’m honest I love the potential for earnings — and it’s feels like there is some gamification built in.

So lets talk specifics… what actionable things have I been working on…

Track your time, data is key

The thing that makes this whole endeavour work for me is treating it like a business. I want to translate delivery into income — and make a living off it. I was very specific in how I worded that, its not time into income— its delivery to income.

The ideal scenario is that my content makes ongoing passive revenue until the end of time — but thats not realistic and even if it were, I’m nowhere near that yet. I need to be aware of how much time I’ve invested into every course — end-to-end, and how much return is generated as a result.

Students generally only see the number of hours of videos and labs in a course. But there is so much more — research, outlining, slides, lab design, coding, recording, editing, uploading, quiz questions and even marketing. I need to know, a total of all of those elements and track that against income earned. Using this data I can trend which courses are good earners, and which aren't.

If I don’t earn, i don’t eat — its pretty direct.

I use an application called toggl — it’s available for macOS and iOS, both of which are my platforms of choice. It’s pretty easy to configure, you can setup people, projects and clients. And you can map your time against those entities. It syncs between my devices and comes with good reporting — in short, it just works.

My biggest logistical change early on was becoming regimented with my time tracking. If you are about to start on the freelancing path, become good at tracking time as soon as possible, your sanity will thank you.

Maintain a balance

I mentioned above that I love my work. I love the company and helping others to improve their lives via self-improvement.

I’m learning, I’m helping others to learn, and I’m getting paid for the privilege. It’s addictive and with that comes some concerns. I’ve found that it’s easy to drop any notion of work-life balance when that work is your thing. I’m lucky, my partner is super-supportive — both to make me happy and because she sees the potential for our financial success. If anyone is at a similar stage to me, or about to start, my advice is simple — set boundaries and establish some form of routine. I’m not saying don’t adapt and have a flexible schedule — thats one of the benefits of freelancing. What I’m cautioning you on, is set up a structure to avoid 70-hour weeks — unless you want that — which might be the case.

Whats Next?

My plan is continue doing what I’m doing — releasing great technical content. But at the same time, aim to put in place some planning and systems to support me. I’m still working on my technical setup, recording studio and workflow — more details on those in upcoming posts.

In the short term, I’ll be writing about the financials involved — I’m still pondering how much detail to provide (if you have any comments on this, give me a yell). And I’m also planning detailing whats involved at a high level in creating a course. A blow-by-blow from initial idea, to downloadable content.

If you have any suggestions or specific questions you want answered, drop me a line and I’ll do what I can.

As always, if you found this useful please tweet, Facebook share or medium recommend — it all helps me increase my reach, which puts food in my mouth.

And of course, if you are involved in tech and/or cloud — consider buying my courses here and here.



Adrian Cantrill

Technical Trainer, Cloud Architect, Tech, Productivity & Efficiency Obsessed wannabe minimalist.