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Work • Purpose

The Challenges of Choosing a Career

Our brains are fatefully badly equipped to interpret and understand themselves. We cannot sit down and simply enquire of ourselves directly what we might want to do with our working lives – in the way we might ask ourselves what we would favour eating. The ‘we’ retires, falls silent and fragments under examination. At best, our deeper minds let out staccato signals as to certain things that appeal to, or appal them. We might find ourselves saying: ‘I want to do something creative’ or ‘I don’t want to give up my life to a corporation’; ‘I’d like to make a difference’ or ‘I want meaningful work.’


Such aspirations may be reasonable, but they are also foolhardy in their vagueness. The prospect of having to build a career on their foundations can rightly induce panic; not having a robust plan swiftly puts us at the mercy of the plans of others.

We’re liable to blame ourselves and what seem like our exceptionally obtuse minds. But our incapacities are not unique. We’re simply encountering at an especially stressful moment a basic problem of the human organ of thought. Our minds do not surrender answers to direct questions very easily. The same fractured replies would emerge if someone were to demand that we tell them what love really is or what constitutes friendship. We would feel baffled and put upon. We most probably wouldn’t be able to come up with remotely sensible analyses – despite one striking and central fact: we are bound to have a lot of ideas lurking somewhere about the constitution of love and friendship, for we have all lived through plenty of their examples.



We necessarily already possess an immense amount of relevant material for framing extensive and highly penetrating answers. We’ve had so many fleeting thoughts and insights, we’ve known situations both good and bad which could feed into profound responses. Yet somehow our experiences are too easily blocked from coalescing into robust replies. The problem is that our sensations have been left scattered in our minds. We haven’t been able to collect them, sift them, see the connections and evolutions; we haven’t had the time or encouragement to consider what each one is telling us and how they all stack up together. And yet, if we felt more dextrous and confident, we would all have the capacity to come up with insights of superlative value (the people we call great writers are in the end merely people who’ve known how to manipulate the butterfly nets required to catch their own flightiest, airiest, shyest thoughts).

There are so many things we already know without knowing that we know them – because we haven’t been trained in the art of gathering and interpreting our experiences. What is a beautiful city like? What is an ideal holiday? How does a good conversation flow? The questions may sound daunting, but we have answers to them already – for we all harbour, somewhere within our memories, recollections of well-being as we walked the streets of a capital, or felt our senses reopen in a new climate or registered our sympathies expanding at a table of friends. Our belief that we don’t know is merely a symptom of tendencies systematically to underrate our own capacities. With touching regularity, we dismiss the fact that we already contain within ourselves the power to address the grandest themes of existence.


Instead, from fear and habit, we turn away from inner exploration and reach for platitudes which we suspect won’t do justice to our impressions, sensing that our real feelings are hiding somewhere in tangled pre-verbal form, yet hoping that our questioner might leave us and make someone else feel inadequate.

So there’s ultimately nothing very special (and therefore nothing especially worrying) about our inability to give a direct or neat answer to an enquiry about what we might want to do with our working lives. It’s merely one more example of our minds’ unjustly weak self-reflexive muscle.


Because these minds do not easily surrender answers, and yet the material for an answer is in them, we should take the time to consciously collect relevant evidence, create a library for it, pore over it and analyse it, and so ensure that stray thoughts and fleeting sensory impressions can one day be assembled into clear lines of argument. There may be a few complexities to doing so (we will address them in a minute), but the chief obstacle to getting started is the melancholy feeling that it would be peculiar and unnecessary even to do so. A search to understand our working characters has to begin with a basic acknowledgement of the natural vagueness and intellectual squeamishness of our minds – without our falling prey to a sense that our furtive mental inclinations are shameful or indicative of any sort of individual weakness.

When addressing the question of what we might do in our work, we should have the confidence to believe that large portions of a sound answer are already in us. But the best way to proceed is not to try to head for a conclusion too quickly, because the data that can contribute to a reply hasn’t been correctly tagged within us; doesn’t know its own nature or its potential to guide us and has to be disentangled from cobwebs of forgetfulness. We must patiently trust that we have already picked up a great deal of information and experience relevant to determining what kind of work we should do, but it has arrived in guises we won’t automatically recognise. Instead, in so far as it is there, the information has been encoded in us in those superlative indicators of career aptitude: distinctive feelings of pleasure, enthusiasm or distaste in relation to many rather minor tasks and challenges – that can appear to be wholly disconnected from anything resembling a fee-paying job.



Paradoxically, it’s not our direct past thoughts about work that are typically most useful in guiding us to new more fulfilling work. The underlying question is about work we can love not work we have done – and so we need to get to know a lot about what we love and why before we move too quickly to the formulation of a career plan. We might begin by zeroing in on that storehouse of incidental career insights: childhood. When during these long and now perhaps rather distant years did we feel particular tremors of excitement? We should let our minds relax and surrender the smallest most incidental details. Perhaps it was lovely lying on the bedroom floor, in the old house (we must have been eight) cutting out pieces of paper from a coloured pad and arranging alternating strips.

Sometimes you used to particularly like just drawing straight lines across a blank piece of paper. Perhaps there was a jumper you especially responded to, it had yellow circles on the front; or you really liked running round some gorse bushes in the garden of a hotel you sometimes stayed at when you were little; or it was very special when your bedroom was extremely tidy. It was awful (maybe) at school when you had to do a joint project and your designated collaborator wouldn’t accept your ideas about the size and shape of the presentation document, or about the order of the slides. Or you hated the way some people always kept their hair carefully brushed, or you loved the time you chatted with a friend about your fantasy desert island.


In such memories, we pick up on key incidents in the history of our intimate feelings. Something – we might not know exactly what – struck us as lovely or distressing. These very modest fragments hint at major tendencies in our nature that are liable to be still active within us, but not at an operative level. We will have to proceed slowly. It might take many months of careful reflection to uncover and define some of the central ingredients of our nature that can eventually function as important guides to a good working life.

It’s not only the past that we need to investigate. We should start to collect and analyse our present sensations. Because the mind is so prone to wiping out its own nascent autobiography every few hours, we should keep a notebook handy, so that we can trap a feeling and then return to it later, attempting to make connections with other experiences we have registered. We should proceed with some of the patience of an ornithologist lying in the heather waiting for a sighting of a rare migrating bird. The people who have perhaps most adroitly pioneered a careful method of data-collection have been writers. Almost all of these types have kept notebooks, not because of how much they felt (constant sensations are universal), but because of how valuable they understood their apparently minor thoughts might be – and how aware they were of the cost of our brains’ amnesiac tendencies.


The great 19th-century French novelist Balzac was an inveterate note-book scribe. He was fascinated by human character, and in particular, by how the way people move and the expressions they exhibit give away key things about their personalities. With this theme in view, he became a constant observer of the mannerisms of people he saw in the streets of Paris or met at dinners and in offices. His notebooks tell us:

‘Her movements are not equally distributed over her whole person; she advances in a single block at each step like the statue.’

‘He walks like a despot: a menacing suggestion of security and strength in his slightest movements.’

‘A  brusque movement betrays a vice.’

‘The way this woman saunters around, she can flaunt it all while revealing nothing.’

But Balzac didn’t stop there. These moments of experience couldn’t really honour their role until he worked out where they would be useful. In his case, this meant finding them a place in one of his stories. Though this concern might seem localised, he was stumbling upon a task that is really for everyone. We too need to trap and analyse our sensations, assembling from a thousand diverse hints the material that will form not so much a work of fiction but something far more important: the fabric of our own future working lives.


So far we’ve been collecting feelings. But there is a next step. The mind needs to connect and generalise outwards from these feelings – while keeping in mind that their implications are almost always indirect. For example, the pleasure of reading a magazine shouldn’t automatically be taken to imply that we must logically try to work for a magazine. Our satisfactions deserve to be examined a little more closely in order accurately to reveal the real range of options before us. When they are attended to properly, the sensations around magazine-reading typically contain a compression of a number of agreeable feelings not indelibly associated with the professional structure of a career in consumer publishing: it might be that we are being drawn to something about the paper stock, or maybe the pictures of interiors or the tone in the problem pages or an atmosphere of dynamism that promises to compensate for a gap in our own background. These pleasures might have occurred while reading a magazine, but they are not – it emerges – especially tied to magazines. Our initial analysis may have passed too swiftly over the real import of our sensations and can lead us in dangerously false directions. In fact, properly sifted, our feelings might prompt us towards a career that has nothing at all to do with magazines: we may be more suited to a stationery firm, a psychotherapy practice or an industrial design studio. The information relevant for guiding us to these careers just happened to manifest itself in the back issues of Bella or Better Homes and Gardens.

This is partly why we should for a long time be so careful not to think with ourselves or others about specific jobs – and should instead focus on qualities within jobs. We should not rush to conclusions like ‘graphic designer’ or ‘teacher’ but rather stick for as long as possible with the pleasures that jobs contain, captured by words like: order, leadership, meaning, calm, team-spirit…


At this point we need to invoke the idea of an inner dialogue. As we proceed, one side of the mind must generously, but insistently, question the other. The observer self should ask the everyday feeling self: ‘so you found this nice, what was it really about the experience that pleased you, it wasn’t everything, it was something more specific. Could you go into greater detail?’ And the feeling self can say: ‘I don’t know, I’m not sure. It was just sweet’. And the observing self can come back: ‘give it another go. It’s fine that you are unsure, we’ll circle around for another approach. Remember, that other time, there was something a little bit similar but not exactly the same. What if we compare them’. And gradually the initial hints yield up parts of the information they contain about what really makes us happy or upset – and hence edge us a little way further forward towards understanding who we can and ideally should be around work.

It isn’t only pleasurable sensations that hold out clues for the future. Envy too is a vital, if more unexpected guide. Shame is a natural response to feelings of envy. However, to feel embarrassed by our envious moments risks encouraging us to repress them – and therefore, to lose out on deriving some hugely important lessons from them. While envy is uncomfortable, squaring up to the emotion is an indispensable requirement for determining a career path; envy is a call to action that should be heeded, containing garbled messages sent by confused but important parts of our personalities about what we should do with the rest of our lives. Without regular envious attacks, we couldn’t know what we wanted to be. Instead of trying to repress our envy, we should make every effort to study it. Each person we envy possesses a piece of the jigsaw puzzle depicting our possible future. There is a portrait of a ‘true self’ waiting to be assembled out of the envious hints we receive when we turn the pages of a newspaper or hear updates on the radio about the career moves of old schoolmates. Rather than run from the emotion, we should calmly ask one essential and redemptive question of all those we envy: ‘What could I learn about here?’



Even when we do attend to our envy, we generally remain extremely poor students of envy’s wisdom. We start to envy certain individuals in their entirety, when in fact, if we took a moment to analyse their lives we would realise that it was only a small part of what they had done that really resonates with us, and should guide our own next steps. It might not be the whole of the restaurant entrepreneur’s life we want, but really just their skill at building up institutions. Or we might not truly want to be a potter and yet we might need in our working lives a little more of the playfulness on display in the work of one example we know. What we’re in danger of forgetting is that the qualities we admire don’t just belong to one specific, attractive life. They can be pursued in lesser, weaker (but still real) doses in countless other places, opening up the possibility of creating more manageable and more realistic versions of the lives we desire.

We must learn to tease out insights concealed in apparently tiny movements of satisfaction and distress scattered across our lives. Once we see how vague our minds really are – and how naturally tricky it is for us to piece together the answers to complex but highly important questions about our futures – we can gain a new perspective. We start to appreciate that our career analysis is going to take time, that it has many stages, that the reach for an immediate answer can backfire – and that it is a strangely magnificent, delicate and noble task to work out what one should most justly do with the rest of one’s brief life on earth.

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