Humanist, family man, seeker and learner. 3X Founder (2 exits): Cogsy, Conversio & WooCommerce. I wrote and published Life Profitability. Ex-Rockstar.

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Rules

I was writing my second post for the day just now.

For a split second when I was done, I considered not publishing it today and instead schedule it for tomorrow. (Or worse, just keep it in the backlog for a rainy day.)

Somewhere along the way, I had internalised the supposed* content marketing best practice: picking a consistent publishing cadence and sticking to it.

Something about creating expectations with your audience and then delivering on them. Blah, blah.

In being free, I quickly asked, "Who made this a rule for my blog?"

Unless I had made the rule (which I had not), the only obvious thing to do was hit publish immediately, which I did.

And I'll double down on that by publishing this post as soon as it's done.

*I say supposed not because I think it's bad advice or that it wouldn't work. But it's unchallenged and invalidated within the context to which I almost applied it.


h/t to Andy Hawthorne.

I stumbled upon his blog this morning and read a few of his blog posts.

I noticed his haphazard writing cadence, which undoubtedly influenced my awareness to say, "f*ck it" in publishing my post.

Andy's writing cadence emboldened me; maybe his way is a better rule for me to live and write by.

Maybe this wasn't Andy's intention when he wrote "What's The Point Of Blogging?" but this resonated with me:

That's what makes blogs valuable. Not because they're definitive. But because they start conversations.

In this case, it wasn't a single blog post, but the very way in which he was blogging that has sparked me to add to the conversation.

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Being Free (Part 2)

This is a follow-up on the original Being Free.

Having gotten into a bit of a groove of writing (and publishing!) here regularly, I've overlooked one of the things that used to trip me up so often when I was writing to achieve a goal.

Picking a good headline.

Sheesh. It's the bane of my existence.

Every single time it became a rabbithole of overthinking and bouncing around between different perspectives or frameworks to pick the best one.

Impulsively I always have a semi-decent and often catchy headline in mind.

Then I realise it's so personal and abstract that it's likely only catchy to me.

I then remind myself that if I can only be clever or clear, I should probably be clear, which means the next iteration is literal and mundane. (Or just literally mundane.)

It's generally at this point that I involve AI in brainstorming other options. Irrespective of how I try to tone down the objective to gamify my headline for our algorithmic overlords, all of the suggestions are perfectly fine and have equal ability to go viral. At that point, I feel all of the ick.

In the last week, I've just picked the first headline that intuitively resonates with me most.

That feels more interesting and authentic.

Plus, I'm not publishing short-form content here or hiding the majority of my writing behind a click. In both those cases, crafting the perfect headline makes sense.

Instead the headlines here are only signposts to say, "A new post starts here."

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Local Consequence

This is one of those perspectives that I suspect I can exclusively have in hindsight and this season of my life.

At any other point in my journey, I prioritised other things to the extent that I neglected even considering this perspective. Therein probably lies some of the sentiment I attach to this today because I wish I had clearer thoughts about this sooner.

In this moment, I'm energised, inspired and ready to ambitiously pursue building something in South Africa, for South Africa. I want to contribute to something that benefits a greater community/society beyond the direct stakeholders or shareholders of the project.

When I look back though, WooCommerce could've been that in many ways especially considering how the platform has grown since Automattic's acquisition.

I wonder what would've happened had WooCommerce stayed independent and importantly stayed a South African corporation.

Instead of jumping on the remote working and distributed work trends so quickly, I wonder what impact we could've had if we prioritised training and hiring South Africans.

I wonder what could've happened had we helped independent retailers and small businesses in South Africa with free software and services so that they could jump into ecommerce sooner. Would we have seen some local DTC brands use that momentum to grow into multinational empires?

So many positive second-order effects could've occurred had we decided on a more South Africa-first mission.

There are many ifs, buts and maybes in all of this, and the level of my speculation here makes this a personal thought experiment only.

I don't have any regrets, and as I think about building in South Africa, for South Africa in the future, revisiting some personal experiences helps crystallise what could be possible if specific perspectives get enough oxygen at the very start of the journey.

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Belief

A big part of our world today is about making others believe what you believe.

Capitalism thrives on sales and marketing, which are both a function of great storytelling.

Becoming really good at this is a predictable way to make progress and accumulate wealth.

An obvious and linear rationale would suggest the paths where you can garner the most believe, is also the path to greater progress and wealth.

I would suggest that the path where no one believes what you believe is possibly the more meaningful and rewarding.

Naysayers are inevitably stuck in the status quo which informs current beliefs.

When you’re trying to push beyond that, your conviction should exceed those limiting beliefs inherent in the status quo.

The biggest challenge is maintaining the passion of your conviction when the first person says they don’t agree and believe what you believe. When that happens, you need to find a second and third and fourth person who might believe in what you are convinced about.

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When money is not enough

Money can buy many things.

Often on the road to making more money, we buy more and/or more expensive things.

And we agree that the smarter is often to save or reinvest that money into something that can make even more money.

Capitalism is beautiful in that way; it can keep on compounding forever. And it can do so exponentially if you keep adding more fuel to the flames.

The even smarter play is when one starts to use money to buy back time or meaningful experiences with those people who matter most in life.

Eventually though even the richest of the rich gets to a point where their financial means at least partly makes them lonely.

As a millionaire, it is easy to throw a party and get people to attend. It’s harder to make them your friend. But money can go a long way to plaster over those cracks.

Money loses it efficacy when I can’t use it to change the society I live in.

Looking at this with my South African tinted glasses: I can use money to insulate myself against many of the challenges in our country. But, what I ultimately desire is to live in a country that is free of crime. That is only achievable (and realistic) when we eradicate poverty and inequalities.

My money is definitely not enough for that, and no well-known, super rich individual can buy that outcome. Changing the status quo requires a collective effort that involves money, but it is not the primary thing: