Conversational Tools

I don’t think we’re ever really having the same conversation.

It’s like sitting in a theatre watching the same play but from different seats, distracted by different things. Maybe you’re focusing on one actor, while I’m captivated by the lighting.

Jonathan Haidt uses the metaphor of the rider and the elephant. The elephant (our emotions, intuitions, and embodied experience) is doing most of the habitual and automatic work. The rider (the conscious mind) tries to explain it afterward.

Inside my head, it feels like there’s a committee in constant debate. Each member has their own agenda, and their words float around, interrupting and overlapping. When I speak, it’s not a clean stream of thought—it’s fragments trying to make sense of each other. Dipping in and out of connection with my elephant.

I don’t have access, but I am as sure as I can be that the same thing is happening in your head.

So when we talk, it’s not just me talking to you, it’s my inner committee talking to yours. No wonder we miss each other.

That’s why we need better tools for conversation. Tools like Interpretive Charity, Transcription, Summarising, Questions, Reframing… and teasing out meaning rather than thinking we can just force it on each other.

To truly hear.
To truly listen.
Because sometimes… we’re not even in the same conversation.

Truth is conversational. 

Catalyst

 I use social media as a catalyst for real-world interaction.

I’ve been writing a blog since 2006 called Swart Donkey. That name came from my surname before I took my wife’s (Black) and because I’m stubborn, noisy, and ignorant… but loyal and willing to put in the work.

I enjoy sharing my thoughts openly and honestly. I write about things happening in my life and the observations I make, always aware that it's a public space. And I know people won’t read everything. You can’t stress too much about trying to be interesting to everyone all the time. Just be yourself. The right people will connect with the parts that matter to them.

What I love about this is that when I speak to someone in person, even if they didn’t read everything I’ve shared, something will have resonated. That’s where the conversation starts.

When I was posting regularly, I found that the people who were reading, or even just skimming, would pick up on the bits that mattered to them. And so we’d go straight into a meaningful, open conversation.

Because I was open, they felt safe to be open too. I’ve had some of my best conversations this way. Not because I was trying to sell something or manipulate anyone, just because I was being real.

And I think we can use artificial intelligence in a similar way. These language models are brilliant at connecting ideas through analogies.

Let’s say I’m trying to explain financial planning, and you’re into rocks, diamonds, star signs, or you’re a Star Wars fanatic, whatever it is. The model can help me use your language to explain my world. And that creates connection.

But for me, it still comes back to real-world interaction. These tools are like GPS, they’re useful to look things up, but they don’t replace the journey.

We become the things we repeat. And we become like the people we spend time with. That deep connection comes from ongoing, human conversation. From engaging, unpacking, repacking, learning, unlearning.

That’s what makes us human. That’s what excites me.

So I’m going to use AI as a catalyst for connection. To spark better relationships, not replace them. Because that’s where the magic is: around the fire, eye to eye, seeing and being seen.

 

Stay Grounded

There’s a big difference between embodied knowledge and surface-level learning. 

Think about how we used to find our way home. You’d either know the route or use a physical map. That’s embodied. Now, with GPS, it does the work for you—you follow the instructions without really learning the route. This is one of the core fears people have about artificial intelligence: Will we be replaced? If something else is making the decisions, what value do you add? 

But I’m not scared of that. Just like I’m not scared of investing. 

I don’t panic that there are a thousand PhDs trading in the markets—because I’m not trying to out-trade them. I’m not a trader. I invest because I believe value is created by companies doing real things: building products, serving customers, solving problems. When I invest, I own a slice of that. I’m not gambling on price movements—I’m backing something real. 

It’s the same with decision-making and Artificial Intelligence. Own a slice of yourself. Be the person in the room. 

When something becomes embodied, it’s because you’ve done it so often it becomes part of you. You don’t have to think about it—it’s second nature. That’s mastery. That’s magic. It lets you move fast, connect dots, and act with intuition. 

It’s like language. Words only have meaning when they’re shared. You and a close friend can say a single word that carries a whole story. That’s relational depth. That’s how embodied learning works—you repeat, you refine, and it sinks in. 

Eventually, it changes how you respond. Your reactions are no longer deliberate—they’re instinctive. That’s the gift of repetition, of depth, of care. 

But here’s the key: Stay embodied. Be aware of the habits you’re forming. Watch what you repeat—because what you repeat becomes who you are. 

Learning something deeply is hard. But now, with the tools we have, it’s more possible than ever. The opportunity is there—if you’re intentional. 

That’s why I don’t panic—about money, or Artificial Intelligence, or being replaced. I get my money a job. I let it work. I stay grounded in relationships. And I focus on what I value. That’s the difference.

Building and Rebuilding

A big part of life is who we partner with. I have gone through difficult break-ups and a number of years of losing myself in the process of building or rebuilding a picture of the life I wanted. In 2011/2012 I used yoga and my art studio as tools to find myself again. 

One of the investment lessons I had learnt is that you should never be a forced buyer or a forced seller. When you want anything too much, and when it becomes your absolute focus, you can lose focus on everything else. If you are in a corner, and you have to make a decision, that may be the most important time for you to make the opposite decision. When you feel like that is the only thing that matters, at the cost of everything else, then it may be time to walk away. 

I had to really dig deep and come to terms with myself, and so I went to the mountains. I went to Austria, and it was just a magical time. As a South African boy, one of the things that blew my mind was REAL snowflakes. Crystals of fragile beauty. Snow with those mathematical patterns that cast spells as they stop time in their gentle floating till they softly butterfly kiss and lie with the ground. I had seen blobs before. The wet and soggy sort that grinds London to a halt like summer sweats or any other extremes. In Austria, there were magical mornings with clear skies and silent walks. The Yoga Teacher Training I did was over the year end, and a bunch of Swamis came from all over the world to join the small group I was in for the period between Christmas and New Year.

Kuiering v Pricing

Stillness can come not through the absence of thought, but through a point of focused engagement. 

I am at my happiest when I am absorbed in a deep and meaningful conversation with someone. My favourite word is Kuier. It doesn’t have a direct translation, but I interpret it as a warm spending of time. There is catch-up. There is content. There may be wine. 

Yet the point of focus is really an appreciation of the other human being rather than being defined by another goal. An attempt to see each other. Like the wonderful greeting... Sawubona... I see you. 

I get into a state of flow by diving into learning things. When I feel a sense of meaning soaking in as I chip away at complexity. Flashes of insight before I get swallowed once again by confusion and doubt. Wondering in the grass rather than lost. Stumbling. Grappling. Connecting. 

Everyone finds flow in a different place. Which is why relationships are one of the essential basics to come back to. To invest in. To make yourself available to people. Partly so that when you need them there is pre-loaded reciprocity. We can tell if someone is interested in us simply because they want something now. 

Part of Kuiering is a lack of urgency. Part of pricing is manufactured discontent and immediacy. Kuiering is comfortable where it is. Pricing creates a feeling of wanting to be somewhere else. Kuiering releases expectation. It notices. Pricing creates expectation. It contrasts. Kuiering needs a person. Pricing needs a problem. 

I am lucky to have a wide circle of friends. I find each of them is able to see me in a slightly different way. I understand, and see, and kuier with, myself better through those relationships.

No better place to be

Shifting Winds

When you make choices, you narrow future choices. When you get on a path, you seldom get an opportunity for broad re-evaluation. An opportunity to say, “right, I am going to start from scratch.” 

When attempted a clean slate in 2014, I removed the stake in the ground of where I physically had to be. Normally that stake is your job. If you have kids, their schools. If you have a house, you can rent it... so maybe that is a medium rare stake. You can also change jobs and schools. The change is not a trivial one. 

I packed up a single week’s worth of clothing, carrying my world on my back. Australia and New Zealand chose themselves as my first destination because of a wedding invitation. 

Ironically, just before I left, I met my future wife. She was heading in the opposite direction. She is an Anthropologist and was transitioning from being an academic to engaging with the corporate world. She was shifting from living for the love of learning to a pragmatic and purposeful engagement with applying ideas. 

When I came back, we had to figure out a balance of two visions of the future. A challenge in building autonomy is our decisions impact others, particularly if we want to share our journey. 

How do we agree on the stakes? Our choices are path-dependent, and what happens affects what happens next. We are never in complete control. There is an element of randomness to it all. Within those constraints and shifting winds of change... we get to have an influence on the direction.

...and he's off

Shared History

How many of our decisions are inherited? How many are embodied? Things we do well. Things we do badly. Not many of our decisions are made with a deep understanding of all the other decisions those decisions affect. That is too high a benchmark. 

What we do matters. Actions have consequences. Yet, not everything is cause and effect. We are just one element heavily affected by the ways we were taught. The repetition of parents, teachers, mentors, coaches, family, and friends. 

Sometimes it takes events happening to you in later life to trigger patchy memories of something that happened early on. Maybe we hear our parents' voices coming out of our mouths? Maybe we see the expression of a sibling in the mirror. Sometimes I can’t even see the expression, but the muscle memory makes me think of my brothers. 

We are very connected. We are built in a world where money is dependent on skills and knowledge, and being paid for those skills within enclosed containers. Skills, knowledge, and barriers (to entry and exit) can compound in the same way wealth does. 

Subtle skills like network building, trust, and the ability to communicate, depend on the deep work of being able to understand other people’s problems from their perspective. A lack of shared history makes that challenging.

Unintended Consequences

Working to See

We can live very different lives, and have such varied values, that massively competing worldviews can lead us to conversations where it becomes clear we are struggling to see what the other person is seeing. If the two sets of decision-making framework have little in common. The two people might even be very close. They may even be in love. Yet they do not see the same thing even when it is in front of them. 

Hello in isiZulu is Sawubona. Directly translated, it is “I see you”. Seeing someone means you are sufficiently interested in them to do the work of understanding the building blocks of how they construct their world. Through curiosity and care, deep relationships gently unpack what words, sentences, tone, chunks of meaning, triggers and backstories, create the exchanges each person has with a shared reality interpreted differently. 

Money is a blunt tool for this. You don’t have to do the work if you measure your respect for someone by how much they charge, get paid, or own. Instead of relationships where people see each other, they can become job descriptions and conspicuous expectations. Mapping life through things you can count. Success as a life CV of achieved milestones... houses, schools, job titles. 

In truth, a really well-lived life might be difficult to express except to the person who walked with you. Except to the person who saw you.

Armenia's Symphony of Stones

Feeling the Choices

Local markets should be more responsive to changes in preference, because they are able to respond to tacit knowledge. The stuff we can’t put into words. The stuff we don’t always understand ourselves. Our inconsistency. Our moods. 

Local markets mean relationship building and consequences. Huge markets become more abstract. If you sell someone something that isn’t a good deal for them (because you need/want the money) and it affects them badly, size matters. In a huge market, you disappear in search of the next sucker. In a local market, you still have to engage with the people. 

Local forces commitment, recognising that what we do matters. The boundaries between client, colleague, friends, and family blur. It gets complicated. Dealing with strangers is cleaner. It is transactional. Local and intimate means getting involved in the nitty gritty. Local means we experience the results of each other's decisions. Local means wrestling with issues. 

Standardization can give comfort. Where you do venture away from local to explore, some recognition is useful. When you (think you) recognise something, you don’t have to give it thought. Conscious choice is hard. 

Daniel Kahneman talks of “thinking fast and slow”. You want to embody a lot of decisions and make them fast. Jonathan Haidt talks of our rider (head) and elephant (body/habits). We think the rider is in control, but it is mostly the elephant. 

To embody and relax, we have to trust. It is hard to trust when you haven’t done the necessary wrestling to deep soak shared agreement.

International Standardization

Decision-Makers

Joint decision-making is complicated. We make mistakes when we make our own decisions. They are our mistakes. They reveal information about our habits, values, character, drivers, desires, fears, knowledge, ignorance, and personalities, but they are also wrapped up in noise. 

We are complex and inconsistent. If someone else is going to make decisions for us, the further they are away, the less they will see the consequences and responses to the decisions they make for us. Central Decision-Making scales both impact and mistakes. 

If you look at the typical democratic political process, the issues are incredibly complicated when it gets to elections. How many people read and engage with the manifestos of the politicians, and grapple with what they are promising? How accurately does the manifesto reflect their intentions? Their ability to deliver? 

If you wrote your own manifesto, how closely would that reveal your real behaviours... or would it (more likely) reflect a promotional version of what you (in your head) want? 

Information gets lost as you add distance between decision-makers and consequences. Ideally, in local markets, small decisions can be made that reflect the stuff we can’t even put into words. There is relationship building. There is understanding. There is the ability to adapt. 

As soon as markets scale with central decision-makers, they become abstract. People become categories. Voters become power bases. Actions have consequences. It is important that decision-makers feel those consequences.

What we do, matters

Messy Trade-offs

Sometimes you have to do things. If you are fortunate, what you have to do depends on what you want to do. There are realities to accept once you have figured out what you want. Trade-offs. Each opportunity taken closes doors to other opportunities. The tricky bit is negotiating through complex competing relationships and trade-offs. The deeper your network of meaningful connections, the more you have to take into account the desires of others. A lot of my anxiety comes from the managing of expectations. If no one expects anything of you, and your actions do not impact anyone else, then you can do what you want. If you cut yourself off from the world. If you engage, it is messy. A friend of mine took this approach when he started work. He said, “you have to do a good enough job that you don’t get fired, but not so good that they come back”. It is comfortable under the radar. That strategy did not last long. Eventually, he wanted to engage, and people started coming back. A life worth living is messy.

Under the Radar

Winking in the Dark

There is not enough work. Much of the work there is does not pay enough to have some left over to build capital. It is not simply a case of willingness to work. You must find a job that matches your skills and knowledge. Then it depends how many other people could do the job, and whether the employer/client specifically wants you. Ideally this would all be neatly mapped out like GPS. Insert destination, and a road map is provided. The challenge is we all need to eat. In a pure play meritocracy with 7.8 Billion people, there is for all but the Djokofednadals, always someone better. We operate behind smoke and mirrors to protect our containers. A friend told me about a reality show called “dating on the spectrum”, and how young adults with autism deal with the unpredictability of dating. A world where you hope someone stops “looking for someone better”. In some ways their yesses are yesses and noes are noes, and they deal with it. Imagine a world with full transparency where we were comfortable being open with our asks and offers. It would be pretty uncomfortable, but we would do less winking in the dark.

Winking in the Dark

Single Serving

We do not have full knowledge of other people’s stories. It helps to build an environment that supports repeated interaction. Connected stories. 

The hardest part of making money is building a relationship with decision-makers with money. Finding clients. 

A decision-maker will do the hard work of deciding they trust you enough to give you money. That is emotional work. They do not need to do that initial heavy lifting again if trust is maintained. Build deep relationships. Superficial relationships will leave you constantly searching for new clients. If you are serving them once, but then maybe they never want to see you again, because you have not acted with integrity, and they regret their initial decision.

Sharing Interests

People are interested in people who are interested in them. I have a deep reserve of inner confidence, partly because my Mother was always fascinated in, and supportive of, anything (and everything) I found interesting. My curiosity always had an army of motherly reserves. The South African bubble I grew up in has some resistance similar to British reserve to faking and overenthusiasm. I didn’t read the book “How to win friends and influence people” (Dale Carnegie) for years because the title sounded very “American” and fake. It is, I discovered, a brilliant text with some very practical observations on reality. One of those realities is we respond to people who show interest in us. Who are interested *because* we are interested. We recognise that indicates a deeper level of loyalty and willingness to put effort in, in order to share our worlds. If you want people to be genuinely interested in you, be genuinely interested in them. Yes, that takes effort. It shows.

Got my Back

Trusting the Container

The Holy Grail is a direct, sustainable, relationship with decision makers with money, where you have their trust and confidence. Trust that you intend to solve their problem. Confidence that you can. Relationship building is one of the strongest barriers to entry. Trust is built from multiple layers and signals to show that the words and ideas being exchanged mean the same thing to both people. A lot is lost in translation between worlds. This is why nepotism and prejudice are so powerful. In a world of complexity, friendship, community, and emotional connection are a way of cutting through the noise. A lot of business has nothing to do with business. The specific problem being solved is far less relevant, than the sustainability (and containability) of the connection. Building trust in the container of the relationship.

"The Damsel of the Sanct Grael"

Rossetti (1874)

Allowing for Extra

How do you start? Building Capital so that you can gradually become less dependent on your earning ability, seems like a game reserved for the wealthy. Advice is tricky because we have different lifeboats in a shared storm. When people talk of being “self-made”, they are often referring to whether, or not, they inherited Capital or a pre-packaged business from Mom or Dad. It is more complicated than that. Most of us have weird relationships with money. Wrapped in our sense of worth. In our relationship with our parents. In their relationship with their parents. In our politics. The advice I give is deeply wound up in my own story. Our self is a bigger container. The bubble we grew up in. Mine is based in Apartheid and Feminism. One based on inequality and gender roles. For me, starting starts with constraint. Having a firm and absolute hold on what “enough” looks like. Then not feeling like more than that is better. I wasn’t trapped in debt, and had the option of choosing a path to develop skills & knowledge to get an income. So my first steps were pragmatism, spending discipline, and delayed gratification. Building a buffer. A few months spending in the bank. Then putting the extra to work. I realise that extra is a foreign concept for most. That is what needs to change.

Sustainable Relationships

When organisations and groups are small, it is possible for the people in charge to understand the dynamics and treat everyone as individuals. The key person can have lunch with every new joiner. They may even have a role in picking all of them. Work with all of them at times. Know their names. Understand the complexity of their story. In small groups, each combination of members has its own character. Each combination of two. Each combination of three. Four. Five. When it is relatively small, you don’t need prejudice. You don’t need roles. You don’t need grades. You don’t need standardised controls and comparisons. As soon as an organisation gets beyond a certain fuzzy size, it needs to turn into an institution. Every decision becomes precedent setting. You need to be able to articulate reasons, cause, effect, and attribute value add to ensure fairness. A friend of mine regularly tells his kids, “If life was fair, you would be far worse off”. There are benefits to scale, but there is danger in turning people into numbers. Dunbar’s Number is a theoretical limit to the number of people with whom an individual can sustain meaningful social relationships. It is usually considered somewhere around 150. Who are the 150 people you understand reasonably well as individuals?

Share of Wallet

The hardest part of making money is finding customers. It is the same thing as getting a job. It is preferable to get to come back tomorrow rather than looking for new employers every day. Ideally you are able to get a “share of wallet”. This is the amount of a customer’s regular spending they will direct to the problems you solve for them on a regular basis. Like a salary. That’s where relationship building and trust come in. We all specialise. We have to. So we are incompetent in an almost infinite number of ways. But we understand our problems. Especially our problems that are recurring. If we know someone can solve them, there is no reason to look for greener grass. Particularly if the problem is not the thing we are passionate about, but a distraction from our true purpose. If the relationship with the problem solver makes us better at the things we care about. A “Target Market” is a group of people (1) with money, (2) with the problem you have the skills and knowledge to solve, and (3) who you understand well enough to see the world from their perspective. It’s no coincidence that people with wallets get seen.  

Throwing Name

For 5 years I raised money every November for Movember. In the first year, I raised more by growing a moustache than I had as part of a dedicated Youth Council in a full year’s effort. It blew my mind. Hours selling hot dogs, arranging charity dinners and “expanding Rands” versus a few emails and some fancy dress. I sharpened my self-mocking for money over the next few years and learnt a few lessons. (1) Don’t make the one time a year you contact someone, a time you are asking them for something, (2) Don’t always ask the same people, and (3) Be interested in and support the causes of other people. People like people who are consistent and interested, rather than only there when they need help. This is analogous to new tools like LinkedIn. Don’t take it seriously only when you need a job. It takes time to become a contributory member of a community. To be trusted. Relationships and Networks are the backbone of privilege. But now tools are there to democratise that, and change the game. If they are used authentically. If they are used as a conversation rather than a request. Be part of the conversation.

Easy Money

Consenting Adults

Some people like hierarchy. That’s okay. Everyone has their kinks, and anything that goes on between consenting adults is fine. It’s the consent part that bothers me. I believe in institution building, but I worry about the power of “legal people” over people. When the institution gets so big that the individuals become abstractions. Roles, categories, functions, grades. Turning people into numbers for memos to pass up to boardrooms. Particularly when the negotiating power is lopsided, and on one side there is a person “speaking for the institution” (be it a Country, Company or a The People). For markets and communities to function well, there has to be full transparency and a sense of peers working together. Otherwise it is just bullying. Using the fact that someone has limited job opportunities or capital to incentivise them to do as they are told. 

Need a Crown?