The Jabber

If your decision was plastered on a street-pole headline tomorrow, would you stand by it? Exploring the Warren Buffett ‘newspaper test’ and why comfortable transparency is the ultimate goal of a sovereign life. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit keepjabbering.substack.com

After the high of our annual conference, the crash has arrived. Exploring why we feel ‘the wall’ mid-week, the importance of the Monday Rule, and how to find the ‘rest station’ between the sprints of life. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit keepjabbering.substack.com

Exploring the frustration of Max Verstappen, the ’losers' limp,’ and why the pursuit of perfect regulation is creating a new kind of sporting mediocrity. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit keepjabbering.substack.com

Max Dowman scores at 16 and the media crowns him. But history shows that early brilliance is often a mirage. We explore the ‘survival bias’ of the Premier League and why the ‘slow burn’ beats the ’flash in the pan.’ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit keepjabbering.substack.com

Exploring the conflict of social media ‘shorts,’ why taking guests out of context is a long-term brand killer, and how to build an engaged following without selling your soul to the scroll. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit keepjabbering.substack.com

Exploring the cost-benefit analysis of work travel, the ‘bubble’ of the conference circuit, and the unseen weight placed on the partner who stays behind. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit keepjabbering.substack.com

Exploring the ‘uncanny valley’ of perfect nature reels, why my dog’s bark stayed in the edit, and the mathematical value of being unpolished. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit keepjabbering.substack.com

From CVs for 12-year-olds to the ‘open day’ gauntlet, we look at the institutional stress-test of high school applications and why a ‘no’ might be the best thing that ever happens to your child. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit keepjabbering.substack.com

Exploring the power of the ‘half-full’ flip, the endurance of hardships through the lens of Viktor Frankl, and why ‘this too shall pass’ is the ultimate mathematical truth of history. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit keepjabbering.substack.com

Schools and workplaces love to use the word ‘voluntary,’ but the subconscious pressure to conform is a powerful engine. This episode explores the conflict of the Grade 7 camp, the ‘hidden curriculum’ of institutional bonding, and why teaching your child to say 'no' might be the best high school prep there is. This is a public episode. If you would like to discuss this with other subscribers or get...

Pure commission is a gamble on your anxiety. In this episode, I share a personal business pivot: why my work colleagues and I chose a balanced salary/incentive model, and how ‘lifting the weight’ of lopsided risk has unleashed a new wave of energy. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit keepjabbering.substack.com

What do you do when something you said or wrote no longer fits the reality of today? We discuss the ‘contradiction trap,’ the importance of staying kind when things go sideways, and why the only way to stay true to yourself is to keep speaking, even when the script changes. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit kee...

We hit 10 subscribers. In this episode, we talk about why the ‘initial friction’ is the hardest part of any pivot. We explore the philosophy of compounding - not just in finance, but in showing up, building trust, and honoring the few before you reach the many. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit keepjabbering.su...

Is the world actually worse than it’s ever been? This week, inspired by a thought from Vestact’s Byron Lotter, we look at the historical perspective of struggle. From near-misses with conscription to the modern career grind, we explore why our current ‘shitshow’ is actually a sign of the incredible freedom and choice we often take for granted. This is a public episode. If you would like to discuss...

What happens to your ‘sovereign values’ when your income is no longer guaranteed? This week, we discuss the intense psychological shift of moving into a commission-based role. We explore how to resist the urge to make money the ‘purpose’ of our work and why focusing on the craft is the only way to survive ‘year one’ of a career pivot. This is a public episode. If you would like to discuss this wit...

Is the ‘logistical tax’ of modern parenting higher than it used to be? We dive into the relentless schedule of the modern family. We compare the ‘free-range’ childhoods of the past to the curated logistics of today and discuss how to maintain your own sovereignty while being the ‘engine’ for everyone else. This is a public episode. If you would like to discuss this with other subscribers or get ac...

As my son enters his teenage years, I find myself drafting a ‘survival guide’ for him - only to realise it’s exactly what I need for my own mid-life pivot. We discuss dreaming big, the danger of "wishing it away," and why being yourself is the only way to stay sovereign at any age. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, v...

What happens when the ‘outsider’ finally gets invited inside? This week, we discuss the Bloomberg insight into Bitcoin’s institutional era and how it applies to our personal lives. We explore the internal hubris and external jealousy that follow success, and why staying grounded is the only way to avoid becoming a victim of your own wins. This is a public episode. If you would like to discuss this...

We all want the harvest, but few of us want the first year of a lemon tree. This week, we explore why gardening is the ultimate metaphor for business and personal transitions. We discuss the Fool's Garden "Lemon Tree" syndrome and why the most important growth happens underground before you ever see a single piece of fruit. This is a public episode. If you would like to discuss this with other sub...

We think we grow out of star charts, but adult behaviour is driven by the same simple rewards. This week, we unpack a recent change in a gym reward program and discuss why 'almost free' is psychologically more expensive than 'free.' It’s a lesson in habit-building, momentum, and the high cost of minor inconveniences. YouTube · Substack This is a public episode. If you would like to discuss...

What happens when you present Michael Burry’s data to a crowd of Bitcoin "HODLers"? This week, we explore the hilarious and frustrating reality of the Dunning-Kruger effect. From Bitcoin price points to global energy debates, we look at why we’ve traded nuance for echo chambers. YouTube · Substack This is a public episode. If you would like to discuss this with other subscribers or get acce...

Is it the work, or the worry? This week, we explore the "Sidewalk Theory" - that moment when we stop to watch the changes instead of driving them. Drawing on a classic Jeff Bezos insight, we discuss why the present moment is the only place where stress actually disappears. YouTube · Substack This is a public episode. If you would like to discuss this with other subscribers or get access to...

A 4.5-hour drive offers plenty of time for reflection. This week, we get raw about the transition from a team-based corporate culture to the solo-driven world of commission. It’s a talk about identity, the "Creative Wall," and the reality of batting for yourself. YouTube · Substack This is a public episode. If you would like to discuss this with other subscribers or get access to bonus epis...

When self-control fails, the contract begins. This week, we explore the "Tech Agreement" - an AI-assisted family contract designed to teach an 8 and 12-year-old the value of moderation in a digital-first world. YouTube · Substack This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit keepjabbering.substack.com

This week on The Jabber, we trade the cricket pitch for the Rollercade. We discuss the transition from primary to high school and the literal struggle of letting go of the safety rail in middle age. A lesson in core strength, family memories, and why the kids have it right when they refuse to fear the fall. YouTube · Substack This is a public episode. If you would like to discuss this with...