12 months in 60 seconds

It’s been just over a year since I last wrote a post for this blog – quite a surreal realization to have. It’s amazing how much time you can lose when you don’t have a day-to-day structure that creates space for stuff like this.

Over the last few months its become clear that I need to spend more time writing – with the data and experiences I’ve accumulated, the best thing I can do with it is to share it out more regularly. Subscription tools have also come a long way in the last 12 months, and I’m considering starting a paid email subscription offering.

Before I can do that, though, I need to actually re-discover and refine my ability to write on schedule. It turns out I have no shortage of things to say, I just tend not to find the right moment to say them (or consider them important enough to say).

To that end, I put out a call to my audience on Twitter (which I barely use anymore) and they came back with about 20+ topics and questions I’m in a position to cover:

Based on that, I think I’ve got a bunch of content worth producing. Before I get to it though, I wanted to briefly close the gap between my last post (“2019+“) and right now. Since I wrote that:

  • The global COVID-19 pandemic happened.
  • For the first time since living with my parents, I moved back into a non-apartment building. It was actually quite a realization that, between 2008 and 2020, I had spent all 12 years in various apartment blocks around Cape Town.
  • My business has grown from just me, to 4 people total. We’re still doing roughly what I was doing a year ago, but now that there are more of us on it – the possibilities for future growth are a lot greater.
  • I’ve undergone something of a transformation in the last 6 months. The responsibility of building a business from the ground up has forced me to adapt in ways I wasn’t expecting.
  • As I write this, we’ll end this September having prototyped an entirely new done-for-you service in the digital marketing space, which I think is pretty exciting. Doing something fun that a customer pays you for = winning.
  • The reality of running a business (and having to lead and direct a team) has focused me in a way I’m very grateful for.

I think those are the most noteworthy developments. The next few months present challenges all of their own, but I definitely feel more equipped to handle them now, than I did when I wrote the last post on this blog!


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

And I’ve changed. In future, I might write more openly about the life I came from, the demons I’ve wrestled with over the years, and the moments of breakthrough that have set me free.

April 2018: “Oh boy, where to begin

This is that moment.

I’ve been agonising over this topic for years. There are so many places to begin, and so many bases to cover, I don’t even know if I can get through it all in one go. I do have to start somewhere though, and if nothing else, I’m finally tired enough of feeling this way. So much so that I’ve stopped caring about what the fallout might be.

Whoever thought apathy would be a useful tool in untangling the damage done by a lifetime of depression?

When I started freelancing last year, I set myself a few tangible goals. First was building a runway – enough money to cover me for a couple of months, and give me some breathing room. The next, to set a time and date to pause and reflect on where my life is going.

That time and date is right now. To prevent last-minute second-guessing, I planned this situation three months in advance, letting all my clients know I’d be offline in September. I booked accommodation and transit two months in advance, and when the day finally came to actually go on this holiday, my past self left my present self no way out.

And now I’m sitting in a guest house in a town I haven’t been to before, with nothing other to do than tackle the single largest monster in the bestiary: I’m 30, still single (against my will), and have a lifetime of damage to account for before I can begin to move forward with my life.

The objective truth: I’m bad at relationships. I haven’t had any that lasted more than a few weeks. I’ve turned down good people in favor of damaged people, I’ve constantly sabotaged my own happiness, I’ve hurt people I loved in the process, and I’m frankly amazed that anyone puts up with me at all.

I’ve spent long enough blaming other people for this (and honestly, a few of them deserve it), but I can’t keep running from this forever. I have to come clean to someone – even if it’s just this blog – and fully account for this breakdown in my life.

Over the years, I’ve built up the most complete picture of my life that I could – always operating in objective mode where possible, trying to see my life not only from my point of view, but also from the perspectives of others. What follows is the most complete, honest account I can make.

This is difficult to write. My better judgement and my emotional distress are at war right now, and every bad instinct in me is telling me to stop. Obviously, I’m crying throughout this whole thing, and I have to blink every few seconds so I can actually see what I’m doing.

That detail is important, and I include it deliberately. I’m not going to deal with a near-lifetime of suffering and keep my cool, and there isn’t anybody alive that could claim the same.

But I don’t need sympathy, or pity. If there’s one thing I’ve learned how to do over the last 15 years, it’s to deal with destructive emotions. It’s part of the problem really: Having learned so completely to rely entirely on myself.

No analysis would be complete without examining my origins, so I should start in the 1980s, with my parents and the circumstances under which they met.


My mother came from privilege. Her father was a relatively wealthy property owner, and from what I can tell, she was pretty much raised by her peers – picking up a lot of destructive behavior along the way. The most dangerous by far: A seductive, manipulative streak. She knew how to push people’s buttons (mine, too, decades later).

That property wealth didn’t go very far – my maternal grandfather burned through all of it on some sort of legal vendetta against the NG Church. I think that’s where my mother inherited her blind arrogance from – and not much else.

My father was the product of many generations of working-class families. This traces all the way back to the 1850s, when my paternal ancestor landed in Cape Town and found work as a farm hand. My grandfather worked the mines, and my father was one of three siblings.

The black sheep of the family, it turned out. He didn’t get along with his parents at all, the least favorite of three. He met my mother in high school, and you can pretty much see where this is going:

A rebellious young man eager to break with family tradition (“prove them wrong”), meeting a manipulative women of some means (that the parents don’t approve of), equally eager to live the rest of her life off the backs of other people. They married as soon as they were able.

Neither of my parents will admit this, I’ve never posed the question directly, and I’ll frankly be happy to have the truth of this go to the grave, but: I don’t think I was planned.

Or rather, I wasn’t planned mutually. In the years since, knowing a bit about my mother’s friends and the way she operates, I’m fairly convinced I was a surprise pregnancy, engineered on her part to entrap my father.

That’s the sort of thing gold-digging, manipulative narcissists do. It’s also the sort of thing the South African court system let her get away with in 2003 after she illegally took me out of the country, violating joint custody orders (far as I know, anyway), using forged signatures on the affidavit for my passport.

It should also come as no great surprise that, as soon as I aged out of the maintenance agreement, she couldn’t wait to get rid of me – going as far as threatening her new husband with divorce if he didn’t kick me out of the house he was paying for.

December 2007, what a month.

Those were the conditions under which I came into the world – none of which I was directly aware of for the first 11 years or so. I first knew something was wrong when my parents finally divorced (late 1998), and I was in the room when my mom pulled off her wedding ring and threw it at my dad.


It’s at this point I want to introduce Barney (not his real name), one of my early childhood friends.

In a lot of ways, our lives would have followed parallel tracks. We went to the same primary school in the same small town, bonded over computer games and fantasy roleplaying, and would probably have followed similar paths in our lives had things not gone so wrong.

I use Barney as my yardstick – a measuring device from the same control group, a person that shared some of my formative experiences. I don’t think I’ve told him this directly, but I occasionally measure my personal progress against his, and use his examples, experience and ideas to set better guidelines for myself.

Having a stable, “known good” reference to develop my life against has been a big help. I’d go so far as to call him a role model.


May 2001 was the last time I had any real friends. Despite the family drama, my life was mostly great up until that point. I had gone to the same primary school from grade R through 7, the single longest period of stability in my childhood.

Academically, I was doing really well. In grade 1, I scored highly enough on my tests that the school advanced me straight to grade 3 the following year. By grade 7, I was scoring high marks in class without having to do much homework.

Socially and creatively, I was doing relatively well too. If it weren’t for the five years that followed, I’m convinced I’d be a different person right now.

In mid-2001 my mother remarried a middle aged civil engineer. Another black sheep among several siblings who spent most of his life working, only marginally getting along with his large Afrikaans family. Another person she could manipulate.

By the end of 2001 I had changed schools, finishing my grade 7 year in a different town. Not only did the schools change, the culture changed too. Where I had formerly had a friend circle into “nerdy” things like computer games, this new school was far more athletically inclined. I didn’t fit in at all, and made no new friends there.

It got worse in 2002. My stepfather, being a career loner, followed the work wherever it led. He agreed to take up a project in Zambia. So we packed our bags and drove in his doublecab bakkie all the way from Bellville, through Johannesburg, Beitbridge, Harare, and into Zambia.

My mother’s grand plan at the time: Home schooling. She was excited about the idea of finally playing “mother” to these kids. That excitement came to an end a few weeks in, when it became apparent that it would require a lot more effort from her than she realized. A few weeks into 2002 I found myself on the way back to South Africa, to attend a boarding school in Bloemfontein.

In case you want to know how a narcissist thinks: Her decision to home-school me was justified on the basis of keeping the family together. Her decision to then send me away was justified on the basis of getting a well-rounded education. After my life imploded, she “apologised” to me and said she really shouldn’t have sent me away, as if that was enough to undo the damage.

This is really where the trauma begins. 2002 was the year that broke me. I’ve written about this a few times, but it’s gotten no easier since then, and I doubt it ever will.


The reason for Bloemfontein is that my mother had a sister there. She was also putting two kids through schools – cousins, 1-2 years older than me. She was a teacher herself, a committed marathon athlete, and unstable enough to exercise herself into an early grave. I don’t know what demons she was running from, but I’ve chosen not to find out.

Boarding school is hard at the best of times. It’s harder when most of the children in your group are rowdy, violent, aggressive farmers-children types. It’s harder when the school has a proud sporting tradition, and participation is mandatory. It’s harder still when bullying is tacitly encouraged (to “toughen kids up”).

It’s hardest when you don’t fit in. Starting a few weeks into the grade 8 school year meant I was always the outsider. Having my parents be two countries away, and my aunt dealing with her own troubles meant I had nobody to rely on.

Fun fact: It didn’t affect me directly, but in 2003 a scandal broke. The boarding school had an on-premise chapel, run by a man who produced and disseminated child pornography with the knowledge of the school faculty.

By the end of the first term, my academic scores had bottomed out. I couldn’t deal with the class work at all, between the intense isolation and constant bullying by my peers.

I still remember emailing my parents (mom and stepfather, in this context) every week, telling them that I hated being here. My stepfather kept those emails. In 2003 he produced them and chastised me for the language I used, which is of course the reasonable thing to do after putting a 12-year old child through hell.

Actually, another fun fact: my stepfather is a spineless dipshit. He took matters into his own hands during 2002: He called the school, threatening legal action (and/or going to the press) if something wasn’t done about my situation.

That sort of thing doesn’t go over well in an environment where the school management is knowingly abetting a pedophile, the school’s athletic reputation is on the line, and it’s toughened bullies all the way down the leadership structure. On top of everything else, I now had a target on my back, thanks to a cowardly blowhard trying to solve problems by shouting at the manager.

That asshole made my life worse in 2002, and not for the last time either. But I digress.

By the end of the second term, my parents finally relented. I could leave the boarding school and live with my aunt, but I had to finish the school year there.

At that point I was already going downhill. I skipped classes. I shoplifted. If I carried on long enough, I’m pretty sure alcohol and drugs would have been next in line for me, but mid-2002 put a stop to that.

My aunt (the athlete) had planned to attend an annual athletics meet in Bellville, so one of the first things I did after moving in with her was to accompany her, my two cousins, and my uncle down to the Bellville Velodrome.

I wasn’t an athlete – and had zero interest in the meet – so I was left to wander around the field by myself. I don’t know about today, but back in 2002 that was still a fairly safe thing to do, especially with lots of families around.

When I trace my life story back, it comes to this one particular day. The trauma had been building for months. I’d been uprooted twice, relentlessly bullied, and I was starting to go down a self-destructive path.

But there’s this moment that’s forever burned into my memory, and I genuinely think this was the thing that changed me.

I remember sitting on the grass embankment across from the stadium. There were families, kids scattered around. It was a warm day. From where I sat, I could see down the road, past a building I recognized on the other side of the road.

I knew the route by heart, and if I wanted to, I could have walked all the way from the Velodrome, down the highway, and up to the address where I had been living just six months prior.

(CW: self-mutilation)

In those six months, everything had been taken away. I was caught in a living hell, and all my pleas fell on deaf ears. I had no friends. The adults in my life didn’t seem to care, the pain had already started to numb me, and so without really thinking about it I picked up an empty coke can, twisted and bent it so that the metal split open, and used the sharp edge to carve a checkerboard pattern into my left arm.

The thing I remember most: Nobody cared.

For the rest of the day, that week, and two weeks thereafter, I walked around with visible scars on my arm. Nobody at the velodrome (none of those families) stopped me. My aunt didn’t check up on me, either. I so desperately wanted someone – anyone – to free me from the nightmare I was in, but nobody came.

I was thirteen. I was somebody else’s responsibility.

That’s why I’m doing this, by the way. That’s why I write these posts, and openly talk about my mental health. I know what it’s like to live in that hell, and pass a thousand blank faces who see you, but don’t acknowledge you.

I know what it’s like to have everthing fall apart inside you, and yet still have to look people in the eye and pretend that everything is okay, because showing weakness is not an option – it would just give the bullies another reason to pick on you.

I was the scared, lonely kid at a public sports event, blood running down self-inflicted wounds on his arm, unable to arouse any interest or sympathy for it. That was really the moment that killed me inside, and as I write this in 2019, I can’t honestly say I’ve recovered.

None of it got any better from there. A couple weeks after that, I was on my way back up to Zambia for the mid-year school holidays.

On a bus.

By myself.

My mother saw fit to put her 13-year old son on a bus from Bloemfontein, via the Johannesburg terminal, through Beitbrige and Harare, through to Lusaka, and pick him up there.

Fun fact: You can be an unattended 13-year old at four different African border control posts and none of the guards, workers, fellow passengers or anyone else will question it. At least, they didn’t back then.

For years afterwards I was actually kind of proud of that. I was the tough kid who was able to travel two countries on his own, wandering around the border posts and major bus terminals completely consequence-free.

A few months later, my boarding school did interschool rugby against Pretoria, and we took a train through to the same Johannesburg station. I’ll never forget the scolding I got from the coach about wandering off on my own – it made no sense to me at the time, given that I had just had free reign of that terminal a few months before.

It was only a few years ago, when I told that story to someone else, that their horrified response indicated that maybe something was wrong. That’s been a major theme in my life as I’ve started to work through this stuff.

By the end of 2002 I had experienced an overwhelming amount of trauma, most of it a blur. In 2003, my parents returned from Zambia, and I was “reunited” into a home I didn’t recognize anymore. For every year since then, I felt like I was permanently disconnected from everything around me.

I made no new friends for the remainder of my school career. My odd behavior in 2003 prompted my mother to send me for counselling, and I was diagnosed with clinical depression. My treatment lasted exactly one month, until she decided she’d suddenly discovered Jesus on this, and we could simply pray away the bad feelings.

It’s obviously completely coincidental that her approach to fixing the problem was rooted in her denial at having caused it in the first place, but then that’s what narcissists are great at: dodging responsibility for their own fuck-ups.

My experiences in 2002 drilled several lessons into me, and being a formative year, they’ve stuck with me through to this day:

  • Adapt, conform, lie if you have to, but don’t show weakness.
  • Adults are not to be trusted – they don’t know what’s going on inside you, and they certainly don’t care.
  • Don’t bother making friends, you’ll just end up losing them anyway.
  • Generally, people don’t share your interests, and couldn’t ever understand you – so there’s no point in opening up.
  • Always expect things to go from bad to worse.

It’s pretty obvious (from an objective viewpoint) how those ideas might make it difficult to form any sort of relationships – even friendships. For a long time, it wasn’t even obvious to me that anything was wrong with those beliefs. They reflected the world as I understood it, and led me to adapt myself for survival.

To this day, I don’t have any friends. What I mean by that is: Everything I know about the world tells me that friendship is a set of voluntary, enjoyable social obligations. You feel like you have friends, you share things with them, you understand each other to some extent, you’re happy to see them, and they’re happy to see you.

I don’t have that. Whatever part of me would normally derive joy from that is absent – burned out of me by years of trauma and neglect. Whenever someone’s being friendly to me, I immediately assume they want something from me. There could be no other reason for reaching out.

J: Hey man how are you?
W: Hi. I’m on leave πŸ™‚
J: Ah cool, enjoying it?
W: So far yeah. What’s up?
J: Awesome. Just wanted to find out how you are?
W: Haha. Usually there’s something up, is all.

Discord, 7 September 2019

That exchange is dated yesterday. “J” is a person I’ve known for years, we have a bunch of things in common, we get along really well, we’ve worked on some creative projects together, I’ve even checked in on him occasionally, but the moment he reciprocates out of basic human decency I figure he wants something.

This is what depression does to you. I didn’t even think twice in that exchange – I just assumed there was some way I could be valuable to him, that his reaching out had some other motive behind it.

My whole life has been this way, and this is the part where I finally get to the heart of this post: My inability to form relationships.

All of that background story was part warm-up to tackle this beast, part illustration to help you contextualize everything that comes next. Some of it probably wouldn’t make sense otherwise.


All told, in my life so far, there have been 6 encounters that I would broadly define as relationships. Given that I grew up in complete social isolation with only the internet for company, quite a few of those existed purely online – a strange world to the uninitiated.

I should sidebar here for a moment and mention that (a) I’m gay and (b) all six were men. Between my manipulative, narcissistic, liar of a mother, and an overbearing female bully in primary school (seriously though Sarah, fuck you, wherever you are), I’ve spent my whole life viewing women with mistrust. I might not even have turned out gay if it weren’t for the path my life took. I might yet find my way “back”. Quite a thought.

The most recent quasi-relationsip came to an abrupt end in February 2018, and it’s taken me this long to fully process it. It came as quite a shock to me, given that I’d been building towards it for years (solid friendship, mutual interests, lots of time spent together), doing everything right that I possibly could, and thinking it was going well. I only broke through that fog this last weekend, when I finally realized that the problem wasn’t with me.

That was quite a milestone: After 12 years of failed relationships, to finally have one end because the other person wanted something else. I would have resolved it a lot quicker if he had actually been honest about that, but then that’s another one of those problems I keep causing for myself: I select poorly.

When you’re depressed, there’s a special sort of void that opens up inside you. It seems boundless, omnipresent, and ultimately becomes part of your life. You never really get a grip on the edges of it, and despite how miserable it makes you, you can’t muster a meaningful defence.

Because you can’t describe it, it starts feeling like nobody understands you. There’s a well of sadness inside you that can’t be reasoned with. Every time you try dealing with it, you fail. You’re inhabiting the same mind that’s trying to destroy you. Your efforts are sabotaged from the start.

Other people will see the symptoms, sure. Maybe you’re withdrawn, erratically emotional, clingy, have problems with abandonment, seek comfort from destructive sources, work yourself to death, and so on. They’ll try to help, but every attempt ends in failure, and you start blaming them for not understanding your suffering.

It’s nobody’s fault, of course. You’ve been set up to fail by your own mind. You have no framework for evaluating success, no way to recognize progress as distinct from your constant nightmare. No matter what anybody else does, they’re not going to get through to you that way.

Over time, that leads to contempt. You start deliberately isolating yourself, closing off avenues that might otherwise help. You start pretending, because there is no other way to relate to people without them taking pity on you.

And so you learn to build masks. You invent a personality that appeals to other people. For a while, it seems to work, but it never lasts. You have a deep, unfilled well of desires you can’t communicate, you get frustrated, and you start taking it out on the people who love you.

Until, eventually, they stop.

Broadly speaking, that’s been the last 12 years of my life. Every friendship, relationship, or whatever other -ship between 2007 and 2018 has followed a variant of that pattern.

In a few cases, the problem was definitely my selection. I’d overlook all sorts of red flags and warning signs for the sake of just having somebody I could talk to. In other cases, I drove genuinely good and patient people away by a combination of my self-inflicted grief and paranoia.

I regret all of it, and it hurts to think about, but right now that’s a good sign. For years, I wouldn’t think about it at all, and was largely unable to actually process painful emotions. I’d usually game, eat, or masturbate them away whenever they came up. Substance abuse, in other words.


In the last few years, I’ve been increasingly fixated on the idea of “who I might have been”. What path would my life have taken, if it hadn’t gone so spectacularly off the rails in 1998?

This is where I reintroduce Barney. He hasn’t authorized me to tell this story (and that’s not his real name anyway), so I’ll keep the details brief.

At some point between 2001 (when I left South Africa) and ~2010-ish (when we met up again) he had apparently fallen in love with a girl. That came to an end when she cheated on him, and it left him devastated for a while.

In the last few years though, he met another girl – randomly, one night, at a bar. They hit it off, one thing led to another, and they’re in a stable relationship right now. If I were a betting man, I’d wager they’re on the road to getting married.

There are so many things in Barney’s backstory that I didn’t have: Parents who gave a shit, friends who stuck around, stability at home and in school. To the best of my knowledge life didn’t beat him up nearly the same way it did me, and when it did throw him a few punches, he had the necessary strength and support to recover.

I’ll never begrudge him that, though – it’s not his fault my parents were a wreck. If anything, it’s the one piece of my childhood I’m grateful for: The afternoons, nights and sleepovers with friends at his place, getting to see for myself how a more-functional-than-mine family actually looked like. I think those were the first seeds of doubt that eventually led me to question everything else.

But that’s not something I can ever have. As much as analysing my past has helped me to get a grip on my present, I can’t let it dictate my future. This is one of those truly rare instances where Twitter delivers solid gold.

I came across that a few days ago, and it’s been acting on my perspective ever since. Resolving my feelings towards my last failed relationship, the post I did about depression this morning, and this insanely long essay right now are all born out of the same desire: To document my life so far, so I can close it out and start putting it behind me.

In future, I want to be the person that squared up to all the bullshit life dealt him, worked to overcome it, and left something behind to help others do the same. If nothing else, I won’t let my depression be the thing that takes me in the end.

I feel relieved to have finally written all of this out. For the 2008-2018 period (my 10 employed years) I never considered publishing anything this personal online, believing that it would somehow undermine my career prospects if people knew how fucked up I was inside. At the very least, it would contradict the image I carried at work.

I’ve given some thought to “closing advice”, if there is such a thing to be found here: what to do if you think someone in your friend circle might be depressed.

Chronic depression is not an “illness” in the same way other illnesses work. There’s not so much a “treatment” to “fix” it, as there is a set of lifestyle changes that need to happen.

The first one (and honestly, the most impactful) is to simply understand the depressive’s point of view. I’ve done my best to lay out my own experiences, and they won’t apply to everyone, but it helps if you know the nature of the beast your friend is fighting: Themselves.

Depression is irrational. Everything will be totally fine (job, love life, future, family, church, whatever), and your friend will still be miserable. “Cheering them up” won’t go the way you think it will – that’ll just remind them that they’re unable to be happy like other people.

Doing “nice things” that put them on the spot won’t really help either. The fixes for neurotypical sadness backfire spectacularly when you’re trying to help someone who’s mind is set on destroying itself.

The only thing that’ll ultimately help, as far as I can tell: Rebuilding your mental software from the ground up. Challenging every depressive thought with a strong counterpoint. Deliberately and consciously carving out new mental reflexes. Training yourself to see things in a new way, based on everything you know to be the “normal” you want.

And as someone caring for a chronic depressive: Just being there is good enough. Give them a reason to refute the dark voices in their head (their own voices, for the most part). Whatever bad things they believe about themselves and other people, just be a reliable counter-example to that. It will take courage, effort, and time – maybe longer than you’d ever think – but the situation can improve.

Many years ago (must have been around 2011) I met a guy online, in the wake of another relationship imploding. He lives a full hemisphere away, and we’ve never met in person, but he’s been a constant presence in my life.

We’ve had major arguments, I’d block him for months at a time, but we’d always cool off and reconnect eventually. I think he knew, intuitively, the sort of demons I was wrestling with – and he had patience with me. That one connection, formed and maintained over the years, was all it took to ground me in a basic fact that most people take for granted: I’m worthy of friendship, even when I’m at my worst.

I still have a long way to go, but I know for sure it would have been a much more difficult journey without that, and I’ll be grateful to him for the rest of my life. If nothing else, try being that person for your depressed friend.

That’s all I have the energy to say on this subject. I hope tomorrow is better for all of us.

15 years of depression

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

UPDATE: This post ended up preparing me to tell the full story. I hope it helps: 2019+

Hello, my name is Wogan, and I was diagnosed with clinical depression at age 13. It’s taken me more than 15 years to start dealing with it, and I’ve learned a bunch along the way. Part of my process in de-fanging this monster is to talk about it in public.

Most of the conversations I’ve seen relating to depression frame it as something you “have”, or “suffer from”. There’s you, the person, and then there’s this foreign invading entity, the depression. Through a combination of therapy and medication, you can exorcise the demon and return to health.

That hasn’t been my experience. It’s possible that I’m an even-more-abnormal case: my depression was diagnosed at age 13, but went largely untreated until my mid-20s. My mother, unable to deal with her parental failure, passed it on to me by pretending I was totally OK.

Humans are essentially moist robots: We have leanings inherited from our genetics, but a great deal of our socialization and behavior is programmed. Sometimes passively (by observing and imitating), sometimes actively (by deliberately trying to learn new attitudes or skills).

My formative years (6-18) were a combination of positive influences and absolute trauma. I owe a lot to the positive male role models (uncles, church leaders) that, through example alone, set good examples for me: Being honest, constructive, taking responsibility, etc.

My trauma: Being ripped away from all of that, over and over again. My family moved around a lot: I attended 7 different schools in 6 years. This, again, boiled down to a parental decision: My mother didn’t put my well-being first, so I was forced to constantly adapt.

That constant adaptation destroyed quite a few things. I went from a normal, healthy, happy boy to a depressed, overweight, socially awkward teenager. Through my entire high school career I made no friends. I missed out on crucial formative experiences.

My depression formed quickly: through my 12th birthday I was still doing relatively OK. By my 13th, being dumped in a boarding school 2000km away from anyone or anything I knew, I was already starting to break. A few months in, I had self-mutilated for the first time.

Later that year it was my stepdad who noticed something was wrong. If he had his own shit together (and didn’t defer to my mother for fear of ending up divorced) I might have gotten the treatment I needed the following year. That didn’t pan out, and I had to fend for myself.

That prolonged depression, exacerbated by constantly denying treatment and moving around to new places, eventually changed me in a way that I’m still dealing with today. The depression went from a potentially-treatable illness, to a chronic reprogramming of my personality.

Most people who know me think of me as a hard worker – for many years, I’ve put in really long hours, and achieved quite a few things in my career. What they don’t know is that it’s an unhealthy obsession with being infinitely adaptable and socially useful underpinning that.

That’s one of the things I figured out really quickly after my mother kicked me out of the house (another star parenting move): By being useful to others, I didn’t have to focus on anything about myself. Fantastic trait to have in a new hire, desperate to not be fired.

Over my first few career years, that became integral to my personality. It eroded my social and romantic skills (not that they were fantastic to begin with), and replaced my entire worldview of one consisting of work. Work (and earning income) came to define everything.

How bad did it get? After 6 years, having earned several increases and promotions + on a solid career track, I still woke up every morning thinking I might get fired. One morning I was unable to log on to my email (temp glitch) and my first thought was “They’ve just fired me”.

When I mentioned that to my new manager (about 2 years later) he was taken aback. He knew what I could do, and couldn’t conceive of a situation where I’d be summarily fired like that. That was the conversation that made me realize something was horrifyingly broken inside me.

There are a lot of “worst” parts to consider here: That it got so bad, that I got so good at hiding it that people didn’t think anything was wrong, that I hadn’t even noticed how far down the hole I was. Mostly, though, that I started taking anti-social behaviors as normal.

And that’s the truly pernicious part about depression, especially untreated: You stop thinking of it as a thing you have, and start thinking about it as the person you are. You even learn to live with it – laugh, smile, have friends, present a picture of normalcy to the world.

That’s how you get Robin Williams, Chester Bennington, Avicii: People who appear to be top of their game, likeable and successful, relatable and entertaining, while their own brains destroy them from the inside out by constantly telling them the wrong “truth” about themselves.

That’s where I started dealing with it, though. Within another 2 years, I had worked up the courage to do the unthinkable: Resign from my first job and go freelance. I drafted that resignation letter at least five times, and put it off for months, hoping I could defer entirely.

And even though I recognize I’ve come a long way since then, I still have a long road ahead. The most basic things (like deciding not to work) is still really difficult. Acknowledging people’s basic positivity and learning to trust external feedback – still a challenge.

Having dreams, creating the time and space to work on them, and then not following through for fear of everything falling apart – that’s my real struggle right now. Every piece of creative work I do is preceded by days (weeks!) of internal emotional wrangling.

So how to fix any of this? I always, openly, and loudly recommend seeing a mental health professional. A few, even, if the first one doesn’t really work for you. Your brain is the most sophisticated computer you’ll ever operate – there’s no shame in maintaining it.

But that’s not your day-to-day: when you’re faced with hundreds of decisions and some incredibly powerful conditioning that tells you all the wrong things. I’ve lived in that headspace for decades, and to this day, I still make occasional, unconscious, self-destructive choices.

Relaxing and “taking it easy” aren’t going to cut it. What you really need to do to yourself is deprogramming (look up any cult documentary). You need to consciously, directly challenge the things you believe to be true. You need to find people who will help do the same.

You need to give your best self a fighting chance against your depressive self: Diet, exercise, hobbies, time spent with friends, all of it adds up. You’re basically a houseplant with emotions: get water, get sunlight. Consciously put yourself in better environments.

A big part of those better environments: Better people. For years, I made the mistake of seeking out people that accepted me for who I was. That’s comfortable, but it’s your mental health at stake here. Find responsible, honest people that want to help you succeed.

Finally: Writing. Even if you don’t do it every often, take some time every once in a while to record your thoughts and feelings. Save them all up. Look back at older ones every now and then. If you’re doing this right, you’ll notice how your mindset shifts over time.

I normally try to end long posts like this on a positive note, but honestly, that’s not the space I’m in right now. Instead, I’ll point out that 0800 567 567 is the SADAG Suicide Crisis Line, and that there’s no shame in seeking help for the issues you’re facing.

Pantheon of Unfulfilled Desires

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There wasn’t a NoScriptShow episode this weekend, and that’s entirely my fault. The hectic work schedule was one thing, but there’s been a lot more going on in the back of my mind of late. Every year (sometimes twice a year) I do a sort of 360 audit of my life.

It’s a fairly existential thing: Reflecting on what I’m doing, where I’m going, who and what I am, where my strengths and weaknesses are, and how I’ve changed (or not changed) over the last few years. My intention in doing this is to constantly discover my optimal path.

And by that, I mean: Where do I spend my time, energy and resources, and to what end? What do I expect to get out of my work/life/hobbies, and are they actually fulfilling? Am I paying a hidden opportunity cost, overlooking something that might be better?

And every year, (usually!) without fail I’ll come across an insight that changes the way I look at myself. This year, the realization was that I’m actually profoundly risk-averse, and the circumstances that pushed me into freelancing are rooted in a much deeper problem.

I’m not sure where in my past it originates, but one of my driving forces in the last 10 years has been work. Specifically, doing really good work. I’ve been told (quite a few times) that people admire my work ethic, attention to detail and the effort I put in.

But that’s always come at a cost, and up until this point I was relatively okay with making that trade. This year, for some reason, less so. Maybe this is part of growing up? Maybe I’m just getting more grumpy πŸ˜‚ – but my cost/benefit preference is definitely changing.

In truth, I think my work ethic is symptomatic of two underlying issues that I’ve never really dealt with. First there’s my dad, who idolizes people who basically work themselves to death (and he’s made jokes about that on occasion) – there’s lots to analyze there.

But more importantly, it’s a very deep-seated need to solve problems – something I once thought was purely noble. I see problems in the world, I try solving them. Relentlessly. And luckily for me, with my skillset, profitably.

It’s the “why” that’s eluded me for quite a long time though, and it finally clicked for me in the last week that it’s actually a form of risk aversion: I’m working so hard, so passionately on other people’s ideas as a hedge against taking any risks of my own.

There’s lots of things I’ve wanted to do for a very long time, yet I never seem to find the time to do them. Which is a big fat self-delusion, of course: Priorities can be shifted, choices can be made and time can be opened up for the things that matter.

So long as I’m burning myself out trying to solve someone else’s problem, I’m sort of protected (irrationally): If it works out, great! If it doesn’t work out, also great – it wasn’t my risk to take, I did the best I could, I can console myself with that.

As a result, no matter how good/interesting/unique/challenging/fun my own ideas are, they come second to other people’s ideas. Much less riskier to do something that someone else wants, vs striking out on your own.

My freelancing over the last year has actually been an extension of that. Fulltime employment is only a drag because I don’t get to choose the problems I want to solve. Freelance, I have that choice – and it turns out I choose far more work for myself than I can handle.

All to avoid taking the actual risks of spending time on the things that I actually want to work on.

Last year, I could kind of argue that my full-time job was very demanding and left little time. This year, I don’t have the luxury of that same excuse.

I’ve done quite well in the last year, which is not a boast – more of a cry for help. Even as I write this post now, I’ve got a bunch of work to get done ahead of a 10am call tomorrow, meaning I’m going through the night again.

Something inside me has definitely shifted though. Maybe this week has been the final straw, or maybe I just had the capacity to really reflect on all of this while doing mindless, repetitive spreadsheet work.

Regardless, I’m going to have to decide what to do with this new perspective. I’ve already decided to take the month of September off, and in practice this means doing a lot more work right up until the end of August.

Beyond that, I don’t know. In one sense, this has always been “the plan”: Work hard for a year or two to build up a cash reserve, then start taking bolder risks with my time – working on things of my own.

Turns out most of that work is going to be psychological. So many of my decision paths are irrational, so much of my behaviour remains self-destructive. And this is to say nothing of my health, which hasn’t really improved in the last year. Probably for obvious reasons.

My first objective, though: Take something from the pantheon of unfulfilled desires and make it real. I have some real cowardice when it comes to this, but I can already sense the consequences of not following through, and I have no desire to go down that road.

2019 Q1 Review

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So those first three months went by pretty quick!

Towards the end of last year I set myself a bunch of goals for 2019 – a New Year’s Resolution, but with some measurable criteria. The idea was that I’d check in every quarter to see how I’m doing against those goals.

I’ve also managed to miss my last few weekly updates (with semi-legitimate reasons), so I figure I’ll do this all in one go: Catch up to where I am now, and look at where I thought I might be, this far into 2019.

On my March 17th update I set myself the task of analyzing the manifesto of the Christchurch Shooter:

For my part, I’m working through the manifesto myself, attaching commentary and context on a lot of the arguments within it.

I never ended up finishing that analysis. Load shedding carried on for the following week, and the disruptions were hard to deal with. I ended up rearranging my days around the times I’d have power, with all my devices constantly charged up so I could keep working in the dark.

An unanticipated side-effect of the loadshedding was losing all my connectivity. This was more emotionally taxing than I thought it would be.

My apartment has a fiber connection delivered via ethernet, and there’s apparently no backup generation for that. Fair enough – that’s why I have a Rain 4G SIM, but as it turns out, the towers themselves are not equipped to survive. Usually they would go down within 30-45 minutes of the loadshedding window starting.

That left my FNB/CellC/Vodacom-roaming setup, which routinely failed too. So most nights I spent a large portion of it trying to work offline (which is hard, being a web developer and all) while literally coding by candlelight.

Still, I carried on. By the end of the week I had a bunch of notes drafted and was ready to publish the first round of info on the site, when I learned that New Zealand had banned the manifesto.

I agonized over it for a while, and eventually decided not to go ahead with publishing anything. In the end, as much as I stand for the freedom of expression, I’m also pragmatic. Potentially painting a target on my back is not the smartest move here.

The next few weeks are pretty much a blur to me, even now. It turns out that work stress accumulates, and eventually takes over your life: I lost my routines and schedules, simply stumbling from one day to the next, constantly feeling like I was behind on everything.

(Not to mention, incredibly stressed.)

But then my leave arrived. Even though I had intended on finishing far more work than I did before my leave, it simply didn’t happen. I ended up eating into my leave for two additional days, trying to catch up, but didn’t get anywhere. And then I had to fly up to Pretoria, which physically removed me from my environment. That’s the only thing that actually ended up helping.

Right now I’m still technically in the middle of my “leave period” – the two weeks I set on the calendar (first in a year of freelancing) explicitly to relax and recharge. I haven’t been able to stick to all of it. As I write this, I’ve spent the last two days dealing with issues to the point where I may as well be back at work full-time.

This whole experience has helped, though. If nothing else, I’ve learned that I absolutely have to set guardrails for myself. Left to my own devices, with no structure enforced anywhere, I’m liable to continue working until it kills me.

The hardest part of that, for me, is disappointing customers. For the last year I’ve managed to do a lot of good work for a bunch of great customers, but being a one-man show is inherently unscalable. Sooner or later, it was bound to happen: I’d have to turn someone down that I really didn’t want to.

That happened this month. It was agony. I hate leaving work unfinished, and I hate disappointing people, but I ultimately have to honor my prior commitments first. I had to take the (very gracefully offered) out from one of my favorite clients. It really sucked.

Still, that was a necessary step, and it’s made a few things easier since. At the very least I can be sure I’m on the right track: Growth is sometimes uncomfortable (even painful), but that’s how you know you’re pushing yourself forward.

And then I turned thirty.

For the last few years, my birthdays have been relatively uneventful. I’d take the day off (usually) and go have a quiet braai at my dad’s place. This year, I learned that I share a birthday with a new (and really good) friend, so for my 30th I resolved to do it differently.

That ended up being 5 days in Pretoria. In no particular order, my 30th involved:

  • Flying up to Pretoria on a plane that wouldn’t start on the first try
  • Riding the Gautrain with half the carriages missing their aircon (stuffy, sweaty fun)
  • Met my NoScriptShow co-host and learned that I’m taller in person than he thought
  • Played some proper old-school video games (1980s NES titles!)
  • Met another internet friend and recorded a podcast episode as a group
  • Spent an evening getting moderately drunk with great conversation at what amounts to a secret hideout in Pretoria (never knew this place existed)
  • Started working on ideas for a movie that may or may not materialize, we’ll see
  • Spent my entire Sunday at a large (40+) family gathering of predominantly Tswana folks, had great food and fantastic conversation
  • Got pulled over and extorted by the Tshwane Metro Police on the way back to the airport Monday morning, and
  • Made it through airport security after they had called for boarding on my plane (first time ever)

Ultimately, a far more memorable 30th than I otherwise would have had, and I’m grateful for all of it. Even, in some weird way, the criminal cops: I can now honestly say I’ve now had that happen to me. Feels like I’m not a true South African unless the cops have fucked with me in some way.

So now I’m back to normal, but with a few different ideas about how I’ll manage my time. For one thing, I’ll need to constantly combat my tendency to over-work. I keep telling myself that just a few extra hours effort will make a big difference, but by the third day I’m spinning out of control again.

I’ll also have to learn to be okay with losing. I hate losing, but if I keep trying to win these short-term battles I’m absolutely going to lose the war. My health has suffered in real ways from my workload, and I need to make a serious change.

Mostly I need to learn to be okay with not being the hero. That was something I realized when I had to let that client go: While I do take pride in delivering good work, there’s a dark side to that. When pushed, I’d sooner take on more work than I can handle, just in order to be the one that solves the problem. That shit has to stop.

I’m coming up on a year of doing freelancing – it’ll be official on the 1st of May. I can honestly say it’s been eventful, I’ve been pushed, I’ve learned a few things, but still have quite a way to go. The master plan has always been to build up some sort of cash buffer, to free up time to work on more sustainable income streams. I’ve got something resembling that buffer now, so it’s time for the next phase. I just have no idea how I’m going to do this yet.

Q1 Review

So now for the actual review on my stated goals:

1. Launch a SaaS

This is ultimately still “in progress”. Spending some time in the trenches at different sorts of businesses has given me a bunch of new ideas, and has helped me refine my understanding of how to spot opportunities.

The biggest thing I have to overcome is my tendency to see every problem as a software problem. There’s much more value I can add through more scalable means, like producing educational content.

I’ve also now got a few months of managing two actual SaaS platforms (one customer each) under the belt, and the experience has been informative. It’s a bit like looking after a sick animal – it needs constant attention and care, or it’ll throw up all over everything.

Mostly, it’s taught me that I need to build something that I can scale to multiple customers, then find a way to support without it killing me. It’s quite a challenge, but I think I might still manage it. For easier income though, I’m thinking that producing something educational might also be worth it.

2. Blog More

I set a fairly ambitious goal here: 3 posts per week for 2019. I did pretty well at first, but it became difficult to sustain that output.

By now, I should have published 51 posts, but I’ve only managed 12 posts. Most of those have been weekly personal update posts.

The problem here is that I don’t often have that many things I feel like I need to say. The weekly update is a decent format for producing something, and I’ve gotten feedback from a few friends that they look forward to reading it, but that wasn’t my intention in setting this goal. I wanted to be pushed to produce useful content.

I suppose the error there is that I need a clear topic to focus on. Last year I did a bunch of writing for an ICO blog, and having clear topics and deadlines helped me push the work out. It’s another reason I think an educational-content product might be smart: If I have a clear reason to churn out 500-word articles, I’ll be setting myself up much better.

But of course, the main thing has been work stress. I keep prioritizing other people’s problems above my own, and since those never seem to run out, I’m constantly putting out fires. It’s a personality flaw I’m working on.

3. Read More

I’ve actually managed to finish a book! Best Dick, by Mike Sharman. Even though half of the advice in there wasn’t applicable to me, it was quite an entertaining read, and I got a lot out of it.

I haven’t tracked all the time spent reading articles online (I do that quite a lot), but then this goal was more about books than anything else. There, I didn’t complete as much as I wanted.

For the next quarter (which we’re already a third of the way through!) I’m going to make more leisure time for myself where I can actually get through a few books. At this point it’s a question of mental health more than anything else!

4. Develop Routines

I have a simple routine that I’m supposed to complete every day: Take a blood sugar reading first thing in the morning. This is my log for that activity so far:

The pattern is actually pretty clear – I do very well on my habits until the work stress takes over, which then blows everything out of the water. When work calms down, my habits become easier to maintain. The most recent stats for April are entirely thanks to taking leave.

What’s supposed to be happening here is that my habits, routines and healthcare all take precedence over my work. Work is infinite, my time is not, yet somehow I keep ending up with work being the priority.

I did eventually realize that it’s basically my ego driving that, and I’ve now got a new angle of attack for solving this problem: I need to stop caring more about work, than my health. Seems rational and obvious, but when I’m in the thick of it, it’s very easy to forget.

That’ll be my biggest challenge this quarter: Keeping watch for the idea that I need to do just a bit more work and everything will be okay. That’s a seductive, destructive little demon in my internal pantheon, and if I don’t get rid of it, it’ll take me down eventually.

So I think that’s pretty much it – the major events of the last few weeks, a review of the quarter itself, and some ideas for moving forward. Onwards!

It’s Good to be Home (#7 of 52)

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A Saturday post on an actual Saturday – madness!

Last week was hectic – pretty much a repeat of the week before. The second half of my first-ever full-time on-site consulting gig drew to a close, but not before leaving me with a task list a mile long. It turns out that delegation really is an important part of building a business – including delegation to my future self (or I’d go insane).

At least I’m home now! Slept in my own bed last night, which was glorious. Overslept, really.

So it should come as no surprise that my habit tracking went to shit again over the last week. It’s pretty obvious to me now that maintaining these habits does require a bunch of external inputs (namely, being home every morning), and it further diminishes the notion that I’ll take up digital vagrancy at any point in the future.

At least I recovered from that gastro bug, which was no fun at all.

The last week also presented me with an opportunity that I’m now seriously considering: Taking on a full-time role at the company I consulted, to help them fix their IT and systems, helping them get to the next level.

In many ways it’s my dream job – it won’t last forever, I’ll have a meaningful remit, the authority to implement the changes that make sense, and I’ll walk away from it with quite a lot to show. For the first time, I’ve got tangible validation that my skillset is, in fact, pretty rare – and I’ve now got an opportunity to really use it.

It’s also causing a massive internal debate, once again ripping up the floorboards of all my assumptions.

On the one hand, as a career move it makes total sense. Pushing out and establishing myself as an independent consultant here will pay huge dividends well into the future. The job itself is challenging, but not impossible. The tradeoffs may well be manageable, too, and it’s likely to open up new career paths and opportunities in the future.

But on the other hand: Do I really want to do this?

A big part of leaving full-time employment was specifically to push myself into new areas of personal growth. All things considered, this job wouldn’t really be that much of a push – it’s something I’m good at, and can do at length, but it won’t be as personally challenging as a total career change.

Doing this well (and establishing those new opportunities for myself down the road) will only serve to further draw me away from the reasons I quit this world in the first place. Five years hence, I’ll find myself doing the same things I was doing five years ago, and again I’ll feel disappointed at my lack of taking actual risks.

I recognize that I’m really lucky to even be in this position: Openly debating whether or not to take a potentially career-defining job, over doing something completely unrelated for a career. But I’m also the one that has to wake up and do this job every single day, and at some point I also have to consider what I want for myself.

Nothing’s been decided yet, other than the fact that I’m thinking through all of this very carefully. In the end, I doubt I’ll walk away from the opportunity – it’s more likely that I’ll deliberately carve out the time for the things I really want to try.

Everything else in the last week has really just been implementation details. I’ve once again found myself hand-rolling a 2-tier analytics and reporting stack, purely because rolling out any of the free tools would have added far more complication too early in the process:

Most of my week in one simple diagram

Question: How do you link records between two systems when no correlation or shared key already exists? Answer: You create a system that goes hunting across two databases, following ever-broadening match rules in an attempt to best-guess what those correlations should be. A solid week of my life for the first version of that.

I’ve also regained an appreciation for communication as a skill. It’s actually pretty important that people talk to each-other, and not past each-other. The latter is how you end up with organizations that make absolutely no sense.

Finally, I’m continually vindicated of my decision to leave full-time employment. We’re about 10 weeks away from my 1-year anniversary, and a part of me was worried that I’d come to regret the decision to leave. So far, no such luck.

Other than that, not too much to report. I’m doing badly on my reading goals – Best Dick is still on my reading list, and I haven’t touched it for at least two weeks. I’m at least keeping up with 1 post per week on blogging, even though the goal was 3 per.

Mostly I’m still trying to manage an escalating-workload situation. A big part of my paranoia thus far has been the upcoming CIT payment, and to what extent that’s going to eat into my cash buffer. At one point I was within striking distance of having a 6-month buffer built up, but that’s about to be wrecked. I just hope the damage isn’t too bad.

I’m also dealing with the growth question – and if I want to do any of that at all. It goes against everything in my nature to see a problem I can solve, and then walk away from it – but I’ll have to start doing that in order to maintain my sanity. I’m confident I could spend the rest of my life fixing things and getting rewarded for it, while never managing to pursue the things I’ve wanted to do since I was a child.

Or maybe now is the right time to accept that not all dreams come true, and go with what’s actually around me.

Like I said – hectic week.


New episode of The Noscript Show came out today. We missed a lot of international tech topics in the pursuit of dealing with local issues, the peak one being loadshedding – and how we absolutely shouldn’t have had to deal with it.

The Helderberg Dev Meetups were postponed last week (bad scheduling) but are back on as of the 19th. I’m still not sure whether or not I’m preparing anything for it, but I’m looking forward to a relaxed evening of chilled conversation.

In the coming week it’s back to something resembling business-as-usual, as I attempt to negotiate an exit path for a project that’s dragged on far too long, and start onboarding my second (!) part-time freelancer. I guess this is how we all learn!

Still learning (#6 of 52)

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It’s time for another weekly update! And this time, yes, it’s on a Sunday. My Saturday was purely for switching off, and I have zero regrets about that.

A whole bunch of new things have happened for me during the last week, mostly in the form of my first-ever full-time on-site consulting gig.

First, my habit tracking went to shit again:

This has mostly been a function of not being at my regular desktop PC every morning. Opening a browser window (which I do hundreds of times a day) and seeing my stats is the #1 motivator for recording habits. Since going on-site with my Macbook (and without the everyday.app extension) I’ve just skipped over it entirely.

Last year, I did a couple of “trips” from my native Strand into Cape Town, and treated each one like a mini-digital nomad experience.

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.

2018 Retrospective

This time around, I figured it would mostly be the same: I’m on-site at a customer for two solid weeks, so I booked an Airbnb way in advance and planned to set up there for the duration. But there were a few differences.

First and most importantly: a schedule. I committed to being on-site at 8am every morning, leaving at 5-ish (just like a regular working day), which meant adjusting my schedule a little further back than I’m used to.

That, in and of itself, has been a challenge. 6:30am mornings are not the norm for me, and I can’t say I’m a huge fan. Nevertheless, it’s been a productive week – and working these regular hours for a short burst is somewhat refreshing. As is being in an office full of motivated people.

Until Thursday evening.

There’s a running joke in my circle about the Republic of Helderberg, and the fact that travelling to Cape Town is pretty much like visiting a foreign country. It turns out I needed to update my shots, because it was on Thursday evening that I ate something which profoundly disagreed with me (I think it was the Long Street KFC).

By Friday morning, the early stages of gastroenteritis were in motion. I made it as far as 2:30pm before the headache/nausea/joint pain/disorientation phase kicked in, and I ended up leaving early, heading straight to bed in the Airbnb at 3pm.

That was something of a low point for me, with several factors converging at once. I was:

  • Sick and tired (literally),
  • In an unfamiliar bachelor flat,
  • In the middle of a town I’m rarely in, and don’t much know,
  • Facing the prospect of spending the rest of the weekend cooped up,
  • Potentially having to grind through a bunch of work on the Mac, and
  • Having all of these thoughts while lying on an uncomfortable bed

This was the side to the “digital nomad experience” I hadn’t yet encountered: when things go wrong. Assuming I did ever want to travel the world and set up shop anywhere I go, it stands to reason I wouldn’t be 100% healthy the entire time. I’d absolutely catch bugs, get sick and miserable, and end up in this exact situation.

By 7:30pm I had called an Uber to take me back to Somerset West.

So that was the first big learning this week: Either I was never suited to it, or I’ve just missed the window – but when it comes to feeling that miserable in a foreign setting, I can’t handle it that well. Between the loss of habit tracking and bailing out at the first sign of trouble, I’m a lot less confident now in my ability to city-hop in exotic locales.

Which is not to say I don’t like travel – I still love seeing new parts of the world. It’ll probably be as a tourist, though, and I think I’m fine with that.

The second big learning is putting expiry dates on contracts.

Without going into too much detail on this, it turns out that no matter how good you are at what you do, sometimes you’ll run into clients that just cannot get things back to you on time – and that can really throw out your planning.

As I write this, I have a contract “out” (for signature) that would commit me to a few hours/month of support work for the rest of the year. When I drafted it in December last year, it made total sense – and as of February it still isn’t signed.

Having now looked at my workload, I’ve decided to take 2 weeks off in April – which will be complicated if they suddenly sign that contract.

I now completely understand why a lot of firms do “quote valid until x date” – time marches on, and the longer something goes unresolved, the more of a risk it becomes. So this is one of those things that I’ll be factoring into every document going forward, no matter how sure I am that they’ll sign (and I was pretty sure of this one).

But the third, biggest learning of the week: I’m really into digital transformation.

When I went freelance last year, I had to decide how to market myself, and I ended up going with the option that I was most familiar with: Digital marketing.

As I’m closing in on the first year though, I can honestly say that this project has been the most exciting – working directly with business leadership to assess, roadmap and then implement a transformation strategy. Even better that it’s a small, flat business without many legacy systems or processes.

If the next 6 months go well, it will (hopefully!) mean a great case study into practical steps for making businesses more efficient. That, and an already-long-overdue update to my “company” website.

This isn’t quite where I expected to be a year into freelancing, but I’m not complaining at all.

Another few highlights from the last week:

New Noscript Show episode (2019-006). These recordings are basically a form of therapy for me nowadays. And this was a good one – a range of eclectic topics and nothing taken too seriously, except for the part where we’re (Odin and myself) collectively frustrated with the lack of basic financial literacy.

Feeling more confident in having taken this risk. There’s an unexpected side-effect to having a company account and InContact notifications – every few days I get an SMS telling me some automatic payment has gone off, along with the remaining balance in the company cheque account (which pays my salary).

It’s begun serving as a constant reminder that I’m generally doing okay, and I’ve become a lot less stressed about finances (and finding new work) over the last week as a result. This wasn’t advertised on the freelancing brochure, but it’s been a great psychological bonus.

Reached level 17 in Overwatch! And enjoying every minute – Blizzard really did a great job on this one. After a solid run as a Pharah main I’m now experimenting more with Orisa and Mercy to round out my personal roster. At this rate, I’ll be eligible for competitive games in no time.

In the coming week I’ve got another round of office hours, during which the rubber hits the road on a chaotic (and ambitious) digital transformation project. My excitement level for this is 10/10.

The longest year of 2019 (#5 of 52)

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Is it just me, or was January unreasonably long?

Technically speaking I’m writing this post on a Saturday, in that I woke up late and haven’t gone to bed yet. The calendar will tell you this was written on Sunday though – it lies.

The last week was particularly hard on me, as evidenced by my habit tracker.

Every morning, I need to take a fasting blood sugar reading in order to adjust my treatment. I’ve been really good with that since starting the tracking, managing a fasting reading every morning for a straight month – but in the last few days, that became difficult.

Whenever I have a bad week, it seems to throw everything else out of balance. The first thing to go is perspective – I get stuck on a particular problem and don’t really notice things like the passage of time, or that adhering to my habits have become a problem.

In this last week, I can clearly attribute that to something: A poorly managed project – with at least half of the blame falling on me.

In September, I picked up a project that was meant to take two months at the most, but as of end-January we’ve still not managed to go live. The application is a line-of-business app for a major enterprise, and like most major enterprises, timelines can sometimes stretch out a lot further than you might think.

In this case, there’s no one single reason why it’s taking this long. The scope has kept changing, but that’s par for the course when developing an all-new process in a shifting landscape. Feedback has been slow, but it’s impossible to align calendars. Getting it deployed has been a challenge, but there are so many parties involved in simple IT change requests that no single one of them has unduly held up the process.

As it turned out, by mid-January they had managed to finally get our first version out for testing with some of their internal customers. The feedback ended up requiring a whole new set of changes, which was scoped and priced and scheduled for delivery over the last week.

And this is where I hit a brick wall. I’ve worked on this project long enough now to have developed some really negative feelings towards it. The launch has been delayed time and again, the stakeholders and priorities have shifted back and forth, and my main concern remains launching a decent product – which seems further and further away.

But the blame for this one falls squarely on me, for once again trying to handle more than my fair share of work. The time to outsource it was actually mid-January, but after the week I just had I can’t afford to not pull the trigger on this.

Which I’m now doing. It’s a new milestone: I’m outsourcing the first bit of work I feel comfortable with, mostly because it’s starting to drive me insane and just getting a fresh set of eyes on it will already be a big relief.

Looking back on the week, though, I could have caught this one a lot sooner. I got stuck in a negative feedback looped that completely drained my energy:

  • I have this very important thing to do
  • I really don’t want to do this, it’s gotten too difficult
  • But I also can’t do anything until I do this
  • It’s already 1pm, I need to start
  • It’s already 5pm, I’ll have to work this evening
  • It’s 2am, I need to push through to the morning
  • It’s 4am, I can’t do this anymore
  • I woke up late this morning and I have a very important thing to do

Remarkably unproductive, but not the first time I’ve dealt with this feedback loop. Despite my own self-sabotage I’ve managed to get a lot of it done, including a monster VueJS refactor:

But I could have done more, had I been sufficiently motivated to tackle this yet again. I’ve just run out of motivation at this point, and it’s finally forcing me to evolve.

One upside to this: It’s forcing me to think outside the box. My problem has always been that I’m good at figuring out solutions, but bad at letting things take place beyond my control. If I ever want to grow an actual business (and not just grind out code for the rest of my life), I’ll have to learn how to delegate, and this is forcing me into that position now.

This one problem has really shaped most of my week, and it’s drained me far more than is reasonable. I’ve already decided that next week will be better: I’m travelling for work, and spending time out of the house is just what I need right now.

In other news:

My self-imposed Twitter limitation continues to work. I still open up the app several times a day, but most of what I’m getting are SABC News tweets (of which there are few), and I haven’t been tempted to dive back into the burning garbage vortex.

CIT is turning me into a libertarian. I’m a few months away from clocking my first year as a freelancer, but my financial year-end comes up on 28 February, at which point SARS gets to take 28% of my profits for the year. Let’s just say it’s shaped a few of my pointier opinions about taxes.

Ghost in the Shell: ARISE is actually pretty good. After trying to watch it in 2013 and being roundly put off by the Microsoft Surface product placement, I’ve kept away until this week. A more detailed post is in the works, but for now, I have to admit it’s got a whole bunch of merit all on its own.

I’m starting a new business venture! What started out as a semi-serious joke is now materializing into a new business, with a few potential projects lined up. With any luck I’ll be able to share more details by the next weekly update.

… and saying goodbye to my first client. The first customer I ever signed was for a retainer that they ended up not using as much as they thought they would, so cancelling this was really more of a formality at this point. But that’s another milestone I crossed this week: Ending a contract before its due date.

Next week, I’ll be doing my first ever full-time on-site consulting gig focused on the things I actually enjoy doing: Assessing business operations and guiding teams towards improving all of them. I’m already mentally drafting the case study πŸ™‚

Saturday #3 of 52

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2019 is officially back in full swing – it’s been a rollercoaster of a week, and looking at the work that lies ahead of me I’m legitimately worried I might be working too much again. As it stands, I need to put at least a half-day of effort in tomorrow (breaking my own no-work-on-weekends rule) if I want to stay ahead of my current workload.

This is reflected in my habit tracker for the last week, where I was only able to stick to one of them reliably!

Captured from everyday.app – highly recommended!

The worst part: I wasn’t nearly as productive as I’d have liked. I lost a lot of time with constant context-switching, being knocked off-course by incoming requests, and proper analysis paralysis. In other words, the back-to-work blues.

As my work’s gotten back to full swing, I’m having to re-engage my planning brain (to make sure I don’t go crazy), and I’ve had to adopt two strategies to stay on top of things.

A daily Inbox Zero habit

An inbox is basically a task list of indeterminate length. Until you actually go through the emails in there and map out the time it takes you to do things, there’s no way you know how much work you’ve really got on your plate.

So for that reason, I’ve focused on reducing both of my inboxes (work and personal) to zero every night. It’s become my new ritual for closing out a day, since it usually results in a list of to-do’s for the next morning – meaning I don’t have to think about how to start my day.

Even without Inbox Zero, it’s usually a good idea to end your day with a brain dump of everything you know you need to do the next day. It saves time and maintains momentum between “breaks” (ie eating and sleeping for the night).

I’ve found that most useful when paired with the second strategy:

Task Time Planning

Task lists are sweet little lies we tell ourselves – potentially days worth of work hidden behind one-line items. They get much more concrete when you do two things:

  1. Estimate how many hours a task will take you
  2. Add all of them up and try to fit them into your workday

So that’s what I did on Wednesday evening. I took a few hours to go through my inboxes, and eliminated everything in there:

  • Archived any emails that I didn’t need to respond to
  • For tasks, I noted down the task outside the email, then archived the email
  • For meeting invites, I made sure they were either on my calendar or rejected with an explanation

And then for each task that came in, I gave some thought to the hours it would take. I ended up with around 60 hours worth of work planned out (a solid week of effort plus overtime), and that was before I factored in all the other work I had planned elsewhere!

Most of my work runs in cleanly-defined contracts (I call them “obligations”), which mean I get to put together a table like this – charting hours per project per workday, with weekends hidden:

Freelancers can be really busy people!

And now it becomes really clear how busy I am! After I sat and charted out all my obligations (retainers, contracts, ad-hoc work, internal allocations for product development, marketing and admin) I found that I’ll only be back to “normal” at the end of February!

But I also felt relieved that the situation had been managed. Just having a plan – and some visibility into your immediate future – makes things a lot more manageable.

And then, finally, there’s the Eisenhower Matrix, an idea which has genuinely helped make the world a better place:

Borrowed from Develop Good Habits.

Urgent is usually pretty easy to discern: Things that have to be done right away, or a bad thing might happen.

Important is a little bit harder – it implies that there’s a reason beyond the completion of the task itself, which is undertaken as part of a larger plan. Developing a good sense of what’s important is, itself, quite important πŸ™‚

In my case, I have a relatively clear idea of where I want my working life to go. I know that long-term, the sustainable path is to develop and market products (not services), so that I can generate value without constantly investing effort. I’ll likely always be doing some sort of consulting work, but it would be nice if I didn’t have to do it – that would let me pick the best projects and truly do my best work within them.

So even though they don’t address any burning needs at the moment, spending time working on “unprofitable” product development is really the smarter move over the long term. The work won’t be urgent for a while, but it’s important to do it every day.

Between those strategies, I finally felt like I had regained control over my workload by Thursday morning. Consequently, those were the two most productive days of my week.

Then there were another few wins, thankfully unrelated to work:

The Noscript Show is now syndicated everywhere
We’re finally on iTunes, which also means we’re on Pocket Casts – apparently making the show even more accessible. I also managed to put up a basic website with all the pertinent info in one place: noscriptshow.com

Laravel Quickstart has backup!
I think there’s been enough idea validation here to move on to the next phase – designing the prototype and outlining the functionality for the first Quickstart. That’s begun with the help of a frontend developer, who I won’t name in public without approval πŸ™‚ Between us, we’re hoping to get the first version of this out a lot quicker!

Planning a podcasting info resource
Moving even further away from software, I’ve been looking at putting together a podcast learning center of sorts. The idea would be to offer once-off flat-rate access to all the information (with the price increasing over time as more info is added), and the focus would be on getting first-timers to the point where they’re producing their first podcast successfully.

It turns out there’s a lot to know – and even more questions you don’t think to ask until after you’re in the thick of it, so I’m hoping I can put something valuable together that will save everyone some time!

Finished Ghost in the Shell season 1 again
I rarely count shows as a win, but there won’t ever be a day where I don’t recommend Ghost in the Shell to people. Just skip over ARISE, that was an unintentional mistake.

Next week will be a proper grinder of a week, so I’ll probably get a head start on it by clearing up some of the smaller work items during the day on Sunday. All things considered, it feels good to be back in the driver’s seat again.

51 to go! (#1 of 52)

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I blinked and missed the first week of 2019 – it’s going to be a pretty short year, at this rate!

At the start of this year’s blogging adventure I figured I’d borrow a strategy from Charl’s personal blog, in which he (generally) does a weekly post to recap what happened during that week.

That’s usually the reason I wrote so little last year: I keep busy with a lot of stuff, so much so that picking one topic to write about causes analysis paralysis. So I end up writing nothing instead, a sub-optimal outcome.

The first week of 2019, for me:

Most of my customers came back online by yesterday, and I’m already planning out my workload for the year. Last year, my strategy was to just take on every piece of work I conceivably could – this year, I’m limiting my billable work and planning to take time off instead.

To that end, I mapped out the 2019 year in several different configurations, until I landed on the one that was optimal for my planning. And actually relatively sad:

The entire 2019 calendar year

That’s my 2019 tracker. It includes all 365 days of the year, marks out weekends (gray), public holidays that result in time off on weekdays (P) and my minimum-acceptable-leave dates (L) – calculated and distributed in such a way that I have sufficient capacity every month to hit my financial targets through billable work.

The sad part is seeing the year laid out like that. 250 weekdays, 104 weekends, 11 public holidays, and that’s 2019 all done!

Where the planning part comes in: If I have a really good quarter, and bring in amounts above target, that means I can “afford” to slow down later in the year and focus that time towards building my own products. It’s a mindset made possible by the insane amount of hours I worked last year, and the resulting cash buffer I built.

I’ll only feel confident once I go through February though. Bare minimum, SARS is going to take a full month’s pay away from me in one shot. Once I sort out my tax predictions for the next fiscal year I’ll actually be in a position to predict things.

Then there’s the minimum-acceptable-leave idea: I have to take time off. It’s an ongoing problem with me, so much so that I’ve sought therapy to help me manage the anxiety involved. I tend to overthink negative outcomes, and then to mitigate those I’ll work myself to death (literally) to compensate.

On top of those handful of [L] days, there’s the weekends (during which I absolutely should not do billable work), and public holidays (the same), meaning that of the 365 days in the year, only 250 (68.5%) should be productive.

It’s a nice plan on paper, for sure. Whether or not I stick to it will be a different story. One of the downsides of being a freelancer is that you’re 100% responsible for the opportunities you create, and sometimes that requires you to put in effort above and beyond what a regular 9-5 will require of you. So we’ll see what happens!

Other stuff of note:

Helderberg Dev Meetup: I’m giving the first talk of the year today (Progressive site enhancement using VueJS), which as of this post I still technically need to prepare for!

Laravel Quickstart: I’ve seen some early interest in the idea, even though I haven’t done much to market out the page yet. I’ll be doing that by outlining my first product, and publishing those details to a good-looking storefront – then there’s something more tangible to talk about in public.

everyday.app: This indie-built daily habit tracker (hi Joan!) has already been very useful. Simply by replacing the home tab on my browser, it encourages me to review my habit completion status often!

Makerlog: I’ve signed up (@wogan) for one of these public to-do trackers, and I’ll be using it for Laravel Quickstart work (when I work on it). With any luck, the daily reminders from everyday will nudge me into making at least one update per day here, and progress will be made overall.

On to the next week of 2019!