Deep Life Reflections: Friday Five
Issue 125 - Wicked
What if the world you trained for isn’t the one you have to live in?
Welcome to Issue 125 of Deep Life Reflections, where each Friday I share thoughts on how to live more deeply, inspired by literature, cinema, and experiences.
This week, we explore the terrain of generalists versus specialists and what it takes to succeed in a complex and unpredictable world.
Join me for this week’s Friday Five.
1. What I’m Reading
Range. By David Epstein.
Do you consider yourself a generalist or a specialist in your career?
Perhaps that’s an easy question to answer. Perhaps not.
For me, it’s a bit of both. I spent two decades building a specialised set of skills in ‘executive communications’—writing speeches, presentations, and company-wide messages for senior leaders, and developing the strategies to support them. But my earlier years were anything but specialised: selling advertising space over the phone (total sales: zero), managing projects, and even running my own restaurant.
In reading David Epstein’s Range, I recognised that path straight away. “A rapidly changing world demands conceptual reasoning skills that can connect new ideas and work across contexts,” he writes. “The ability to apply knowledge broadly comes from broad training.”
In Range, Epstein argues that breadth, as well as a journey of experiments, is more likely to help you find your place in the world than early specialisation. He uses two familiar examples to make the point. Tiger Woods, who trained almost exclusively in golf from the age of two, as the archetypal specialist; and Roger Federer, who played several sports at a high level before committing to tennis, as the generalist. Across industries, Epstein found people’s career stories looked far more like Federer’s than Woods’s. Those people experimented, zig-zagged, and tried different paths before finding the right fit. Most of us, whether we realise it or not, are probably more like Federer.
One of the most interesting ideas in Range is Epstein’s distinction between the types of problems we face.
“Kind problems versus wicked problems”
Some are “kind problems”—closed, stable, and predictable. The rules are clear, the patterns repeat, and feedback is immediate. Chess is a classic example. So is playing a musical instrument in a set style. These are domains where the link between practice and improvement is direct, and where specialisation shines. Classical musicians often say they cannot improvise. They can interpret notes masterfully, but that’s because they operate in a stable and predictable environment.
Django Reinhardt, the jazz guitarist who revolutionised the virtuoso guitar solo, once said when asked if he could read music, “Not enough to hurt my playing.” He learned by uninhibited experimentation and even influenced Jimi Hendrix, but always within the fixed boundaries of music—a kind environment where skill compounds through repetition and refinement.
Then there are “wicked problems”—complex, unpredictable, and often unique. The rules may change at any time, the feedback is delayed or incomplete, and past solutions don’t always fit the present.
Three examples of wicked problems today:
Building a meaningful career in industries that didn’t exist ten years ago
Knowing which information to trust in a world of deepfakes
Deciding when to stick with a goal and when to walk away
Here, deep specialisation alone can be a trap, because it can commit us to a narrow path that no longer leads anywhere.
In a wicked world, it’s breadth—the ability to draw on different fields, to connect ideas across contexts, and to adapt—that gives us the edge.
We can all embrace breadth and the journey of experimentation without feeling left behind. Specialisation still has its place. We all specialise to a degree at some point in our lives, as I did. The trick is knowing when to narrow our focus, and when to pull back and draw from the wider field of our experience.
Nothing we’ve learned along the way is wasted. There’s always something to draw on. Even those £0 telesales in advertising taught me something: don’t do telesales.
Fortunately, I found areas where I was better suited—and built skills I still rely on today.
We all have range. More than we think.
2. What I’m Watching
The French Connection (1971). Directed by William Friedkin.
“That son of a bitch is here. I saw him. I’m gonna get him.” — Jimmy ‘Popeye’ Doyle
It’s the last line of William Friedkin’s multiple-Oscar-winning The French Connection, and it sums up the character perfectly. New York City Narcotics Detective Jimmy ‘Popeye’ Doyle—played by the late, great Gene Hackman in his breakout role—is no meticulous specialist. He’s impulsive, prejudiced, obsessive, and volatile. He doesn’t think in systems or operate in predictable environments. He reacts, adapts, and keeps pushing forward. Above all, he’s relentless.
The film was released at the dawn of the 1970s, which I firmly believe is the greatest decade in cinema. New Hollywood was in full swing—young, ambitious directors like Coppola, Scorsese, and Spielberg were taking their cameras into the streets, creating morally ambiguous characters we’d never seen before. The French Connection led the way, with its young, risk-taking director drawing inspiration from the energy and realism of the French New Wave—Godard, Truffaut—and bringing that restless style to American cinema.
On the surface, the film is about a major drug trafficking case: $4 million worth of heroin smuggled from Marseilles to New York, hidden in a car. Doyle and his partner, Buddy ‘Cloudy’ Russo (Roy Scheider), close in on the ringleaders. But the pursuit is elusive. Every lead slips away, much to Popeye’s growing fury.
New York has never looked so grim. This is no love letter to America’s most famous city. Shot in the dead of winter, it’s grimy, freezing, and stripped of any glamour. I felt cold just watching it. The crew felt it too—cameras and equipment often froze in the frigid temperatures. Like Truffaut’s The 400 Blows, which revealed a Paris far from the postcards, Friedkin’s New York is filthy, stripped-back, and dangerous, acting as a metaphor for Popeye’s mind.
In the character of Popeye Doyle, we have a portrait of obsession. And this is at the centre of the film. Doyle is deeply flawed— his judgment is questionable, his morality ambiguous, his policing often reckless. And yet, we root for him. Because he acts. He’s no Gary Cooper in High Noon, standing tall in clear-cut moral territory. This is a messy world—a wicked environment—and in that environment, it’s Doyle’s imperfection, his instinct, and his refusal to stop that pull him closer to the arrest.
Hackman is superb as Doyle. A natural pacifist, he initially struggled to inhabit the role’s violence and aggression. Friedkin pushed him hard, and Hackman almost quit on the second day. But he persisted, dug deep, and delivered a performance that won him a Best Actor at the Oscars and a little bit of cinematic immortality.
The film’s most famous moment—an 11-minute chase that begins on foot and explodes into a breakneck car-versus-train pursuit— is still fantastic. Part of its power comes from how real it feels: Friedkin had no permits from the city, so he shot it guerrilla-style with stunt driver Bill Hickman (fresh from Steve McQueen’s Bullitt) tearing through Brooklyn traffic—and pedestrians—at genuine high speeds, which is very obvious on watching. In one brilliant anecdote years later, Friedkin recalled getting permission to film on the elevated train after handing a New York official—who had dismissed the production as “crazy”—$40,000 and a one-way ticket to Jamaica.
Friedkin admitted in his memoir that he regretted the risks he’d taken, calling them incredibly irresponsible, and said that if he had the chance to do it again, he wouldn’t.
Like many great films of the ’70s, The French Connection is rooted in fact. It’s based on Robin Moore’s 1969 book The French Connection: A True Account of Cops, Narcotics, and International Conspiracy, itself drawn from real detectives and real cases. Friedkin’s version—like the stripping of the drug car in the final scene—strips away the glamour of the crime genre and neat, tied-up endings, replacing them with grit and an ending that feels intentionally unsatisfying, mirroring real-life.
That’s why the film still endures more than half a century later. It’s about a flawed man in a chaotic world, willing to act without certainty.
And in wicked environments, that’s sometimes the only way forward.
3. What I’m Contemplating
I’ve been enjoying a solid run of 1970s cinema during these past weeks—The French Connection, Taxi Driver, and One Flew Over the Cuckoo’s Nest to name a few.
I’ve always been interested in the context in which films are made. Just as I used to say in my executive communications days when someone asked me for help with a phrase or sentence, I’d ask, “What’s the context?”
The French Connection emerged in an America where trust in institutions was crumbling. The Vietnam War dragged on, the Pentagon Papers had been leaked, and Watergate was just around the corner. Half a century later, in 2025, we have a very similar set of circumstances, just a different set of names.
Audiences back in the early 70s were ready for anti-heroes: flawed, morally ambiguous figures who looked nothing like the polished ideals of 1950s cinema. Doyle fit the moment perfectly—a cop who bent and broke the rules as it suited him. A year later, Clint Eastwood would bring his anti-hero to the screen in the form of Harry Callaghan—Dirty Harry. Another character walking a moral tightrope.
Rather than Alien vs. Predator, or Batman v Superman, a showdown between Popeye and Callaghan would be the better entertainment for me.
Which brings me back to David Epstein’s Range, and his idea of kind and wicked problems. How do we act when the world refuses to follow the rules? In such a world, developing range—in thought, in experience, in our responses—seems to be more essential than ever.
4. A Quote to note
“A man with a watch knows what time it is. A man with two watches is never sure”
- Lee Segall
5. A Question for you
If you could master one new skill this year, what would it be, and what opportunities would it create for you?
Thanks for reading and supporting Deep Life Journey. If you have any reflections on this issue, please leave a comment.
Have a great weekend. Stay intentional.
James
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