“You’ve changed your earrings.” I was sitting opposite a prisoner I worked with regularly, and he’d noticed I’d switched from sleepers to studs. He also observed that I’d caught some sun, my hair was lighter, I had a scratch on the back of one hand.
This level of attention was one that my closest friends and family members would struggle to match. That it came from a convicted sex offender held under an indefinite detention order (so still considered too dangerous to release into the community) was more than a little unnerving.
Behind bars, though, there’s not much else to do but watch others. And on the streets, heeding the subtlest of shifts in your associates or the environment can be the key to survival. That’s how criminals hone their keen observation skills – and many other strengths.
As a forensic psychologist, I’ve spent plenty of time working with prisoners. It’s always struck me how detail-oriented, resourceful, creative, adaptable and driven these men* can be. If they’d grown up in less aversive environments, I’m sure some of them would probably be running ASX 50 companies instead of, say, drug trafficking operations.
What’s this got to do with creativity?
Creativity is usually considered a force for good – and something that can help your work stand out in a sea of AI-generated content. But burgeoning research in the field of malevolent creativity recognises that it can be just as easily harnessed for antisocial or destructive purposes. For that reason, studying the ingenuity of criminals can be instructive.
Criminals routinely devise complicated schemes, fashion unconventional solutions, and adapt to difficult (seemingly impossible) circumstances. By exploring how they create, innovate, and strategise, it’s possible to glean useful creative insights – even if you don’t necessarily endorse their criminal actions or the harmful outcomes which eventuate.
Here’s how prisoners colour outside the lines – and what we can all learn from them:
Notice the small details
The case study
Acute observational skills allowed con artist Frank Abagnale to impersonate professionals by mimicking their behaviour, speech, jargon and mannerisms. Abagnale, who told his story in Catch Me If You Can, claimed to have logged millions of air miles by impersonating a Pan Am pilot, and says he variously passed as a doctor, university professor, and a lawyer. He also passed millions of dollars of bad cheques.
Many of his claims have since been called into question, raising the possibility that his biggest con was, in fact, turning a made-up story into a bestselling “memoir”. Nevertheless, Abagnale wrote, “Observation is a skill that can be developed, but I was born blessed (or cursed) with the ability to pick up on details and items the average man overlooks.”
The lesson
Pay attention to the smaller details that other people might miss. Detailed observation can lead to richer and more authentic storytelling. As Joan Didion did, keep a journal so you can record moments which might otherwise be lost to poor memory.
Dream big
The case study
A 1973 mugshot taken in New Orleans showed a moustachioed Raymond Stansel looking sullen. He’d been arrested on marijuana smuggling charges, and was found with large sums of cash, unused cheques on a Swiss bank account, and a passport indicating he’d visited a dozen different countries in a month. Stansel posted bail. His trial was scheduled. But then he went missing, presumed drowned, while scuba diving in Honduras. Only four decades later did it come to light that the fugitive had in fact made his way to Far North Queensland. Here, he’d taken a new name and reinvented himself as a highly respected cruise operator and environmentalist on the crocodile-filled Daintree River – before dying in a car accident on the Mossman Daintree Road.
Successfully faking your own death and getting away with it? The odds are stacked against you. Yet one of the hallmarks of a criminal thinking style is something called super-optimism. On a scale designed to measure this tendency, high scorers act as if they’re wearing a “bullet-proof” vest, in the sense that there’s no way their plans can fail. Overconfidence and unrealistic plans aren’t always a good thing – but sometimes self-belief and a little bit of luck can help you pull off something big.
The lesson
We’re conditioned to be rational, realistic, and measured when setting goals. Yet thinking on a grander scale can sometimes yield outsized results. It works for the smaller stuff too. For example, one weight loss study found that people who set ‘unrealistically high’ goals in relation to their weight loss displayed ‘more effort’ and greater short-term weight loss than their peers with more modest weight loss aspirations. For writers, dreaming big might involve pitching those top tier publications. Self-publishing that book. Scoring that impossible-to-get interview. Don’t wait for permission from the gatekeepers. If you want to break into, say, travel writing, you might need to take a trip under your own steam in order to create a couple of clips for your portfolio.
Be resourceful
The case study
In 1962, three prisoners used remarkable ingenuity to escape from the supposedly inescapable Alcatraz prison, located on an island in the middle of San Francisco Bay. During the six-month planning phase, they’d fashioned a drill from the motor of a broken vacuum cleaner, used more than 50 raincoats to build a raft and life vests, and made dummy heads of plaster, flesh-tone paint, and real human hair to fool the night guards.
The Guilford Alternative Uses Test is one assessment of creativity which asks participants to think of as many uses as possible for a simple object, such as a brick, paperclip, or shoe. Prisoners would ace this test. Some of the inventive things I’ve seen behind bars include bongs made using shampoo bottles or salt dispensers, syringes hidden inside cut-out compartments in books, slingshots made from the bars of a refrigerator, and shivs (improvised knives) crafted from toothbrushes or T-bone steaks.
The lesson
Prisoners don’t wait for the perfect conditions, the right time, or the most suitable tools. They just get on with it, demonstrating repeatedly that where there’s a will, there’s a way. For tips on getting started, read this post.
Regardless of what anyone else thinks, criminals prioritise the things which are most important to them. Creativity can flourish amid constraints, as an increasing body of research reveals. For example, one review of 145 empirical studies on the effects of constraints on creativity and innovation, found that individuals, teams, and organisations benefited from constraints in terms of coming up with more innovative solutions.
Almost everyone can become more resourceful by leaning into – rather than railing against – constraints. I hate interruption and used to demand long stretches of unbroken time and concentration in which to write. While that’s still my preferred way of working, I’m learning to embrace small snatches of stolen time in between appointments, or while commuting, or after everyone else has gone to bed, to knock big jobs over, bit by bit.
Play to your strengths
The case studies
Small-time crook Jack Karlson played his theatrical talents to his advantage long before the Democracy Manifest arrest which turned him into a meme. In 1968, in Sydney, the self-described actor and artist walked out of court by impersonating his own arresting officer in order to escort his co-accused, and himself, to freedom. (To read more about Karlson, read Mark Dapin’s Carnage or stay tuned for the documentary due to be released in 2025.)
Sadly, I learned Karlson had died two days after this story was posted. I sometimes wonder if he was descended from Claude Duval, a 17th-century French highwayman, who used his charm, dramatic flair and love of dance to rob stagecoach travellers without resorting to violence.
Other criminals wield their intelligence as their weapon. Known online as Dread Pirate Roberts, physics graduate Ross Ulbricht exploited the anonymity provided by the dark web to create Silk Road. A massive online marketplace where users bought and sold drugs, false identification documents, and computer hacking software, Silk Road used the Tor network which enabled anonymous communication. This innovative use of technology allowed him to circumvent traditional law enforcement methods – at least, until his arrest in 2013.
The lesson
We’re often taught to remedy our deficits. But it’s just as important to play to your strengths. Writing is a diverse field with myriad skills that can differ significantly from one writer to the next. Some writers excel at research, analysis, and breaking complex information down. Others are skilled at capturing dialogue; others at setting the scene. And so on.
As an introvert, I sometimes wonder why I persist with travel writing gigs. Unlike my more extroverted colleagues, I inwardly groan when I see a famil (press trip) itinerary loaded with drinks, lunch, dinner and other social engagements, all of which satisfy hosts and PRs, but don’t contribute to the stories I’m writing.
I used to beat myself up for not wanting to be more sociable. But as Sophia Dembling writes in The Introvert’s Way, “our brains generate their own heat … too much outer stimulation and we blow a fuse”. So, I’m a little kinder to myself these days. I extricate myself, where I can, and fall back on other introvert strengths such as deep observation and reflective storytelling.
Go for broke
The case study
Trembling with adrenalin, John Killick waited in the exercise yard at western Sydney’s Silverwater Correctional Complex on March 25, 1999. He was doing a long lag for bank robbery and had noticed a sky thick with helicopters flying in and out of construction sites ahead of the 2000 Olympic Games. ‘I’d watched the guards closely and I could see they weren’t taking any fucking notice of the choppers coming over,’ he told Mark Dapin, in Prison Break. (Those observation skills again!)
According to an audacious plan he’d cooked up with his then-lover Lucy Dudko, he knew she was, at that moment, enroute to him in a helicopter she’d hijacked at gunpoint. Dudko demanded the pilot land within the prison grounds, allowing Killick, under a hail of bullets from prison officers, to escape. It was an incredibly risky plan. But he and Dudko remained on the run for 45 days.
The lesson
You’ll often need to take risks to bring your plans to fruition. The very nature of creative work demands it. Sometimes your gambles won’t pan out. Sometimes they will – spectacularly. So don’t play it safe. Find ways to beat the procrastination that keeps your work from seeing the light of day.
Entrepreneur Steven Kotler noted that there is a deep and meaningful connection between risk taking and creativity. “It’s one that’s often overlooked,” he writes. “For starters, creativity is the act of making something from nothing. It requires making public those bets first placed by imagination.”
* I work mainly with men.
Over to you … Are there any other lessons you’d add to this list?
While you’re here … Prisoners don’t get hung up on perfectionism either. So don’t let finding the ‘perfect’ story or writing the ‘perfect’ pitch hold you back. In my free resource Pitching for Publication, I present three pitches that landed assignments, and ongoing relationships, with editors. I also highlight the many embarrassing mistakes that an editor could have seized upon if they’d really wanted to strike me out.
