Over a decade ago Oliver Burkeman wrote what I think is one of my favourite short op ed pieces of all time on the topic of how ‘everyone is totally just winging it, all the time’. The piece was well-shared at the time, in large part I think down to the fact that it touched on a fundamental insight that many of us intuitively know but which nobody ever voices out loud – that, as Oliver puts it, we’re all ‘energetically projecting an image of calm proficiency, while inside we’re improvising in a mad panic’ and that ‘there’s no institution, or walk of life, in which everybody isn’t just winging it’.
This might sound like a terrible thing, but I’m here to tell you that its not. In fact I believe it to be one of the most valuable tools we have for living productive, fulfilling lives filled with learning. I don’t mean that we should be regularly undertaking overtly risky adventures or projects with little or no knowledge (hello Dunning-Kruger), but I do mean that there are real benefits to always operating at the edges of what you know or feel comfortable with. David Bowie articulated it brilliantly in this richly insightful clip in which he gives advice to young artists:
“If you feel safe in the area that you’re working in, you’re not working in the right area. Always go a little further into the water than you feel you’re capable of being in. Go a little bit out of your depth and when you don’t feel your feet are quite touching the bottom, you’re just about in the right place to do something exciting”.
It’s quite the analogy. The moment when we’re standing on tip toes, still connected to the sandy sea bed, to then taking one step further into the sea and suddenly we’re swimming.
Educational psychologists call this ‘desirable difficulty’, or making learning activities intentionally challenging in a way that promotes better long-term retention. When your brain is faced with a desirable difficulty it releases neurochemicals that enhance attention and memory consolidation (as if your brain is saying to itself, ‘this is important!’). The discomfort we often feel when faced with new or challenging tasks is a sign that the brain is actually rewiring itself, shifting from efficient paths to generating new ones in a process called neuroplasticity. Every time we tackle something which is at the edges of what we know we are laying down new neural pathways rather than travelling familiar neural highways. This is why deliberate learning, and working consistently at the edge of competence, is such a powerful lifelong habit. It trains the mind not only to learn new things, but to stay good at learning itself.
You might call this learning like an athlete – committing to systems and regimes that continually push us into territory at the edges of what we’ve previously been capable of. An example of this might be developing a daily or weekly habit of learning something new and different. This works because systems (like developing habits) are more powerful than big goals which can feel distant and unreachable. It works for me because it helps me to feel like I’m constantly developing my toolkit to deal with the uncertainty and diverse challenges of working for yourself. The paradox is that in the modern world stability doesn’t come from treading familiar paths, but from continually teaching your brain to embrace its own discomfort.
The critical balance of operating at the edge is that between skill and stretch. Psychologist Lev Vygotsky called this the ‘zone of proximal development’ which describes the space in which a learner can achieve more if supported to move beyond what they can already do unaided. In the today’s world this support may come from people but increasingly it may also come from AI. I also find that this balance between novelty and familiarity promotes a kind of pattern synthesis or an ability to connect unrelated ideas, most often by taking concepts or principles from previous projects or things I’ve written about and using them to give me a fresh way of thinking about a new or different challenge. In this sense, what feels like risk is actually the necessary condition for originality.
Operating at the edge of what we’re comfortable with also helps us to move more fluidly between different modes of thought, or what psychologists would call our cognitive range. Cognitive scientist Scott Barry Kaufman has written about how creativity relies on being able to seamlessly shift between divergent thinking (generating lots of possibilities) and convergent thinking (selecting and refining the best ideas). This is also a classic part of Design Thinking. Most of us tend to favour one side of that spectrum. We’re either comfortable exploring widely or disciplined at narrowing down. But I think working beyond your comfort zone forces both to coexist. When you stretch into new domains, your brain encounters unfamiliar constraints and unexpected patterns, and in the process of reconciling them it learns flexibility. Each time you push into something unfamiliar, you’re adding knowledge but you’re also expanding your mental range of motion.
This is all to say that operating at the edge is expansive in so many ways in both work and in life. In life it keeps us alive to possibility. It builds our empathy and tolerance for ambiguity. This may mean learning a skill that feels alien to our identity, or spending time in spaces or with people that unsettle our assumptions, or curiosity in domains adjacent to our areas of expertise (horizontal learning), or routines that generate surprise.
In work it stretches what we can do but also what we take notice of and see. It expands our sense of potential. Choosing projects where the outcome isn’t certain, or tackling challenges that haven’t been solved before, or collaborating with people who think in unfamiliar ways. The impact of these small acts of deliberate unfamiliarity accumulate over time.
Bowie was, of course, famous for reinvention and following his own path, and I think there’s also something interesting in how this practice changes how we see ourselves. When psychologists talk about ‘self-expansion’, they mean the process by which we broaden our sense of self by acquiring new perspectives, skills, and resources, often through novel and interesting activities or close relationships. It’s a kind of slow evolution of identity through challenge and new experiences. A kind of growth. But one in which it’s not only us growing, but the world that we inhabit.
I’ll leave you with a quote from the artist Georgia O’Keefe, whose life was also characterised by continual reinvention and challenge. She broke through in a male-dominated art world in early 20th-century New York, moved to New Mexico later in life due to ill health and burnout, and all her life treated uncertainty as evidence that she was doing something worthwhile:
‘I’ve been absolutely terrified every moment of my life, and I’ve never let it stop me from doing a single thing I wanted to do.’
A version of this post appeared on my weekly Substack of AI and digital trends, and transformation insights. To join our community of over ten thousand subscribers you can sign up to that here.
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