Notes from ‘How to find fulfilling work’

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Introduction
This book, from the self-help series of The School of Life, not only provides some actionable insights in finding fulfilling work but also, provides a brief history of our attitude towards work and its meaning in our lives.
It begins with an unfulfilled work life, of course. As much as it is important to be grateful to have a job, it is also, equally catastrophic to be too grateful that can eventually, turn into complacency making us settle down for mediocrity. We must be self-aware of our choices when building our work life. The below passage echoed the thoughts I had when I was working as an IT consultant back in India a few years ago.
I assumed I should be grateful to just have a job, let alone a ‘good’ one. So I focused harder on trying to fit in, and when that did not work, I lived for the weekend. I did this for ten years, burning the candle at both ends. Eventually, it caught up with me. I became chronically stressed and anxious.
The problem was that all the alternatives – changing career, starting over again – seemed impossible. How could I trade in the security of my comfortable life for uncertainty? Wouldn’t I be risking all the progress I had made? I also felt guilt that I should even be searching for such luxuries as ‘meaning’ and ‘fulfilment.’ Would my grandfather have complained at such fortune? Life appeared to offer an awful choice: money or meaning.
History of Work
The desire for fulfilling work – a job that provides a deep sense of purpose, and reflects our values, passions, and personality – is a relatively modern invention.
Open Samuel Johnson’s celebrated Dictionary, published in 1755, and you will discover that the word ‘fulfillment’ does not even appear.
For centuries, most inhabitants of the Western world were too busy struggling to meet their subsistence needs to worry about whether they had an exciting career that used their talents and nurtured their wellbeing. One of the earlier schools of thought suggested the ‘grin and bear it’ approach: the view that we should get our expectations under control and recognize that work, for the vast majority of humanity – including ourselves – is mostly drudgery and always will be.
Forget the heady dream of fulfillment and remember Mark Twain’s maxim, ‘Work is a necessary evil to be avoided.’ The best way to protect ourselves from all the optimistic pundits pedaling fulfillment is to develop a hardy philosophy of acceptance, even resignation, and not set our hearts on finding a meaningful career.
However, today, the spread of material prosperity has freed our minds to expect much more from the adventure of life. There is an emergence of two new afflictions in the modern workplace, both unprecedented in history: a plague of job dissatisfaction, and a related epidemic of uncertainty about how to choose the right career. 
Never have so many people felt so unfulfilled in their career roles, and been so unsure what to do about it. Added to this is the death of the ‘job for life,’ now a quaint relic of the twentieth century. In its place is a world of short-term contracts, temping, and nomadic career wanderings, where the average job lasts only four years, forcing us to make more and more choices, often against our wishes. Choosing a career is no longer just a decision we make – often frighteningly uninformed – as a spotty teenager or wide-eyed twenty-something. It has become a dilemma we will repeatedly face throughout our working lives.
Although the search for a fulfilling career has only become a widespread aspiration in the West since the end of the Second World War, it has its roots in the rise of individualism in Renaissance Europe. This was the era in which celebrating your uniqueness first became fashionable. We are the inheritors of this tradition of self-expression. Just as we seek to express our individuality in the clothes we wear or the music we listen to, so too we should search for work that enables us to express who we are, and who we want to be.
I was scared about contemplating anything but law. Law identified me; indeed, I thought it defined me. Many lawyers are like this – it is your label, it is who you are. To lose that identity was going to make me feel naked and empty. If you are not a lawyer, what are you? Who are you?
However, when somebody asks us the deadening question ‘What do you do?’, let us set our sights on giving an enlivening answer, which makes us feel that we are doing something truly worthwhile with our lives, rather than wasting away the years in a career that will leave the bitter taste of regret in our mouths.
We experience unfulfillment when the work and self are not aligned.
The job is interesting, but it is rather conventional for the kind of person I am. I feel it is not the permanent me.
On the face of it, I look like a very conventional person, yet I still regard myself as deeply unconventional. Paradox is too strong a word, but there’s a tension there.
Karl Marx, one of the first social thinkers to take the subject of career choice seriously, saw that the erosion of feudalism and the rise of wage labor in the eighteenth and nineteenth centuries offered some hope for change. Each worker had ‘become a free seller of labour-power, who carries his commodity wherever he finds a market. That sounds like progress. However, he also pointed out that this was an illusory freedom because most of the possibilities on offer were back-breaking industrial jobs that turned people into slaves of the capitalist system, ‘which, vampire-like, lives only by sucking living labor.’ The nineteenth century may have been the era of Dickensian poverty and hellish laboring in the mines and textile mills, but it simultaneously witnessed a revolution in career choice through the spread of public education and the invention of the career open to talent.
It was increasingly common, especially in northern Europe, for job selection to be based on merit and qualification rather than bloodline or social connections. Here, at last, was a chance to scramble up the social hierarchy – though you were most likely to benefit if you were a middle-class man.
For most of history, people had little choice about the jobs they did. Work was a matter of fate and necessity rather than freedom and choice. Since the industrial revolution, however, the range of career opportunities has expanded beyond recognition. We need to understand not only the origins of our new era of choice but how we have become psychologically tyrannized by our hard-won freedom.
You do not realize how hard it is to be free.
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Picture Courtesy: Found on my LinkedIn timeline that I feel is relevant to this blog post.

Challenges involved in choosing a career
Beneath the sheer number of possibilities lie three fundamental reasons why career choice is often such a conundrum: we are not psychologically equipped to deal with the expansion of choice in recent history; we are burdened by our pasts, especially the legacy of our early educational choices; and because the popular science of personality testing rarely helps us pinpoint fulfilling careers. As we gradually grasp how these forces shape our lives, we will discover that being able to identify the causes of our career dilemmas is the beginning of moving beyond them.
1. Plenty of choices
How much choice have you had over your working life compared with your parents or grandparents? In all probability, you will have had the good fortune to enjoy many more opportunities than your forebears.
My father had arrived in Australia as a refugee from Poland in 1951 and had little opportunity to pursue his talents as a mathematician, linguist, and musician. I, on the other hand, had career possibilities that he could never have hoped to imagine. Moreover, yet there I was complaining, in the National Gallery in Canberra, feeling perplexed – almost paralyzed – by the array of choices before me.
Although a life without choice is almost unbearable, says Schwartz, we can reach a tipping point where having an abundance of options becomes an overload. ‘At this point, choice no longer liberates but debilitates. It might even be said to tyrannize.’
Schwartz believes that similar effects can arise in the realm of career decision-making, since we now have so much more options than in the past, having left behind the days of Benjamin Franklin. ‘One effect of having so many options,’ argues Schwartz, ‘is that it produces paralysis rather than liberation – with so many options to choose from, people find it very difficult to choose at all.’ A second effect is that ‘even if we manage to overcome the paralysis and make a choice, we end up less satisfied with the result of the choice than we would be if we had fewer options.‘ His main explanation for this apparent paradox is that we can always imagine having made a better choice so we will regret the decision we did make, and thus feel unhappy about it. We get so worried about regretting making a bad choice that we may end up making no decision at all, and remain frozen in our current unfulfilling career.
Are there any solutions for dealing with the choice overload that afflicts modern society? Schwartz makes two main suggestions. First, we should try to limit our options. Second, we should ‘satisfice more and maximize less.’ By lowering our expectations, we can avoid much of the angst and time-wasting that arises from having an excessive choice. What we need to do is narrow down the choices by thinking more deeply about the core elements of a fulfilling career, and then devise concrete ways of testing out which of them best suit our aspirations.
2. Educational choices made in the youth
We find ourselves following the furrows of a career track with origins deep in our personal histories, which can prevent us veering off in more adventurous directions. The way that education can lock us into careers, or at least substantially direct the route we travel, would not be so problematic if we were excellent judges of our future interests and characters. However, we are not. The result is that people so often find themselves stuck in careers that do not suit their personalities, ideals or expectations. Their educational choices and opportunities have come to haunt them.
I am not going to be the same person I am at 16 as I am at 45. I am going to have different values, opinions, and motivations.
Family pressures and expectations can also shape our early educational and job decisions, especially for the children of immigrants or those with high-achieving parents. Although family opinion might shape our choices as impressionable youths, as we get older this influence gradually fades away.
This kind of thinking resembles what economists describe as a decision based on ‘sunk costs.’ The sunk costs are just too high to ignore. This sense that we might be squandering everything we have struggled to achieve is one of the greatest psychological barriers facing those contemplating a career change. If you have spent years working your way up the ladder in law, advertising or any other profession, and then realize you are miserable and want to leave, you will hardly be consoled by a friend who reassures you that it was ‘all part of life’s journey’ or that ‘nothing is ever wasted’.
On a similar note, when I implemented the KonMari method of decluttering my home, one of the theories the founder, Marie Kondo suggested was to let go off things that we still stick to due to ‘sunk costs.’
The upshot is that we can find ourselves in a constant struggle with our pasts, unable to make a decision to try something new because of an allegiance to the person we have been, rather than to the person we hope to become.
We are caught between two forms of regret. On the one hand, the regret of abandoning a career into which we have put years of time, energy and emotion. Moreover, on the other, the possibility of looking back on our lives in old age and regretting that we did not leave a job that was not offering us fulfillment. The latter, according to the latest psychology research: the most emotionally corrosive form of regret occurs when we fail to take action on something that matters deeply to us. The philosopher A.C. Grayling has come to a similar conclusion: ‘If there is anything worth fearing in the world, it is living in such a way that gives one cause for regret in the end.’
There comes the point when splitting up is probably the healthiest option, painful though it may be. We all change: we learn more about ourselves, and shift our priorities and perspectives, under the challenging tutelage of human experience.
Fear of failure is close to being a universal affliction. It can be consoling to know that we are not alone in our uncertainties. Even if we know that others share our fears, and are similarly riddled with doubts behind a carapace of outward self-confidence, we still need to understand why anxiety about the career change looms so large in our lives.
That is the problem with the ‘plan then implement’ model: it rarely works. What happens is that we find ourselves in new jobs that don’t suit us, because we have not had any experience of what they are like in reality. The job matches our checklist, but we fail to fall in love.
Alternatively, we spend so much time trying to work out what the perfect career would be, ceaselessly researching or getting lost in confused thoughts about the best option, that we end up doing nothing, overwhelmed by fears and procrastination, trapped by the paradox of choice.
It will gradually become clear that our greatest hope for overcoming our fear of change and finding a life-expanding career is to reject the traditional model of the career change, which advises us to plan meticulously then take action, and replace it with the opposite strategy, which is to act now and reflect later. We must adopt Leonardo da Vinci’s adventurous credo, ‘experience will be my mistress.’ It is a bit like dating. So maybe it is not about thinking and planning, but about doing lots of job dating, trying things out until you feel a spark. We must enter a more playful and experimental way of being, where we do then think, not think then do.
By far the biggest mistake people make when trying to change careers is to delay taking the first step until they have settled on a destination. The only way to create change is to put our possible identities into practice, to work and to craft them until they are sufficiently grounded in experience to guide more decisive steps. We learn who we are by testing reality, not by looking inside. Reflection best comes later, when we have some momentum and when there is something new to reflect on.
This ‘act first, reflect later’ process includes some interesting ideas as follows.
a. The Map of Choices is designed to enable you to reflect on where you have come from before you focus on where you are going. You start by spending ten minutes drawing a map of your career path so far. On this map, you should indicate not only the jobs you have done but the different motivations and forces that have shaped your route. If a major career decision was influenced by the prospect of more money or status, show it on your map – similarly if you were driven by your talents, passions or values. There may be general patterns you can see, such as the way you never stay in a position for more than a couple of years, or that you seem to have fallen into most jobs rather than choosing them.
b. Imaginary Lives is a thought experiment which aims to take your ideas a stage closer towards specific job options. Imagine five parallel universes, in each of which you could have a whole year off to pursue any career you desired. Now think of five different jobs you might want to try out in each of these universes. How does each career measure up against the two motivations in the previous activity that you chose to prioritize in the future? If you decided, for instance, that you want a combination of making a difference and high status, check whether your five imaginary careers might provide them. The point is to help you think more deeply about exactly what you are looking for in a career, the kind of experiences that you truly desire.
c. Writing a Personal Job Advertisement allows you to seek the advice of other people. The concept behind this task is the opposite of a standard career search: imagine that newspapers did not advertise jobs, but rather advertised people who were looking for jobs. You do it in two steps. First, write a half-page job advertisement that tells the world who you are and what you care about in life. Put down your talents, your passions, and the core values and causes you believe. Include your personal qualities. Moreover, record anything else that is important to you. Keep it at the level of underlying motivations and interests. Make a list of ten people you know from different walks of life and who have a range of careers – maybe a policeman uncle or a cartoonist friend – and email them your Personal Job Advertisement, asking them to recommend two or three careers that might fit with what you have written. Tell them to be specific. You will probably end up with an eclectic list of careers, many of which you would never have thought of yourself.
d. Experimental projects take three main forms, in descending order of personal challenge: radical sabbaticals, branching projects, and conversational research. They are designed to suit different kinds of people, with different career ambitions, at different stages of their journey. All of them, though, can help pinpoint which of our possible selves offers the greatest prospect for fulfillment.
(d1) The key to finding a fulfilling career is to experiment with these possibilities in that rather frightening place called the real world in the form of a ‘radical sabbatical.’ The radical sabbatical involves granting yourself a dedicated period for action-based projects, such as shadowing or accompanying people in their work or volunteering in an appealing organization. We may not even realize that we are unfulfilled until we immerse ourselves in an alternative world.
(d2) A second and more common form of experimental project is the branching project, or what Ibarra calls a ‘temporary assignment.’ Apart from options such as work shadowing or volunteering, we could do a training course that gives us a taste of a different career or do an initial, scaled-down version of a prospective job. In effect, you will have taken some small and relatively unrisky steps, but which have led to big results. With each step you take, more confident you will feel, making the journey easier as you go along, and circumventing your inbuilt evolutionary aversion to risk.
(d3) A final form of experimental project is conversational research. Perhaps less daunting than a radical sabbatical or a branching project, it can be just as effective. It simply requires talking to people from different walks of life who are engaged in the types of work you might imagine doing.
One of the best ways to escape the confines of our worldview is to shift our peer group and talk to people whose work experiences and daily lives are very different from our own. Conversational research is also a particularly good strategy for making discoveries about careers that are difficult to test out in branching projects. Such conversations bring us closer to understanding the realities of a career change, with all its pleasures and pains. Furthermore, studies of career change consistently show that most people find new jobs through personal contacts rather than official channels and that shifting career require developing new social networks. Conversational research creates openings in both these realms.The purpose is not only to give you surprising ideas for future careers but also to help you see your many possible selves.
Seize this very minute; What you can do, or dream you can, begin it; Boldness has genius, power, and magic in it. The quest to find fulfilling work begins with acting, but is resolved by reflecting.
3. Personality tests
An important reason why the search for a fulfilling career can feel so difficult is that this apparently ‘scientific’ approach to career advice seldom provides the answers we hope. To explain exactly why this is so, we need to return to the roots of career advice itself.
One of the darker secrets of the history of career counseling is that it originated in the vogue for phrenology in the US in the nineteenth century, which itself had roots in racial theories suggesting that the superiority of whites over other races was evident in their finely shaped skulls. The interesting – and somewhat alarming – fact about the MBTI is that, despite its popularity, it has been subject to sustained criticism by professional psychologists for over three decades. One problem is that it displays what statisticians call low ‘test-retest reliability.’ The second criticism is that the MBTI mistakenly assumes that personality falls into mutually exclusive ‘either/or’ categories.
According to official Myers–Briggs documents, the test can ‘give you an insight into what kinds of work you might enjoy and be successful doing.’ Its success is primarily due to ‘the beguiling nature of the horoscope-like summaries of personality and steady marketing.’
Human personality does not neatly reduce into sixteen or any other definitive number of categories: we are far more complex creatures than psychometric tests can ever reveal.
Given that scenario, it is best to follow one’s gut and intuition. We know what’s best for us. Keep a diary/journal. Write down what you enjoy and analyze them to see if there is a pattern that connects all. Use MBTI as a guideline but, always trust your intuition.  On a sheet of paper, write down – or describe in pictures and diagrams – your responses to the following: What are the three main reasons why you are feeling confused about where to go next? What are your three greatest fears about changing career? What are the three biggest practical challenges you face?
We need to boldly go where most personality tests fail to take us and explore exactly what kinds of fulfillment we wish to seek in our careers. 
In addition to the above three, there are other challenges as well.
4. Money
Everything was determined by money or rather a lack of it.
We typically get caught in what psychologist Martin Seligman calls a ‘hedonic treadmill’: as we get richer and accumulate more material possessions, our expectations rise, so we work even harder to earn money to buy more consumer goods to boost our wellbeing, but then our expectations rise once more, and on it goes. None of it does much to boost our sense of having a fulfilling and meaningful life, and may well contribute to higher levels of anxiety and depression since we are forever yearning for more.
It is a powerful appetite which has no inbuilt mechanism to alert us to when we have had enough; we want more and more – especially, it seems, just that little bit more than everyone else. Although we have relative material abundance, we do not, in fact, have emotional abundance. Many people are deprived of what matters. Lacking emotional security, they seek security in material things. So we may be looking for fulfillment in the wrong places – in having rather than being, in accumulating possessions rather than in building nurturing, empathic relationships.
If we truly aspire to live the good life, then we would be rash to allow money to be our primary goal. What would you most like to change about your attitude to money?
Choosing a career for its monetary rewards is the oldest and most powerful motivation in the world of work. ‘Men have often criticized that money is the chief object of their wishes and is preferred above all else, but it is natural and even unavoidable. For money is an inexhaustible Proteus, ever ready to change itself into the present object of our changeable wishes and manifold needs. Money is human happiness in the abstract.’ So does this mean we should place our hopes for career fulfillment in substantial salaries and big bonuses? The answer is no.
The lack of any clear positive relationship between rising income and rising happiness has become one of the most powerful findings in the modern social sciences. Once our income reaches an amount that covers our basic needs, further increases add little, if anything, to our levels of life satisfaction.
What seems to matter to people is the quality of their relationships in the workplace: both ‘respect’ and ‘the people you work with’ head up the list.
5. Status
Like the ancient Romans, we still have a strong yearning for reputation and glory. However, as the eighteenth-century philosopher, Jean-Jacques Rousseau warned, ‘this universal desire for reputation,’ in which we judge ourselves through other people’s eyes, is fraught with dangers. We can easily find ourselves pursuing a career that society considers prestigious, but which we are not intrinsically devoted to ourselves – one that does not fulfill us on a day-to-day basis.
Our peer group shifts and the status we seek is forever just beyond our grasp, much like the ‘hedonic treadmill’ that continually raises our expectations as consumers.
The writer and spiritual thinker C.S. Lewis identified this problem when he said that most of us desire to be a member of an ‘inner ring’ of esteemed or important people, but we ‘will reach no “inside” that is worth reaching’ since there are always more rings within it. The lesson may be the simple one that we should not be so concerned about what other people think about us.
6. Meaning
One of the greatest frustrations is that it is often difficult to see, in concrete terms, what difference your work is making. A second challenge is the tensions that can arise between making a difference and making money. Enterprise and ethics do not easily mix.
Rather than hoping to create a harmonious union between the pursuit of money and values, we might have better luck trying to combine values with talents. This idea comes courtesy of Aristotle, who is attributed with saying, ‘Where the needs of the world and your talents cross, there lies your vocation.’ That may be the single most useful piece of career advice to have emerged in the past 3,000 years.
Five different aspects of what can make a job meaningful: earning money, achieving status, making a difference, following our passions, and using our talents. They are the psychological underpinnings of the work we do, and why we do it. Both money and status are known as ‘extrinsic’ motivating factors since they are about approaching work as a means to an end, whereas the remaining three are ‘intrinsic,’ with the work valued as an end in itself.
Clarifying our thoughts on where our priorities lie can help us develop a personal vision of what meaningful work looks like, so we can narrow down the career possibilities and make the right choices.
As we explore each motivation, in turn, we will discover not only their individual challenges and the tensions between them, but that there is no single blueprint for a meaningful career. It will also become clear that pursuing a career mainly because it offers the tempting rewards of money and status is an unlikely route to the good life. Passions and Talents are the most likely way to satisfy our hunger for fulfillment.
It is an increasingly common desire, even in our age of rampant hyperindividualism, and one that resembles the ancient Greeks’ aspiration to perform some virtuous and noble deed that would give their lives a sense of purpose and ensure their immortality in historical memory. We want to be able to look back in old age and feel that we have left our mark.
Most people intuitively know that making a difference is a promising path to a fulfilling career. Moreover, it is borne out by the evidence. A major study of ethical work by Howard Gardner, Mihaly Csikszentmihalyi, and William Damon showed that those doing what they call ‘good work’ – defined as ‘work of expert quality that benefits the broader society’ – consistently exhibit high levels of job satisfaction. The moral philosopher Peter Singer argues that our greatest hope for personal fulfillment is dedicating our lives – and if possible our working lives – to a ‘transcendent cause’ that is larger than ourselves, especially an ethical one such as animal rights, poverty alleviation or environmental justice. Such views build on deep traditions of religious thought that promote the idea that giving to others through our work is spiritually uplifting. As Martin Luther King said, ‘Everybody can be great because everybody can serve.’ As Simon Sinek said in one of his interviews, ‘only service can save us.
The emergence of new economic sectors such as social enterprise raises the question of whether it might be possible to enjoy both the intrinsic rewards of being true to our beliefs and the extrinsic rewards of earning money. Although we may believe that there are no ethical careers that can easily accommodate our talents or expertise, almost any professional skill can be applied in a job that makes a difference: Where do your talents meet the needs of the world? While an ethical career is one intrinsically rewarding path to the good life, there is also the option of focusing on your passions and talents. Forget money, status or even making a difference: do what you love and what you are really good at.
The prize of meaningful work goes to those who pursue intrinsically rewarding jobs that make a difference, use their talents or reflect their passions – or that involve some intoxicating combination of the three. Although we all desire money and status to some degree, a career decision driven primarily by these extrinsic motivations is unlikely to offer sublime depths of meaning to our lives.
7. Alternate interests
While some people swear that transforming their hobbies or interests into their jobs was the turning point on the road to fulfillment, others claim that it was a terrible mistake. You might love building model trains, but starting up a company selling them online, with all the stresses involved, could drain all the joy from your passion, and make you nostalgic for those rainy Sunday afternoons tinkering with engines when you had no sales figures to worry about. Mixing work and play are usually worth the risk of potential contamination.
8. Specialization
There is a further dilemma awaiting those intent on pursuing their talents or passions in the workplace, which is whether we should aim to be specialists, directing ourselves towards a single profession, or aim to become generalists, developing our various talents and passions across several different fields. I think of this as the question of whether we should aspire to be high achievers or ‘wide achievers’.  
For over a century, Western culture has been telling us that the best way to use our talents and be successful is to specialize and become an expert in a narrow field. This ideology is to a significant extent rooted in the division of labor that emerged during the industrial revolution, which split most jobs into tiny segments to increase efficiency and production levels. So now many people find themselves funneled into working in a limited field.
Specialization may be all very well if you happen to have skills particularly suited to these jobs, or if you are passionate about a niche area of work, and of course, there is also the benefit of feeling pride in being considered an expert. However, there is equally the danger of becoming dissatisfied by the repetition inherent in many specialist professions. Moreover, our culture of specialization conflicts with something most of us intuitively recognize, but which careers advisers are only beginning to understand: we each have multiple selves.
A master in the art of living draws no sharp distinction between his work and his play; his labor and his leisure; his mind and his body; his education and his recreation. He hardly knows which is which. He simply pursues his vision of excellence through whatever he is doing and leaves others to determine whether he is working or playing. To himself, he always appears to be doing both.
We have complex, multi-faceted experiences, interests, values, and talents. It raises the possibility that we might discover career fulfillment by escaping the confines of specialization and cultivating ourselves as wide achievers. Only then may we be able to develop the many sides of who we are, allowing the various petals of our identity to unfold fully.
There are two classic approaches to being a wide achiever: becoming a ‘Renaissance generalist,’ who pursues several careers simultaneously, or a ‘serial specialist,’ who does one after another. 
The first option is modeled on the Renaissance idea that to be fully human we should do all we can to foster the array of our individual talents and the many dimensions of our personality. Perhaps the greatest Renaissance generalist of them all was Leonardo da Vinci. He was not only a painter but also an engineer, inventor, natural scientist, philosopher, and musician. History has never seen a more accomplished wide achiever. Leonardo’s Vitruvian Man, arms stretched out wide, is the quintessential symbol of the Renaissance wide achiever. Leonardo was an early example of what is today known as a ‘portfolio worker,‘ a term invented by management thinker, Charles Handy. Personally speaking, I would like to call myself a renaissance generalist. I am an HR consultant, who is interested in singing, playing piano, and writing. A portfolio worker develops a range or ‘portfolio’ of careers, each of which he does part-time, and possibly on a freelance basis. Handy believed that this was a smart survival strategy in turbulent economic times, reducing the risks of unemployment. However, we need not think about portfolio working only in such negative terms. Adopting the more positive Renaissance perspective, pursuing several careers at the same time is a way of thriving and being true to our multiple selves.This approach to being a wide achiever makes sense in a world where the retirement age keeps shifting back and working lives are getting longer: there is more space in which to fit several careers. Even making one substantial career change can free us from a profession that has lost its attractions and allow us to explore other sides of who we are.
Becoming a Renaissance Generalist provides plenty of challenges, not least amongst them the prospect of financial insecurity if you are juggling freelance jobs. So you might feel more comfortable indulging your various talents and passions by becoming a serial specialist.
There are so many interesting things out there – why do just one forever? Everyone should up and quit their job at least once in his or her life. I have done both – quit my job and pursue several things simultaneously. I wonder which category I would fall into. Another example is Helene Godin, who was a successful lawyer for over 20 years and quit one day to pursue baking. Our motivations and ambitions evolve throughout the course of our lives, and we are often poor judges of our future interests. The route of a serial specialist may be just what we need to nurture our many talents and passions, and to lead the many lives that lay dormant within us, like seeds beneath the snow.
9. Self-confidence
People are much more sensitive to negative than to positive stimuli. There are a few things that would make you feel better, but the number of things that would make you feel worse is unbounded.
Evolutionary biologists have attempted to explain why we have this strong negative bias that means we focus much more on potential drawbacks than benefits. They speculate that it may be because we are products of the primal terror experienced by our hominid ancestors. So when it comes to a career change, we are psychologically disposed to magnify everything that could go wrong. Similarly, when thinking about whether a new job might suit us, we are more likely to highlight our personal weaknesses than our strengths.The result is that we tend to exhibit extreme caution, and remain in jobs that – at least regarding fulfillment – are long past their sell-by date.
Without self-confidence, we are as babies in the cradle. – Virginia Woolf.
10. Worldview
Our worldview is a psychological straitjacket that restricts us from pursuing new possibilities. It is our underlying mental frame of reference and belief system. The problem is that we may rarely interact with those who see the world very differently. As Tolstoy noted, most people ‘instinctively keep to the circle of those people who share their views of life and their place in it’. The result is that our existing priorities and values are constantly reinforced. In certain ways, internet filters also, create an echo chamber preventing us from serendipitous encounters of ideas.
11. Nature of work
Meaning is not sufficient for human fulfillment. Most of us also want to enjoy our jobs on a day-to-day basis. That prompts another question about the jobs you tried:  Which gave you the best ‘flow’ experience? Flow has the potential to provide this sense of daily enjoyment and can help us choose effectively between the options. It is now widely accepted as one of the most fundamental indicators of ‘life satisfaction’ or ‘happiness.’ A flow experience is one in which we are completely and unselfconsciously absorbed in whatever we are doing. As Csikszentmihalyi puts it, we are ‘so involved in an activity that nothing else seems to matter.’ When this happens, we are ‘in flow,’ a state that athletes often describe as being ‘in the zone.’ He says that we enjoy such activities because they are ‘autotelic,’ or intrinsically motivating: the action is valuable in itself, not a means to an end. In a typical flow experience, we feel totally engaged in the present, and future and past tend to fade away – almost as if we were doing Buddhist meditation. One of the curious characteristics of flow, according to Csikszentmihalyi, is that it is not limited to ‘high-end’ professions like being a surgeon, but can equally be experienced by butchers, welders or farm workers.
What kinds of activities typically give us flow? It most commonly occurs when we are using our skills to do a task that is challenging, but not so hard that we fear to fail. Flow is also enhanced when we are creative and learning new skills when we can see the immediate impact of our actions, and when we have clearly defined goals.
The implication of the flow theory is that we should aspire to be working in a career that offers us a high flow content. However, this is the point at which it gets controversial. Csikszentmihalyi and many of his followers claim that almost any job can be altered so that ‘its conditions are more conducive to flow.’ Even an apparently mundane job such as being a supermarket cashier, he says, can be approached in a way that makes it brimming with a flow. So we may not need to change our career at all if we are feeling miserable in it: we just need to give ourselves more challenging tasks or focus on the creative aspects of the work. However, the majority of jobs cannot be magically transformed to provide better flow experience. Most workers, especially those in bureaucratic organizations or who do repetitive tasks, just don’t have that much scope to alter their jobs. People who feel unfulfilled in their jobs are unable to adjust them sufficiently so that they can squeeze substantially more flow from them.
It is so important to conduct branching projects: to discover whether a career has high flow potential for you is to have a go at doing it. You can then choose between the options on the basis of which is most likely to put you in the zone. The idea of flow can help us make career decisions in two other ways. First, through conversation. When talking to people whose jobs interest you, don’t just ask vague questions such as ‘What’s it like being a taxidermist?’; Ask them about flow – how often do they have that sense they are in the zone, and what precisely are they most likely to be doing when this occurs? A second strategy is to become a detective of flow in your life by creating a Flow Diary. Spend a month keeping a daily note of the kinds of activities that give you flow – whether it is writing a tricky report at work, or cooking a Sunday lunch for a dozen people. You can then use this knowledge to help identify potentially fulfilling careers.
12. Desire for both stability & freedom
In deciding which career to pursue, we need to find a way to balance our twin desires for security and freedom. Most of us want some stability in our working lives, especially in uncertain economic times. At a deeper psychological level, from the moment the umbilical cord percent and we are cast out into the loneliness of our individuality, we are in search of emotional and material security. Although we may find it in a loving marriage or membership of a community, it can also be found in the workplace through a steady job that not only gives us a guaranteed paycheck at the end of the month, but can also provide a network of friendships, a sense of identity and a feeling that we are valued.
It was this overwhelming desire for security – rooted in a turbulent wartime childhood – that kept my father working at IBM for half a century.
We consider it a price worth paying for a position that offers us an attractive financial package – the classic Faustian bargain of the modern workplace. Sociologists might alternatively suggest they are the unlucky inheritors of the Protestant work ethic, an ideology that emerged in seventeenth-century Europe, promoting the belief that hard work was good for you and would bring you closer to God. The legacy today is that we feel guilty if we are not putting in long days with our nose to the grindstone. In reality, nothing is more damaging to the adventurous spirit within a man than a secure future.
All work is a form of voluntary enslavement.
Flow is not everything. Necessary, yes. However, sufficient on its own, no. We could be doing those challenging and creative flow tasks, yet still not find our work ultimately rewarding, because it does not embody our values or offer any of the other profound forms of meaning explored earlier.
I used to experience flow when writing academic articles and lecturing, but I still didn’t want to work as a university professor.
What we need are both flow and meaning. Even this heady combination is not enough for the deepest forms of fulfillment. There is one more element we must consider, which is whether a job can offer us the liberating gift of freedom. Michelangelo’s sculpture The Captive Slave, seemingly half-finished, shows a figure attempting to free himself from the stone. This work of art is about the struggle for freedom in everyday life.
There are many ways to free our spirit, from inventing our job to unchaining ourselves from the culture of overwork by living a simpler life with more space for pursuing our passions.
The Anarchist Alternative, or How to Invent Your Job: While security may be at the foundation of our hierarchy of needs, human beings are equally driven by the quest for individual freedom. For decades, industrial psychologists have observed that job satisfaction is directly related to ‘span of autonomy,’ meaning the amount of each day during which workers feel free to make their decisions. The desire to ‘be your own boss’ is very common indeed. So if you’ve ever felt frustration at your lack of autonomy, and crave the independence of working for yourself, then you might have an anarchist lurking within you.
It may, however, be possible to feel freedom working in a big organization, especially if you can choose your daily tasks and targets, and are offered benefits such as flexitime. Many firms pride themselves on how much autonomy they give their workers. However, if you seek genuine autonomy, you are much more likely to find it by joining the 20 per cent of Europeans and North Americans who are self-employed. Moreover, the chances are that it will be good for you. ‘Working for yourself makes you happy,’ according to the UK’s Work Foundation.
Being self-employed is wonderful yet awful. There’s no holiday or sick pay, no security. No development opportunities are offered, and there’s nobody to tell you if you are doing a good job or even notice how hard you are working. Work easily bleeds into before breakfast, after dinner and weekends if you are not careful. If things go wrong, there’s no one else to blame or to discuss things. Having said that, you can manage your diary, build relationships with the people you want to build relationships.
It’s helpful to remember that the security you think you are missing out on by not working for a corporation is non-existent. Once you have tasted freedom, it is almost impossible to turn back.
The most radical form of self-employment is to invent your job – a bespoke career. This is an aspiration with origins in the Renaissance ideal of expressing individuality and uniqueness. A bespoke career sometimes described as a ‘customized job,’ is one which you design yourself to suit your particular interests, talents, and priorities. Typically they cannot be found in a standard career guide. Needless to say, these are not professions featured at any careers fair. The internet has revolutionized the possibilities for custom-designed jobs, especially for those with a little entrepreneurial flair. They also usually involve being self-employed, so you can decide exactly when and how you work. A further opportunity has emerged from large companies and organizations farming out a huge portion of their work to freelance consultants, following years of down-sizing. So you might be able to work from home for multiple employers, perhaps from several countries, and take a midday bubble bath without anybody knowing. This all leaves us with a question to ponder: If you could create a bespoke career, what would it look like, and what branching projects would help transform it into reality?
Another efficient way to free our spirit is to become an adherent of simple living, one of the fastest-growing religions of our post-industrial age. By doing so, you would be joining a venerable tradition of individuals who have voluntarily turned against materialism and consumerism in pursuit of a more meaningful – and cheaper – existence. Think of the nineteenth-century American naturalist Henry David Thoreau, who spent two years conducting an experiment in self-sufficiency in the 1840s.
You’ve probably experienced the phenomenon whereby an increase in your salary fails to lead to any increase in your savings because your spending mysteriously expands to fill the space of your available income. Well, the reverse also applies. When your income goes down from working less (or maybe from taking a salary cut to do a more fulfilling job), as a general rule your daily living expenses – on things like food, clothing, and entertainment – will naturally contract to fit your new financial circumstances, and yet you will not feel any worse off. In fact, it is quite likely that you will feel life is better than ever since you will be luxuriating in an abundance of that most precious commodity, time. We must apply the ‘waste not, want not’ ethos of our parents’ generation. We will get so much pleasure in not spending money. We will also, become more creative and be focused on what we need versus what we want.
Making a transition towards simpler living requires embracing Picasso’s philosophy: ‘art is the elimination of the unnecessary.’ One worthwhile experiment is to keep detailed accounts for a month of all your expenses, labeling each item as a ‘need’ or a ‘want,’ and in the following month trying to halve the spending on our ‘wants.’
It is important to recognize that our jobs can cost us money: Think how much you spend on what Joe Dominguez called your ‘work uniform’ (suits, dresses, shoes, bags), on commuting to the office, daily snacks, and on luxury, vacations to help you recover from the stress. Should you be paying so much to be in work?
Simple living also has more general applications to a career change. And a knowledge that you can live lightly could make it easier to shift to a job with less pay but more meaning.
‘Without work, all life goes rotten, but when work is soulless, life stifles and dies,’ wrote Albert Camus. Finding work with a soul has become one of the great aspirations of our age.
If we wish to experience career fulfillment in its most sublime form, we ought to do everything we can to work in a way that suits who we are, with all our quirks and qualities. If we have a choice between security and freedom, choose freedom.
13. Multi-tasking to save time
According to psychotherapist Bryan Robinson, we should be asking ourselves questions like ‘Do I find myself doing two or three things at once, such as eating lunch and writing a memo?’ and ‘Do I put more time and energy into my work than into my relationships with loved ones and friends?’ Answering yes could mean we are sliding into addiction, especially if we are regularly putting in a lot of ‘voluntary hours’ beyond official duties.
Of course, working a twelve-hour day does not necessarily mean we are workaholics: it might be a reflection of the fact that we have found a stimulating and absorbing vocation. Anxiety about money is the major factor preventing most people from following Bertrand Russell’s advice and reducing their working hours, so they have enough time for creative idling.
14. Work-life imbalance
If the expansion of public education was the main event in the story of career choice in the nineteenth century, in the twentieth it was the growing number of women who entered the paid workforce. However, this victory for women’s liberation has been accompanied by severe dilemmas for both women and men as they attempt to find a balance between the demands of family life and their career ambitions.  This kind of dilemma is typical for anybody trying to ‘have it all’ – to pursue a fulfilling career while also being a dedicated parent. Despite these challenging realities, having it all had become a widespread aspiration in Western society, especially since the 1980s when the phrase was popularized and became associated with the ideal of the ‘superwoman’ who had well-adjusted children, a great marriage, and a top-flight job.
If you are finding it hard to have an enjoyable and successful career while also bringing up children, remember this: it is not your fault. The time strictures and emotional strains you face are in large part a consequence of social and cultural factors that make it extraordinarily difficult, particularly for women, to have it all. This is not your work crisis; it is society’s crisis.
One aspect of the problem is that men’s attitudes towards family life have not changed sufficiently to keep pace with women’s emancipation. The French philosopher and feminist Simone de Beauvoir recognized this back in the 1940s. When discussing the significant increase of women entering the paid workforce during the early twentieth century, she pointed out that ‘it is through gainful employment that woman has traversed most of the distance that separated her from the male, and nothing else can guarantee her liberty in practice.’ She saw that the majority ‘do not escape from the traditional feminine world’ of childcare and housework, even if they have a job. No wonder Erica Jong declared that liberated women ‘have won the right to be terminally exhausted’.
A second factor compounding the problem is that the way work is structured is out of kilter with the realities of raising children. For instance, even when fathers want to get involved in childcare, employment laws in many countries only grant them a few weeks of paternity leave.
‘Can women have it all?’ is the wrong question. An underlying assumption in most books and news articles about how to have it all is that this is primarily an issue for and about women.
Focusing on women while neglecting the role of men also reinforces the cultural norm that it is mothers, rather than fathers, who should be adjusting their lives to the complexities of managing both a career and a family, and making compromises where necessary.
Another reason for the work-life imbalance is when people feel safe at home and not in the workplace.
It is possible to find work that is life-enhancing and broadens our horizons and makes us feel more human. The concept of work-life integration comes to the rescue in such situations. We must be able to bring our whole selves to work to be able to love what we do.
Having it all does not mean you must have it all at once. An alternative approach is to avoid the juggling act by adopting the philosophy that having it all does not mean you must have it all at the same time. This requires stepping back to take the long view. Imagine your life as a series of phases, each expressing a different dimension of who you are – something like Shakespeare’s Seven Ages of Man. The idea is to have a fully committed career phase, where you throw yourself into work, then switch to a phase of dedicated parenting, and perhaps return to work again at a later stage. A radical new experience like having children might leave us utterly exhausted at the end of each day, but it can also free our minds, encourage our creativity, and stir us to experiment with the worker bee buzzing in our souls. This idea is similar to being a serial specialist, discussed earlier.
Conclusion
In the end, we may decide to shift our priorities: instead of thinking that the goal must be to find fulfilling work, our ambition could be to seek work for a fulfilling life.
The philosopher Bertrand Russell can help us explore the issues. In his scintillating 1932 essay ‘In Praise of Idleness,’ Russell shocked the establishment by arguing that ‘there is far too much work done in the world’ and that ‘immense harm is caused by the belief that work is virtuous.’ He saw no good reason why people should be sweating away producing so many consumer products that added little to the quality of life. Like many progressive thinkers of his era, including the economist John Maynard Keynes, he was convinced that economic growth and technological advances had made it possible for most people in wealthy countries to enjoy a decent standard of living by working no more than four hours a day. Russell also thought we should recognize the virtues of leisure. By ‘leisure’ he didn’t mean passive pastimes, but rather activities that could expand our human potential: reduce screen time and actually, get involved with life.
In a world where no one is compelled to work more than four hours a day, every person possessed of scientific curiosity will be able to indulge it, and every painter will be able to paint without starving, however, excellent his pictures may be. There will be happiness and joy of life, instead of frayed nerves, weariness, and dyspepsia. We might more realistically consider the possible benefits – and costs – of shifting to a four-day week, a popular aspiration since the 1970s, and one that employers are increasingly willing to accept.
I think my kids would rather have more father than more garden.
Seeking work for a fulfilling life is a common strategy for the art of living: you hold down a job that leaves you sufficient time and energy for a serious free-time pursuit. A meaningful job need not be one that completely consumes your whole life. Moreover, fulfillment remains possible if we are willing to break down the conceptual barrier between work and leisure. So-called ‘leisure activities’ may not offer us hard cash, but they can provide many of the other benefits of a fulfilling career if we pursue them with dedication. Through his poetry, Wallace Stevens was able to obtain social status, respect from fellow poets, and a sense that he was using his talents and following his calling. So let’s not be so hung up on the traditional idea that a career necessarily involves earning money.
 What we might think of as the Holy Grail of profound work: a career that is not just fulfilling, but that additionally feels like a ‘calling’ or ‘vocation.’ This raises the first question: how can we discover our true vocation in life?
A vocation is not something we find; it’s something we grow – and grow into.
A vocation is a career that not only gives you fulfillment – meaning, flow, freedom – but that also has a definitive goal or clear purpose to strive for attached to it, which drives your life and motivates you to get up in the morning.
Aristotle was the first thinker to recognize it explicitly, writing that every person should have ‘some object for the good life to aim at concerning which he will then do all his acts since not to have one’s life organized given some end is a mark of much folly.’ The German philosopher Friedrich Nietzsche similarly stressed the beneficial effects of having a mission to guide us: ‘He who has a why to live for can bear with almost any how.’ In the 1940s, the Austrian psychotherapist Victor Frankl suggested: ‘What man needs is not some tension-less state but rather the striving and struggling for some goal worthy of him.’ What people require is ‘a goal that like a magnetic field attracts their psychic energy, a goal upon which all lesser goals depend.’
If we want a job that is also a vocation, we should not passively wait around for it to appear out of thin air. Instead, we should take action and endeavor to grow it like Marie Curie. How? Simply by devoting ourselves to work that gives us deep fulfillment through meaning, flow, and freedom. Over time, a tangible and inspiring goal may quietly germinate, grow larger, and eventually, flower into life.
Indeed, the inconvenient truth is that there comes the point when you need to stop thinking and just do it. Carpe diem – seize the day – before time runs out on you. Writing your obituary is a startlingly effective way to help avoid a corrosive feeling of regret that you did not take your life in new directions when you had the chance. Most of us live bound by our fears and inhibitions. If we are to move beyond them, if we are to cut the rope and be free, we need to treat life as an experiment and discover the little bit of madness that lies within us all.
‘A man needs a little madness, or else he never dares cut the rope and be free.’
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