Being (Un)Successful

An unsuccessful person's take on what it means to be successful.

I recently told a friend who claimed that aloneness is related to success that that’s not necessarily true. My own case – alone but not successful – disproves, or at least weakens, that. To which he said that some people would consider me the epitome of success.

Fortunately, he was smart enough to get what I meant; after all, much the same held for him. And to see that it’s not just false modesty or humble bragging – which is contemptible, neither here nor there, trying to have your cake and eat it too. That it’s not enough to boast; you also want to come off as modest while doing it.

And yet, it’s true enough that a lot of people, myself included, apparently seen by many from outside as successful, are pretty much anything but.

What does it mean to say that I am or am not successful? To answer the question, positively or negatively, I must have some meaning I attribute to that word. So how do you define what it means to be successful?

A seemingly logical way to go about it is to pick a metric and quantify it. You’re successful if you have so many millions (or billions) of dollars, or so many million ‘followers’ or ‘fans’, or if X number of people acknowledge you as their boss. Three standard metrics – wealth, status, or power.

That’s a pretty crappy measure, not least because it’s arbitrary – who decides which metric matters? Whatever metric you pick will likely have both false positives and false negatives. The false positives being countless number of rich or famous or powerful people I personally wouldn’t consider successful. And what about false negatives, say someone like Witold Pilecki, Franz Kafka, Vincent Van Gogh, Boyan Slat – neither rich, nor famous (at least in their lifetime, and perhaps in some cases, even now) or powerful?

Perhaps you could try this in terms of how much impact a person has. All three – wealth, status, power usually are a cause or a consequence of impact, that is to say, either wealth/status/power lead to impact, or impact leads to wealth/status/power. And this covers the false negatives as well – people who make impact without much wealth/status/power.

But this brings its own problems. How much impact is sufficient – who decides that, and how? How can you ever measure impact satisfactorily? Is impact ‘bad’ and ‘good’, and how do you distinguish? And what kind of impact matters – deep impact, affecting a few individuals but affecting them deeply, or wide impact, affecting many people, but shallowly? But most importantly of all, any definition should still remain personal – who the hell is someone else to tell me whether I’m successful or not?

A good definition should be general, something everyone can use. And yet, this one should also be personal – because my success or failure is something I decide for myself. Which leads to a general principle that anyone can apply, but in their own personal way, to arrive at an individual answer for themselves.

There won’t be a single definition of a word like successful that everyone will agree on, and that’s not a problem. In fact, I think of more value than a definition with the greatest consensus is a definition that helps me answer the question of whether I am successful.

Which leads me to put forth what I think is a decent definition of success – impressing yourself. If you can do that, you’ll probably consider yourself successful. And that’s the sense in which I’ll use the word successful throughout this essay. Impressing is more than satisfaction; it’s a stronger word. You can be satisfied with yourself without being impressed, but if you’re impressed, you will be satisfied (which doesn’t mean you stop aiming for more, just that you think what you’ve already done is good).

How do you impress yourself? You can do that by either doing something cool, or by having really low standards, so that anything impresses you.

Doing and Becoming

What makes someone successful? Which is to say, what will it take them to impress themselves? This question isn’t in the sense of what traits are needed to be successful? It’s in the sense of what do you need to become to classify yourself as successful, or what do you need to do to classify yourself as successful?

The very idea of what constitutes success depends on what you value, because that’s what you’ll find impressive. Wealth or brawn or intelligence can just as easily be something looked down on as it can something admired. Rich people often try to pass off as ordinary while poorer people might try to project wealth.

But when I say ‘what you value’, what exactly is being valued? Is it the ‘doing something’ or is it the ‘becoming someone’? To take the example of wealth – is it the fact that a person did something to earn money, or is it the fact that he is a rich person, that he has a lot of money? Hence the two questions in the paragraph before the preceding one – becoming someone v/s doing something.

Intuitively you’d assume doing things is more impressive, but people seem to be more easily impressed by ‘becoming someone’ than by doing something. Someone might have done great work, but the moment they get a Nobel or a Pulitzer, it’s then that they suddenly become successful. Their achievements by themselves didn’t do much; it’s the becoming a Laureate that did it.

I find award functions funny for this reason – often no one in the audience has a clue what the person did, but they’ll clap and be impressed anyways because he’s getting an award. Such touching faith that the award recognizes merit faithfully, or more likely, simply never having given this a thought. It’s a common sight because it’s not easy to separate doing something and becoming someone. They’re equated too readily, the implicit assumption being that you had to do something to become someone.

I doubt anyone would like to admit they’re impressed by superficial titles – it’s nicer to dress it up as merit. If you asked someone why they’re impressed because you’re an alum of a top-ranked college, or an employee at a top firm, if they stop to think about it, they’ll probably tell you it’s because you must have done something impressive (worked hard, been smart or something similar) to be someone like that.

The idea is that ‘becoming someone’ is a causal effect of ‘doing something’. Deeds, things you do, lead to things you ‘become’. Of course, there are cases where it’s pretty easy to see this is not really true – nominated positions or figureheads come to mind.

So where this is going is that, in most cases, if you probe deeply enough, you’ll find that what people value, or claim to value, is the deed, the ‘doing something’. And if what you consider success derives from what you value, and people value the ‘doing’ (the value of the ‘becoming’ being simply derived from that), then differences in conceptions of success arise due to differences in how people value deeds.

An easy way to see this is to take a phenomenally rich person, like Jeff Bezos or Bill Gates. I’m sure there are many reasons to commend them, but I’ll stick to a 1-dimensional model of wealth for simplicity. Now if I think that money is a dirty thing – and that is again mostly because of what you have to do for it, that you have to cheat or deceive to be rich, then I won’t value wealth, and I won’t consider them successful in the least and the matter ends there.

If I do value wealth – again because of the deeds that go into it, perhaps believing that to earn wealth you must do something valuable enough that people are willing to pay for it, so if you are rich it means you’ve done a lot of such valuable work, I’ll consider them successful. Their kids are probably wealthy too, though not to the same extent; yet would I consider them successful? Inheriting wealth doesn’t command the same value as earning it. Which is to say that simply ‘being’ wealthy isn’t enough to be successful.

That aligns pretty well with how I defined success. I can’t imagine anyone being impressed with themselves by inheriting wealth, but I can imagine being impressed by earning it.

And it’s worth pointing out that this conception of being successful has nothing to do with what other people think of you. It isn’t about doing what you want, or even what makes you happy (though presumably, if you think you’ve done something impressive, you’d be happy – more on that later). It’s having done something that impresses you yourself.

Pseudo – Impressive

So the answer to the question of why people would have different standards of what being successful would mean to them is that the value assigned to the deeds that go into such success differs from person to person.

Why does this differ? It’s another involved question, one I don’t want to get into here. At a high level I’d guess it’s that the things someone values, the traits or principles they consider important, are the currency they use to assign the worth of something. Someone who valued compassion might not think much of a particular businessman as someone who valued innovation or daring.

But another reason is probably that you don’t know something you’ve never done. Not its worth, nor its difficulty, nor how it feels to do. Someone might consider killing a human a tremendous thing; one used to it might call it a day’s work.

My own example illustrates the point better than anything I’ve come across. The idea, or delusion, that someone who has cleared a bunch of examinations or landed a job that a lot of people seem to want is brilliant. The judgment here again hinges on the value you assign to this particular deed.

I generally prefer abstractions over personal examples because the latter seem to derail most conversations. In this case, it’s often mistaken as modesty, which it definitely isn’t, or as pretend-modesty, which it isn’t either. Or people attempt to ‘console’ you, trying to assure you, sincerely or insincerely, that no, you are brilliant. If you can avoid these diversions, you come to the point – which is whether such achievements are really impressive or not.


I strongly believe not. Rarity by itself doesn’t make something valuable; just because there are few of something in existence doesn’t mean each of those things has great worth. That’s for the supply side of the equation – reducing supply doesn’t raise value, even if it can raise price, because the two aren’t the same.

“Beautiful things of any kind are beautiful in themselves and sufficient to themselves. Praise is extraneous. The object of praise remains what it was—no better and no worse… Does anything genuinely beautiful need supplementing?… Are any of those improved by being praised? Or damaged by contempt? Is an emerald suddenly flawed if no one admires it?

Marcus Aurelius

Raising demand doesn’t raise worth either – were the whole world besotted with something, it wouldn’t necessarily raise the value of that by a jot, even if it did send the price skyrocketing. Praise and contempt are, in a sense, a rise and fall in demand – and yet, the worth of the emerald remains the same.

Artificial tests – the man-made tests that we game – be they examinations, interviews, follower counts, rankings, bestseller lists and so on, are the prime example of something of no worth by itself, yet something that impresses. Of no worth by itself primarily because it doesn’t do anything useful (at least not directly – it can at best be a means to something useful). And the reason it doesn’t do anything useful is because it’s artificial, something you do only because you’re supposed to in order to get something – were it not for that, you’d never do it.

The artificiality of a test is a measure of how much and how specifically you’re supposed to prepare for it. The best tests are the ones you don’t have to prepare for – not because they’re easy, but because they’re natural. They test something – whether it’s knowledge, skill, strength – such that those who possess it inevitably ace the test, even if they haven’t explicitly tried to. The best exams, for example, are the ones that align closest to ‘learning’ – where someone who’s understood the subject, regardless of whether he really ‘prepared’ for the test, would do well on – not the one who’s memorized tricks and likely questions.

An artificial test is easy to spot. It makes people do something that, left to themselves, they’d never do in a million years. A test of rock climbing, of running, of weightlifting, of singing, of football or tennis – what you do in the test is far closer (though probably not the same, and that’s because the very fact of preparing for a test induces some artificiality) to what you do for fun. Whereas what you do for most standardized tests is completely alien to what you’d do by yourself (even if you happen to like what you read, is that really how you’d have gone about it without the test ahead of you?)

Not all tests have to be artificial. There’s a difference between a test of speed like a race, a test of strength like a weightlifting competition, and the typical standardized tests for colleges and jobs. The difference is how easily you can game it – the easier to game, the more artificial. It’s rare for a slow runner to win a race using tricks, rare for a weak person to win a powerlifting competition using hacks, but extremely easy – and dare I say common – for a stupid person to win tests claiming to test knowledge of something, or looking for creatures with a particular pattern in their CV or who fit into a particular ‘organization culture’.

The reason for that is that to win such a test, you don’t really need to win by being the one who’s learnt the subject the best – if you did try that you might well be more likely to lose. You just need to be the one who’s learnt the tricks of the trade – what’s more likely to be asked, what the person in front of me would like to hear, how I should dress up my content to win. Whereas, a runner or lifter might slightly improve his outcome through some techniques, but that can’t change a weak player into a winner.

It’s a rare skill, difficult but not impossible, to design tests that can’t be gamed, where knowledge wins over memorization and hacks. I can recall a handful of courses where I had professors who could do that – and all happened to be STEM or economics / commerce, not a single from ‘soft’ subjects – probably because your answers in STEM mostly don’t depend on what your examiner thinks or believes.

Looking at what someone’s made – whether it’s art, music, code, handcrafts, hardware, literature – is a much more reliable test. It’s genuine – it’s what they spend their time on, typically without being coerced to, and it’s often useful – people derive value from the creations.

There’s another defence of standardized tests, that they ‘test’ something, some trait, that they filter for people with particular characteristics. Some might claim knowledge, some determination, very ambitious or deluded ones claim to test your character. Whether they really do so is questionable – not just because they’re gamed, but because a trait like determination is highly context dependent – a person showing determination for one thing mayn’t show it for another. What they definitely do test is how well you game tests. What you measure gets managed, and the measure becomes an end in itself.


To return to an earlier question – if I choose to not live under delusions, if I know that I have not done anything impressive, even if others might happen to believe so, where does that leave me?

That leaves me wherever I want to be. After all, there’s no reason I need to do anything worthwhile at all, if I don’t want to. If I’m at peace with that fact, if I know my reality and accept it cheerfully, then the matter ends there.

If I think though, that I want to do something better than what I’ve done, that opens up more questions. In the first place, why haven’t I done it already – what has stopped me? If, as you might think to yourself, or as people might try to assure you, you are brilliant, talented, intelligent – then the question arises – what makes someone think that? The proof of the pudding is in the eating, where then is the proof of my supposed brilliance? Perhaps they are mistaken, or at least exaggerating. It’s easy to misinterpret this stripping away delusions as self-loathing. All it is is seeing myself as what I am, not what others tell me, not what I want to be, not what I think of myself, but what I actually am.

Which is not to say that not having done anything impressive yet implies that I can’t or won’t do so in future as well. It doesn’t, although it doesn’t imply I will either. It’s simply that living in the future – specifically riding on the achievements one thinks one can potentially do – is a pleasant escape from the reality of what you have done and what you are doing, which, unless you will otherwise, soon metamorphose into what you will be doing.

it is dangerous to venture. And why? Because one may lose. But not to venture is shrewd. And yet, by not venturing, it is so dreadfully easy to lose that which it would be difficult to lose in even the most venturesome venture, and in any case never so easily, so completely as if it were nothing …one’s self.

Kierkegaard (from Amjad Masad’s essay)

Assuming that I think I want to venture, and yet I haven’t done so, is it worth trying? To try is to possibly lose, certainly to spend effort and years, with possibly nothing to show for it at the end of it. A certain cost, and an uncertain benefit. To not try is to apparently not lose, to avoid the cost, but to definitely accept that I shall get no further, and that perhaps is a bigger loss than any.

Originality in choosing problems seems to matter even more than originality in solving them. That’s what distinguishes the people who discover whole new fields. So what might seem to be merely the initial step — deciding what to work on — is in a sense the key to the whole game.

How to do Great Work – Paul Graham

Of course, even if you do decide to try, you don’t really know what you should try, where you should start, and perhaps that’s the hardest part of it all. The alternatives are either to sit around and mope in the expectation that one day it’ll drop into your lap, or to keep going on, even though you don’t know where it is you’re going.

But on the road that I’m on I must continue; if I do nothing, if I don’t study, if I don’t keep on trying, then I’m lost, then woe betide me. That’s how I see this, to keep on, keep on, that’s what’s needed.
But what’s your ultimate goal, you’ll say. That goal will become clearer, will take shape slowly and surely, as the croquis becomes a sketch and the sketch a painting, as one works more seriously, as one digs deeper into the originally vague idea, the first fugitive, passing thought, unless it becomes firm.

my torment is none other than this, what could I be good for, couldn’t I serve and be useful in some way, how could I come to know more thoroughly, and go more deeply into this subject or that? Do you see, it continually torments me, and then you feel a prisoner in penury, excluded from participating in this work or that, and such and such necessary things are beyond your reach...

Such a person doesn’t always know himself what he could do, but he feels by instinct, I’m good for something, even so! I feel I have a raison d’être! I know that I could be a quite different man! For what then could I be of use, for what could I serve! There’s something within me, so what is it!

Vincent Van Gogh, Letter to his brother Theo

I wonder how many people do find that out in their lifetime, even among those relatively few who make the effort to. Van Gogh, who wrote even better than he painted, spent years drifting from and failing at one endeavour or another, only seemingly succeeding a couple of years before ending his life – perhaps that’s why he could write about it so deeply.

People who do great work are not necessarily happier than everyone else, but they’re happier than they’d be if they didn’t. In fact, if you’re smart and ambitious, it’s dangerous not to be productive. People who are smart and ambitious but don’t achieve much tend to become bitter.

How to do Great Work – Paul Graham

None of which is to say that there’s any onus to choose a particular way, or to strive to be successful. It really comes down to individual choice. Perhaps any choice is simply an attempt at maximizing one’s happiness; for some it might be through work, for others it lies outside work.

Paul Graham writes that people who are smart and ambitious but don’t achieve much tend to become bitter, and it’s easy to imagine that – I don’t doubt it. Napoleon, who held the stick from the other end, had another take – ‘Men of great ambition have sought happiness . . . and have found fame.’ That people who are ambitious, in the search for what makes them happy, end up finding something else entirely – presumably not what they sought, but nevertheless perhaps alluring enough to distract them from it.

What it comes to is that, if you’re not ambitious, you don’t need to work towards anything, beyond the bare minimum you can’t avoid, if that’s what you think makes you happy. If you are, you probably will work; whether anything comes of it is another question, and whether, even if you do achieve something, that makes you happy is yet another question.

If you do choose to work, at any rate you do get one answer. If I ever get the temptation to think that I am talented, brilliant, whatever I or others choose to tell myself, all I have to do is to look what I’ve actually done to know whether any of it is true.