Hi, I’m Jack
I am a coach working with leaders from London to Prague to Bangkok. I write life advice grounded in research and real world experience. If one thing captures the essence of what I do, it is the opening lines of the 700 year old Dante’s Inferno:
When I had journeyed half of our life’s way,
I found myself in a shadowed forest,
For I had lost the path that does not stray.
I help you rediscover your path. Why? I believe my purpose is simple: “to educate the world that life is amazing.”
I’m in the process of writing a book for those of us who are ‘half of our life’s way’ - around age 30 - who want to rediscover meaning and direction. Until then, read my articles and let me know what you think.
The Original Mid-Life Crisis Was Not About Porsche 911s and Buying Red Trainers
We are all familiar with the stereotype. The 50-year-old guy buying a Porsche 911 and a pair of red trainers. But this halfway-point-of-adult-life is too late for a crisis. Why have your mid-life-crisis when your kids have already left home and you have just the twilight of your career left?
I’m sitting in a café in Brera, Milan. A small wooden table, the legs balanced on the cobbled streets. I’m alone. Liv flew back to Bangkok this morning. In front of me is a plate of pasta, half eaten. In my hand a book. A book, half in Italian with English translations alongside it. I’m halfway through it, but I again flick back to the first page, re-reading the sentences I’ve underlined.
Nel mezzo del cammin di nostra vita,
mi ritrovai per una selva oscura,
ché la diritta via era smarrita.
When I had journeyed half of our life’s way,
I found myself within a shadowed forest,
For I had lost the path that does not stray.
The Divine Comedy, Dante Alighieri, Canto I (14th Century).
The Original Mid-Life Crisis
We are all familiar with the stereotype. The 50-year-old guy buying a Porsche 911 and a pair of red trainers. But this halfway-point-of-adult-life is too late for a crisis. Why have your mid-life-crisis when your kids have already left home and you have just the twilight of your career left?
But, the original mid-life crisis was not about sports cars and colourful trainers.
The original mid-life crisis is and always will be around your 30th birthday. And it isn’t reserved for men. In Dante’s time – 14th century Renaissance Italy – life expectancy was 60 years old if you were rich. So half of our life’s way was very much your 30th birthday.
We Have A Child’s Brain Until Our Late Twenties
Dante was onto something from a neuroscience point of view as well. In our 20s we look outwards for validation. We look to the world and say, ‘who do you want me to be.’ Up to our 30th birthday, our brain is constantly building neural pathways, solidifying them and pruning unused connections.
As we progress into our 30s, our mind shifts and with a fully developed pre-frontal cortex we move into a more reflective state.
With reflection comes early signs of wisdom, we usually begin a journey of realising that the identity we have created for ourselves is based on following the world’s expectations. Satisfying parents, then teachers, then friends, then universities, then organisations.
When we reach half of our life’s way, our brain supports us to move to an introspection unavailable to a teenager. ‘Who am I?’
My Shadowed Forest
As I read and re-read those sentences in the Divine Comedy, I reflect onto the last few years of my life, my shadowed forest and my path. It would be easy to say my ‘shadowed forest’ was working my career and realising I was selling unhealthy food to children. Yet, it would be too easy to say that – I loved my time there, the pace, the people, the challenge.
I found myself within a shadowed forest.
Too often we try to point at one single cause – it is easier for our brains to understand that. For me, it was more a feeling that the world has always given more to me than I have given in return. My career has always been about learning and my personal growth. I have never looked at my years in consulting and corporate and thought, how can I make the world a better place. My shadowed forest was not burnout, it was not a slap around the face, it was a mismatch between potential and purpose. Yet knowing something is not the same as doing.
I needed agency and as is usually the case, inspiration came from adventure. Sat in the driver’s seat of our Toyota Hilux, the white paint stained red by the desert dust of Namibia, Liv and I listened to the incredible Greenlights by Matthew McConaughey. As the hours of bumps passed underneath us, I knew that as soon as we returned from that trip I needed to do what he’d done since his mid-twenties. Not to take as many drugs or play the bongos naked, but to start recording my life by journalling. That was my Greenlight, my first drip in the bucket.
“We cannot fully appreciate the light without the shadows. We have to be thrown off balance to find our footing.”
Matthew McConaughey, Greenlights
Catch The Drips And Let Your Purpose Take Care Of Itself
You won’t be as clear headed as Steve Jobs, having epiphanies to make the world’s best computer. Instead, the first step out of the forest is to figure out who we are, and that starts with what we love. Don’t spend your time ruminating over lack of passion, spend it recording what you love, what you are passionate about. Move the bucket to catch the drips.
Drips are those small moments when you quietly think to yourself, ‘that’s cool’. One drip into the palm of your hand quickly evaporates. Quickly forgotten. Catching the drips in your bucket means noting things down with intention. Journalling or sharing your curiosities with someone.
In Milan I’m catching drips. One morning I am at the Veneranda Biblioteca Ambrosiana checking out Leonardo da Vinci’s journal of inventions (read more about da Vinci’s amazing range in this previous post here) . The next morning I’m with the incredible Nikos where we discuss our Wildest Dreams. That evening, I meet an old friend Francesca for dinner and talk about life. The rest of the time we walk around the city, exploring.
Catching drips.
Those small moments for me are my inspiration. Reading and learning about the renaissance history, brainstorming the future with an amazing Greek guy, sharing life’s challenges with a good friend.
Drips are those small moments when you quietly think to yourself, ‘that’s cool’.
When you are present enough to catch a bucket full of drips, the water can be used to wash away the dirt which covers the path.
The bucket of drips has led me down this path of studying, researching, coaching. On a Monday morning 18 months ago, I was paid handsomely to check my emails and talk to my team. Instead, I am sat here writing a blog post that might be looked at by up to 100 people, perhaps half will make it to this sentence, maybe less. I don’t have clarity on where it will lead, but I know I’m moving towards something that matters.
The pasta’s finished. A light breeze moves through Brera, sliding the napkin off my lap and onto the cobblestones. I take a sip of water, glance again at the underlined lines in Dante. I’m still here, in the shadowed forest. But light is filtering through the canopy now, and the path ahead is just a little more visible. And that’s okay. Have your crisis early. Get your bucket, I’ve got mine and I’m catching the drips.
Deepen Your Curiosity
This week I feature two incredible books – The Women, and Wild Swans – in their own way the protagonists tell the story of entering their shadowed forest, losing the path, and finding their way out in their 30s. To read more about how we learn more from stories than textbooks, check out the bonus blog on the website.
Divine Comedy, Inferno by Dante Alighieri.
The Women by Kristin Hannah.
Wild Swans by Jung Chang.
We Need To Rebuild Our Tribes. Not By Blood, But By Choice
Humans are wired for tribes. When we belong, we thrive. The Industrial Revolution broke our tribal bonds – replacing community with control. Today, we must consciously rebuild our tribes, choosing where and with whom we belong. Whether in companies like Ferrari or leadership retreats in Thailand, modern tribes still make greatness possible.
Lessons From Leaders
“Le fabbriche sono fatte di uomini, di mezzi tecnici e di muri. La Ferrari è fatta soprattuto di uomini.”
“Factories are made of people, machines and bricks. Ferrari is made of mostly people.”
Enzo Ferrari.
"The strength of the team is each individual member. The strength of each member is the team."
Phil Jackson.
“If you want to go fast, go alone. If you want to go far, go together.”
Often cited as an African proverb, though its exact origins are unclear.
“It's better to hang out with people better than you. Pick out associates whose behaviour is better than yours and you'll drift in that direction.”
Warren Buffett.
We Are A Tribal People.
100,000 years ago, tribes worked. Living in small, close-knit groups of kin, Homo sapiens came to dominate all other hominid species and animals, eventually migrating out of Africa 50,000 years ago.
Hardwired to live in groups of 30-150 people, who stand beside us come rain or shine, we developed language, culture and imagination. These unique skills were the backbone of our superpower – our ability to work in teams.
The Gorilla Debate
Consider a male gorilla. Now consider a strong man, say Dwayne ‘The Rock’ Johnson. In hand-to-hand combat, who would win? Well, most likely the 200kg gorilla would outlast Hollywood’s finest, weighing 120kg. Now, consider Tom Holland, Spiderman, weighing in at 65kg. Without his spiderweb spinning fingers, he would be crushed by the gorilla. Obviously.
What if Tom was joined by an all-star cast of your favourite 100 light weight actors – I’d include anyone from the Superbad movie, maybe as bait. The gorilla would no sooner have beat its chest before our all-star cast of talented men would’ve formulated a plan and taken the gorilla down.
Act 1: Tribes At Their Best
70,000 years ago, tribes slowly walked out of Africa, travelling a few kilometres each year as they searched for greener pastures.
Tribes worked. They survived the polar ice caps expanding to cover Chicago, New York, the UK and Central Asia. 20,000 years ago, how would the Rock have made himself a warm jacket, whilst hunting woolly mammoths, fending sabre tooth tigers, navigating the Bering Strait Land Bridge? He wouldn’t. He would be dead. Our small, determined, collectively organised ancestors did survive though.
These unique skills were the backbone of our superpower – our ability to work in teams.
Once the ice thawed, climates became ripe for farming, and humans began to thrive with populations booming across the globe. In these farming civilisations, we were still tribal, still in groups of up to 150 people.
Humans had the same brains as we do now, they were smart. These were not cavemen. If you took a human baby and teleported it from the Fertile Crescent in 9,000 BCE and dropped it in Bangkok with me – it would fit right in. It wouldn’t know the difference.
Act 2: Tribes Start To Unravel
Our environment has changed, but our emotional brain has not. Now, as I sit on my balcony in sunny Thailand, I couldn’t tell you the name of any of the 150 people that are most proximate to me right now. Hang on, my wife came home, there’s one, and my cat, if he counts? Two. So, how did we get here?
The Industrial Revolution began in the United Kingdom and spread throughout the world in the 1800s. Incredible progress was made to human civilisation, but at a cost. Tribes began to wither, fray, and move to the ever-growing cities. Mass migration on a scale never seen before, saw humans organised into working units, led by managers. Manage comes from the French word ménager, meaning to handle horses. Factories didn’t need tribes, they needed output, and like animals, humans were another capital investment.
The dimmer switch was turned down on the human spirit at this time, a little bit of light lost behind the eyes. We lost connection, we lost rest, we lost play, we lost our tribe. Where tribes had leaders who inspired and protected, the industrial age gave us managers who treated us like bricks and widgets.
But all was not lost. Over the coming centuries emerged visionaries who remembered that the essence of the tribe is people.
“Factories are made of people, machines and bricks. Ferrari is made of mostly people.”
Enzo Ferrari.
Three days ago Liv and I visited the Ferrari Museum at Maranello, just outside Modena. I was taken back to my childhood. I loved supercars, with posters of Aston Martins and Ferraris on my bedroom walls.
Maranello was full of Italians. Proud of their heritage, they flocked in and surrounded the beautiful cars dotted throughout the museum. In the first room there were some old car shells from the 1960s. Beautiful, curved metal, shaped incredibly by hand. Printed on the wall above it was that quote from Enzo Ferrari. He knew that people are at the heart of a great organisation.
Act 3: Tribes Reimagined
The 21st century is just beginning – we have a wealth of opportunity ahead of us. We will not win by being tribal in the traditional sense of the word. Tribalism, belonging to one group, is always going to draw us in, but now we need to lean into a multi-tribal world. No longer do we belong to one village, community or race. We choose to belong to sports teams, workplaces, universities, nations, continents and the world.
Diversity is being in the room; inclusivity is belonging in the room.
Enzo Ferrari understood it, he understood that to consistently add the most value to the world, we need to bring diverse individuals together to become one tribe.
I started writing this piece two days after returning from our leadership retreat. Bringing together incredibly high performing people in Thailand, Patrick and I guide these 25–39-year-olds through growth of both the body and mind.
This is the 21st Century tribe. Lebanese, English, Czech, Straight, Gay. The 21st Century tribe is founded on diversity and succeeds on inclusivity. Diversity is a statistic; inclusivity is connection that drives collective progress. Diversity is being in the room; inclusivity is belonging in the room. Inclusivity is a mindset, of coming together despite our differences and because of our shared values.
There is far more power to belonging to a tribe of your choosing.
As a species our minds and bodies have not changed for 100,000 years. Our environment has been in constant flux. Over the last half millennium we have dropped the very essence of what makes us human – the tribe. In its place came isolation, loneliness, and the myth of the self-made individual. We don’t need to go back to tribes based on blood, on religion, on borders. There is far more power to belonging to a tribe of your choosing, one whose people come from different places, who have had different hardships, who have different goals in life.
We now have this amazing ability to fly halfway around the world and discover places where we truly belong. I think it is okay that we are less close to our hallway neighbour. What is not okay, is to not take advantage of the wealth of communities that exist to cater to your passions, your interests and your needs.
Deepen Your Curiosity
The Evolution Of The Human Brain - William H. Calvin PhD on page 17.
History of the World by Andrew Marr.
Sapiens by Yuval Noah Harari.
Wildest Dreams Come From Range
From Fuxi to Da Vinci, Leibniz to Claude Shannon - human progress has always been driven by those who crossed disciplines. They weren’t specialists. They were explorers. They followed curiosity, saw patterns others missed, and made creative leaps that changed the world. In today’s age of AI, complexity, and constant change, it’s not your niche that will define you - it’s your Range.
Lessons From Leaders On Range
“Smart people are a dime a dozen, they don’t usually amount to much, the real key was being creative. And whether it is Leonardo da Vinci or Benjamin Franklin or Steve Jobs, these are people who love to seek patterns across nature. They were interested in everything you could possibly know. By seeing those patterns, they made mental leaps that others didn’t do.”
Walter Isaacson.
“Time you enjoy wasting is not wasted time.”
John Lennon.
“Modern work demands knowledge transfer: the ability to apply knowledge to new situations and different domains.”
David Epstein, Range: Why Generalists Triumph in a Specialized World.
“Learn how to see. Realize that everything connects to everything else.”
Leonardo da Vinci.
“The creation of something new is not accomplished by the intellect but by the play instinct.”
Carl Jung.
Range Comes From Curiosity.
As a child I never believed I was amazing at any one thing. For Sunday league kids football I was a goalkeeper, then a defender and occasionally a forward in six a side. I could spend hours building Lego sets, arranging toy soldiers into imaginary battles, or piecing together puzzles of the world map and its flags.
In secondary school, I was popular, but not one of the cool kids. In class I was smart, but I never received the attention or pressure of being the smartest. My academic journey was never a straight line. Final exams had ups, downs, and several resits.
What I was great at was curiosity. Sometimes it got me sent out of class for talking too much or asking the wrong question. I wasn’t the best at any one thing, but I had a quiet superpower: I was fascinated by people.
I spent the summer break of university working for an eccentric American who owned a handful of engineering factories in Birmingham. I loved it. I was good at designing logos, understanding finances and organising machinery layouts. I was great at getting on with people – whether the eccentric American or the factory workers. This was one of my first data points that it was valuable to be good at many things.
I moved into consulting where I would have amazing conversations with business leaders and industry experts. Why was I good at it? I knew how to connect with people, to connect disparate ideas together, and to move fast. Whilst consulting, I discovered the phenomenal book Range by David Epstein. He challenges the myth that specialisation is the only path to success. Instead, he argues that generalists – those who dabble, explore, and connect dots across fields – often thrive in complex and unpredictable environments.
Generalists – those who dabble, explore, and connect dots across fields – often thrive in complex and unpredictable environments.
It made me look back at my experiences in a different way.
I knew that what I was doing, this ranging, exploratory type of work was beneficial. Why else would we place so much trust in general practitioner doctors – highly trained generalists who help us navigate complexity?
Range helped me to make sense of me loving Lego, blowing things up, history books, geography lectures, ski mountaineering, piano playing, cooking, drawing, being outdoors, being indoors with friends, economics, politics, sociology, psychology, strategy, communication, critical thinking. I’ve always been an easy-going person, willing to share, willing to try something because ‘why not.’
Looking back, I wasn’t born with Range – I built it. As a school kid, my Range looked like curiosity. As a consultant, it became understanding and insight. Today, it’s my ability to hold multiple perspectives, to move from abstract to practical.
I am finding my Wildest Dream in my Range. Yesterday evening Liv and I spent an hour building Lego – a Viking Village to be exact. It was such a throwback to childhood. My Wildest Dream is not to build a Lego Viking village for a living, but maybe it’s to build something new and novel.
Leonardo da Vinci lived through the Renaissance in the 15-16th centuries. In 2013 he shot back into the limelight for posthumously becoming the artist of the most expensive painting ever. $430m for the Salvator Mundi. I urge you to explore his story. Da Vinci wasn’t just an artist; he was a bridge between disciplines, the original interdisciplinary thinker. He was Range. He was the ultimate master of Range. His contributions to scientific discovery, engineering, military equipment, human anatomy and biology are incredible. He had such a diverse range of interests, curiosities and skills. Diversity which only he can make overlap.
Da Vinci wasn’t just an artist; he was a bridge between disciplines, the original interdisciplinary thinker. He was Range.
Never look at your hobbies and think it is getting in the way of something. If you love yoga and baking and piano playing, keep doing it. Maybe you won’t open a yoga retreat or an Etsy baking store or become the next Ludovico Einaudi. But those passions? They shape how you lead meetings, how you connect with people, how you see the world. That’s value.
I’ve been playing piano again. Not to perform – just to enjoy the process. That small creative act reminds me that our Range, our inspiration, lives in the margins, in how we choose to spend our time when no one’s watching. What hobby, what curiosity, could you return to?
Today I see range in my great friend James, a Gen-Z renaissance thinker. Able to talk, communicate and share stories in sport, philosophy and technology. Excelling in building deeply technical AI models and working with stakeholders in Australia, Dubai and Finland. James has a deep sense of Range.
He is the Gen Z AI-Renaissance man. What is his Wildest Dream? To contribute to multiple humanity wide challenges. Humanity wide challenges, that is a Wildest Dream. But, multiple, that is only achievable by someone with Range, by someone who has developed their passions across multiple disciplines.
Range is when the 17th century mathematician Gottfried Leibniz was inspired by the 4000-year-old concept of Yin and Yang.
Leibniz was a true Range master of the 17th century. He moved effortlessly between disciplines. Inspired by ancient philosophy and the concept of Yin and Yang, he made groundbreaking discoveries in mathematics and logic.
Yin and Yang are foundational concepts in Chinese philosophy, representing complementary opposites – light and dark, active and passive, expansion and contraction. According to mythology, eight elemental symbols were first developed by Fuxi, an ancient cultural hero. He observed the natural world and understood that these dual forces, Yin and Yang, were the building blocks of creation. The eight elemental symbols of Heaven, Lake, Fire, Thunder, Wind, Water, Mountain, and Earth were each made of solid (Yang) and broken (Yin) lines.
Leibniz was a true Range master of the 17th century. He moved effortlessly between disciplines. Inspired by ancient philosophy and the concept of Yin and Yang, he made groundbreaking discoveries in mathematics and logic. One of his most enduring contributions was creating a simple numerical system using just 1s and 0s. One century later, George Boole would be inspired by this binary system to create Boolean Algebra.
In the 1930s, Claude Shannon took a philosophy and mathematics class at the University of Michigan and learnt about Boolean algebra. As an engineer he applied this idea of binary logic to electric circuit boards. 1s and 0s, Yin and Yang, on and off. Shannon was another Range master, making contributions across mathematics, information theory and cryptography. It might surprise you to learn that Claude.ai is named after Shannon.
From Fuxi to Leibniz, Boole to Shannon – Range has always driven progress. What began as ancient philosophy became mathematical logic, then evolved into the language of circuits, and now powers the digital age. Range is more than having a hobby. It’s how civilizations leap forward.
In times of uncertainty, Range becomes a competitive advantage.
We are living in challenging times. Challenges are just challenges – they are neutral, they are a construct of our mind. It is up to our interpretation on how we live through them. In times of uncertainty, Range becomes a competitive advantage. Like Da Vinci, we each carry the potential to overlap our own unique mix of skills – to find creativity in the collision points of science and art, philosophy and tech, the ancient and the future.
Each of these humans, Da Vinci, Leibniz, Boole, Shannon, have advanced human civilisation greatly, lived through challenging times and approached it with a sense of exploration. Each of these humans explored beyond their primary discipline, they found range in invention, in philosophy, in art, in engineering. In sketchbooks and circuit boards, in conversations and curiosity.
The artificial intelligence revolution is just beginning. The 21st century is just beginning. This is the renaissance for us, Millennials, Gen Z, Gen A. This is our time to get involved in transformational challenge. Be a warrior. Get outside. Find challenges and challengers that are worthy of you. Do not hold back, do not be meek. Seek courage to grow, to learn, to develop, to explore, to adventure, to meet people. Read books, talk to people you disagree with. Find your Range.
So, what is your Wildest Dream? What Range will you need to build it?
Deepen Your Curiosity
My favourite learnings on range:
Range: Why Generalists Triumph in a Specialised World by David Epstein.
The Knowledge Project with Shane Parrish - Episode 121 with Walter Isaacson: Curiosity Fuels Creativity.
The Lost Leonardo - Documentary Trailer.