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.
What Is Your Wildest Dream?
Creating a Wildest Dream doesn’t mean fanciful living in the future. It means stopping to reflect, to think, ‘where do I want to go,’ because only then can we know and be truly conscious that the steps we take today, and tomorrow are in that direction.
Dream (Old English): joy, mirth, merriment.
Dream (modern): A cherished aspiration, ambition, or ideal.
Welt (Indo European root for Wild: 4500 BCE): woodland, untamed land.
Wild (modern): not domesticated or cultivated, uninhabited, emotionally intense, or enthusiastic.
Wildest Dream: a bold and aspirational ambition, sitting in the uninhabited part of your mind. In its purest form, it is unconstrained and deeply personal.
Lessons From Leaders
“All men dream: but not equally. Those who dream by night in the dusty recesses of their minds wake up in the day to find it was vanity, but the dreamers of the day are dangerous men, for they may act their dreams with open eyes, to make it possible.”
TE Lawrence.
“Whether you think you can, or you think you can't – you're right.”
Henry Ford.
“The people who are crazy enough to think they can change the world are the ones who do.”
Steve Jobs.
What Is Your Wildest Dream?
What does wild mean? It means uninhabited, inhospitable, impassable, unknown. Wild. You can only be brave enough to get there when you are totally uninhabited by restricting thoughts, negative people, dreary circumstances of reality. In Thailand on our annual leadership retreat, we answered the question ‘what is your Wildest Dream?’ We answered the question in the sea with the rain falling on our shoulders. The preparation was critical.
We finished eating lunch an hour ago. I look around at everyone, seven good men at the table, all fully bought into the change process. I’m so excited for the next part. I want their lunch to go down and be digested properly.
The rain starts, often that would be a hindrance to leadership development. Perfect. I stand everyone up and I just say, ‘to the beach’. ‘Will we get wet?’ Asks someone, ‘yes,’ I reply. We walk, with me speeding up, to the beach – it is just 20 metres. Down on the beach I gather everyone in a circle. I want to pump the blood up, get people moving.
“The dreamers of the day are dangerous men, for they may act their dreams with open eyes, to make it possible.”
TE Lawrence.
‘Max, give us an exercise to do.’ Max obliges and gets us to hold our arms horizontally, making the shape of a cross for one minute. Aching arms, ‘Patrick give us another exercise.’ We run on the spot doing high knees. Carter, Luke and Rami all give us push ups, squats and lunges. I’ve left Nate to last before me, he usually has a wild card. ‘Do roly-poly’s’ says Nate.
My eyes get wider as I see Nate doing one, getting covered in sand. I love it. It feels almost primal, childlike, and hilarious, watching everybody getting sand in their hair, down their back. It’s my turn. ‘I want everybody to jump in the sea, and I want you to grab the shoulders of someone opposite you in the sea and just shout! Shout and whoop in their faces!’
We get so primal, so wild, so unknown versus our usual environment.
‘Come in close guys, get in the circle, let’s just float here in the sea.’ Everyone comes in, a bit tense from throwing themselves in the sea, but ultimately relaxed, a thousand kilometres away from sending emails. I say, ‘what is your wildest dream?’
‘What is your wildest dream?’
Your Wildest Dream. This question is best thought about after a deep period of reflection, a quick period of dopamine release, a total reset of our brain. The magic, the courage, the uninhibited dreams that flowed from my friends’ brains and came out of their mouths was wild. Creating solutions to humanity’s greatest challenges, building an independent architecture practice, creating an interactive documentary to change a million lives, taking a business franchise to Africa from Turkey. Wild. Crazy. Totally out there, yet in that moment, we all believed it, we all felt it, we all knew we had the courage, creativity and grit to achieve it.
Your Wildest Dream is what sits in the rusty recesses of your mind. It is the tiny thought that you might have entertained once, but perhaps not shared with many people, if anyone. It’s that crazy thought that seems completely unachievable. It might be as crazy as flying to the moon, or as down to earth as living by the sea. We all have them. We all have excuses we tell ourselves that means we don’t entertain the thought. ‘I have a mortgage, I need to hold onto this job, I don’t know what will happen, the other candidates are more qualified than me.’
It is the tiny thought that you might have entertained once, but perhaps not shared with many people, if anyone.
I just finished reading Chasing Daylight by Eugene O’Kelly, the CEO of KPMG who was diagnosed with terminal brain cancer at 53. He quit his job right away and lived out his final 90 days with the positive intention with which he led his company. “After I was diagnosed, I came to consider consciousness king among virtues. I began to feel that everyone’s first responsibility was to be as conscious as possible all the time.”
Creating a Wildest Dream doesn’t mean fanciful living in the future. It means stopping to reflect, to think, ‘where do I want to go,’ because only then can we know and be truly conscious that the steps we take today, and tomorrow are in that direction.
Maybe it’s time. Maybe it’s time to go back to that thought you once dismissed, the one that felt too bold, too uncertain, too ‘not me.’ Maybe it’s time to entertain the possibility that it’s not crazy – it’s just unclaimed.
Deepen Your Curiosity
My favourite learnings on finding your wildest dream:
Chasing Daylight by Eugene O’Kelly.
Podcast - What your dreams are trying to tell you about your waking life with Dr Rangan Chatterjee and Dr Rahul Jandial.
The Alchemist by Paulo Coehlo.
Steve Jobs by Walter Isaacson.