The Strategic & Motivational Benefit of Brooding

How to know what to do, when you don't know what to do.

Brooding with Dr Jason Fox by dangerlam

Are you feeling lost? If so, felicitations! You are potentially on the brink of new wisdom and insight.


This is of course only comforting in hindsight.

Feeling lost can be incredibly discomforting. The ensuing darkness and doubt can cripple your confidence, and the absence of any meaningful feedback loops can erode your sense of progress (and the intrinsic motivation progress brings). This is all amplified if you’re responsible for leading a team.

Thus, when confronted with the infinitely complex and ambiguous nature of an uncertain future, it’s also only natural to crave clarity.

A sense of knowing what to do next.


So how do we find this clarity?


How do we truly know what to do next?

If you’re leading an organisation and looking for the classically obstinate defaults, you might try:

  • denying any need to change — retreating to the comfort and convenience of the familiar, and deriving clarity from what has been done before;
  • demanding to see evidence before making decisions — masking a fear of the unknown as ‘prudence’, and deriving clarity from limited evidence filtered through cognitive bias; or
  • delaying any action until others have lead first — it’s so much easier to follow, to just ‘wait and see’, and to obtain clarity passively rather than proactively.

But none of these strategies are particularly appealing to a pioneer. Nor are they particularly useful as a means of leading us closer to relevance.

And yes there are a heap of placating strategies out there for you — but I don’t peddle in banalities. Or at least, I hope I don’t.

I’d like to offer you a different approach: antifragile brooding.

But first, let’s be clear. Unless you’re cleaning your spectacles or distilling gin: —


Clarity is a dangerous illusion


Oh, clarity. The comforting quality of things being certain and definite — how we crave it.

And yet, true clarity is ever fleeting and unattainable. Like a will o’ the wisp, we infinitely seek it. And yet we may never grasp it, and we may never know the perfect truth. As renowned psychologist Daniel Khaneman writes in Thinking, Fast and Slow:

“Our comforting conviction that the world makes sense rests on a secure foundation: our almost unlimited ability to ignore our ignorance.”

But what’s more, our very seeking of clarity is philosophically dangerous.

Happiness, security, certainty, clarity are all concepts we yearn for. And these are all concepts to which our yearning is also our undoing. As my intellectual crush Oliver Burkeman explains in The Antidote:

“…We seek the safety and solid ground of certainty, of knowing how the future will turn out, of a time in the future when we’ll be ceaselessly happy and never have to fear negative emotions again. But in chasing all that, we close down the very faculties that permit the happiness we crave.”

Or, as Alan Watts observes in The Wisdom of Insecurity:

“The desire for security and the feeling of insecurity are the same thing. To hold your breath is to lose your breath.”

This is perhaps why there’s some part of me that always chafes when the default advice for obtaining clarity includes things that only serve to exacerbate our inherent insecurity, and distract us from meaningful progress. Things like setting clear and specific goals, having a detailed plan, ‘dreaming big’ or visualising success.

It’s also why part of me deflates when potentially pioneering leadership teams succumb to overly quantified reassurances, seeking clarity through probability and prediction (rather than possibility and experimentation). Seeking easy answers, rather than better questions.


To obtain clarity, we must embrace ambiguity


Just as Burkeman advocates for a ‘negative path to happiness’ — in which we learn to be willing to experience more negative emotions, so as to fully experience happiness — it may be worth embracing ambiguity as a means of obtaining clarity.

Here we take an approach that is much more meandering. Much more tolerant of uncertainty and the uncomfortable state of not knowing.


And besides — ambiguity has its benefits


Getting lost is a good thing.

When pioneering, you’re venturing beyond the established default and into unprecedented territory. With no map to follow. You’re almost guaranteed to feel lost from time to time.

In fact, I find it more worrying for those who don’t manage to occasionally find themselves lost. They instead cling to the safety rails of life, never straying too far from convention. They ‘know’ what to do, because they haven’t genuinely considered any alternatives.

Finding yourself knowing that you don’t, in fact, know what do means:

  • You are more aware of the areas in your life where you need to seek more information. This helps you prioritise your active quests;
  • You have the opportunity to step back and reflect/reconsider before making a potentially foolish or ignorant decision; and
  • You have the delight of being able to refer (to) someone else with more expertise, who may be better placed to serve meaningful progress.

Benefits aside, ambiguity is still unsettling


Getting lost should only ever be a temporary experience — something to otherwise punctuate meaningful progress.


Is ‘action’ the antidote for ambiguity?


In a nutshell: yes.

Almost everything is a bit clearer on the other side of action. We’re all much wiser after the fact — even if it’s simply knowing what not to do.

Science has practiced this for centuries — it’s called experimentation. To take a particularly Apollonian view on things, it could be argued that the bulk of human knowledge has grown through our ability to posit testable hypotheses, conduct experiments, review evidence, and evolve our collective reasoning. In recent times, Eric Ries has popularised this concept with The Lean Startup. Here we seek to minimise ambiguity by rapidly prototyping — accelerating our learning by launching minimum viable products and obtaining market feedback quickly.

This is all great, of course, but: —


We must beware the extremes


There’s always a risk we can swing the pendulum too far. To go too lean, and to think too fast.

Swing too heavily into theoretical (the thinking), and nothing gets done — we all just have a good time swilling cognac and postulating about possibility while the world moves on. But swing too far into practical (the doing), and we end up perpetuating mediocrity — making ‘shit’ happen, as it were.

Activity might precede clarity — but it may also perpetuate a certain type of ‘clarity’ we’ve become accustomed to. Constant activity crowds out curiosity and the opportunity for slow, thorough thinking. We do the science, we conduct the experiments — but with none of the wonder, imagination or artistry needed to truly pioneer. It’s iterative, but not innovative.

To pioneer and bring about something new from naught — we need a precursor to action. Something that comes before the doing.

And so here’s what I do, to know what to do, when I don’t know what to do:


Antifragile brooding


When I don’t know what to do, I brood. And I do it just as the dictionary says:*

brood |bruːd|
verb: think deeply about something that makes one unhappy, angry, or worried.


* Yes, brood also means to sit on eggs to hatch them. #analogical


When faced with a perplexingly ambiguous challenge — when I don’t know what to do — I court discontent. I positively cultivate it.

Beneath my dapperly debonair veneer, I percolate in the complexity and angst of ambiguity, until things become so dark and bitter that I reach a point where not doing something is worse than carrying on with the default. Where the fear of change is trumped by the fear of regret.

It’s my most effective form of procrastination — thanks to an approach much inspired by one of the most significant books of our times: Antifragile: things that gain from disorder. In this, the maverick Professor of Risk Engineering Nassim Nicholas Taleb presents the concept of ‘antifragility’ — the distinct opposite of fragility, and something beyond resilience or robustness. ‘The resilient resists shocks and stays the same,’ Taleb states. ‘The antifragile gets better.’

When thoughtfully pioneering, one does not simply leap to solutions, jump to conclusions, or skip to quick fixes — we distrust them. As Taleb observes, ‘The strength of computer entrepreneur Steve Jobs was precisely in distrusting market research and focus groups — those based on asking people what they want — and following his own imagination’.*


* Also, as Scott Belsky says: ‘When 99% of people doubt your idea, you’re either gravely wrong or about to make history.’


But what are we left with, if we can’t quickly validate our ideas through focus groups and prototyping?


A whole heap of doubt


Ambiguity is antifragile: the more you know, the more you know you don’t know.*


* As Aristotle once quipped (sans the ‘ambiguity is antifragile’ bit).


Brooding is not everyone’s cup of tea. Here we take a hunch — our quiet dissatisfaction combined with an intuitive reckoning that things could be significantly better — and temper it with new perspectives.

We invite challenges to our fledgling idea — for our thinking too, is antifragile. It’s strengthened by exposure to a diversity of different perspectives (and a healthy dose of doubt). What this looks like for me is reading more broadly, having more conversations, and generally seeking to disprove my hunch.

While brooding, I’m seeking to build optionality — a state in which we have multiple pathways available to us, and the ability to choose how to best progress (based upon information and insight as it emerges). Through deep percolation on an idea, we have the opportunity to future-pace what progress might look like along each pathway. 

Like the pings of sonar, we rapidly prototyping each path in our heads to see what might go wrong, and where the pitfalls may lie. We ask ourselves ‘what if?’ repeatedly, and we allow time for emergent thinking to be steered by our imagination.

And we do this in contrast to the default option of doing nothing different. Perpetuating the default, and the consequences of choosing to not choose an alternative.

At any given moment in time, I am quietly dissatisfied about dozens of things. If they had clear and simple solutions — I’d be in action already.

And then, through this near-constant brooding, sometimes I get to the point where I have dialled up my discontent to the tipping point of—bah! Fuck it! The pain of not doing is worse than any of the potential alternative pathways ahead.


And then I know what to do.


And so I enthusiastically do that thing, throwing myself back into the joys of pioneering meaningful progress, until I next myself wondrously lost again.


Here’s to brooding your way to new motivation and clarity.

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