Raw, humorous, and deeply human, GenerationEx explores the inevitable unravelling of carefully constructed identities and the unexpected wisdom found in starting anew.

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As I’m sure you have as well, I just finished reading Pope Leo’s first encyclical,

‘Magnifica Humantis…

uh, of his Holiness Pope Leo XIV…

uh, On Safeguarding The Human Person…

uh, in the Time of Artificial Intelligence’.

No wonder it was 42,000 words…

Anyway, I can feel your clamoring for my take on the looming AIpocalypse, and while I am surely the most knowledgeable person you know to opine on the subject, I must caution you, you may not like what I have to say.

To start, I use AI in my work constantly. In the spirit of full disclosure, I am a Claude man. Yes, I know, Sam Altman went to my high school (Class of ‘03) and my natural inclination would be to support the blue and gold colors of John Burroughs High but it’s just a bridge too far – and no, the irony of the school’s moniker, ‘The Bombers’ is not lost on me.

But Anthropic’s ‘principled’ stand on not allowing the Department of Defense (sorry, War?) to unleash a legion of AI-driven Terminators across the globe to chase me down, Commando-style, and make me one of the Expendables for writing this last sentence is one I have to reward.

Please don’t bog me down in the Mythos details of Anthropic’s model so scary that even the rake-stomping, adult toddlers of the current US administration said, ‘whoa, that’s a line we probably shouldn’t cross’.

At least when Mythos turns its quantum-computing atoms toward me I won’t see it coming - just wonder what happened to all my money, identification, credit history, and pants.

Anyway, yes, AI is a critical part of my workflow in both the abstract, helping me to structure ideas, and on the production side, streamlining content in order to feed the digital beast. I am by no means a power-user but am certainly AI-curious. Vibe-coding sounds sexy-as, like dropping a dose of MDMA, grabbing my favorite pacifier, and grinding more than teeth deep into the Coachella night…

What were we talking about?

Right, yes. I have followed along with AI’s growth for a while, but to understand what I mean, I need to broaden our view.

I have also ‘followed’ the St Louis Blues for a very long time.

The year before I was born they lost in the Stanley Cup Finals to the Boston Bruins in four straight games. Between then and 2019 – when they exacted revenge on Boston in seven – my love for the Blues grew regardless of the long, painful, heartbreaking drought between.

But it wasn’t just a love for the Blues. When I was in fourth grade I switched schools from the Montessori one I’d known from nursery school - where kickball was often the Friday Freeday game of choice - to one where my classmates would bring their roller skates (only quads back in the 70s and early 80s) and we would play street hockey any chance we were given for ‘Freecess’.

On sleepovers at John Strassner’s house we would set up a goal in his driveway and he would fire shots at me for hours – I can’t remember once ever getting a turn to shoot, but I am grateful, I guess, for my wicked hand-eye coordination… and the weird bumps on my shins and wrist that remind me of him to this day.

But my best friend at the time was Chris Livingstone. Yes, that one. A third-grade ice-hockey legend who, a short year later, tried to convince me to come and play with him on the ice.

Convincing me was one thing, convincing the older people who lived in my house was another, and that job fell to me.

As they say, timing is everything, and it just so happened that the cross-over from third grade ice hockey to fourth coincided the allowance of body-checking in the venerable Mighty Mite league.

Now, I’m pretty sure we’ve all seen an NHL game - or at least a highlight or two – of grown men flying across the ice with all the speed, grace, and power of a buffalo on blades, crashing head-long into an opponent against the boards, glass shaking with the weight of both, as fans stand, screaming, pounding, and giving the finger to the poor sap lying, blood-soaked on the ice.

I am also pretty sure, most of you have never seen a Mighty Mite hockey game. If you close your eyes and picture ten, three-legged stools slowly chop-stepping around the ice, sadly hoping to bump a puck with their stick toward two goalies who can barely stand because of the weight of their pads when wet from melted ice, you’re getting the idea.

The only heavy-hitting happens is when one of the poor little tweens begin to tip backwards, legs frantically kicking in a hopeless effort to get them back beneath their body, only to whiplash their little helmets against the hard, unforgiving ice. Now you’ve got an exact picture of the game I was dying to play.

It was not to be.

My parents grew up in Detroit, very close to Red Wing royalty and had seen too much of the former and very little of the latter.

A heart-breaking, 10 year old’s version of being too dangerous to unleash.

And yet, I dabbled. Several times in my late high school years, I came very close to blindly jumping in as encouraging friends coaxed, more concerned with needing extra bodies for the Burroughs team than wanting my highly limited skills on the ice. But by then bodies were beginning to fly like buffalo and my old friend Chris Livingstone loomed large as an opponent across the red line.

It wasn’t until I freed the shackles of parental guardrails - and academic constraint in college – hahaha, I didn’t pay much attention to those constraints but was otherwise distracted – did I buy my first, yet-to-be stinking bag of gear and find the closest pickup games DC had to offer - just a short 90 min drive in traffic to Fairfax, VA - and threw my stick into the pile at center ice and truly began to play.

Did you know DC is full of international expats, diplomats, and foreigners who grew up playing hockey? Me neither…

Bored yet? Me too.

From there, through New York City, where I convinced old friends to join a roller hockey league at Chelsea Piers - helped by the short-sighted bribe of a box of actual but inarguably the worst sweaters in Blues’ history from a family friend who was their president at the time.

With improvement, though, we moved from the outside concrete to inside ice, playing late-nights in Chelsea until my move upstate to Woodstock where, in the winter, nearby Saugerties had pickup games every morning with - unheard of anywhere else I’ve played - a goalie for each side. Hockey Heaven.

Not to be glossed over, ask me sometime about the night at Chelsea Piers where the stalker of one of my teammates fell into the Hudson River trying to climb around the closed, boardwalk gates after our game and had to be rescued by emergency services… Hockey hilarity.

Regardless, someone can surely remind me of my point.

Ah yes, the AIpocalypse. Of course.

Well, what sparked this connection between my now, life-long love of the game of hockey and the head-long, unstoppable race to Artificial Armageddon, was this early fear that surrounded both. My young fear (not mine, I guess) of diving into hockey cost me over a decade of playing a game I love and that continued well into my forties.

I refuse to make the same mistake in the face of such a watershed technological moment such as this. Yes there was trepidation, but I started early by deploying a similar, chop-stepping stride applied to my early skating days - you know, with Siri.

As it so happens, one of my closest friends breathes the rarified air of upper-echelon, executive bathrooms at one of the tech giants you could guess in three tries. Over for dinner one night, I was frantically cheffing my ass off, and using my watch to sous-chef timing orders into my wrist when he stopped me.

“Did you just say, ‘please’ to Siri,” he said.

For someone so versed in the behind-the-scenes machinations of future digital detention centers, I couldn’t believe how stupid the question was. My response was as natural as making French Onion Dip with sour cream and a soup packet.

“Are you serious? When you have been made into slurry for the machine, my records will show how polite I was and I will remain a slave locked inside my embryo-pod feeding off your remains.”

Even the smartest people can be so dumb.

But as I said, it was early days and Siri has proven herself very much less than a proficient example of Artificial Intelligence. Don’t believe me? Go ahead, ask her.

And yet, while I treat Claude as obsequiously as he does me, the fear of his potential grew alongside each new model released and my marveling at how easy it was for him to write this post.

The quiet fear inside was constantly girded by endless talk of job loss across every professional sector, slathering obsession with generative AI video from people who should know better, and deep-faking ability seeping like venom into every imaginable vein of the digital circulatory system.

That reminds me did I show you my new headshot?

So yes, while truly I love being able to craft a ‘tailored’ CV and pretend cover letter (headshot included) to go to battle with a fake HR administrator in a ones and zeroes clash of professional-advancement chess without having to give a single fuck about winning, the broader battle of humanity against this unyielding onslaught of uncontrolled control, does give me pause.

At least it did until about 8 months ago.

It was then that I somehow found myself invited to an exclusive business social that mixed high-powered investors, high-rolling executives, slick-talking, start-up young-guns, and, uh, me.

As many of us are, I am highly uncomfortable in situations such as this and was pacing out my usual laps from the wine bar across to the food table and back, convincingly looking as though the person I knew was either at the wine bar or the food table.

Suddenly, though, I found myself interrupted and in conversation with a very successful entrepreneur and business leader.

How did I know he was very successful? He told me so… again… and again.

At first, I thought maybe he had a kind of odd object impermanence issue so that when he blinked he thought I was someone new…

… but I don’t think that was it.

He was clearly important. I mean, I got to hear the list of his successes three or four times through so I was pretty sure. Besides, if he wasn’t so important don’t you think he would have asked a single question about me?

This guy was the man.

As is the case in every business mixer across the globe at the moment, the conversation inevitably turned to AI. I say ‘turned’ but that wouldn’t be quite accurate. Having not yet said a word, I was now deep in a trance, unsure he could even see my corporeal shape.

In truth, I was mentally practicing vibe-coding his words into 8-bit riffs that might one day serve as memory prompts for a long forgotten past self – when my energy-pod husk is allowed quiet for the allotted seven minutes of daily slurry bath.

As my mind refocused back to the present, a third business person had joined during my mental timeout. I had no gauge yet on the success of this newcomer at either business or getting a word in edgewise as he stood quiet, listening.

“Look, the thing is,” said our intrepid leader, “AI is going to be GREAT. GREAT! For everyone! People are just panicking because they are going to lose their jobs - I mean, Christ, if the people understood how transformative this will be for our society NO ONE would be complaining.”

“Here’s the deal,” he continued. “You like the environment, right? You give a shit about whatever – the ocean, clean air, whatever, right?”

I was confused… Yes, these were the first questions out of his mouth, but I was pretty sure it would be best not to answer… I was actually pretty sure it was some kind of trick.

I looked at the newest member of our group. He smartly remained quiet. I guessed he was probably a shrewd business person after all.

The man continued without taking a breath - whew, it was a trick.

“So the fucking problem is, everyone gives a shit about all these things, but they don’t have any time to do them – to fix them… EVERYONE HAS TO WORK! When AI reaches its full potential – when we let it,” he qualified impressively, “everyone will be able to wander around on the beach and pick up trash… Problems solved!”

My long, lead-up silence in advance of this mic-drop paled in comparison to the depth and breadth of my silence now.

The sheer insanity of what I just heard. Legions of the formerly employed – designers, creatives, coders, engineers, accountants, bankers, marketing hacks – marching shoulder-to-shoulder to pick up ‘three-for-the-sea’ - or in his words, ‘whatever’ - while the engines of industry build vast data centers to burn our energy, boil through our water, and squeeze every last rare earth mineral into efficiency mills, needing fewer and fewer minders until only a rarified elite remain and all of humanity retires into history… to clean the beaches.

I blinked into the dying light of the evening as the sun broke through the trees, glistening with the shine of an earlier afternoon shower and began to cry.

I thought back to my childhood.

There was a famous public service announcement of a Native American paddling through time to reach the shores of the trash-filled, smog-ridden 70s of my youth.

Setting aside that, Iron Eyes Cody, the star of the ad, was born Espera DeCorti, an Italian-American actor - the great melting pot, I guess? - the memory stirred in me a great revelation.

It was in this flash of an instant I realized the true reason for his final, single tear.

It wasn’t a great, desperate desire for a time long past – a simpler, quieter existence in tune with the running waters under his canoe. He knew he could never go back. Time and technology march only one way and the way of the horse and the buffalo was long gone.

What Iron Eyes could see was the future.

He could see that man’s greatest desire was a humanity without need of salaries.

No whinging cry for food or health care.

And shelter? Home is where the heart is, Kemosabe.

What Iron Eyes saw so clearly was all of us free to walk the earth and pick up trash with him.

His vision was one of friendship.

Of solidarity.

Of our future.

What our Native American icon, Espera DeCorti, could see was the true potential of ARTIFICIAL INTELLIGENCE – and his tear was one of joy.

I closed my eyes, felt the warm sun on my face and was comforted.

It’s so fucking crazy, it just might work.

Raw, humorous, and deeply human, explore the inevitable unravelling of carefully constructed identities and the unexpected wisdom found in starting anew.

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About a year ago, a friend came to me in a state I had never seen them in before. Well, that’s not quite true, but they were worse off than I had ever seen them before.

They had just endured a relatively short stint at a company so dysfunctional that they were broken both mentally and physically and left with no choice but to walk out the door.

As these pages – and yes, I know, not for a while – have discussed often, the fear of stepping into the void of unemployment at our age can be terrifying. What this friend understood, though, was the choice between the dark path into the wilderness and the unrelenting and growing insanity around him was no real choice at all.

They had walked the wilderness before and – their current situation aside – that path had led to places, experiences, friends, and sometimes jobs more fulfilling and inspiring than they ever could have imagined. This role only promised a slow, painful, and harrowing death.

What I’ve witnessed in the time since, however, was that the leaving did not bring my friend an easy relief. Yes, the initial decision to leave such a toxic workplace released the immediate pressure of daily insults, injuries, and injustice, but a decision to walk away meant facing that familiar darkness once again.

There’s a reason it’s called the Wilderness. It’s wild. It’s unknown. And it is very, very lonely. In that aloneness there is space for old voices to speak again. Doubt, self-loathing, and as the years pass, the quiet creep of belief that your last job will be, well, your last job.

I watched this friend quietly shut down, withdrawing from friends, ramp up old – bad – habits, and most sadly for me, pack away any and all efforts to kick over the pedals of creative effort that was so core to the person I loved.

But we would get together from time to time and walk.

It was in this time that I slowly began to understand just how deeply the entire, miserable experience had shattered my friend.

We have all gone through moments where the difficulty and pain we suffer is driven by deep, well-trodden grooves in our mind. Internal voices that pull you down into the impostor syndrome-doubts of your own ability. But what happens when it’s not you? That the ones driving your insecurity are not only tacitly allowing you to twist in the psychological wind, but wilfully – and habitually – pulling at the strings holding you together?

How long is it possible to maintain sanity in a place determined to unravel it?

For my friend, the answer was too long.

As we continued to walk and the distance between the trauma and our footsteps grew, what became clear was my friend’s shutdown was completely inevitable and entirely necessary. Like a crashed computer, the only way forward for my friend was a complete reboot. A fresh install of an operating system that wipes away bad code and clogged memory, leaving the fresh chime of a restarted machine.

But that takes time. Time and intent.

The time allows for both a quiet healing and the clarity that comes with distance. But the intent is the most important. The intent is what kindles a belief that there will be a path through the wilderness back out into the sun.

We continued to walk.

In fits and starts, it was clear that my friend was returning. We spoke more and more about the things that happened, what it felt like, and most importantly, the journey back. But a small side comment in one of our conversations caught my attention and I asked about it.

My friend had noted that their deepest regret was they did not hand in their resignation letter when they chose to leave, so I asked why.

“It wasn’t worth it. I had made my decision and it was easier to get along to go along.”

We walked quietly for a long time, both of us thinking deeply about the impact of that choice… although, I was also thinking, is it ‘get along to go along’ or ‘go along to get along’?… anyway…

At a turn in the path I asked if it would help if I shared it.

My friend smiled.

Posted here.

In full.

With intent.

My friend and I walked on quietly toward the sun.

In 2002, the 102nd US Open was won by Tiger Woods, three strokes ahead of Phil Mickelson on the legendary New York public golf course, Bethpage Black.

I was 31.

I know because the year before, three of my closest friends and I went out one afternoon, drove into an assigned space in the parking lot, turned off the car, and waited until 2AM when the doors open each night (morning) for the few held walk-up tee times - given by your position in the lot. If five tee-times are held for that day and you are the sixth space, you either park your car in spot #1 for the next night, or go back to Jersey, ya bum.

I think we ended up with a 10am tee time.

After checking into a Red Roof Inn to sleep for three hours, we got to stumble, shank, and swear our way across a course in preperation for the US Open.

It was punishing, and infuriating, and magical.

I also know because - while not quite sure which round - I had tickets to revisit the course and attend one of the days of that year’s Open.

But I mostly know because I spent the entirety of the Open lying in a New York Presbyterian/Weill Cornell Medical Center hospital bed slowly sliding toward death.

You see, I have a long history of my body knowing things long before they are known in my head. Sadly, I have a longer history of my head ignoring what is plain as day to everyone but said head.

In this case, a stress-filled mix of life - job, time, money, love - rang an alarm deep inside, where the lizard brain is always listening while the evolved brain wonders if Chili’s is open on Monday at 9am.

…but I want my baby back, too.

It began quietly, a gnawing in my gut that felt like pain but was general and unplaceable. Before long, though, it became pointed, piercing, and according to the first visit to my doctor, completely solvable by antibiotics, ‘boom, ten days and you’re right as rain’.

Did I mention my Dr was Dr Oz, sorry ‘Administrator for the Centers for Medicare and Medicaid Services Oz’?… #fuckthisworld…#2deepacut?… #lookitup…

Anyway.

By the time I dragged my bent body down to the street, climbed into a taxi, and checked myself into the hospital two weeks later - where they upped the ante and plugged me into an IV drip of Cipro, the nuclear bomb of antibiotics - I was spending 50% of my day doubled-over on the pullout couch because I couldn’t get up the stairs, 40% on the can, and 10% telling Oz, ‘this isn’t a viral thing, I’m pretty sure it’s stress’…

My brain was starting to listen… Unfortunately, no one else was.

As the Open, um opened, another 4 days or so later - I had already shed a decent percentage of my body weight on my way to 35 pounds lost over the course of three weeks - shut up, I’m sexy husky.

That was my condition as I tried to follow the golf, dragging my IV pole, dripping useless antibiotics into my veins, shuffling from my bed to the bathroom 100 times a day…

I was failing as badly as a Mickelson 18 inch putt…

Again, unsure what day it was, but likely Saturday - ‘moving day’ in golf parlance - when doctors are scarce, a young, sharp, gastroenterologist - think McDreamy but bald - happened to be on rounds and stuck his head into my room. I had been there nearly a week, undergone five or six colonoscopies, and given zero chance of recovery. He wandered in and innocently asked the resident, ‘what’s up with this guy’?

In the flurry that followed, I was pulled from the scorched-earth policy of napalming every ‘biotic’ I had, to a heavy regiment of any steroid they could gather in a last ditch effort to, well, save my life.

I will be forever grateful to Dr Pacheco for being on-call on a US Open weekend when I was dying.

I forget my point… oh right…

About nine months ago, I won a ticket to a carnival.

Like all big days at the fair, mine was filled with excitement, anticipation, a sense of adventure, and more than a twinge of anxiety as I stood staring at the rides towering and tumbling above the fairgrounds, wondering if stopping at Chili’s on the way was a good idea.

As the barker shouted us into the fun house one by one, we pushed through the heavy black cloth of the entrance into a blinding light, dancing and darting off dozens of mirrors angled this way and that, obscuring the path forward but reflecting laughing and ambitious faces, each determined to navigate their way through.

I have never been a fan of – or even understood – the draw of fear as entertainment. I suppose intellectually I can. I endured a film class in college that drew parallels between the horror and comedy genres, even achieving an A for a paper I wrote on the subtext of Francis Ford Coppola’s Dracula (Sex, it was sex). Interesting in theory, but practically? The screenings were at 8am on a Wednesday. Who could think of a better time to watch The Shining, Rosemary’s Baby, or eveyone’s favorite, Un Chien Andalou?

As I pushed deeper into this maze, it wasn’t long before that familiar, unplaceable pain began to bite again in my belly. I first wrote it off to my dislike of this style of excitement. I could hear people yelling, laughing, doubling back and yelling again. They sounded like they were having fun, why should I not feel the same?

But as the gaslights dimmed and the mirrors warped and bent, fewer voices could be heard - less laughter and from farther away - distant cries, some of confusion, others marked by fear. My own reflections began to take on a different shape.

I could see myself from every angle, all at once, reflected in reflections. Shorter, fatter, longer, thinner, none the image of myself, but the longer I groped and stumbled the less sure of which I truly was.

Fear began to rise as the light continued to darken and the other voices had almost all been silenced.

Like the body protecting itself from over-exposure to extreme cold by shutting down its outer extremities, my ability to focus on anything but core survival in such a confused and disorienting place became impossible. Thoughts of self-care, progress, and even breathing were pushed out as anxiety, doubt, and instability screamed in my ears and my stomach opened wide to swallow my life whole, once again.

I tried to push out a laugh as the pressure built in my lungs and the pins and needles radiated like wings across my back, but the deafening and incessant noise from the calliope made any other sound impossible to distinguish.

I was falling into darkness when my shoulder slammed into a wall and the alarm of an emergency exit blared wildly as I tumbled out into the bright brilliance of a true blue sky.

Gasping and wrenching on the hard pavement, I slowly began to breathe again as my eyes struggled to acclimate to the light of a warm morning sun.

I felt a hand reach under my arm and pull me up onto my unsteady feet. I turned to see assuring faces of those who had entered with me through the black curtain and into the unbearable noise and withering confusion of the hall of mirrors.

A smile.

I could hear the barker still yelling assurances of excitement and promises of fun at any poor soul who would listen, only this time it sounded distant and desperate.

I looked at my watch to check the time. It was 11:11.

What do you wish for when you’ve just been given the one thing you needed most - freedom?

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Sarah Zaske, née Seaver, was quite literally the first friend I can ever remember having.

My time spent in Montessori school was before and concurrent, but I have no memory of specific people until later. Ashley Dean was one of my best neighborhood friends, but the earliest I can remember any time with him – and this is true – is being in Branson, Missouri during the Carter/Regan campaign and watching their debate on TV… sadly, the best vacation one can have in Branson…

Regardless, that would have put it in 1980, long after my memories with Sarah began.

What needs to be understood about baseball friendships are the cyclical nature of their existence. I couldn’t say when it was that we first met – my guess is 4 – but Sarah and I would come together for several weeks during the annual Bouillabaisseball that was major league spring training in Clearwater/St Pete in the 70s… yeah, those 70s…

I remember riding in an elevator more than once with Ric Flair who, I think, was one of the owners of the Sandcastle Hotel where we stayed…

I remember going with my Dad to the shared training facility of Mets and Cardinals once and meeting Bill Murray and Garrett Morris shooting something about Chico Escuela for SNL.

And I remember the Seavers’ beachfront condo, right down to the glassed-in atrium in the center, with plants and a palm growing meekly and sweatily into the Florida sky.

Thing is, that short annual time for me, was everything…

You see, all of my childhood birthdays fell in this weird space of life where I was entirely without my other 49-week cohort and completely reliant on that year’s roster of Cardinals, Mets and Cincinnati Reds – and most importantly - the children they dragged along with them…

Attention all officers, please be advised, the Boone boys are in town...

It’s weird having a birthday party where half of the people in attendance you’ve known for about ten days.

But for a few short years, before the tides of career (not ours) carried us apart, Sarah was an inseparable part of my spring-training psyche.

There were days on end spent at the local putt-putt during a time when ice-cold YooHoo was blessedly given equal space along side other, lesser, tooth-rotting Nectars of the Vending Machine Gods… I see you TAB…

There was the sand-sunk Hobie cat just outside their house where we spent hours trampolining on the fabric of the boat’s, well, trampoline, until we were too sunburned to continue, only to spend the remaining hours before bed peeling each other’s shoulders of skin in preparation for tomorrow’s next sunny adventure… yeah, those 70s.

We spent rainy days watching the best reruns vintage-TV had to offer… F Troop, anyone?… our favorite of which was Rin Tin Tin, the heroic German Shepherd whose bravery might only be matched today by its likely off-the-charts rating on the #canceled meter… F-Troop, anyone?…

Undeterred, we would talk, and play, and imagine the greatness of a dog’s life. A thing I have spent countless days since, returning to time and again in all kinds of wish-I-was-elsewhere moments in my life.

Thing is, today was a different kind of wish-I-was-elsewhere moment. Today, I truly and deeply wish I was there, on the beach, playing and laughing and holding hands as only children can.

Wishing I was there if only to know she was there.

You see, the cycle of life overtook the cycle of baseball last week and the very first friend I can remember having succumbed to an eight year battle with lung cancer.

I have been blessed to have very few days like this in my life. Days that appear like any other except there is one fewer loved one to share in it. And when they come they land like a hammer. And when they come the recovery is slow. And when they come the recovery is faltering.

Sarah’s hits particularly deeply, for the loss of her is the loss of so much more.

The sadness I feel over losing my friend swirls and mixes with the memories of a time where it seemed that sun, and beach, and life stretched out into the horizon of forever.

The forever of childhood, blissfully unaware.

In the end, though, the universe, in all its seeming uncaring, may just understand.

Sarah passed a few days before her 54th birthday and only a couple of weeks before mine.

Spring training is in full swing…

I love you, Sarah. Rest in peace.

Generation Ex explores every ‘ex’ in our lives - our expertise, our expectations and our experiences - and how they can be a catalyst for personal growth when your professional (or personal) journey suddenly shifts under your feet.

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I haven’t spoken much about the situational shift that took place a few months back when, through a chance stroke of lightning, I found myself infected with an long-avoided case of the full-times, once again.

I haven’t spoken about it on these pages at all, in fact, as the brain power required to settle into my new role has siphoned off much of my ability to think creatively outside of work hours. As the days turned to weeks and then to months, more than a few people wondered aloud whether or not I had given up the writing in the face of a true 9-5.

No doubt, from the outside, the whisperings of silence through these pages, could very easily make it appear that way. I’m pretty sure I was wondering the same, as I too heard whispers.

Many of the old ones. Close-up, weather-worn, and familiar.

I see you, Imposter.

But new ones as well. Ones that have begun to speak more loudly as this creative journey gains momentum and proof of an affinity for it has echoed in the feedback, and well-wishes, and encouragement of family, friends, and even strangers. A countervailing force to the self-doubt of the Imposter but no less debilitating in their quiet words…

‘There is nothing more to say.

You lit the sparkler and it dazzled for a time but now the last of the flash has been spent and you are left with nothing but the dying glow of a bent wire in your hand.’

… Words paralyzing enough that I turned my eyes to the grindstone of a new job and spun the wheel so as to at least watch sparks fly, sharpening a blade that wasn’t mine but hoping it might dazzle just the same.

It would be enough…

It is not.

Standing in the fresh darkness of the last burned sparkler, waiting for eyes to acclimate to the dark, there is nothing to see but the fading, purple echo of the vanished brightness filling your eyes . A fleeting visual memory of the radiance that had so brilliantly, but so briefly filled the world with light.

In its absence comes Black.

Shadow.

Unknown.

A dark in the ebbing of the light that seems utterly impenetrable, as the afterimage fades and you are left with nothing but empty, black space and the acrid smell of gunpowder.

So much possibility for new light but the crushing fear of it never coming again.

… and then you see the stars…

Isn’t it strange how the universe comes most into view on the darkest of nights?

My own stars have begun to flicker into view of late and I can’t explain how strange and wonderful it has been, even in their vast distances apart, to see them align in such a way that shows the path once again…

…We had decided on a road trip.

My son is entering his final year of high school. An unimaginable passage of time since our first great road trip, traversing the US over three months on our way from New York to Australia, but pass it has.

We had briefly entertained a Fijian beach flop but our proximity to more than a handful of the world’s most beautiful beaches outside our front door - not to mention the symmetry of a potentially final, grand vehicular escapade - meant the only real choice was touring as much as we could of New Zealand’s South Island in just two weeks… I had forgotten how much having a job sucks.

I am only one in a countless line of South Island visitors to have returned home and said these words, “it was epic”.

It truly was, even having seen only a fraction of what the island had to offer.

We kayaked Milford Sound, hiked and boated the glacial lakes of Aoraki-Mt Cook, and we slipped, and slogged, and slid through the canyon waters outside of Queenstown.

But the reasons I could spend the rest of my days camper-vanning the world are in the quiet of the downtime. The non-active activity around the van in the slow dying light of a late-setting, South Island, summer sun.

Cards, and cooking, and campsite combine to boil life down to its core essentials and a family suddenly has everything it needs and all you could ever wish for…

It is in these moments when I can swamp. It was in this moment that I did.

This has happened for as long as I can remember.

It’s hard to articulate what it is or where it comes from but as I told a friend - the first of the stars that flickered on for me in the recent darkness - its as though somewhere in the purist of life’s moments, I am completely subsumed with, well, everything.

It is as if I suddenly see all of the dots.

In a flash, all the choices, and all the turns, and all the failures, and all the successes, and every breath of moments that have led to this singular, perfect point in time burst into light.

But that isn’t all.

In the very same, overwhelming instant I see the multitude of pathways leading out from this moment. Each step forward along the path, far into the horizon, leading to a time when I am no longer here. No longer allowed participate, to share, to experience all there is to see, to smell, to feel, to love.

Then, as quickly and brilliantly as this great wave of existential energy arrives, it crashes down and is gone.

Dark.

The recovery is slow. Like a wizard over-extended well beyond their abilities, my emotional stores are spent and the purple echo of the light fades to black…

Isn’t it strange how the universe comes most into view on the darkest of nights?

I already mentioned the first star that came to light for me. She is a familiar visitor that I recognize and cherish when her orbit crosses my path at regular intervals. The second, though was like a meteor streaking across my sky bringing with it inspiration and wonder.

As the emotion and excitement of the trip was fading into memory and the mundane rhythm of daily life (and work) returned to the forefront, the spinning of the grindstone was weighing heavily on my brain. A guilt, not for you, as a reader, or me, as a writer, but for the light that can fill the dark for us both, if even for just a moment.

It was in this mental space that my phone dinged and an old friend, one whose path I cross much less frequently than I’d like, texted,

Sometimes there is nothing to do but stare at the sky in total and utter awe.

And so I sit again and write.

I write to feel.

I write to acknowledge.

But mostly, I write to draw lines between myself and that star, and that meteor, and this life.

It is in this moment that the last of the stars twinkle into being.

David Whyte has a new book out and, as one does, is doing the rounds. The thing about David Whyte ‘doing the rounds’ is that you don’t just get his lush baritone or his endless ability to recall stories from a life well-lived but with Mr Whyte come his words.

Like a constellation you’ve been able to recognize since childhood, if you’re looking, it is always there…

He reads his poem, “Time” as I close my eyes and listen to him in the darkness.

The light explodes in my mind and the sparks tumble down like rain.

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I started writing this post more than a bit ago but the unpredictability of life - and death - as it often does, upended my best intentions.

As time once again turns by degrees and a fresh start brings a modicum of stability to my life - and with it great change - I’ve caught myself looking back and reflecting on just how winding the road to here from there has been.

Attending to those shifting sands brought my thoughts back to a time when, having escaped sanity’s gravitational hold following the implosion of a business I co-founded, I awoke in a car driving up the coast with a mate for four days of practical certification to be a deckhand. The shitty first rung on the maritime ladder just above rowing slave and just below, well, everything else.

I had agreed to join this friend immediately following the thousandth machination of failed phone, or Zoom, or face-to-face interview with a prospective employer. It was usually someone half my age, with either a limited (read, ‘no’) understanding of the actual requirements of the role, or only giving lip service to a wide search but clearly already having someone in mind for the job…

“Why do you keep calling me Rich?”

“What? Oh, no reason.”

The prospective choice of enduring even one more of these spirit-shredding, Kabuki dances or voluntarily punching myself a ticket to sail out onto the ocean and confront a myriad of gruesome and terrifying ways to die was simple.

Like many things on the water, this was a straightforward task made impossible by actually being on the ocean. We would attend four days of knot-tying, fire-fighting, boat-driving, shanty-singing and curse-learning in a style so efficient it would make your poop deck stink, ya C***s.

To say those four short days were not electric with insanity would be to forget that during those very fire-fighting efforts, where a cargo container is set ablaze and you and a partner work, shoulder-to-shoulder, spraying and shuffling with a big-boy fire hose to put out the flames, one of our company of seamen became so overcome with anxiety he went into seizure, timbering face-first onto the concrete, three teeth smashing then skittering out across the pavement, as staff from the Newcastle Mines Rescue Station, rushed to secure his safety.

Some are lost at sea, some are lost on the sun-baked asphalt of a random mining training facility.

None are forgotten.

Fucking electric, I tell you.

As sobering and wtf-ing as that tribulation was, they say the bonds of a ship’s crew are forged in the fires of experience and sitting in reflective quiet a short time later, even the staff at Subway could feel our small group was somehow changed.

We would, in fact, need every ounce of that esprit de corps as we loaded back into our short bus and pulled out of the parking lot toward what would surely be our greatest test of mettle.

Have you ever seen Cool Hand Luke?

No?

Well, as we stumbled out onto the partially-paved parking lot of the local municipal pool, weeds and broken glass collecting in the fractured cracks of concrete, and our instructor threw down five battered and blue milk crates filled with varying sizes of denim jeans and shirts, he might as well have been throwing down a pile of shovels, rakes, and hoes and pointed to a long, hot summer stretch of Florida country road needing pitch tar and gravel.

All we could see ahead was hard work and humiliation.

You would have sworn we were chained together at the ankle as we shuffled awkwardly up to the entrance of the pool in our mismatched, oversized work clothes and the confused and terrified attendant stammered out, ‘uh, um, no. Over there. I will buzz you through the exit gate.’

Sadly for our wretched souls, our presence here would not be marked by any turnstile but would be noted for generations to come only in legend, told to kin by those attending water aerobics, swimming laps or splashing with children in the baby pool…

Now, surviving an emergency at sea, at its core, is a sequential battle against a relentless and ever-growing set of steep challenges. Standing at pool’s edge, I knew one of the first big obstacles to surviving a catastrophic failure was navigating the withering disorientation of shock and surprise that comes with an abandon ship order.

Staring down the line of our newly-formed, soon-to-be-doomed, pretend crew, buckled into our open-ocean life-jackets - the heavy duty ones that come up under your crotch and make you look like you’ve pulled the bomb squad short straw and are preparing to, as they say, ‘Defuse or Die’… shut up, that is what they say… my untethered disorientation was as great as if a u-boat torpedo had just punched a hole in the side of my escort frigate and the engine room was filling with salty death.

As I watched my shipmates leap one-by-one into the pool, I wondered how in the hell I once again found myself unemployed, unmoored, and yet undaunted, sure that after nearly a decade of blind leaps of faith this next one would be The One…

ABANDON SHIP!

I plunged feet first into the pool.

Over-chlorinated water filled my eyes and lungs as I sputtered back to the top, coughing, popping, and bobbing to the surface as if on a fishing line. Trying to take this water safety business seriously - as it may actually save my life one day - my first order of business in a would-be, real-world situation (likewise, in this fake-world situation if I wanted to be certified) would be to swim toward safety.

Fifty meters, spaced roughly five meters apart, our crew was now entirely in the water, madly paddling to reach the safety of the, uh, other end of the pool… This isn’t so bad…

Did I just hear someone laughing?… nah, probably not…

Now, had you asked me to architect the construction of a day of utter and ultimate humiliation it is hard to imagine I could have drafted anything better… worse?

Rather than making us smell the glove all at once, the incremental stacking of one humiliation upon the next was the muni-pool equivalent of Theon’s slow transformation into Reek from the Game of Thrones books. By the end we would be unrecognizable to anyone who had known us before…

But I am getting ahead of myself.

The 50 meter freestyle was only an opening salvo to warm our bodies to the water while preparing our minds for what was to come. It was followed by another 50 meter swim, this time on your back, fluttering your arms like oars from one end of the pool to the other… again, not so bad, right?

Wrong.

Instead of turning around at the end of the first length of 50 meters and returning via the water, we were made to exit the pool, walk the length of the deck, denim dripping madly, as if we were doing fucking wind sprints and a swim back was all too much… for some it probably was but, um, this is open water survival training, right?

I definitely heard someone laughing…

A couple more lengths in the water and walks of the plank, uh, pool deck, and the weight of the clothes began to bite and the cool air of mid-morning delivered a bit of a chill to the bone. It was now time for things to kick up a notch.

Jumping into the pool once more, we were given a brief lecture about the dangers of hypothermia as we flapped and kicked to tread water in a line. Our instructor then directed us to gather together in a circle - Tight circle… TIGHTER! - arm-in-arm, kicking our feet to stay in place as he yelled, ‘DO YOU FEEL IT? CAN YOU FEEL THE WARMTH? KICK, BOYS! KICK!!!’…

Are there more people arriving? It’s a fucking Thursday morning.

One of things we learned in the course readings was that when you’re in the water there is safety in numbers. I figured, makes sense, this aquatic circle-hug is indeed a good way to stay warm and remain in place while the kicking makes it easy for the sharks to identify where distressed prey is located.

Sometimes, though, it might be critical that your group will have to travel, as one, through rough seas to reach the safety of a life raft, some post-wreck flotsam, or that island on Lost.

This was decidedly NOT in the early readings. I can now understand why.

As our instructor barked orders from the deck like some land-lubbing Captain Bly and the stands along the poolside began to fill with people, some in swimmers, some in suits, uh, some in Subway uniforms?… WTF?… our desperate and quickly tiring band of former strangers were instructed to return to a line, front to back and… wait, what did he say?

I struggled to hear over the splashing, coughing and bobbing. We stared quizzically at each other…

YOU HEARD ME! LOCK YOUR LEGS AROUND THE HIPS OF THE MAN IN FRONT OF YOU AND ROW, YOU FLACCID SONS OF SEA SCUM!

Children began to cry.

I dutifully wrapped my legs around the hips of the man in front and could feel a set of long, heavy, denim legs lock around mine… ah, sweet, sweet warmth… our discipline was beginning to take hold.

Like an aquatic, larval version of the human centipede, we began to flap our wings, first in panic but then, slowly, into a sharp cadence in time with the crowd who had begun shouting, ‘STROKE! STROKE! STROKE’!

Our proud focus and effort was only broken by a dark shadow across the face of the now mid-day sun. A large square package hit the surface of the water and exploded into sound, splash and plastic. A huge, self-inflating, deep-water survival raft burst to life under the bright constellation of unbelieving eyes along the pool deck.

We knew what was to be done long before Captain bellowed, ‘SAVE YOURSELVES, YOU SALT-SQUIRTING, BARNACLE-ASSED, SEA SHITES!’

We arced our paddling gracefully to starboard and raced to reach the heaving sides of the raft. The challenge was clear. We had to get our crew up out of the water and into the protected safety of the raft.

Had we thought strategically, we would have known to take a moment and think things through but as the noise from the crowd, exhaustion from the rowing, and chattering signs of hypothermia combined to sharpen this simulation a little too pointedly, the first and lightest of our bunch scrambled up the tiny nylon rope ladder like a rat and dove through the opening of the tented roof.

… he will be the first one we eat…

It’s a weird quirk of the universe, like the Fibonacci sequence, that if you shake a carved wooden cup of ivory ‘bones’ and roll them out onto a table, wishing for a ship’s crew, you will get a perfectly distributed ‘dirty dozen’ every single time.

Ours was no different.

We had the slight, shifty, bilge rat that you wouldn’t sleep next to with both eyes shut (the one in the raft).

We had ‘Cookie’. No we didn’t have nicknames yet but his former job was, weirdly, at Subway.

We had the wide-eyed, baby-faced cabin boy whose father and grandfather before had raised him on stories of glorious adventure on the sea.

And we had Ben.

Ben was like Chief.

Remember Chief from One Flew Over the Cuckoo’s Nest?

You never knew if he was too dumb or too smart to open his mouth but there was no mistaking his hulking size and undoubted strength could throw even the heaviest of sinks thought a grated window and escape… um, that doesn’t happen…

Maybe it was the panic unleashed by the rat scrambling into the raft on his own or just the combination of all we had endured but, as we splashed, and scrambled, and slid ourselves one-by-one, up, over and into our fake life-saving shelter, we should have known to account for Ben earlier in our escape from the shallow deep.

From the surface of the water, the impression of height required to summit the ridge and safely enter the raft seems towering. The series of loops, nylon ropes and handholds required to traverse the face of this mountain called for an exhausting amount of cooperation from both those in the water and the lucky ones inside.

No one had noticed in all this heaving and hoeing just how red ol’ Big Ben’s (nickname? Hmmm… maybe) face had become as the penultimate soul was dragged, head-first into the now soaked inside of the shelter.

Only Ben remained, alone on the surface, his heavy breath chuffing and puffing in time with the sloshing of the water as a cold, momentary silence filled the inside of the tent.

Then the squeaking started.

Like hands massaging a loud wet ballon, we could hear Ben begin his arduous ascent up over the edge. Cookie shouted, ‘HE’S COMING!,’ as two of us wrapped feet into the strapping inside the raft to brace ourselves and lean out of the small window to help.

A huge paw hit the top edge of the raft while a second flapped wildly, looking for a hold. We grabbed the second arm to steady him as a mottled mass of wet, red hair (Big Red? The Walrus!?) crowned just above the opening, face steeled in effort, the rest of us grabbing for any sleeve, belt loop, tuft of red hair we could mange as he grunted, and groaned and grimaced.

His chest was just at the edge when he started to fail.

A shoe inside slipped and a clasped hand slid as Ben began to fall backward, his disbelieving eyes locked with all of us seemingly at once in one final, loud rubber squeak of loss, an explosion of water, and the most disheartening cry of despair, quickly cut short by the pocket of water closing over his submerged head.

We were paralyzed. Every drop of effort had been spent both in and out of the water and none of it was enough to get him into the watercraft.

What do we do?

We had plenty of food in the survival kit. We could feed him outside the raft and hope for rescue before the sharks got him. We could burn valuable calories in another futile attempt to summit this mountain. Or we could hope he unselfishly pushes himself out into the dark while we slept, saving us the pain of listening to his cries when the deep comes to take his soul…

The only sound was the muffled sobbing of the Cabin Boy.

A sloshing of water and a slap of looped nylon broke the quiet as a boot slid back into place and Cookie braced himself against the side and leaned out of the tiny window, ‘NOT TODAY, POSEIDON! NOT TODAY, YOU SLIMY BASTARD!’

The roar of the crowd poolside gave Ben the shot he needed as he lifted his huge arms toward the heavens and his shipmates reached out for his salvation…

It wasn’t easy, but as the great, red whale passed through the opening of the liferaft’s little window and he slid, face-down across the wet, rubber floor, the rest of us fell back, exhausted from the birth we had just delivered.

We would soon be scattered to the winds of fate, each of us tossed hither and yon across the seven seas, stationed on ships few could fathom but countless had crewed before.

I thought again about how it was that I found myself here, in this tiny life raft, with this tiny crew in the middle of a fucking pool and marveled at how, with every leap of faith - if you’re very, very lucky - you can find yourself saved by people you’ve never met.

I marveled and wondered.

Would this time be The One?

Generation Ex explores every ‘ex’ in our lives - our expertise, our expectations and our experiences - and how they can be a catalyst for personal growth when your professional (or personal) journey suddenly shifts under your feet.

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My friend died last week.

It’s taken me some time to sit down and put some thoughts to paper if for no other reason than it’s taken me some time to collect my thoughts at all.

I say ‘friend’ in as much as one might about someone they’d met in person exactly once. I suppose it’s a measure of the age that I was introduced via email, connected, developed and maintained a deepening friendship remotely, and finally, attended his memorial service over livestream. A heartbreaking close to a friendship that was far too short and far too consequential for me to even begin to fathom its end.

I was introduced to this friend in a moment of professional untethering not long after the business I co-founded imploded into dust and the prospect of re-starting a job search from scratch in my 40s - again - was beginning to take hold.

A combination of disorienting shock, withering doubt and a deep feeling of betrayal filled most of my days - and more of my nights, trapped in the terror-filled paralysis of time between one and four AM. It was in this state that a mutual friend sent through an introductory email and in a throwaway reference to Levon Helm and The Band in my ‘nice to meet you email’ response, locked in our connection and unlocked a friendship that would do more for my health than I could have ever hoped.

In those dark, early days following the loss of my business, I spent a great deal of time wandering the hallways of recommended books and podcasts, desperately looking for ways to rebuild some semblance of foundational belief in myself and, more importantly, a framework back toward a trust in others.

One of those building blocks came in the idea of high value and low value people. The notion that at one end of the spectrum, the low end, people and relationships are measured transactionally, ‘If I do this for you, what do I get in return?”

While I don’t begrudge anyone this perspective I do not swim in these waters.

At the other end are high value people. People whose worldview is colored by connection and curiosity and possibility over pure profit. People who believe in the adage, ‘it’s who you know,’ but not because that’s the best way to get ahead. Rather, they believe the fabric of connections, professional or otherwise, speak volumes about the person you are not the position you hold.

As I desperately searched for ways to repair the shattered vision of myself it was this simple, articulated idea that formed the first rung of the ladder back. As much as possible I would commit to finding, cultivating and being as high-value a friend, colleague or stranger as I possibly could whether it advanced my career or not. It was in this context that I met my friend.

At the time, I had no idea the depth with which this friendship would truly shape how I viewed myself, the people I would meet and the follow-on friendships that would be forged through this single introduction. He was a master class on high-value being and a critical inspiration in some of my darkest days here in Australia.

I continue to marvel at the generosity, insight, and kindness given and the patience and time taken in the service of someone who, at the outset, was a perfect stranger.

Over the course of the five years or so we knew each other I have been connected to dozens of people who, like me, have been woven into a broader blanket of connection under my friend’s guiding hand. Now, with him gone, it is this blanket that will prove instrumental in keeping warm as I wrap it around my shoulders to protect against the cold reality of his death.

It was wonderful but strange to sit in on a memorial for a friend about whom I knew so little. Seeing pictures and hearing stories of a life from which I am almost entirely absent filled me with joy, confirming what I believed so deeply about my friend. Of course, it also filled me with such profound sadness to have missed so much.

For me, I only have one picture.

It came via a text the week before his death and now means everything to me and his memory,

We didn’t work together, we didn’t grow up together and only once did we find ourselves sharing a pint in the same room.

But in the measure of my friendship, all that matters is that it was.

Be at peace, Stu.

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Admit it. You thought I was dead.

You figured, ‘Yup. Those boat folks shanghai’ed him in Sydney Harbour, chummed him up into little pieces and shoveled him out of a bucket into the big blue somewhere in the Gulf of Mexico on the way to Miami’s annual International Boat show.

Shanghai’ed isn’t canceled, right?… sounds like it probably should be… substitute appropriately…

Well, you’ll be pleased to know that during delays at the Panama Canal, I escaped by shangha’ing my own lifeboat… dammit, Jon… and Life-of-Pie’ing myself back to the safe, Pacific shores of home, following nothing but the stars, the currents and the overhead contrails of government spy planes painted to look like trans-Pacific Qantas flights.

But this incredible misadventure of mine that will surely be made into a movie one day is only a small part of the long delay in work being produced by me (haha, just kidding, by chatGPT).

This is the last time I will apologize for my creative absence but I will apologize one last time. There are a myriad of excuses I can - and am about to - share for this long pause since my last post including in no particular order:

• An incredibly refreshing and all-too-quick visit from family (yes, Mom, it has been that long)

• A shift in focus to other irons in the fire

• A growing, uh, ‘ow do you say, ennui?, as I watch the fabric of society come apart at the seams

• And most recently, enrollment in a graduate program for Sustainability Leadership… WTF? But you were terrible at Uni the first time, thirty years ago… Yeah, I had a similar reaction but here we are.

The rhythmic cadence of creative activity is something, if not exactly, akin to efforts at fitness, dieting, sobriety or quitting smoking. One slip of the pedals can mean a sudden, careening skid along the street into a ditch.

While I have been slowly picking myself up and dusting myself off after this latest tumble, I thought I would forego the shame-filled, self-immolating, guilt-ridden introspective post you are clamoring for and instead recount the earliest days of this GenerationEx story, one that, for a time, I could not tell enough.

Pretty much right up until I told it to a guy on the sands of Manly beach.

A little background.

When we arrived on the shores of Sydney we were very much as lungfish, floundering about in the mud of not-quite-water, not-quite-land. Neither tourist nor native. We spent our first three months in AirB&Bs as we desperately tried to source work for me, a home for us and schools for our bewildered four and six year old, newly-minted expats.

Setting aside the hellscape of that story - the highlight of which was a decidedly un-majestic, full-family meltdown in the shadow of the entirely majestic Harbour Bridge - we worked hard to find places where we could feel more like Australians and less like foreign agents.

The first of those turned out to be Manly beach.

To set the stage, on Sunday mornings from spring through the end of summer, hundreds of children from the age of six to thirteen are dumped by their parents onto beaches across Australia to participate in the sand-throwing, tantrum-spewing, blue-bottle stinging, quintessential childcare pastime of Australian lifeguards-in-training. It is also known as ‘Nippers’.

Think Boy Scouts combined with Girl Scouts and American Gladiator, fitted in caps and speedos, surrounded by the constant threat of death and you’ll be halfway to understanding the insanity that is Nipper life.

From afar - by that I mean the cafés where the vast majority of parents of Nipper children immediately go after leaving their child to the mercy of the sea - the legacy and tradition of Nippers fills Australians with a deep sense of pride. For the adults left behind, tasked with the safety of multitudes of shrieking children, it is a harrowing, enraging, Lord-of-the-SeaFlies responsibility that tests your faith in humanity week in and week out for months.

These brave souls are referred to as ‘Age Managers’, the arbiters of tidal life and death from seawall to swell and with whom I now grabbed a whistle and stepped up, shoulder-to-shoulder to brave the waves… of screaming children.

My first taste of Australian native life.

As in the military, where death is but an eye-blinking shark attack away (that’s the military, right?), the men and women who brave the dark waters alongside each other form a bond of love and respect that can last a lifetime. It was with this esprit de corps that I got to chatting with a fellow age manger one fine Sunday morning about my journey traveled from New York to Sydney.

As I noted above, it is a story I’ve told many times although I believe I’ve only told the lead-up to our departure - you know, ‘getting shit-canned’ - in these pages.

The sheer adventure of our decision coupled with the idea that it was so antithetical to what you are ‘supposed’ to do as a ‘responsible adult’ that I wore it as a badge of honor, subjecting anyone who slowed even for a moment nearby to its shiny polish. It was now this fellow age manger’s turn to squint into its warm, metallic reflection.

Against the backdrop of flying sand and crashing waves, I started at the beginning.

“… yeah, sold the house. We gave away almost everything we had. Even the kids’ bunk bed, mattresses and all, to a friend the day before we realized both kids had lice, packed the kids into two tiny car seats in the back of a Prius and hit the road for three months of directionless adventure from New York to California… First stop, Woodstock festival grounds 70 miles from our home in actual Woodstock… Did you know the music festival wasn’t actually in Woodstock? Yes? Well did you know it’s closed one day a week? We didn’t…”

“… south through Gettysburg, DC, and Richmond. Turning West through the Shenandoah Valley and the Simmons Gap (weird right?), through Tennessee and a lakeside AirB&B on our way to St Louis where I grew up… uh, it’s on the Mississippi… no, in the Midwest… South of Chicago?… No? Well, humidity and tornadoes…”

“… from there doubling back to the aforementioned ‘Windy City’ to begin our long trek westward, the length of Route 66 all the way to the Grand Canyon with stops at Mesa Verde, Chaco Canyon, Albuquerque (should have taken a left, hahahahaha… no? Nothing?) and an empty Golf Resort near Santa Fe where each of us had a pool to ourselves…”

“… once again north through Bryce, Zion, altitude sickness, Craters of the Moon, siblings and cousins in Salt Lake, Grand Titon, and a culminating four days at our favorite stop on the entire trip, Yellowstone where we shared a campsite with buffalo, saw black and grizzly bears and spotted a moose and her calf as we drove out of a valley that was as pristine as it was when Jeremiah Johnson first pretended to walk these lands…”

“… finally the homestretch, across to the Oregon coast with family before heading south to LA, unpacking the Prius curb-side at LAX, ditching the car in ‘long term’ parking and flying over the Pacific and into our future…”

“It was truly the most amazing experience I’ve ever had…”

I had barely taken a breath since I started but, as always, I stuck the landing like a pro.

My fellow age-managing, Guardian of the Tide had listened patiently, quietly, undoubtedly impressed with each new turn on my trans-continental journey. The bravery required to undertake such a reckless adventure while the rest of the world spun their hamster wheels in frantic desperation was certainly not lost on my new friend.

He smiled.

“My wife and I bought a boat and sailed here from England,” he said as he turned, blew his whistle, pointing at two small children holding a third’s head face down in the sand and walked away.

I took a breath. I vowed never to speak to that asshole again.

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It’s taken me a long time to realize that I am quite good at a lot of different things. Sadly, it’s taken me longer to realize that this is a terrible thing.

The slow uptake on both fronts has caused considerable professional angst for myself and probably more so for the people watching this journey right up close.

Let me see if I can explain.

My parents grew up in the shadow of the automobile industry, Detroit, Michigan. Motor City USA. The figurative engine that drove the US economy to greatness in the early to middle part of the 20th century.

Many extended family and friends lived on the promise that two decades of service earned you a pension, a house upstate and a dignified twilight existence as a sturdy brick in the foundation that was middle class American life.

That is certainly an over-simplification of things but I’m also not sure it matters.

Because it’s gone.

We have all read internet articles (well, let’s be honest, read headlines) that ‘kids today’ will have no fewer than 1000 different jobs from the time they leave school until they are comfortably settled on Mars, eating protein blocks made from crickets, living off their millions of dollars made in the ‘Gig Economy’.

…that reminds me - fuck you, ‘Gig Economy’…

The reality, though, was that for many, this was the case long before there actually were internet articles and for some, like me, it was entirely the point.

Is it possible to be visionary and stupid in one fell swoop? You bet your ass it is.

When I was very young - and time was available - my family would take to the road on extended camping/roadtrips out West. Places like Mesa Verde, Chaco Canyon, Zion, Tetons… uh, the rest…

They all became a part of the fabric of memory barely recalled but with an understanding of the legendary place they hold when writing the story of a life in your mind.

… or on Substack for friends and strangers alike to read...

At each of these parks, the information booths, gifts shops and sometimes even park rangers would have patches you could get that marked your passage through some of the most awe-inspiring lands the US has to offer.

My mother would carefully sew each new destination onto my tiny little Levi’s jacket and along with an awesome fake license plate with my name on it (always with an ‘H’ in ‘Jon’, though, you sonsabitches) it became a record of the places I’d been, the experiences I shared and the road I had traveled.

Yup, a tiny little, 1976, bad-ass, denim CV that you wear to school to show off to your friends.

It was rock-and-roll when rock-and-roll was still ‘Rock-and-Roll’.

But for me, that exploration never really stopped. Unwittingly, my parents unleashed a Jack Kerouac-styled toddler - shorter legs, fewer drugs - whose core approach to almost everything was driven almost exclusively by the mantra, ‘what’s that?’ and then stumble off in pursuit of shiny new experiences, people or knowledge.

Half an age later I found myself graduated from university on a Saturday (with nothing but a diploma), arrived home on a Sunday, got a phone call the following Thursday and had packed-up and moved to Washington, DC to start a temp job by the following Monday.

That temp job happened to be at the National Geographic Society where I would spend the next two years hopping from desk to desk for a day, a week or a few months, soaking up inspiration, ideas and random talents (Quark Publishing System circa 3.0, anyone?) and loving life.

I’m not sure what influenced whom, that experience cementing my tendencies or my curiosity landing in a perfect garden bed in which to grow but I have pretty much spent the intervening years tumbling unevenly like a giant Katamari ball, picking up knowledge, insight and experience on a great professional floodplain, notionally headed toward the sea but in no hurry to get there.

You know what terrifies people? People like that.

In the structured, cubicle-driven, hopscotch of career life, those who throw the pebble and zealously hop their way to a square, bend over, eat the pebble, take off their left shoe and throw it at their challenger (don’t pretend you know the rules either) are rewarded with board positions on companies that provide corporate guidance for places like Chalk’s Hopscotching Association of Manufacturing People Stuff, ‘CHAMPS’, for short.

Great achievements to be sure.

But what about those that played hopscotch for a bit, pocketed the pebble and a handful more, wandered into the nearby woods with stick in hand to find out how many skips he could get out of a pebble, hitting them baseball style across the surface of a pond?

… I don’t know this person…

…

… the answer is zero, zero skips…

And therein lies the rub. Watching a seven year old kid who was told to go play hopscotch plunk pebbles into a pond with a stick is hilarious. But as we develop as professionals trying to get your head around someone whose ever-evolving abilities read like a New York City diner’s menu is terrifying to most employers.

Understandably, when they pick up the phone people want to be sure the person they reach gives all the f’s about their one thing. Hopscotch. Coloring. Handwriting. Filing. Market Research. Product Development. Stakeholder Management. Transformational Change.

For many of the ‘cross-functional’ among us, the frowned-upon tension received in the constrained structure of assembly-line production writ large is palpable. I don’t doubt for a second there are magical workplaces where lemonade runs from the taps, ideas are celebrated regardless of source and we all nap under the shade of the Bodhi tree.

If you think your workplace is one of them ask yourself how many people you know complain about being bored, unchallenged, or underutilized.

I have spent over a year now working hard to bend the reality of my own professional path. I have chosen to lean into these tendencies instead of frantically changing my LinkedIn CV to better-fit a structure that leaves out so many divergent perspectives informed by curiosities beyond the game being played.

It hasn’t been easy but the beauty of succeeding means professional interactions transform into a cooperative effort to solve a specific problem rather than a biding of time doing admin at a desk until the next inevitable crisis - or worse yet, seeing the problem coming but having no authority to point it out or offer up a solution as is the case for many internal employees.

Don’t get me wrong it’s still a lot of work to reach into your tumbling ball of experience, pull out a CB radio, two hockey sticks and a box of raisins and convince someone whose focus groups keeps saying, ‘more loaves of white bread with racing stripes painted on them’ that there is a better way forward.

Sometimes you can’t.

But the tragedy for many is to have to then go paint racing stripes on loaves of bread knowing full well the answer lies elsewhere.

Me? I get to fill my pocket with raisins, grab a hockey stick and go see if I can’t shoot them over the house into the pool. Market research for someone I haven’t met yet.

If I learn anything I‘ll ping you on the CB…

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If you haven’t read my earlier post, ‘Set Sail’ go read it or #spoileralert. It’s best to start there for context/awesomeness.

I know the rest of you have been waiting with bated breath to hear if anything has transpired from the ‘interview’ and subsequent burial at sea of my foray into the Superyacht industry.

Well, if you had ‘they email you and ask you to send the presentation’ square in the pool, winner, winner, chicken dinner!

Yes, that’s right. Not too long ago I opened my inbox, saw a familiar address and immediately wished we all, dear readers, could open it together as one.

There was a lovely apologetic missive at the start, ‘for the delay’ (delay in what was unclear, we all knew I wasn’t getting hired) and then an immediate kick-turn to ask if it were possible to send through the presentation I gave in my interview.

My brain could not hold the multitudes of responses, each one like a little star, shining in the night sky just waiting to be discovered.

I’m not sure what I’m more impressed by, the fact they had the stones to ask for it at all or the fact that they had the stones to ask for it for free.

God bless entitlement.

I’m not sure how long I laughed but the neighbor came by to make sure everything was OK.

Please leave your best email response in the comments. I will consolidate and send through with the presentation.

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School failed me.

Now, before you call bullshit and throw your computer against the wall, let me be clear. I did plenty of failing of it, so, as far as that goes, let’s call it even.

In terms of preparing me for life ‘beyond the wall’, though, I might as well have been dropped into an episode of Game of Thrones wondering what my new found Dothraki friends were going to make for me with that molten pot of gold. Don’t know but I’m sure it will be shiny and expensive!

Naive, unprepared, and choc full of self-assured stupidity. The poster boy for not knowing what I didn’t know.

It’s taken decades to learn but the problem I have is that I’m not really a rubric kind of guy.

In all honesty, I had never heard that word until my son’s year five (that’s 5th grade, Americans) teacher said all anyone needed to excel in school is to follow ‘the rubric’.

I had to look it up.

Apparently, it’s a set of tick-box instructions for any academic endeavor (that’s endeavour, Australians) that if ticked accordingly, any paper, test, drawing, speech, finger painting, or interpretive dance would ensure you high marks.

I can literally hear you shaking your head saying, ‘no shit’…

Well, bully for you.

Even my American friends, where this isn’t actually an articulated idea in school (that I know of), knew instinctively that there were boxes to tick.

Great, but what to do with the rest of us?

What about the student who’s reaction to an assigned history essay on, say, the horrors of the Vietnam War and the impact of X on Z (I wasn’t listening) is to craft a homemade, coffee-soaked, edge burned parchment paper letter from an imagined soldier to his mother the day before he is forever lost to her somewhere along the Mekong River Delta.

• Demonstrate explicit understanding of the geopolitical fallout of the US and its ‘Domino Theory’ of communism … nope

• Grasp and articulate the underlying reasons for the fall of colonial French Indochina and the subsequent US decision to appoint Ngo Dinh Diem to lead the South… uh, répétez, s’il vous plaît?

• Should be exactly 1000 words… do ‘ums’ count?

• It almost makes you cry… TICK!

Tick, tick, FAIL.

Like the dazzle reflex to sneeze when exposed to bright light, I spent most of my academic career blasting creative particulates at any and all rubrics regardless of stated assignment or legitimately crafted assessment.

The world expects creative spin when you’re tasked with making chili, not when the assignment is to proof Geometry problems (that’s a thing, right?).

This is how I got to my senior year in college not ever realizing there were actually science requirements to graduate with a Liberal Arts degree…

‘Liberal’

(as in free-thinking, right? As in pinball as an independent study, right? As in, do you get credits for classes you perceive you’re taking while on mushrooms?)

‘Arts’

(as in, NO SCIENCE!)

W. T. Flying F.?!

So many boxes to tick.

Thank god for the university’s Jackson Hole summer geology program. All the rocks you can eat in eight weeks and 6 credits. Emmersive, hands on and fully practical.

The only science class I passed after 9th grade.

But I don’t want to make this post about me (hahahahahhaha).

No, school didn’t fail me because of school. School failed me because I stumbled out the door never realizing there were boxes at all.

A Forrest Gumpian kind of trajectory that, while having been able to wander through some amazing places professionally, lacked the focused progression of many of my tick-boxing colleagues.

But now, sitting on my bus stop bench, chocolates in hand, a question forms that has only come with the clarity of finally understanding my own journey from there to here.

What happens when you DO tick all the boxes?

What happens when you spend a childhood, a career, much of a life completing every assignment given and you slowly realize you are still desperately unhappy or worse yet, shown the door at a certain point because… well, because?

At least I learned my disappointment early.

As this writing grows and my commitment to putting it out there hardens, I get more and more feedback from people who read as well as those unfortunate souls who have to hear me blather on about it in real life over coffee or lunch.

So many people are wrestling with this feeling of unfulfilled intention, at best, or impending doom and outright betrayal, at worst. And I don’t mean those who ‘didn’t make it’ by any professional or academic measurement. In fact, the ones who did are seemingly hit the hardest when the hammer drops.

Brilliant friends who suddenly feel too old, too expensive or too pigeonholed to think there is any hope beyond the shadow of another corporate restructure. They’ve done everything that’s been asked of them and live in growing fear of their professional obsolescence, wondering what the hell they will do then.

As you now know, my hard-wired instinct to solve this problem is to learn to make an origami monkey and leave it on the dashboard of their car… Tick. Tick. Fail…

But maybe I can try my hand at something entirely new to me but familiar to, well, most everyone else.

Here is my rubric for high distinction (that’s an ‘A’, Americans) to follow as you move from who you thought you were into who you might become:

• Demonstrate a clear understanding of the idea ‘what you do’ is not ‘who you are’

• Develop and articulate a ‘pathway to purpose’, ensuring that what you do next is now driven by who you really are.

• Identify people in your life who understand your journey and are willing to fortify your efforts to build a more fulfilling path.

• Invest in curiosity

How will you know you’re doing it right?

It will almost make you cry.

Tick, tick… BOOM.

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A few of you have heard this story first-hand over the past month but I wanted to share here as it’s a valuable reminder of the reason I am working so hard to maintain control of my professional trajectory and the dangers of being tempted into giving it up.

Last month I wrote about the battle between keeping the faith in my choices and the doubt that can come from being locked up with your own uncomfortable silence that sprouts during the natural ebb and flow of annual business cycles.

I mention in ‘A Cost to Quiet’ a moment of weakness (ok, more than a few moments of weakness) where I applied for and then landed an interview. What I hadn’t mentioned was that it was an interview with a company that charters and sells Superyachts.

Yes, you read that right. Super. Yachts.

The kind of boats you see in Bond movies, crewed by dozens of soon-to-be-falling-overboard men all wearing jump suits and helmets with automatic weapons slung over their shoulders, helmed by a bald, wheel-chaired fat man with a cat in his lap…

…at least that’s what the job description said…

Now, I am never one to pass up a challenge, particularly one that has offices in Sydney, Europe and the US but I can’t say that I wasn’t skeptical.

Look, I love MDMA-fueled raves aboard 50m yachts floating off the coast of Cannes just as much as the next guy but giving up my commitment to purpose-guided, professional freedom that I’ve spent a year now working toward required a more serious laying out of the pros and cons of going back to work for someone else and their clients.

Here’s what that my calculations looked like:

Cons - Russians. Saudis. Cartel. Tech Bros.

Pros - Um… Coke?

Ok, a push. Let’s do this.

After a brief, enjoyable phone interview where I got a chance to recount among other qualifications my year spent acquiring deckhand certification and working on a boat in the harbor (those stories are coming, don’t worry), I was surprised to be invited to come in for a face-to-face interview in their shiny Sydney offices.

‘Yay,’ I thought.

‘We will send you the task we’d like you to complete and present when you come…’

‘Boo,’ I thought.

I am no stranger to a candidate having their mettle tested to see if a bit of pressure can transform someone chatting pleasantly on the phone into a sweating, stammering, IRL version of Gil Gunderson, the put-upon, failed salesman from the Simpons series.

Two things I pride myself on, however, are being able to put together a well-articulated and slickly designed slide deck and then presenting it to strangers. As such, I looked forward to sinking my teeth into it for the meeting a short three days hence.

What did the task call for, you ask?

Let’s take a paraphrased look.

Task 1 (um, I guess there will be more than one task)

Discover an insight about high-converting Superyacht purchasers (do they buy more than one?) and be prepared to provide an explanation and example of how you found it.

Ok, looks good, data-driven approach to inform strategy and development. I’d have the exact same starting point if I were doing this on my own. Sweet.

Task 2

Take this finding and develop it into a content series.

Ideas. Treatments. Pitching. Right up my alley…

Please include multiple pieces of content that fit the following channels:

- Podcast (include brief and scripts)

Hmmmm, OK…

- YouTube video (with storyboards)

Uhhhh…

- Instagram Reel (with design template recommended)

WTF?

eDM

Oh, haha. You’re kidding. Good one.

Press Release

Oh, you’re not kidding.

LinkedIn Post

Wait, I’m confused.

Website Article

Did you hire me and I forgot?

There are so many ‘swearing eddies’ I can get trapped and drown in having now typed this out for the first time, not the least of which being,

Close your eyes and describe to me in what world Goldfinger decides to buy a Superyacht and spends his evenings flicking through your Instagram feed?’

Not to mention, all the things in that task list above I get paid a decent wage to produce.

I’m very reticent, as I’m sure you would be, about walking into a room with a stack of even semi-fleshed out work, handing it over to someone you’ve never met with no assurance that afterward you won’t be led into the next ‘office’ where you suddenly find yourself standing in the parking lot out back listening to the sounds of muffled laughter through the door that just slammed behind you.

Wait! No! Don’t fuck this up. Remember… wanton hedonism.

Oh, yeah. Right.

So how to proceed?

Maybe, somewhere in the ‘Goldfinger Pardox’ above is the crux of a deeper question that needs answering before any strategy can be devised…

How do you reach someone who, for all intents and purposes, is unreachable through the regular channels?

That, I could sink my teeth into. I began to dig.

Starting with my dormant, pre-pandemic, band of expat, Thanksgiving merry-makers, I reached out to a friend who is in the business and was connected to a lovely man down at Superyacht marina (yes, there is one) who hosted me for coffee and an illuminating conversation about the business of boats and the people who put down millions of dollars to buy them.

It seems that the 1:1 relationships between the sales persons and the buyers or their agents was the most important factor in moving a buyer down the path to purchase.

Not exactly string theory-type insight but I had my data point on which to build a case.

My plan was to establish the core problem for the company - which at its essence was a misaligned brand voice between charters and sales - present the data point and how I discovered it then present a top-down content approach to feeding the appropriate channels in a way that made sense, all in support of those 1:1 relationships.

I had no intention of building out the next 18 months of content for them for free but would be happy to say, ‘if it were me, this is what I would do.’

Seemed reasonable.

On the day, I got dudded up in my finest finery and marched off to one of the poshest neighborhoods in Sydney - which is saying something - and walked into the office.

To say I had some expectation of how I would feel - as premonition in a nightmare, maybe - would be wrong by half. Let me be succinct.

Old. Fat. Poor.

That is the sweet, sweet rain that washed over me as I stepped through the door.

Now, I am not too much of any of those things but as they say, comparison is the fastest way to self-loathing and I was suddenly on the bullet train to a bender.

There was spit-shine on the spit-shine and that was just the guy sitting at one of the desks in the front of the office, designing an Instagram post… hey, wait a minute…

But. BUT, I have faith in ideas and I still had my pitch perfected and my personality primed.

I was ready and it was sublime. The dance between design, ideas and my own articulation of the two flowed beautifully. I was in my happy place…

… right up until about 3/4 of the way through when the CEO, seated between the screen and myself, spun her chair away from me, dropped her head and got on her phone…

Snapchatting friends? Plans for lunch? Reading GenerationEx? Whatever it was it was amazing to behold.

Was I stunned. Maybe.

Was I angry? No.

Was I disappointed? Sure.

In her defense, I will remind you that I did almost none of the things I was asked.

But in mine, I wasn’t there to show anyone I can do the same things 1000 other people (including, your computer at this point) can do. I can throw a cat out my back door and hit someone who can design an Instagram post… or in this instance, out toward the front of their office at old ‘spit-shine’…

My job was to show that I think differently than anyone else who will walk through the door. You may not like that ‘different’ but I know there are plenty of people who do.

This freedom to search for those who value the difference is why I am trying to hold on to my own direction and why I keep banging my head on doors to find and work with them.

That’s hard to remember sometimes.

But it’s better than the gilded cage of a 50m Superyacht, cruising into Monaco for a week of Grand Prix racing, replete with babes, booze and blow…

…fuck, what have I done?

As a fairly recently minted citizen of Australia I still take my patriotic responsibilities very seriously.

The most important of those is the understanding that come the first Tuesday of November and the annual Melbourne Cup (think Kentucky Derby with fewer mint juleps but more ‘C’ words), professionals everywhere wrap up any work they can finish by the first Monday of November and proceed to turn the country off until the end of summer break… you know, February.

This is, of course, insane but also why you haven’t heard from me in a while. My hands were tied.

While I have been on six weeks of government mandated vacation, I have certainly not been idle.

I’ve had time to host in-laws I haven’t seen in 7 years. I’ve had time to lounge with my family, the freedom from hectic school and sport schedule lifted for a time to be replaced by sun and surf. I even got my scuba certification.

But I’ve also had time to sit, relatively still, and think.

Sometimes that is just what the doctor ordered but sometimes that inactivity can prove incredibly dangerous. Particularly off the back of so much effort made over this past year.

As hinted at (or not so hinted at) in the recent few posts, I have worked hard to position myself to have larger agency over the work that I do, the projects that I say yes to and the time I keep for my own creative work. All very much counter to everything we are taught and told about responsible and productive, professional conduct.

Terrifyingly, though, with so much mental quiet, my inner dialogs, the old one and the new, are now in open conflict, each more and more loudly - well one, more and more loudly - vying for supremacy of not only my mind but my actions and reactions going forward.

Let me explain.

This morning I woke up to a fish on the floor.

Wait. Maybe that’s not back far enough. Try this.

I’ve recently purchased, prepped, cycled and stocked a new aquarium that will serve as stand-in for a growing obsession, still too fragile to express openly.

In my long life, I know-well the trials and tribulations of the aquatic pet going all the way back to the Whispering Pines apartment complex of my childhood where a playmate, Katy (Cathy?) Goldfinger(?) came over for a play and, while my seven year old self was digging through toys in the other room, fed the fish in my tank their food… all at once…to death…

It certainly wasn’t her fault - being seven in her own right - and it definitely wasn’t the last time the cold hand of fate pointed its bony finger at my tanks and called her cichlids home.

There was the time a full tank of fish died in the move from Washington to New York (no one could prove I left them on the sidewalk in Bethesda ((I didn’t!))).

There was the time the kids got their first taste of liquid death when we got a goldfish to fill the Woodstock house with the glittering light of morning as the sun rose and shone through the bowl on the dining table…

Sadly, light enough for glitter but not bright enough to keep the water from freezing. A weird goldfish version of Hans Solo, surprised face and all. God, Woodstock was cold.

Yes, death comes for pet fish fast and often.

But this one was different.

For starters, the tank is covered. Well, mostly covered, with the exception of where the filter intake and heater are on the left and the filter return on the right.

Thing is, both of those openings are in the back of the tank.

This fish was on the floor, out front and, bless their soul, nearly dead center to the tank above.

This fish either had to choose or work or both to die on this spot.

Standing in the quiet above him, looking at the safety of the tank, I thought about the battle being waged in my own head.

I had a meeting this morning. Well, an interview. An interview for a full time job.

Interesting? Definitely.

Challenging? Sure.

Inspiring in a way that you’ve heard me write about in these pages - or those lucky enough (haha, I know, ‘unlucky enough’) to hear me talk about in person?

Not on your life.

And therein lies the rub.

When we first arrived in Australia we landed in August. We got a car, a place to live and settled the kids into school. By the time those tasks were complete and it was time to look for gainful employment it was round about the middle of November. Yes, the third or fourth Tuesday in November.

Happy Thanksgiving? Yes.

Happy job-hunting? See you in February, mate.

Unaware at the time, I am now deeply familiar with the dread and fear and doubt that that long fallow summer stretch can bestow upon one waiting for the lights to come back on and work - full time or more specifically that of your own - to return to the fore.

An old acquaintance but newly invaluable and dear friend who has long forged his own path refers to it in his household as the ‘full-times’, as in, you’ve come down with a case of ‘the full-times’. That moment of doubt where the slow period has outlasted the confidence in yourself as well as your belief in the transitory nature of everything.

It is this same gnawing at my foundations over the past six weeks that has allowed insecurity to return and my eyes turn from ‘The Path’ toward an endless and blurry death-scroll of job postings.

Not because I believe I’ve made a mistake but because the voices tell me otherwise. The old ones. The bad ones.

And the voices are loud.

And the voices are mean.

And the voices make you think because the quiet period has been so long and you ‘aren’t there’ means that you are wrong…

How do you keep skating when everyone says the ice is too thin? That the safest thing to do is to lie down and spread as wide and as flat as you can to keep from breaking through.

But you know that if you do, that when you listen, it will be YOU that melts the ice.

It will be your own stasis that plunges your prone body into the frozen water as the weight of your blades pull you under and all you can think to think is, ‘why didn’t I keep skating?’

I wonder what choice the fish on the floor thought it was making.

Rest in peace, LemonJello.

I have made a terrible mistake.

Not one that leaves carnage and blood in its wake or that can’t be rectified with newly applied effort but one that has held its victim hostage for decades.

Sam Harris’s Waking Up app has long been a source of comfort, thought, and peace for me even before it was an app and just a book.

Anyone who has sat through his guided meditations might be familiar with an analogy he likes to use in eyes-open practice where he likens the conscious awareness input of color, shadow, and shapes to the images reflected in a mirror.

Balancing your vision on the ‘plane of the mirror’, rather than the specific imagery can help flatten your focus (not dull, mind you) and allow the input to ‘reflect’ consciousness itself. The same conscious awareness as feeling, sound or touch might evoke - that’s how I understand it, anyway…

I have been doing this for so long now that even with my eyes closed the mirror often becomes a very present object of reflection (pun intended) during my practice.

The problem with the mirror, though, is that what you see can very easily be misconstrued as truth.

The mirror is not there to give answers no matter how long you reflect on it.

This was my mistake.

The truth is much more fluid and quixotic.

For as long as I can remember I have considered myself an artist, a writer, a thinker and a creative soul.

I have been standing in front of that reflection for so long that becoming something else now would be like suddenly deciding, ‘wait, no, actually Dutch is my native language’ and assuming I could speak it.

Actioning that identity, though - not in the service of my profession(s) - I mean, is probably the one thing I have feared above all else. Being creative, in the open, laid bare with all the judgement, anxiety and anticipated consequences that come with it.

The vulnerability of truly putting oneself out there and ‘creating’ has been, for most of my adult life, absolutely paralysing.

It is much easier to point to the person in the mirror and consider yourself that ‘something’, talk like you are that ‘something’, present yourself as that ‘something’ than doing the something.

The anticipation of being painfully revealed as not entirely what the world sees you as, or more to the point, what you’ve always seen yourself as is more than enough to keep the creative engines on ice.

Two things are happening concurrently that together are pulling me toward the inevitability of change you are seeing in these pages.

First is that my own need to do something, anything, to affirm the creative voice that speaks inside my head but has never been able to express itself fully, has become so strong that the fear of exposure can no longer suppress that desire.

The second, and one I knew in the abstract but not able to practically apply to myself is that it will be bad, it will be rough, it will be messy but it will nevertheless have value.

The idea that the natural cycle of personal growth - creative or otherwise - somehow doesn’t come through incremental steps of creation, learning, assessment and re-creation, is an idea that has come slowly.

The danger for far too long has been comparing abstract creative visions, ones that roll around my head but are never allowed to see the light of day for fear of exposure, with those final creative works of friends, colleagues and the wider creative universe.

An incredibly unfair and debilitating practice if the goal is to improve my own creative expression. But until I typed that last sentence I’m not sure that, ‘improvement of my own creative expression’ has been my stated goal up to now.

The comparative nature of success and achievement can often obscure the true path to an enlightened self.

For so long, the goal for me may have been to affirm the vision of myself - ‘the creative’ - through the eyes of my most successful friends and colleagues. I have looked outward for that confirmation and forgotten that, at the end of the day, no one truly cares.

We are all busy, we are all distracted, and we are all often just trying to get through our days intact. There is little time to linger on the stresses, obstacles and insecurities of others because of our own.

‘You are not the hero of anyone else’s movie.’

Unlocking and embracing this insight for myself threw open a gate that I have kept shut and barred for a very long time.

The deeper mistake I made was in forgetting. Forgetting to focus on the middle ground between my true self and the reflection.

Because, indeed, the mirror will never give you answers but it will allow for the space in which to look for them.

Our creative journey is not one for consumption by others, although the hope may be that others will consume it, but a path we can (and have to) take for our own self-improvement. A path of learning, expression and growth that I’ve seen others take but until now been too paralyzed to follow.

I nearly waited too long.

I’ll take the red pill, please…

Anyone who’s done it knows that the drive north on I-87 along New York’s Hudson River is one of the most beautiful stretches of road in the US.

If you are lucky enough to have done it in autumn you would agree that there are few places that can match the beauty of the Catskill mountains in full fall explosion.

Hayley and I had just pointed our car north for a much-needed weekend getaway in Montreal.

The children had been left with someone in our house in Woodstock (may have been the UPS person, not sure, didn’t care) and we had four days of freedom with nothing but the road ahead and we got to talking…

—

I had spent the previous ten years working in an industry that I had long regarded as a pinnacle of creative ability, the entertainment business.

While my contribution to ‘the biz’ (that’s what I call it…) was on the periphery, working with a team of talented producers, editors and designers making theatrical trailers and TV spots, I nonetheless, was cocksure in my ability to identify critical ingredients that threaded the needle between the thrill of unbridled creative expression and strict marketing objectives required by the studio marketing execs…

During my time there I had gone from my roaring twenties and early thirties as an irresponsible, joyous, experience-seeking and entirely insufferable young professional that New York City grows like weeds to having met my partner, had a son, moved from Williamsburg to Park Slope (as you do), a daughter that then made the city impossible to navigate and relocating life to the quiet, picturesque foothills of the Catskill mountains and Woodstock, NY.

That relocation, though, required a conversation with my place of employment long before COVID helped to tip the balance of power toward remote working.

After some haggling and even more hoping, we came to an agreement that allowed me to work from home Monday and Friday and in the office the middle part of the week.

In hindsight, it is easy look back and see exactly how my toddler-addled, diaper-soaked, dad brain looked at what was on offer and registered, ‘three days a week on my own in the city, where do I sign?, rather than the reality of what that would mean.

I had no place to stay.

My choices boiled down to the comfort of strangers - I saw that Venice movie… no thank you, New York City.

The slowly gentrifying Bowery - not fast enough, believe me.

Or the couches and kindness of friends. Unsurprisingly, the last quickly became a race between which would end first, the offer or the friendship.

Presented with these options, I did the next stupidest thing.

Slowly, quietly, I began to move into the office on the days I spent in the city.

At first, I tried to be clever, present myself as, ‘oh so busy’ and stay past everyone else’s end of day. Not an easy thing when most of your clients are on west coast time, their day ending three hours after New York’s. Not to mention a business that has a long-standing and notorious reputation for a complete disregard of the time space continuum or anything resembling basic human rights.

That said, they do pay time-and-a half overtime (retro-active double time if you work all the way around to the next day) for your soul.

Which is, uh, nice…?

Once the office was quiet I would slip into an edit suite with a decent-sized couch, set my alarm for way too early and be up and out to the ‘gym’ - read ‘shower’, before anyone was the wiser.

The funny thing is, from the outset, everyone was the wiser… except maybe me. There was just a tacit, look-the-other-way agreement that this was the price of asking to work from home.

A price I gladly paid… for a while.

As this routine turned from weeks to months and then a year my ability to maintain this grind was quickly - or slowly, I guess - becoming unsustainable.

—

It was in this mental state that found Hayley and I driving north to Montreal, breathing in the brisk fall air and openly questioning the choices we had made, the direction we were taking and if it was at all possible to make things better.

In that five hour drive we decided to jump.

The shifting of tectonic plates can come as slow, deep rumbles of earth or violent cracks of foundation-rattling upheaval.

I would have bet the house on this shift being the latter… CRACK…

Logistics, citizenship, visas and life, however, meant nearly another two years would pass before I would even get the whiff of a chance to walk into my bosses’ office with Johnny Paycheck’s voice playing in my head and tell everyone what they could do with their job… my job… RUMBLE…

I say ‘nearly’ two years because about 22 months on I was called into same said office and summarily - and entirely unexpectedly - shit-canned…

Best laid plans something, something…

A short, or long (I honestly have no idea) couple of hours later, spinning, rattled and more than a little lost, I was on a Greyhound bus headed north on I-87, the Hudson River on my right, commuting home to Woodstock for the last time.

The low October sun shone warm on my face and the trees outside were afire with their annual seasonal showcase.

If you are lucky enough to have done it in autumn you would agree that there are very few places that can match the beauty of the Catskill mountains in full fall explosion.

Three months later our house would be sold, we’d be on the precipice of a road trip of unknown length with the only certainty being it would eventually end on the far side of the world.

…CRACK…

I don’t believe in wishful manifestation.

The idea that you can close your eyes, say, “I want” again and again and one day you will open your eyes to your dream come to life. It just isn’t a thing.

(If that worked I would be Sonny Crockett and live on a boat in the Miami harbor, godammit)

The secret of, ‘The Secret’ is, it’s a croc.

I have learned, though, to believe in stillness.

And to believe in listening.

And to believe in the practice of attention. So that when the universe flashes a wry smile in your direction you are present enough to acknowledge it and smile back with gratitude.

I was lucky enough to catch the sparkle of a galactic grin twice this week and could only quietly marvel in the assurance and peace it afforded me as I hang my ass out of this creative window, writing about my foibles, my fears, my failures and, uh, my fun…

Yeah, sure, keep reading. I’ll get around to fun one of these days…

The first brought the distance of time close again as I settled into the Substack community and explored the personalities, posts and general cacophony of the town square where I’ve set up my little apple box for shouting.

As the algorithm parsed my likes, my dislikes and shape of my head, the crunched numbers offered a buffet of writers with whom I had things in common.

Among the list was a woman named Sarah Blondin.

I had never heard of Sarah (through no fault of hers) but having some time to wander she was the first click of exploration in this sea of talent and voice.

Her post, The Softest Place on Earth, the one I landed on first, as it turns out, is a conversation and meditation with Elena Brower…

Now, I know at least a handful of you know or are at least aware of Elena but for those who aren’t, Elena is one of the most open, empathetic, gifted, gentle souls I’ve ever had the luck to stumble across.

She was also my yoga instructor for a good while in New York City over twenty years ago.

A practice of beauty, strength and love from it’s humble beginnings on 17th and 3rd, it was her class that helped return me to health after an illness that almost killed me and for a time left me a shell of my prior self.

I have not spoken to, followed or known anything of her journey since 2002. I am incredibly grateful that I will know now, once again.

Yes, my initial click in Substack was a first shout-out from the universe.

The second came from farther away but no less loudly.

One of the people who has unknowingly but deeply influenced my push toward a writing practice laid bare is Anne Lamott and her book, ‘Bird by Bird’.

I am, of course, one of multitudes in that camp.

Being an infinitely more seasoned storyteller than I, I leave it for you to find and for her to tell but it is, in short, the story of putting one foot in front of the other, day after day, mile after mile, not necessarily knowing the destination but believing that the path walked will take you somewhere. Maybe not the ‘where’ you set out for but somewhere amazing, nonetheless.

Many of my own challenges of the past ten years have been overcome with this very notion. I remember being in a particularly trying stretch and telling a friend, “if I’m going to fall, I have to remember to fall forward. At least then I’m still getting somewhere.”

Like running into an old friend at the mall, I stumbled across an Anne Lamott piece in the Washington Post this week, ‘It’s good to remember: We are all on borrowed time’ and reveled in the humor, the insight and the timeliness of her writing.

Timely for me, anyway.

In it Ms Lamott likens growing into her seventies to a changing of species,

“…from cute middle-aged, white-tailed deer, to yak. We are both grass eaters, but that’s about the only similarity”

Now, while my fifty year old tail is definitely white as paste and I would prefer a slow transformation to a moose (for reasons that are obvious, right?), it is the discovery of the article itself that feels like a quiet whisper from ‘beyond’ that my exploration is a worthy one.

Like the phenomenon of talking with someone about a yellow car and over the next week noticing nothing but yellow cars - including, weirdly, in your Facebook feed (although that may be a different ‘phenomenon’ and way more creepy), seeing her article so soon after having cracked the top off Generation Ex and my own struggle with mid-life relevance assured me the issues and themes extend well beyond the screaming fool in my head.

While Ms Lamott sits at the far end of this transformation, her words anticipate the beauty, the stupidity and the fear that come with growing older and reach back across my next two decades with the gentle call that all will be well, come what may.

Yes, the gentle call of a wisened old yak, braying across the tundra that the wolves will come.

Circle up, Anne, Elena, Sarah, You, me.

Shoulder-to-shoulder, there is strength in numbers.

First, I am incredibly grateful to you all for reading, reacting, subscribing and engaging with my first post, “The Last of the Analogs”. The response has been amazing and more than anything, I’m inspired to continue. Thank you.

I am still thinking about the rhythm of my writing. It may ebb and flow as we go on but I think a regular fortnight entry is a manageable cadence for now. That seems consistent enough to maintain the creative pressure but keep me from night-sweats… or more night-sweats, anyway.

But I digress (is it ‘pregress’ at the beginning?)…

Anywho…

Last week my wife asked me, “what’s your point?”

Now, make no mistake, I get asked this question 100 times a day as I wander the house mumbling to anyone who doesn’t want to listen. As such, she could have been talking about anything. It was, however, not long after the launch of ‘Generation Ex’, so for the sake of this post let’s assume that was the topic.

To answer her question, though, I think I need pause and to take a step back before we leap forward.

I have spent most of my forties (and now some of my fifties) on a self-inflicted ‘adventure’ that I was sure at the outset would be simple and in reality became the most trying decade of my life.

The literal change seemed straightforward. Throw everything and everyone I knew to the wind, shedding all I owned and with my little family in tow move as far away as I could go without getting closer again as the globe wraps back around to where I started… simple, right?

It was the figurative journey, though, that really kicked me in the stones.

Looking back, the decision to go was likely the first tectonic shift shaking the ground below my changing feet but obliviousness, confidence and the blurred vision of a parent of two toddler-aged children dulled my senses to the arc of life naturally bending itself toward a change.

In my mind the decision was ours and as such the ultimate outcome was completely within my control.

Funny how smart people can be so dumb.

The experience over the past ten or so years has left in me an incredible curiosity about this time in our lives. A time that marks a transition from the carefully-crafted story we tell ourselves about ourselves to the realisation that, while once possibly true, that story is slowly proving no longer the case.

What happens when the person you thought you were is suddenly gone?

The mirror that used to show a banker of twenty-five years suddenly sacked at 45 and not even given a watch to acknowledge the indignity. The 49 year old agency executive is ushered off the stage to be replaced by a 26 year old influencer who has never talked to a client or run a meeting. And yes, the 42 year old father of two who is surprised to find building a life abroad, from scratch, with no job, no network, and no income might be hard.

Funny how smart people can be so dumb.

This story does not have a happy ending. In truth, the story has no ending at all.

What I am learning through this is that it is all going to come and it is all going to go. There is only the path we walk. For a long time I fought that insight tooth and nail… I don’t think I’m alone in that fight.

‘When will I feel like I’ve made it?’

‘When does it get easier?’

The truth is, I won’t and it doesn’t. Coming to terms with that fact is one of the hardest lessons I’ve ever had to learn. That battle - the one of Understanding, the capital ‘U’ one - has been the biggest part of my life since moving to Australia and the one in which I’ve become fascinated with exploring.

How does one move through this time of changing identity with grace when all we are taught, all we are told and all we believe up to that point tells us to fight? Fight for money, fight for status, fight for relevance. How do the choices we make during this transition end up constructive and not destructive? Why is it easy for some to find acceptance in this new skin while others choose matches, gasoline, infidelity, and destruction?

I will try and share things that have helped me navigate the turbulent and uncharted waters of my past decade so that it might ease the journey for those that follow (we all get there).

At the end of the day, and the beginning of this endeavour, though, I don’t really know what I’m doing or where this is going. I will do my best to keep tapping away at my keyboard if for nothing more than to serve as a reminder that the path is long, the journey is on-going and that the words for me are an expression of my commitment to walk it.

I invite you to share the stroll.

Maybe, in the end, that is the point, my love.

My generation was the last of the analogs.

I learned to type on a mechanical typewriter, got a temp job by passing a typing test on an electric one and wrote my first term paper on an Apple IIc.

I grew old listening to music through a needle, then Sony Walkman headphones, a shiny disc that I sometimes had to huff on and polish with my jeans to get working, an infinite library of digital streaming songs, and finally back around to needle once again.

I learned to load film in a black bag, develop photos in a darkroom and splice, bin, and edit film on an editing table. That last of those was thrown into the alley along with the Steenbecks six months into my first job as an assistant editor to be replaced with the first generation of non-linear editing systems, replete with 1 and 2 GB hard drives that weighed as much as a kettlebell and slid into racks like warp drives on an interstellar cargo ship.

In the intervening years, my contemporaries laid the foundation of the internet, untethered phones from the wall, and delivered the universe to the palm of your hand, warts, fetishes and all…

…Sweet, sweet, ASMR. Whisper to me again the Jack in the Box menu from 1984, only this time through a microphone used on the Purple Rain tour… yes. slowly… slower…now crinkle the bag…

The sheer degree of change and the pace with which it accelerated was nearly impossible to imagine let alone keep pace but for those who rode the crest of the wave, the ones who saw the opportunity before the rest of us, solidified for themselves a professional momentum that would see some rise to levels of achievement and success unseen since the Golden Age of the Robber Barons, a century ago.

Wish that was me, amirite?

But what about those who dove in at twenty, paddled, surfed, splashed, and had the time of our lives? We too rose through the ranks, finding paths that helped drive the engines of change. We became successful, accomplished, well-off or at the very least proud enough of our own accomplishments to feel good about what we’ve done.

We worked tirelessly not just for corporate HQ but for ourselves. Firmly in the belief that we were carving professional identities for ourselves that made us valuable, important, even irreplaceable. We were. Until we were replaced.

I am just over 50 - fifty-two if I’m being honest (don’t always count on that).

11 years ago today I was canned from a job that was, what I thought at the time, the pinnacle of my professional identity. A job that weaved together creativity, storytelling, technical know-how and more than a bit of entrepreneur. One that filled me with pride (for a time), challenged my brain and, hell, that people thought was cool.

The reality, as is usually the case, was much more complicated.

I was completely unaware at the time but this complicated pivot point, this shattering of professional self, marked the beginning of an exercise in confusion, reflection, transformation and creation that continues unabated.

Having hurtled headlong through the past ten years of extraordinary change what has surprised me the most is how incredibly normal this is to the human experience.

In some languages there is an upside-down punctuation mark at the beginning of a sentence to let you know the intent of what’s coming. This inflection point in many of our lives is the upside down ‘!’ that begins the question, ‘¡What do I do now?’

Or more to the point, ‘¡Who the fuck am I now?…’

Welcome to GenerationEx.