Ambition v Aspiration (and how prioritising 'achievement' can lead to a really sucky life)

If you fully know why you’re pursuing something, it’s probably not worth pursuing

One of the most important questions anyone can ask themselves is: ‘Why am I working towards whatever it is I’m working towards?’

The typical life-coachy approach to helping people with this question involves attaching actions to ‘core values’.

‘I’m working on being a teacher in a forest school because both nature and education are extremely important to me.’

‘I’m working on making loadsa money because it’s aligned with my core value of providing for my family / teaching my children that love is measured by having expensive things.’

And so on. Grab a goal, tick the ‘is it aligned?’ box, and get on with making a plan to achieve it.

Particularly ambitious people are particularly good at this. They achieve all sorts of things.

Financial planners tend to particularly like these particularly ambitious people. Not least because these people, like the planners, like the plans. They beam at the chance to play ‘discover your purpose’ exercises. They fix their sights and set to work. And they tend to make (and invest) a ton of sweet, sweet, commission-worthy coin along the way.

However, what do you do if your values aren’t so certain?

Or, worse, what do you do if they’re too certain? If they’re beset by the sort of certainty that drives someone to pursue a ‘dream’ for decades, only to be hit with the harrowing reality that they got it all dead wrong right from the start, because they’d confused achievement of things with a life well lived, or what they do with who they are?

Financial planning client rosters are full of people who’ve been absolutely certain that the typical rewards of the conveyor-belt life – from that school, to that university, to that career, to that sort of house, in that part of the country, and so on – were exactly what they ‘wanted’. So certain they dedicated their lives to pursuing them… only to one day wonder why the bloody hell they did so.

What if ambition, while useful in the achievement of narrow goals, were, despite some very loud shouting of the opposite, not actually a very good guiding star for how to live?

How do you square the exalting of fast-track, direct-line, ambition with the reality, I assume well-known to each of you, that the best paths you ever danced along were the ones where you didn’t really know where they led, nor even really why you started dancing down them?

Yet is there an alternative? Doesn’t a lack of ‘drive’ mean slacking about in your pyjamas all day, watching your muscles turn to mush and your brain to blancmange?

Enter Alcibiades

To get a better look at what’s going on here, let’s take a trip to Ancient Athens, to meet heroic heart-throb Alcibiades. Alcibiades was an aristocrat, a general, a close companion of Socrates, and a total hottie.

He had all the resources for a good life. As do pretty much all of us.

He also failed to make the most of them. As do pretty much all of us.

Which is why (with the right guide, which fortunately we have courtesy of Agnes Callard’s Aspiration – a book you should absolutely prioritise reading) Alcibiades’ story is still so instructive.

In Plato’s Symposium, Socrates and some pals were indulging in the popular Friday-night pastime of getting royally trolleyed, while taking it in turns to deliver speeches in praise of Eros, the god of love and desire. Well, except Socrates, who famously didn’t get drunk, or play by the rules.

Socrates is most of the way through an anecdote he’s chosen to deliver instead of the encomium to Eros, when Alcibiades bundles in. He’s drunk. He’s gatecrashing. He’s sporting a ‘bushy garland of ivy and violets and with an abundance of ribbons tied around his head’ (which we’re led to believe cut just the sort of impression then as it would today). And he cuts Socrates off so he can deliver his own speech instead. Everyone else lets him of course, because he’s super hot.

Alcibiades’ speech is in praise, not of Eros, but Socrates. Sort of. He’s mostly chastising Socrates, in a ‘I wish you weren’t so damn wise and virtuous, because it reminds me that I’m not’ sort of way.

‘By Poseidon!’, Alciabiades exclaims [gist: Plato, words: me], ‘what a bastard that Socrates is! Such a clever, clever, bastard. Here I am – me!, Alcibiades! All the boys want to be me, and all the girls (and most of the boys for that matter) want to be with me – and yet whenever I listen to this clever bastard, I become so upset I weep waterfalls.’

‘This man moves me to tears,’ Alcibiades continues, ‘not because of some exceptional, manipulative, quality of his prose. Pericles had that, and stirred enthusiasm. Socrates stirs shame. With what appears to be mere casual chit-chat, this man pierces my general’s armoured shell; with only a little mirror made of questions and silence, he crumbles in minutes an edifice aristocratic manoeuvring took centuries to build, and leaves me feeling as if I’m actually living no better than a slave! Worse than that! He leaves my soul in turmoil, inescapably disturbed by the thought that I am not just a slave, but a slave to the very way of living for which I am so roundly praised!’

Alcibiades knows he wouldn’t feel bad if none of this were true. No one, if they’re genuinely living fabulously, is put out by suggestions that they’re not.

Honour-loving v wisdom-loving

The root of Alcibiades’ turmoil is summarised by the contrast Plato draws out between Alcibiades in his day-to-day actions living an honour-loving life and yet wanting to live a wisdom-loving one.

Honour in this sense can be thought of as the typical dreams of fame and fortune that prioritise the appearance of something over the actual something, much like a bodybuilder’s approach to physical health.

Alcibiades aspired to be a better person in the ways we all know matter most, but frequently forget or don’t fully trust as guiding stars for our ways of living, because they can’t be measured (even though we are fully aware they matter the most, such is the power of the spell cast by the half of the brain that insists on bending reality to fit a model allegedly made to better understand that reality).

But his ambition drove him elsewhere – promising that the path to a better life was actually paved with good looks, riches, job titles, glory in battles, and so forth. The trouble for Alcibiades, as for most of those folk who find themselves asking a financial planner for help, is that by any account he’d ‘won’ the good looks and glory in battle game, but the promised prize of feeling pretty groovy about life hadn’t come with it.

Inside view v outside view

The world sees the shiny, sexy, medal-laden surface of Alcibiades. They see circumstances. Alcibiades sees himself from the inside out. He sees what matters. And what he sees gnaws at him just as reliably as the voice inside the heads of modern multi-millionaire models of ‘success’ that wonder why ‘having everything’ didn’t work out as the world promised it would.

Socrates is even more of a bastard because despite making him feel like he’s lived his whole life in error, Alcibiades can’t help but keep coming back for more.

That should intrigue all of us.

From the point of view of his current struggle, Alcibiades’ life would certainly be easier if he could just ignore looking in Socrates’ little mirror. But something inside him tells him it wouldn’t be better.

He’s drawn to keep trying to live a life of love and wisdom rather than one of glory and honour for a reason. It’s not a reason he can pin down, measure, or summarise in a neat little bullet-pointed list. (It is a ‘proleptic reason’, in Agnes Callard’s terminology).

Alcibiades wants to live expressing values he doesn’t yet embody. He cannot fully know why he wants to embody them, because he won’t fully know until he embodies them. But want them he very much does… even when wanting them makes him feel ashamed and as if being rich, famous, and a massive stud weren’t the unequivocal best way of being… which is a bit awks given he’s devoted his life to that, and lives in a society that treats him like a freakin’ hero for being so damn successful at it.

Living in service of glory, money, or whatnot is entirely different. He fully knows what he values, so he sets his course and charges down it like a greyhound racing after a mechanical rabbit. Get the glory, get the girl (or the boy), get gout and gallstones, and so on.

Ambition v aspiration

Alcibiades is a great example of the difference between ambition and aspiration.

It’s a difference that is at the heart of the screwy way we tend to live with money, and that offers a glimpse of a way to unscrew ourselves.

Ambition drives us. Aspiration draws us.

The difference is not about action (about what you do), but attention (the way in which you do it).

The aspirant sets a course to test out and acquire new values. The ambitious person goes wherever their existing values take them.

Ambition is reasoning from desire (you value money, you run towards it). Aspiration is reasoning toward desire (you have an inkling you’d like to become a different person somehow, you dance toward becoming so). As Callard put it:

When we reason from desire, our rationality consists for the most part in making and sticking to good choices, knowing what is worth sacrificing, taking prudent risks. The excellent decision-maker knows when to jump on an opportunity and when to bide her time.

You’ll no doubt recognise this path, largely because ‘better decision making’ is a billion-dollar industry.

Aspirants, on the other hand, ‘exhibit a distinctive form of rationality that is not a matter of decision at all.’

Callard uses the example of a medical student:

The ambitious medical student is not seeking to acquire a value: she takes herself to have full access, even before entering medical school, to the value of having money, the approval of her parents, or social status. She does not hope that medical school and residency will teach her the value of these things. She hopes only that they will help her satisfy the values she already has. She has too much access to the value in question to count as aspiring toward it.

A different student can go to the same medical school, sit the same exams, and so forth, but do so for entirely different reasons.

The aspirant, as I use the word, doesn’t aim exclusively at any of these things. To be sure, she wants to go to medical school, to pass her exams, to succeed in her residency, to gain a position at an excellent hospital. Perhaps she even wants to please her parents. But her desire for all these things is a secondary manifestation of what she really wants, which is to provide the kind of medical assistance whose particular nature it is the job of her medical education to convey to her. Though she takes herself, before attending medical school, to have some understanding of medicine, she (knows that) she will only really grasp the specific good she is seeking to bring about by way of engaging in the work in question.

You may not be a medical student, but I trust you can come up with a thousand examples of your own. It’s pretty tricky to think of a way in which someone is drawn towards owning a mansion or a megayacht or telling their boss to f-off not because of the envisioned end, but because they have an inkling the character growth they’ll experience along the way will be totally worth it. Much more likely they drive towards these things because of who they already are. And/or because they were bullied at school.

Ambition is great for getting shit done. Which is possibly really great for the whole world if what you’re getting done isn’t actually shit. In a race to build an ocean-cleaning machine between the person doing it as a way to nourish their soul and the person doing it because they’re driven by implacable demons, you know who’s finishing first. But if you’re interested in living well…

If it feels like a decision, it’s a bad one

In my wilder moments, most full of love and seeing most clearly, I find myself feeling that decision-making is hilariously overrated… such that if something feels like a decision at all – if you’re in any way weighing up what to do – it’s a decent sign that you should do neither. You do what you can’t not do, and ignore everything else.

That’s kind of the point with prioritising aspiration over ambition. It’s not a cognitive tug of war. It’s a tilting of attention to one way of living – one existential mode – or another.

Let’s return to Alcibiades:

We can see that Alcibiades doesn’t resemble someone trying to make a decision. Though he clearly struggles, his struggle is not that of someone who has difficulty choosing which of two valuable things he should pursue. The love of honor and love of wisdom that threaten to pull him apart do not present themselves to him in the form of a difficult practical problem. He is not trying to figure anything out. He is just trying to become a wisdom-lover, and his love of honor is holding him back.

Why is this so hard?

Why is Alcibiades’ ambition – so effective at driving him forward – also so ‘good’ at holding him back?

Why, despite having all the raw materials required for a meaningful life, did he, in Callard’s words, ‘nonetheless let himself get sucked back into a life he could see was empty’?

And why do so goddamn many still do exactly this all the goddamn time?

Why, why, why, is modern ‘rich’ life characterised by charging off to accumulate resources, before getting confused by how the accepted ways of applying them don’t really work, getting an inkling there’s a much, much, better way, but then getting sucked back into the accumulating anyway?

Because he is not yet living in a wiser way, Alcibiades cannot fully grasp the value of wisdom. He therefore cannot fully grasp why it is to be pursued. He’s drawn towards it, for sure, but in relation to all the repeated day-to-day actions that most reliably shape our brains, and our lives, aspirant drawings are a lot weaker than ambitious drivings. Especially when, as with Alcibiades, the society in which he lives is geared towards telling him he’s living the best life of any man ever – there must therefore be something wrong with him, rather than the picture of a supposedly ‘good’ life.

This is of course exactly what happens to those in our modern world that have dedicated their lives to becoming rich (note: this is importantly different to ‘being a rich person’, albeit the overlap is almost total). Rich people have all the opportunity to live better lives. But – largely because they are the supposed ‘winners’ of the game everybody is playing – they are also those most heavily sucked back into emptiness.

When you’ve spent your life swimming in water telling you that to live well is to live expensively, you cannot fully grasp the value of living genuinely well. This makes it hard to pursue, despite the fact that all non-psychopaths must feel some draw towards doing so.

If you are thinking the answer is ‘balance’, then stop and try again

The difference between ambition and aspiration in the context of how we live with money is more than a cute distinction. Think that, and you’re liable to think that the sensible call is to be ambitious for a bit – earn a ton of money – and then, once ‘secure’ and ‘free’, ‘one day’ flick to being more aspirational.

Ugh.

No.

That’s not how your brain works. How life works. This myth is not helping you.

From the point of view of your brain, driving down a tunnel doesn’t make it more likely you’ll ‘arrive’ at your brave new world. It makes it less. Because driving with your eyes fixed on ‘one day’ ‘arriving’ somewhere wires you for driving over seeing, for waiting over living. You entrench the worldview that says the Good Life is right around the corner, and you’ll live happily ever after in its cosy embrace, just as soon as these pesky external circumstances have clicked themselves into eternal harmony.

This isn’t about a better way to go about something. It’s about a better way to go about everything.

It’s about clearing your mind so the clash is no longer a clash, because you simply stop caring about the nonsense that you keep getting sucked back to. This is the job of philosophy.

Be moved by what moves you

Thanks to some gentle Socratic prodding, Alcibiades saw that, far from being a great man in command of his, and many other people’s lives, he was a slave to his way of living.

He wanted to escape this prison. He was drawn towards becoming the sort of person who could do so… not by breaking any bars, but merely by having them and their distorting influence on what he believed he cared about dissolve around him.

He failed in this task. (And, more than that, ended up as one of the evilest sh!theads Athens has ever known).

Even with all the riches, social position, and knee-melting appearance anyone could wish for.

Even with Socrates by his side.

As Callard tells us:

The reason Socrates didn’t ‘make’ Alcibiades virtuous is that this is not something one person can do to another. The work of appreciating the value of, say, wisdom is not work that someone can do for or to you. As Socrates was constantly telling people, virtue is not teachable.

You can come unstuck from existential inertia only with a self-propelled change of direction.

It was a strength Alcibiades didn’t have. Class and cash do not buy you character, and time spent chasing the former is time spent not building the latter.

‘Ambition,’ wrote David Whyte,

is a word that lacks any real ambition, ambition is frozen desire, the current of a vocational life immobilized and over-concretized to set, unforgiving goals. Ambition abstracts us from the underlying elemental nature of the creative conversation while providing us the cover of a target that has become false through over-description, overfamiliarity or too much understanding.

The ease of having an ambition is that it can be explained to others; the very disease of ambition is that it can be so easily explained to others.

He could so easily be talking about a financial-planning report and their well-meaning, but meaning-blocking, attempts to over-understand, and over-fit what matters into what can be measured, and summarised in a neat little list or table.

He goes on to describe the people those reports are written for:

Ambition is natural to the first steps of youth who must experience its essential falsity to know the larger reality that stands behind it, but held onto too long, and especially in eldership, it always comes to lack surprise, turns the last years of the ambitious into a second childhood, and makes the once successful into an object of pity.

‘We may direct the beam of ambition,’ he continues, ‘to illuminate a certain corner of the future world but ultimately it can reveal to us only those dreams with which we have already become familiar.’ I hope that this essay has shown you that it doesn’t have to be this way.