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Chapter 2: work: Finding Work

On Career Crises

In 1700, in Western Europe, there were some 400 different kinds of jobs you could choose from. Nowadays, there are approximately 500,000. No wonder if we sometimes have a bit of trouble settling on what we might want to do.

For most of history, the majority of humans have believed that this life is not the only chance we get to fulfill ourselves. There will be other lives beyond death, in which we will be able to correct the errors made here on earth. Career anxiety stems – in part – from a growing inability to believe in next lives.


An average life might be – only – 600,000 hours long. Identifying fulfilling work requires a judicious blending of fear and haste – with self-examination and patience.

We pin our hopes for happiness on Love and Work. And yet in relation to both, refuse to plan methodically, to understand ourselves thoroughly, to train relentlessly and to go into therapy before we act. We worship instinct in precisely the wrong places.

Seldom are we both so acutely dissatisfied and yet so unsure about what would satisfy us as we are in relation to our work. We know only what is wrong rather than what would be right; our displeasure cries out to be heard and yet refuses to point us in any clear direction when we bend down to hear it.


As with relationships, it’s an immense relief – and no sign of meanness – to know that other people are also very unhappy around their work. Not feeling alone is a significant, dignified consolation.

The witching hour for career crises is late Sunday afternoon, usually 5pm: when the vague hopes and sense of possibility of the weekend finally crash into the cold realities of the week ahead. The extent of our despair is a measure of our degree of unused potential.

Career anxiety is our latent talent howling through our minds, desperate not to go to the grave unspent.


The modern meaning of life: that our deepest interests should find external expression in a form that others will find useful – and that will bring in sufficient funds for a bourgeois life. The ambition is enormous, beautiful and worthy of solemn respect for its trickiness.

It is only in very recent history that we’ve even attempted not just to make money at work, but also – extraordinarily – to be happy there as well. How deeply peculiar the idea would have sounded to most of our ancestors: especially the aristocrats who never worked and the working classes who would mostly strongly have wanted not to. Happy work is the genius, malevolent invention of the bourgeoisie.


Our career crises are aggravated by the sense that our talents aren’t real unless a) they make us money b) we mine them full time c) they aren’t just hobbies. Such dogmas are, at the very least, open to question.

We reassure ourselves about the amount of time we have left by pegging our imagined death to the date of the average lifespan, without remembering that long before we reach that terminal point, we will have passed through years of growing infirmity, terror as our friends die off, a sense that we no longer feel at home in the world and humiliating bladder problems. In other words: we must never hold back from a useful panic at how little time there is left.


Given how consequential the issue it treats is, how extraordinary that career counselling should still be the most amateur and haphazard of occupations, about as shoddy as medieval brain surgery. 

Many of us are still trapped within the career-cage unwittingly created for us by some  hasty ignorant choices made by our unknowing 18-year-old selves.

In the utopia, we would start studying ‘What I want to be when I grow up?’ from the age of 5 to 18, one hour a week, rising to three by the senior year of school.


Where your talents and aptitudes meet the needs of the world, that is the zone of our distinctive life mission.

Write down 10 jobs that your acquaintances from university are pursuing that you yourself definitely have no interest in. List the reasons why. Start to understand the particularities of your working identity.

What we want above all is meaningful work – which means in essence: work that either alleviates the suffering or increases the pleasure of other people.



When work feels meaningful, you’d be ready to lay your life down for it in return for a salary roughly equivalent to the minimum wage. When you know it ultimately makes no sense, you quibble over millions. Soldiers vs. bankers.

Envy feels unpleasant and shameful, but it contains vital clues as to your own submerged ambitions. Keep a record of everyone you meet whose job makes you envious. Slowly assemble a portrait of your ideal occupation through an analysis of your envious emotions. Keep an Envy Diary.

We often don’t make any change to our careers because we are fixated on enormous transformations – and disregard the role of evolutions. But a whole new career might germinate from an enrolment on an evening class once a week.


People don’t tend to leave jobs because of the pay or even the office politics. They leave when they are no longer learning.

Reflecting back on our most satisfying childhood interests matters in part because we were at that stage free of the two great anxieties that later inhibit the flowering of our real working selves: the need for money and the longing for status. True success might mean, by 50, having returned in key ways to what it was fun to do at five.

All parents unwittingly (or not) create a sense that certain jobs are not possible for their children: because the jobs are too lowly, or too high – or just because people in our family don’t do that kind of thing. Reflect on 10 occupations that might have been plausible but were (psychologically) off the table back home.


Serfdom had ended in Western Europe by the early 15th century. But it continues as a psychological category in our unconscious. Such things can take a few millenia to work themselves through. It is why we are usually so catastrophically modest about what we deserve to achieve.

It is humbling, not a little ridiculous and yet deadly consequential that the greatest part of our success in life should depend on CONFIDENCE, a subject never taught at school, that sounds like the preserve of dumb self-help manuals – but that will nevertheless determine how much we go on to dare (which is the half of it at least).


If confidence can’t be summoned in more standard, gentle ways, death is always there as a resource to frighten us into productivity.

Change begins when the fear of not acting at all at last outstrips the paralysing fear of making a mistake.

MONEY, CREATIVITY, RESPECT, STABILITY. Rank in order of importance.


Recognise how thin your knowledge of possible occupations may be – because of the unhelpful influence of art (especially film) which relentlessly throws the spotlight in the same few places: doctor, lawyer, politician… How many people have missed their vocation because there have – as yet – been no TV dramas set in the world of logistics.

When we think of changing careers, we’re often held back by the thought of a few friends in particular who we guess would be especially surprised and somehow offended. A career shift might involve, in part, readjusting one’s circle of friends.

Our prospective working selves are like Russian dolls. There are at least five utterly plausible working selves within each of us. We are multiple selves in vain search of singular identities.


On a large sheet of paper, make a map of how you have got to where you are now in the shape of a river; show tributaries feeding the main current and dams where things got blocked or failed.

What job is the person doing whom you would most like to see fail? There are clues here.

Make a list of your fears in relation to work, among them: I won’t earn enough; I will be ridiculed; I will disappoint X; I will be bored; I won’t make a contribution to society; I won’t properly mine my talents. Give each a seriousness score from 1-10.


A palliative nurse described one of the major regrets of the dying as the wish they’d had the courage to live a life true to themselves, not the life others expected of them.

Stop thinking of jobs you might want to do – and start to think of qualities in jobs. In short, not ‘graphic designer’ or ‘teacher’ but words like: creative, leadership, meaning, calm, team-spirit.

We face two tasks: to get on well with our parents. To have a job we like. Parents should never make the choice harder than it is.

What I fear most about my career going wrong is: I won’t earn enough; I won’t be creative enough; I won’t make a contribution to society; I will be a nobody. Arrange according to urgency.


Which of these are you – in the end – best at: numbers, words, images, people?

My mother/father gave me a sense that a good career is… If only my mother/father had really helped me to be a…

The prospect of succeeding is remarkably scary. Who or what experience may have made you feel as though you may not deserve success?

Not having a plan quickly puts us at the mercy of those who have one.

To create; To help; To serve; To teach; To design; To build; To earn; Give a score out of 10 to each.

Email seven friends and tell them you are taking part in an experiment which forces you to ask them what five jobs they believe you might be suited to other than the one you’re currently pursuing.

Every successful business is at heart an attempt to solve someone’s problem: what are – for  you – mankind’s most interesting problems?

Every moment of unhappiness is, potentially, a new business waiting to be born.


In what areas of life are you thought by your friends to be especially ‘fussy’? Treat this heightened sensitivity as a storehouse in which business ideas lie buried.

Look back to the most ‘ridiculous’ ideas for a business you ever had: imagine they were not as ridiculous as all that. Emerson: ‘In the minds of geniuses, we find – again – our own neglected thoughts.’

If I was forced to run a shop, it would sell…

Don’t berate yourself for being preoccupied with your professional future. Don’t let others describe the anxiety as neurotic. Give the agony the time it needs; luxuriate in it. Prepare to spend one hour every evening on it and four hours every weekend.

That you haven’t yet found your vocation is no indication that you will never discover it. Even if you are currently seventy-three.


It’s entirely acceptable to have wasted so much time.

How unusual to seek to be happy through work. We’re trying to do something new and pioneering, like space flight – and there might be accidents on our missions.

A job you love doesn’t mean that there is only job you could love. So it will always be reasonable to have regrets.


It’s easy to imagine that everything has been done and tried: the exciting and simultaneously alarming truth is that we have as yet barely scratched the surface. There are hundreds of years of invention and creativity left in our species.

There’s a temptation to see the immature sides of your parents as stemming from their work – and therefore to discount following in their professional footsteps, thereby perhaps missing out on some potentially rather good opportunities. Don’t have too much contempt for the corrupted familiar.

Be suspicious of so-called “creative industries”: they tend to be far more “industries” than “creative” centres. There are perhaps in the end very few places where you can be both properly secure and properly creative.


We often judge jobs by their beginnings – and therefore do certain careers a bad disservice, while overvaluing others. What the career looks like for the first five years may not be at all what it looks like later. Many of the best jobs don’t have good beginnings at all.

Time to rehabilitate and lend dignity to the notion of regret: of course there will be things we will never get to do… Spread a consoling spirit by learning to ask at parties, with gentle melancholy, not ‘what do you do?’ but ‘what do you wish you might have done?’