Career Choice

Your memories will show you the way.  Scanning random lists of occupations, top 10 lists and so forth, will only confuse – but retracing your history and finding patterns is what will reveal it.  It will be the memories that you most vividly recall, the projects you most looked forward to and enjoyed, the peak experiences you will never forget.  This will not be something new, but something very old and very familiar.

In short: Follow your gut.

This idea is the foundation of all the greatest and most audacious of human achievements – that you know what you need to do far better than anyone else – rationality be damned.  Reason is a powerful tool but the most cruel of masters.

Reason is what dissuaded me from writing.  Reason and failure to immediately succeed or figure out beforehand where exactly in the field I belong.  I didn’t seem to fit into conventional categories, and so I gave up.  I moved on and struck it off my list.  And then of course I complained about not being able to find my passion.  It was right in front of me the whole time – I just had turned a blind eye to it.

So revisit old passions, ones you thought you’d outgrown and left behind.  This is a stressful decision, but it need not be overwhelming.  Be afraid, but look past that fear to the gravity of your destiny – to your few hours and the fact that this is one of the very few truly important decisions you will ever make.

To clarify however, this is typically not a single decision but several.  You choose an initial path that seems in the general direction which your heart is tugging you towards.  Once there, your energy will tell you where to go – towards what increases it and inspires you at an intuitive level.

So while the reasons why we feel compelled to do what we do is difficult to know, the wisdom of following it is well grounded.   So for those who need a “why” for listening and trusting themselves, or for those who are unable to discern exactly what their gut is telling them or who feel conflicted – I share some ideas and suggestions for ways around those obstacles.

A Wise Choice

What is the purpose of human life?  To a certain degree, choice of a profession is subsumed under this larger question – which is the main reason there is such conflicting advice on careers.  It depends on your ends, and it also depends on how ambitious, how uncynical one is towards ones prospects in life, and of humanities prospects in life – particularly those not born to positions of power and influence.

Prior to modernity, when the religious viewpoint dominated, choice of a profession was considered a minor decision.  Our time here on earth is fleeting in comparison with eternity.  There was also less emphasis on individuality and what differentiates individuals, this life was largely simply put up with in anticipation of the glory and paradise to come in the life hereafter.

With the fall of the religious view has come an increasing emphasis on the choices we make about our time, an awareness of the great limitations we have and therefore a great sense of pressure to make the right choices about what to do with our time.

But like every choice, this is one best not made in a vacuum – in isolation from the specific context in which you find yourself – temporally, spatially, and socially.  It is this context which can partially free us from the burden of endless arbitrary decisions.

We are thrown into this world in that we do not choose the time or place we are born into.  We awake to find ourselves surrounded by strangers the bonds of which will follow us all the days of our lives.  This family in turn is part of a larger group with a particular set of values and ideas about what is right and wrong, about what is worthy of praise or blame.  These people try to teach us what it means to be human, and we develop ways of coping with the particular challenges these circumstances present.  As the philosopher Martin Heidegger said, we have been “abandoned to the they” – to the crowd.  We do not learn moral theory from Kant, but from random people who may or may not know what they are doing.

We are also born with a certain temperament and predisposition we did not choose, and are subjected to early experiences we have little control over.  As we cognitively develop we become aware of these things and also aware of the great diversity of times and places into which other humans are and have been thrown, and we develop certain judgements about our own particular destiny.  The size of the gap between what we would have our family, culture and self be and what they are forms our default views of ourselves and other people.  Too large of a gap between self-expectation and our performance and we fall into frustration and despair, too large of a gap between what others are and what we want them to be leads to alienation.  Sometimes the things we most want we can’t have because of our situation or who we are, and other times even the things we want to want we have no real desire for.

We also become aware of our mortality – that we are all under sentence of death, with a sort of indefinite reprieve.  Whether our response is relief or dread, it cannot but frame our experiences.  This knowledge, when internalized, can free us to pursue what really matters to us, rather than being beholden to the they – to the crowd.  Thus these conditions form the basic constraints of our existence, the things over which we have no control.

However, within these constraints we have a wealth of choices and the ability to deliberate on our choices and strike out in a direction of our choice.  Our context provides the raw materials out of which we can shape the life we want and decide on the kind of person we want to be.  While we don’t choose our family we can choose what parts of our family and cultural traditions we want to continue and pass on to our children and which we wish to discard.  Our “throwness” gives our lives context and a certain degree of inherent meaning – we are born not isolated but a part of something larger than ourselves.  We are narrow bridges between two eternities – between our ancestors on one side and our descendents on the other.  We decide in large part what we then pass on to our children, which will then echo on in some form through our ancestors for the rest of time.

So again the question arises: what is the purpose of human life?  I think in some ways it’s been half answered – it only needs completion.

My suggested answer harkens back to the ancient Greeks. Life for them, and Aristotle in particular, was about knowing and then becoming what you are.  It was a fundamental ethical principle “wherein each person is obliged to know and live in truth to his daimon (a kind of spirit given to all persons at birth), thereby progressively actualizing an excellence (from the Greek word ‘arete’) consistent with innate potentialities. The type of happiness they are talking about, eudemonia, translates to ‘meaningful living conditioned upon self-truth and self-responsibility’. It is thus the essence of the two great Greek imperatives: first, to ‘know thyself’ (a phrase inscribed on the temple of Apollo at Delphi), and second, to ‘choose yourself’ or ‘become what you are’.  The self is a mix between what we’ve been given and what we’ve chosen.  The purpose of life as seen by Aristotle was to take what you’ve been given and choose it, to not avoid or shun it but confront and develop it.

However, this wisdom has been lost in the modern era.  In poll after poll, most people choose happiness as their goal.  And I will not denigrate happiness – far from it.  Beyond the pleasant feeling, it leads to better relationships, greater creativity, and better health.  However, there is one fatal flow to placing happiness as a goal: it cannot be attained if pursued directly.  As John Stuart Mill explained:

Those only are happy who have their minds fixed on some object other than their own happiness, on the happiness of others, on the improvement of mankind, even on some art or pursuit, followed not as a means, but as itself and ideal end. Aiming thus at something else, they find happiness by the way.

And studies have born this out (Maus, et al).  The more importance is placed on happiness, the more unhappy and depressed people typically are.  Happiness is a by-product, the result of striving after something else.

And the idea of the purpose of life being to develop and be yourself is intuitive.  It’s addressed in almost all the major religions, and has a long history in philosophy and psychology.  We are given the gift of individuality, of particular talents and energies, and it is up to us to let them wither and die or to grow and develop them – and help others do the same.

This point however cannot really be argued – you cannot logic out the purpose of your life.  It must be chosen.  And in many ways I hate arguing this out rationally – just listen to your gut and tell me that this doesn’t resound with you.  Being yourself is a choice half made – you were given a certain unique nature, to not realize it seems a tragedy.

But lest you fear endless hours navel-gazing, I assure you that both knowing and being yourself are activities.  As Goethe expounds,

Know thyself… simply means: pay some attention to yourself; take note of yourself; so that you may know how you come to stand towards those like you and towards the world. This involves no psychological torture; every capable man knows and feels what it means. It is a piece of good advice which every one will find of the greatest advantage in practice.

One of the advantages of such an outlook on life is how easy it is to place the purpose of work within it.  If such is the meaning of life, then work becomes a means to fulfill the unique potentialities that you’re born with. – it’s an opportunity to express your individuality and make your imprint on the world, to engage in activity in accordance with what is best and truest about you.  Victor Frankl expounds on this:

This uniqueness and singleness which distinguishes each individual and gives a meaning to his existence has a bearing on creative work as much as it does on human love. When the impossibility of replacing a person is realized, it allows the responsibility which a man has for his existence and its continuance to appear in all its magnitude. A man who becomes conscious of the responsibility he bears toward a human being who affectionately waits for him, or to an unfinished work, will never be able to throw away his life. He knows the “why” for his existence, and will be able to bear almost any “how.”

Although individuals are often prone to idleness, our happiest moments rarely happen when we are passive.  Whether in conversation or reflection or physical activity it is these moments that define our lives.

Thus our work can help express who we are or alienate us.  Finding work that does the former is almost always a process, the process of self-knowledge and discovery of the external world.  My purpose here is to provide a general guide to this process, to share how others have approached this question and introduce some of the variables that may be helpful to consider when making such a decision.

Human Limitations:

You want a social life, with friends.

A passionate love life and as well

To work hard every day. What’s true

Is of these three you may have two.

-Kenneth Koch

To choose something is often to exclude another.  We only have so much time, and so much ability to develop capabilities.  I don’t know if the specific choices mentioned above are literally true, but I can say that I’ve never in my life had all three at the same time, and the same is true of everyone I’ve known well.  Regardless, there are certainly many things that are mutually exclusive and some things that we risk by choosing another.  Sometimes choosing a career you’re passionate about involves risking conventional values such as money and prestige, and it’s certainly most difficult when that is the case.  This cuts to the heart of the difficulties of choice.  R.L. Stevenson expounds:

A choice, let us remember, is almost more of a negative than a positive.  You embrace one thing; but you refuse a thousand.  The most liberal profession imprisons many energies and starves many affections.  If you are in a bank, you cannot be much upon the sea.

And Yalom still further:

Decisions are a via regia, a royal road, into a rich existential domain—the realm of freedom, responsibility, choice, regret, wishing, and willing.  Because decisional dilemmas ignite freedom-anxiety, many go to great lengths to steer clear of active decisions. That is why some seek delivery from decisions and, through cunning devices…, force others in their life to make the decision for them. [However], you make a decision even by not deciding or by maneuvering another into making a decision for you.  I always ask my patients [after they accept this]: “Are you satisfied with that?” (with the nature of the decision and with the mode of making the decision).  Did you act in good faith? What regrets will you have in the future? How much will you respect yourself?”

In this life there are no guarantees, and pursuing the best in you often entails both risk and faith that that risk will pay off.  Steve Jobs addressed this often in his rocky and unconventional path to success:

You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.

It’s faith that however odd you may feel yourself to be, that there are others out there who share your same joys and sorrows, that nature created all this wonderful human variety for a reason.

Common Obstacles

However, there are a number of barriers to following your passion, the most common one’s being: money, prestige and gender match.  They played no small part in my initial considerations of my own career decision, but I have since realized their essential folly.  Yes, some measure of money is necessary to live and thrive in any sense, but you can live well in this country for 12,000 a year (I’ve done it – and in northern NJ no less.  Obviously this does not hold true if you have a family).

I think Robert Louis Stevenson’s thoughts on this are most instructive:

A thoroughly respectable income is as much as a man spends.  A luxurious income, or true opulence, is something more than a man spends.  Raise the income, lower the expenditure, and surprising as it seems, we have the same result.  …Indeed, there is nothing so hard to get people to understand as this: That they pay for their money; and nothing so difficult to remember as this: that money is only a cheque to purchase pleasure with.  How then if a man gets pleasure from [his work]?  He might get more cheques by following another [career]; but then, although there is a difference in cheques, the amount of pleasure is the same.  The first gets some of his directly; unlike the second, he is having his fortnight’s holiday and doing what delights him, all the year.

A second and final consideration is also helpful, by Tim Ferris:

An American consultant was at a pier in a small coastal Mexican village when a small boat with just one fisherman docked. Inside the small boat were several large yellow-fin tuna. The American complimented the Mexican on the quality of his fish and asked how long it took to catch them.

The Mexican replied only a little while.

The consultant then asked why didn’t he stay out longer and catch more fish?

The fisherman said he had enough to support his family’s immediate needs.

The American then asked the Mexican how he spent the rest of his time.

The Mexican fisherman said, “I sleep late, fish a little, play with my children, take siesta with my wife, Maria, stroll into the village each evening where I sip wine and play guitar with my amigos. I have a full and busy life, señor.”

The American consultant scoffed, “I am business consultant and could help you. You should spend more time fishing and, with the proceeds, buy a bigger boat. With the proceeds from the bigger boat, you could buy several boats, eventually you would have a fleet of fishing boats. Instead of selling your catch to a middleman you would sell directly to the processor, eventually opening your own cannery. You would control the product, processing and distribution.

“You would need to leave this small coastal fishing village and move to Mexico City, then LA and eventually NYC where you will run your expanding enterprise.”

The Mexican fisherman asked, “But señor, how long will this all take?”

To which the American consultant replied, “15-20 years.”

“But what then, señor?” asked the fisherman.

The consultant laughed, and said, “That’s the best part! When the time is right, you would announce an IPO and sell your company stock to the public. You’ll become very rich, you would make millions!”

“Millions, señor?” replied the Mexican. “Then what?”

The American said, “Then you would retire. Move to a small coastal fishing village where you would sleep late, fish a little, play with your kids, take siesta with your wife, stroll to the village in the evenings where you could sip wine and play your guitar with your amigos.”

Of course that story seems to accentuate the pleasures associated with leisure rather than work, (It’s from his book “The Seven Hour Workweek”, which is another in a long line of self-help books that succeeds by over-promising and under-delivering) but it’s effective at communicating the central point that money is but a means and that most satisfying activities don’t cost much.

The second common barrier is prestige, and there are all sorts of issues with this.  First, prestige often goes to those who do the most annoying work.  Paul Graham expounds:

Prestige is like a powerful magnet that warps even your beliefs about what you enjoy. It causes you to work not on what you like, but what you’d like to like.

That’s what leads people to try to write novels, for example. They like reading novels. They notice that people who write them win Nobel prizes. What could be more wonderful, they think, than to be a novelist? But liking the idea of being a novelist is not enough; you have to like the actual work of novel-writing if you’re going to be good at it; you have to like making up elaborate lies.

Prestige is just fossilized inspiration. If you do anything well enough, you’ll make it prestigious. Plenty of things we now consider prestigious were anything but at first. Jazz comes to mind—though almost any established art form would do. So just do what you like, and let prestige take care of itself.

Prestige is especially dangerous to the ambitious. If you want to make ambitious people waste their time on errands, the way to do it is to bait the hook with prestige. That’s the recipe for getting people to give talks, write forewords, serve on committees, be department heads, and so on. It might be a good rule simply to avoid any prestigious task. If it didn’t suck, they wouldn’t have had to make it prestigious.

Similarly, if you admire two kinds of work equally, but one is more prestigious, you should probably choose the other. Your opinions about what’s admirable are always going to be slightly influenced by prestige, so if the two seem equal to you, you probably have more genuine admiration for the less prestigious one.

Also, the most prestigious are often the most unhappy.  Lawyers are one of the most unhappy professionals, add to that the uncertain and over saturated market for lawyers and the incredible debt that often accompanies law school and you have a recipe for unhappiness.

Finally, on gender type I don’t have tons to say.  Concerns about one’s masculinity or femininity and attraction to the opposite sex are certainly understandable concerns – but I don’t see how going into something that’s not you is any kind of answer or will in any way lead to better relationships.


Positive psychology is all the rage these days but what does it mean?  What does the word “maturity” mean?  Growing up that word always puzzled me, especially because the more serious and boring someone was, the greater likelihood of them being called “mature”.  If that was really what maturity was, I wanted nothing to do with it.

Wisdom (and maturity) is being able to discern what is important and unimportant in a given situation.  I’ve covered a few things I don’t think are important – but what is?

I will update this shortly with a proposed answer, but in the meantime here are some clues:

What Does it Mean to Love what you Do?

How do we find [what we love]? Most of us do what any self-respecting red blooded American would do when faced with a question like this: we’re proactive about it goddamnit! I mean we can’t just sit around waiting for love to find us, we have to go find it ourselves, right? They leave no stone unturned, no activity untried, no speed-dating event unattended. The problem is this: it doesn’t work. Why? Because the stakes for every interaction are too high. If you’re actively searching for that activity you love, for something or someone you’re passionate about, then you’re constantly asking yourself: “Do I love this?”

And that’s a losing proposition from the start.

Let’s say in the spirit of finding something you love, you decide to try piano. You buy a piano and take an hour long lesson. Then afterward you say, “Do I love this?” Well of course not! You’d be crazy to love something after an hour. So you sell the damn piano (it was too big for your apartment anyway) and move on to the next thing. There’s no time to waste right?

After many years of doing this and never finding love, if you’re lucky, you’ll begin to realize that like many things in life what you love wasn’t out somewhere else, hiding where it needed to be found. You’ll realize that the answer was inside of you the whole time. In fact it was right in front of your face. All it required was a little introspection.

It’s dangerous to think in terms of “passion” and “purpose” because they sound like such huge overwhelming things.  If you think love needs to look like “Romeo and Juliet”, you’ll overlook a great relationship that grows slowly.  If you think you haven’t found your passion yet, you’re probably expecting it to be overwhelming.  Instead, just notice what excites you and what scares you on a small moment-to-moment level.  If you find yourself diving into a book about Photoshop and playing around with the program for hours, go for it!  Dive in deeper.  Maybe that’s your new calling.  If you keep thinking about something like putting on a huge conference or being a Hollywood screenwriter and you find the idea terrifies but intrigues you, it’s probably a worthy endeavor for you.

You grow by doing what excites you and what scares you. -Derek Sivers

One thing that Dan mentions that I want to emphasize is that it is highly unlikely to be something brand new, especially if you’re over the age of 25 or so.  The tasks the job involves will be something that there is a pattern of it coming up in your life – so going about looking for a career by looking through descriptions of jobs or careers may not be the most efficient route to finding one you love.  Rather, considering what it is you like and then doing research to find out what jobs there are that involve that may be the best path.

The first thing… is that you already know what it is.  Your bliss is what you’re better at and what you’ve enjoyed more than other people throughout your entire life, but you likely have no idea because you always thought it was normal.  That’s why it’s so incredibly difficult to find out what’s your bliss on your own – you have no one to compare it to, no one to say hey, you enjoy that way more than i do.  The next thing is that your bliss is how you would like to make the world a better place – what gift you’d like to share with the world to make it more enjoyable for the people around you.  So the big question is: if you had unlimited money, time and freedom, how would you spend the rest of your life trying to make the world a better place?  But you have to answer this question like a child from a state of play.  It’s easy to get caught up in “reality” and say that can’t work or that’s not feasible…., because as Joseph Campbell says, “When you follow your bliss, doors appear where before there were walls”

Also consider: what do I want to learn about?

How to Know You’ve Found it

As a lower bound, you have to like your work more than any unproductive pleasure. You have to like what you do enough that the concept of “spare time” seems mistaken… you don’t regard this time as the prize and the time you spend working as the pain you endure to earn it… To be happy I think you have to be doing something you not only enjoy, but admire. You have to be able to say, at the end, wow, that’s pretty cool.  -Paul Graham

“The mark of a calling is a laborious partiality for a vocation, an inextinguishable zest in its technical successes, and (perhaps above all) a certain candour of mind to take a very trifling enterprise with a gravity that would befit the cares of empire, and to think the smallest improvement worth accomplishing at any expense of time and industry. R.L. Stevenson

“Joseph Campbell’s refreshing advice that we should ‘follow our bliss’ is rooted in the belief that deep joy and aliveness are important criteria for whether we are on the path of our calling and is captured in a lovely passage from James Joyce, ‘His heart trembled in an ecstacy of fear and his soul was in flight… This was the call of life to his soul, not the dull gross voice of duties and despair.’  J.P. Neafsey

More on Following your Bliss

“The Spanish philosopher Ortega y Gasset says we fall in love on few occasions in a long life. It is a rare and fortuitous event, and it strikes incredibly deeply. When such love happens, it is for no other reason than the singularity of the object. Only this person. Not attributes and virtues, not voice or hips or bank account, not projections left over from earlier flames or hand-me-down family patterns, simply the uniqueness of this person whom the heart’s eye selected. Without that sense of fate in the choice, the romance of the love doesn’t work. For this sort of love is not a personal relationship or a genetic epistasis, but more likely a daimonic inheritance, a gift and curse from the invisible ancestors.

A similar sense of destiny, if less sudden and less heated, and a similar devotion can mark falling for a place and even for a work, as well as for a person. You can’t leave it, you must stay with it until it’s over, you perform ritual magic devotions to keep it going. The same enchantments occur, the same sense arises that I could live the rest of my life with you, whether “you” is a person, a place, a work. And the similar feeling exists that not only is my life called here, but my death.” -James Hillman

“At every turn in my career, I have faced choices about whether to pursue what seems to me to be boring, respectable… mainstream, and at first glance the better career choice, or whether instead to follow my sense of fun. Rarely have I regretted it in the long term when I have chosen fun.”

“Do work you love. Even if you make less money. Even if you disappoint others. Working a job for which you have no passion is betraying yourself, for eight hours a day.”

An elite education gives you the chance to be rich—which is, after all, what we’re talking about—but it takes away the chance not to be. Yet the opportunity not to be rich is one of the greatest opportunities with which young Americans have been blessed. We live in a society that is itself so wealthy that it can afford to provide a decent living to whole classes of people who in other countries exist (or in earlier times existed) on the brink of poverty or, at least, of indignity. You can live comfortably in the United States as a schoolteacher, or a community organizer, or a civil rights lawyer, or an artist—that is, by any reasonable definition of comfort. You have to live in an ordinary house instead of an apartment in Manhattan or a mansion in L.A.; you have to drive a Honda instead of a BMW or a Hummer; you have to vacation in Florida instead of Barbados or Paris, but what are such losses when set against the opportunity to do work you believe in, work you’re suited for, work you love, every day of your life?

What do you Really Want?

If you’re unhappy, take some time to think about what it is you really, actually want. Not what you’re supposed to want, or what you think you should want because you’d be a different kind of person if you wanted it, but what you actually want.

When you can name it, you can figure out how to get it. But if you don’t acknowledge it, you’ll remain dissatisfied. And this life is too interesting and rich for that.


…the best way to define a man’s character would be to seek out the particular… attitude in which, when it came upon him, he felt himself most deeply and intensely active and alive. At such moments there is a voice inside which speaks and says: “This is the real me!”… When you have found that… follow it. -W. James

There is but one cause of human failure. And that is man’s lack of faith in his true Self. -W. James

We are told that talent creates its own opportunities.  But it sometimes seems that intense desire creates not only its own opportunities, but its own talents. -Hoffer

The intensity induced by an inner inadequacy constitutes a release of energy, and it depends on a person’s endowments and on attending circumstances whether the released energy works itself out in discontent, in desire, in sheer action or in creativeness.  The chemistry of dissatisfaction is as the chemistry of some potent tar.  In it are the building stones of explosives, stimulants, poisons, opiates, perfumes and stenches.  -Hoffer

Passions usually have their root in that which is blemished, crippled, incomplete, and insecure within us.  The passionate attitude is less a response to stimuli from without than an emanation from an inner dissatisfaction… There is perhaps no better way of measuring the natural endowment of a soul than by its ability to transmute [this] dissatisfaction into a creative impulse. -Hoffer

Clarity comes from movement.  You come to know your path by walking it.


Mauss, I. B., Tamir, M., Anderson, C. L., & Savino, N. S. (in press). Can seeking happiness make people unhappy? Paradoxical effects of valuing happiness. Emotion

*While I may appear to be discounting the influence of the environment on what the self is, I am definitely not.  I do believe our fundamental dispositions cannot be created by the environment – they can be destroyed by it but not created.  My interest in writing was biological.  I can still remember to this day the first book that I read, which is amazing because I don’t remember jack shit about my childhood.  My upbringing influenced the types of books I liked and what resonated with me, but not the fundamental interest in words.  For instance, I went to a church every Sunday with a very melodramatic preacher who talked about things like the end of the world and the evils of modernty, which undoubtedly influenced my own interest in “grand” subjects as well as my penchant for generalizations.


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