Winging It

Musings on making it up as you go along.

I’ve been making it up as I go along for most of my life.

When there were exams to pass, chess moves to make, organisational funds to raise, or children under my care who had to be fed or kept safe, I took the opportunities and responsibilities that were mine to take. Carry what is yours to carry, as they say.

But mostly I’ve been winging it.

I say this neither as a confession nor a boast. I think a strong case can be made that most people are winging it most of the time, but we are too invested in a particular version of the idea of competence to admit it.

Winging it is not the same as ‘faking it until you make it’. There’s a place for generative pretending, but the skill of ‘winging it’ is different.

Winging it is about the capacity to demonstrate relevant competence in the absence of presumed knowledge. It’s about knowing what to do when you are unprepared or underprepared, and often doing things well not in spite of the lack of presumed knowledge, but because of it.

Winging it is therefore fuelled by the impulse to inquire and experiment and represents a turn towards reality rather than away from it.

Winging it doesn’t necessarily mean you have impostor syndrome either, though they can co-arise.

I’ve lived forty-six years in a state of mild confusion about what is really going on, and what I’m expected to do, but mostly I’ve enjoyed it, and done reasonably well at it.

I am a D-list celebrity on a good day, I have been known to burn the toast, and I bump into lamposts occasionally. I don’t seek to present myself as any kind of worthy exemplar, but I have recently been wondering exactly how I’ve managed to build a life where I spend most of my time doing what I want to do. I couldn’t have achieved a viable adulthood without a stable society, the love and help of other people, and plenty of good luck, but I was, I guess, involved.

While I might be disorganised, over-zealous, hypocritical, hard to pin down, insensitive, and much else besides, I have rarely felt fake. I believe I’m quite candid, sometimes brutally direct, often over-sharing, and I’m not vain about what I don’t know. I would struggle to explain gravity or the theory of evolution for instance; and though I am a philosopher (of some kind) I have never read more than a few pages of Plato, or Spinoza, or Hegel. My knowledge of classic literature is limited because I was too busy playing chess to read when I was growing up, so I am not ‘well-read’ either.

I don’t really know what intelligence means, and since studying with Howard Gardner I distrust the notion of IQ, but I did get a first-class degree from Oxford, a master’s degree from Harvard, and completed a Ph.D. at Bristol, so I’m passable in a scholastic sense. Even if I do have above-average ‘intelligence’, that’s not where my contribution or efficacy lies. Becoming good at chess gave me intellectual confidence, but I know many people who seem significantly ‘brighter’ or ‘smarter’ in terms speed of comprehension and processing power, and many others who are far more knowledgeable. So it makes me wonder what exactly I bring to the table.

Photograph taken in August 2022 by my son Vishnu, who was then 6.

I wrote about the challenge of figuring it all out in my memoir about what becoming a chess Grandmaster taught me about life. The following distillation didn’t impress the marketing team at Bloomsbury, so this never really saw the light of day, but I do believe each of the following things, and they have shaped how I live.

1. Concentration is freedom

2. It is the mattering that matters

3. Our autopilots need our tender loving care

4. Escapism is a trap

5. Algorithms are puppeteers

6. We need to make peace with our struggle

7. There is another world, and it is in this world

8. Happiness is not the most important thing

Each of these ideas is a whole chapter, and a whole conversation, and together they are a whole book, but you may notice they are all somewhat enigmatic in spirit (which is probably why the marketing team didn’t like them).

The short version of the book as a whole is that…I’ve been winging it, and I’d encourage others to do the same.

I might be some kind of expert generalist, which is mostly about having expertise in one area that you have reflected on enough, and tried to connect to other aspects of life that you develop a broader capacity for epistemic agility, contextual discernment, and knowing which questions need to be asked.

I don’t have a superpower, but if I had to name something that I feel I do well, it’s that I know how to clarify what I’m confused about and follow where confusion leads. I imagine chess played a part in shaping this quality of mind because to be a good chessplayer you have to enjoy feeling confused for several hours at a time. Most of chess expertise is a falsification process, which is based on systematically doubting your ideas, and yet still having to make a move, often without knowing if it’s the right one.

I have always been pretty honest about my lack of understanding, and have some of the qualities of an auto-didact who keeps on asking until some sense of inner conviction arises, or at least clarity about what is unknown or unknowable. I grew into this quality early in my first year at Oxford. I had been struggling with some details about the demand curve in microeconomics and was socially distracted by my new student life, so that week learned helplessness came naturally. I told my tutor, Tim Jenkinson, that I just found it all a bit confusing. He replied that confusion in a general or apathetic sense is a kind of laziness, but confusion about particular things is a sign that you are paying attention, and teachers are often delighted to be asked about hard-earned confusion. This! This bit here. This is what I am confused about. This simple distinction between generic and particular confusion was a kind of revelation.

Ever since then, I’ve been hunting for my confusion.

Annie Dillard captures the spirit of that hunt, in her book The Writing Life:

“Why do you never find anything written about that idiosyncratic thought you advert to, about your fascination with something no one else understands? Because it is up to you. There is something you find interesting, for a reason hard to explain. It is hard to explain because you have never read it on any page; there you begin. You were made and set here to give voice to this, your own astonishment. "The most demanding part of living a lifetimes as an artist is the strict discipline of forcing oneself to work steadfastly along the nerve of one's own most intimate sensitivity." Anne Truitt, the sculptor, said this. Thoreau said it another way: know your own bone. "Pursue, keep up with, circle round and round your life....Know your own bone: gnaw at it, bury it, unearth it, and gnaw at it still.”

I identify with the line: “…the strict discipline of forcing oneself to work steadfastly along the nerve of one's own most intimate sensitivity.” I am sure it can be understood in other ways, but I read it as saying: befriend your confusion.

I may not have realized I have this love of confusion, but a few months ago something was disclosed to me on Bonnitta Roy’s Pop-up School. Bonnie is a remarkably insightful person, and she has been involved in some capacity with Perspectiva’s work for a few years now. She invited me to talk with her students about how being a father influences my work. After one answer Bonnie said to me, in front of the group:

“The thing I have noticed about you Jonathan, is that you lead from your confusion.”

Gosh, I thought, so that’s what I do.

**

This is draft material I prepared while writing Leading from Confusion for Perspectiva and there is a small amount of overlap near the end.

In related news, I’ll also be holding a Leading from Confusion session on Thursday 22nd February at 4 pm UK time (5 pm CET, 11 am EST, 8 am PST), probably on the subject of peace, but who knows? To join this session, please sign up to become part of the Perspectiva community here: