2018 retrospective

This post is more than a year old. The information, claims or views in this post may be out of date.

Image credit: NordWood Themes on Unsplash

It’s been a hell of a year – pretty much like most of the last few years!

Every year, usually between the Christmas and New Year periods (where time stands still) I’ll put some effort into an annual retrospective. Someday, I tell myself, I’ll come back and read some of these, hopefully laughing at the problems that looked so daunting in the past.

The real headline: 2018 was the year I quit full-time employment. It took a 10-year stint (at which I learned much!) and there’s still the ever-so-small chance that all of this falls apart and I have to go back to a full-time job, but for now I’m enjoying the freedoms that come with it.

(And still adjusting to it, 8 months later, really.)

Among other things, I’m trying to blog more. Yes, everyone says that, but I’ve got good reason to: In 2019 I’m starting down the road of product development (the indie hacker dream) and a big part of that is getting comfortable with being public and visible online – something I’ve generally been pretty shy about.

So with that, I need to get a bit more personal on this blog. I’ve written about that before, but the only thing that will actually cure me of this stage-fright is if I start doing it – and this seemed like the ideal opportunity to get some practice in.

January – March

If there was ever a call-to-action, January was it. I’ve been thinking about going out on my own for years, and have occasionally talked about it with friends and family, but it was always with an indefinite time horizon. Somewhere in the future, someday, I’ll take the risk.

By January, things were already heading in that direction at work. I was fortunate to have a long career at a company that I joined in the startup phase, lived with it through the maturity and eventual sale, and I still feel privileged to have done and seen all that I did as a result.

But by end-2017 things were changing in a way that diverged further and further from what I wanted to do with my life, and the likelihood of creating those opportunities were diminishing as the rest of the organization changed. It was inevitable, really – all good things eventually come to an end.

That was all in the back of my mind when my grandmother had an incident, which landed her in hospital for a week. I visited almost every day, and that time spent really put things into context for me. She recovered and was discharged the following week, but it left me to think about a lot – among them, the fact that I was still in a good place to take risks, and the sooner I took charge of things, the better.

In February that culminated in a resignation letter with a two-month notice period (developers are hard to find in South Africa and I still wanted time to figure out what I was going to do). By March, all the financial affairs were in order and I was just running out the clock – writing documentation, doing handovers and last-minute project work.


My last month of full-time employment, and the first month I started figuring out exactly what I was going to do. I had been saving for a few years, and had about 3 months of cash in reserve, but I needed to come up with an actual plan.

I’d be lying if I said I was confident about any of this turning out well. For years, people have told me, asked me, (and at one point actually swore at me) in confusion as to why I hadn’t already struck out on my own. I always told them it wasn’t that easy, I wasn’t ready, and when I was ready I’d do it – but then I never felt ready.

I felt even less ready in February, when I submitted my resignation. If there was anything I was ready for though, it was a drastic change – even if it meant tearing down everything I had built up until that point.

May – August

May was a hard month.

I’ve since learned that there’s a speed to business – it runs in 3-year, 1-year, 3-month and 1-month cycles. Very little happens day-to-day if you’re not actively working, and I’m already a fairly impatient person as it is.

I tried taking the month off, telling myself I needed a break and that I could start working on my business in June. I didn’t listen, though. Every single morning was stressful, and every day I ended up trying to do something – anything – that felt like progress. In truth I was just spinning my wheels.

I did do a lot of reading, though. It turns out there’s an absolute wealth of information on this exact problem (Double your Freelancing, the Indie Hackers forums, etc), and I was soaking up as much of it as I could, just waiting for a chance to use it.

I eventually figured that, worst case scenario, I could go via an existing freelance market and try finding gigs that way. If it meant working really long months for a while, that would still be fine. And if I really couldn’t make it work, I could always just go back to full-time employment – like I said, finding good developers in South Africa is hard.

It was in June that things started to happen. One of my biggest assets, it turns out, was my network and reputation. 10 years of working at company through which many people passed (and got to know me) actually translated into business opportunities.

Mostly it was just a matter of me being available whenever the opportunities came up, and to capitalize on them as quickly (and as well) as I could. By the end of June, two months into this new adventure, I had managed to invoice about 60% of my target monthly revenue.

By July, it was over 100% of target, and by August, with all my NET 30 invoices coming in, I was able to pay my salary entirely from my own revenue for the first time.

That was the actual life-changing moment for me this year – the realization that, all on my own, I was capable of providing a good enough service to paying customers, and earn a living off that.

I still had no idea where I wanted to go with things though, and spent the rest of the year simply taking up as many work opportunities as I could find.

September – November

An entrepreneur is someone who works 80 hours a week for himself so he doesn’t need to work 40 hours a week for someone else.

Unknown Author

These three months were the hardest I’ve worked in years, but also the most fulfilling. For the first time in ages, I was able to bring all of my skills to bear on solving problems – and it felt great doing it.

It was pretty hard work though. The total time spent was well in excess of regular 40-hour workweeks, and that’s before considering all the admin that goes into making the “back office” stuff work. A trial by fire for sure, but right now it’s paying off.


Which brings us to this month, which I had originally anticipated would be quiet, but instead turned into one of the busiest months of the year. I’m still not complaining, though. This year was a big one in terms of personal growth, and that’s the big thing I’ll continue pushing for in 2019, learning an all-new set of skills in sales and marketing.

All of that was just my working life, though. 2018 was also the year I did a few other things:

Sought Therapy

I’ve become a firm believer in therapy. My psychologist had a good take on it: People will spend thousands to maintain their cars and homes, but will refuse to spend hundreds to maintain their hearts and minds.

In my case, there was a lot of anxiety to work through (obviously: I was making a major life choice), but that also cascaded down into a ton of lifestyle and social issues I had to deal with too.

Started a YouTube channel

I quit Twitter because it wasn’t a great place to have longer-form conversations, but that was after the first few episodes of what we’ve called the “Noscript Show”. The irony is not lost on me: We set out to create a tech podcast, but by the second episode it was more interesting to talk about current affairs and social issues, of which only a few are technical.

It’s been a big deal for a bunch of reasons – one of them being my continuing paranoia about putting too much personal stuff out there. It’s been fun to do, though, as a regularly-scheduled event. And there’s always stuff to talk about, which is great.

Co-ran the Helderberg Developer Meetups

If I’m being honest it’s Charl that does most of the organizing (I need to do better in 2019, sorry!). I do have a legitimate excuse in that I quit my job this year and have had to scramble to make ends meet, so I’m hoping that 2019 goes much better.

We meet once per month at a nice spot in Somerset West, and we supply some great snacks!

If you’re interested, the Meetup page is here. Right now I’m planning on delivering a VueJS talk in January – progressive site enhancement in Laravel, with a live demo.

Digital Nomad dry-runs

There’s something appealing about the Digital Nomad lifestyle: The idea of being able to work from anywhere, taking your laptop and business with you to exotic locations. I’ve always thought I might try that out for a year – even on a South African passport, there’s lots of places you can enter for at least a few weeks at a time, and see more of the world while you work.

As it turned out, my living situation was perfect for this. Since I live in Somerset West and have to meet customers in Cape Town every couple of weeks, I started treating them like mini-nomad trips. I’d pack as if I was travelling, and plan to work wherever I Airbnb’d.

It was an informative exercise for sure. One thing I learned: It’s difficult for me to get into a really productive flow state without a comfortable environment. Doing emails, calls, quick bug-fixes and coordination while on the move is fine, but if I wanted to develop actual software I’d need a quiet place to do it.

On the flip side though: Just being out travelling was much better for my overall well-being. Even if I only get an average of 2-3 productive hours/day, doing that while being parked in new places, seeing new things, and meeting new people makes it all worthwhile.

By end-2019 I will need to decide what my next year looks like, and I’m hoping to be in a position where I’ve got that flexibility. Before renting a new place, I’ll first try spending a few months travelling about a bit. If all goes well!

Quit social media

Facebook’s just about run out of goodwill with me, and I’ve ended up completely cleaning out my profile. I’ll still keep it (I need access to the developer tools), and I may use it for pure marketing purposes down the road, but as a social network, I’m done.

I quit Twitter too, and right now I’m still on the fence about it. I know I need to build an audience and social media is a good way to do that, but I really prefer the idea of subscriptions and newsletters over the noise that is social media. At best, the integration to WordPress and Medium will stay up, tweeting stuff out to my ~900 (as of today) followers.


So this is the part where I decide on my new year’s resolutions – since on new year’s day itself I’m likely to already be busy trying to make them happen!

1.Build and launch a SaaS

Any size, any MRR, any feature-set, any market: I just need the experience of building, launching, getting customers, and everything involved in making a good SaaS business work. I’ve done a lot of reading up on this subject, and I have a lot of opinions, but they don’t mean anything until I execute.

2. Blog more

For personal as well as professional reasons, I’ll be trying to push a lot more stuff through this blog (mostly personal, insight etc articles) and Medium (mostly technical articles), with some cross-posting to other sites.

The only tangible goal I’m setting at the moment is 3 posts per week, which should be easily attainable given my typical workload.

3. Read more

If you want to write, read. I’ve got a collection of books that I’ve accumulated over 2018 (a mix of business, technical and fiction), which I really need to start reading at some point.

In the absence of the Twitter-storm of constant content, I’ve found myself turning to local news in an attempt to plug the gap, and most of that is noise anyway. So from today onwards, my Kindle stays charged and loaded, and will accompany me wherever I go.

4. Develop routines

Easily my biggest challenge in 2019 will be routines and discipline. If I want any sort of business to work, I need to take a process-driven, methodical approach to things. I have a bad habit of simply diving head-first into things that are interesting in the moment, when the real long-term gains may come from the stuff that is difficult and boring in the moment.

I’ve already addressed this somewhat, with a new approach to capacity planning. Making it work is a whole other story though!

Every now and then I’ll look back and think about what might have been (a bad habit sometimes, but necessary to develop an appreciation for opportunity cost), and I think 2018 panned out in the best possible way, given the options.

I still don’t know exactly where I’m going, but I have a fair idea of how I might get there, and at least enough of a roadmap to get me started. If this year has taught me anything though, the key is to always be prepared. Wishing for a future won’t get you what you want, and life has a tendency to laugh at the most well-laid plans.

Onwards to 2019!

Published by

Wogan May

By day, I run a software development agency focused on business tools, process optimization, data integration and automation. By night, I build tools and platforms that serve online creators.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.