A version of this essay appears in our new book, The MR PORTER Guide To A Better A Day. Proceeds from the sale of the book will go to our Health In Mind fund, which supports men’s mental and physical health initiatives.

One of the most successful stories we’ve ever published on MR PORTER – depending on how you judge success – was about success itself. The headline, “Five Habits Of Successful (And Famous) Men”, is, let’s face it, borderline clickbait, if not the very definition of the term. But that’s beside the point. The point is: wouldn’t you click it? Or at least be tempted?

The truth is, as I learnt in the course of commissioning and editing hundreds, if not thousands, of such pieces, that “success” is one of those words that has a certain amount of cut-through, as your friendly neighbourhood social media manager might call it, in this overwhelming and oversaturated digital world in which we now live. Clearly, “success” pushes a button in people’s minds. And why shouldn’t it? We are a culture that admires success above all things. We ask our children to aspire towards success, via tests and examinations, and we expect our cities and states, countries and industries to exemplify it through positive growth figures, and we panic en masse if they don’t always materialise.

In the past 20 years, we’ve developed a preoccupation with the TV talent show, a format which, via a long procession of choreographed tear-jerking moments, has developed one of our favourite narratives: Success Against The Odds. But that’s just one of the many flavours of success we now enjoy as entertainment. How about Success At A Young Age, which has given us the excellent novelist Ms Sally Rooney and the talented bedroom jazz virtuoso Mr Jacob Collier? Or even the idea of Failure As Success, which you might use to describe the philosophy espoused by journalist Ms Elizabeth Day in her popular podcast How To Fail.

This isn’t a new preoccupation. Call it natural selection, call it capitalism, call it pack mentality – we’ve always been interested in seeing who comes out on top and how we might follow in their footsteps. But, says Mr Jamie Millar, a fashion and fitness writer whom I often commission on this topic (he is the man who gave us “Five Habits Of Successful (And Famous) Men”), our obsession with success is particularly pronounced at the moment.

“Success narratives have become more compelling, or urgent, in the modern neoliberal era, in which we’re all at the mercy of the market, and the weight of individual responsibility is crushing,” says Mr Millar. “I don’t think there’s anything inherently wrong with wanting to be better or more successful. But it’s hard to know what I really think, because the cultural programming is so pervasive. And the flipside is disturbing. The implication is that you’re not fine as you are or not ‘living your best life’, which is an insidious phrase. If you’re not successful, then it’s your fault for being lazy or stupid and not the rigged market.”

Mr Millar is right. Success is everywhere, all around us, particularly in the form of one of our other cultural obsessions: data. With an endless stream of metrics and analytics at our fingertips, success has become not a vague idea, a thing that is yearned for and dreamed of over the course of a lifetime, but a quality that is measured day by day, hour by hour.

The practices of crunching statistics and interpreting and reporting them is a large part of what we do in the modern workplace, but it’s also invaded the personal sphere, thanks to platforms such as Instagram, Twitter and Facebook, which, with their individual sets of measurements, can quantify things that were previously unquantifiable. Such as how much your friends like your new haircut, or how impressive your holiday is, or – and this is the aggregate of all individual social media successes – how interesting and attractive you are. Success narratives have made us professionalise our private lives.

There’s a popular myth that Eskimos have 100 words for snow, and that tells us a lot about how they perceive the world. It’s a complete lie, of course, and it doesn’t. Yet, I can’t help thinking about this story when I look at lists of the different data points I have available to judge the performance of an article, video or photograph on MR PORTER. What is really meant by “reach”, “bounce rate”, “engagement”, “dwell time”, “product views”, “completion rate”, if not “success”, “success”, “success?”, “success?” and “SUCCESS!!!”?

By continuing to develop and venerate such terms, we’re talking up the idea of success and turning it into a bigger, more nuanced, more confusing concept. We’re also trying to rip it into its component parts, to understand it. But still, it seems, no matter how many metrics we have, the nagging question persists: what is success?

What I’m getting at here – or rather, what has slowly dawned upon me in my own career – is that chasing success is one thing, but feeling successful is another. Typically, I must admit, I do an awful lot of the former and not much of the latter. And I doubt I’m alone in this respect. I tend to find that most successes come with their own dose of anxiety. That was good, but what’s next? Will this be the last good thing that happens to me? Will I be able to go one step farther?

I often wonder whether that’s because we first learn about success through the idea of prizes: sports trophies, marks in exams, report cards, fellowships, getting jobs, promotions, pay rises. Such clear indications of success are a hallmark of young and early adult life, but they tend to dry up eventually, or at least the rewards of doing a good thing well become more subtle, as success builds upon success and the onus upon the successful is to praise and reward others, not get a pat on the back themselves.

I realised this recently when I signed up for a weekend course in wine appreciation (nominally for fun, but probably, honestly, to look clever in restaurants). What I was really shocked by was not the fact that they make dessert wine out of rotten fruit (and it’s delicious), but the sense of elation, and relief, that I felt when presented with the multiple-choice exam at the end of it all – the glee of knowing that, if I knew all the right answers, I would get a mark and a badge. The road to success, in the sphere of wine school, felt so clean, so simple and so satisfying. And then I felt ridiculous. Why did it take a – let’s face it, completely unimportant – quiz to make me feel this way?

The reason, clearly, is because the notion of success in the 21st century has not only become more urgent, but in its all-encompassing nature, more diffuse, to the point where it’s not always easy spot it and properly celebrate it when it happens. Is it about nailing your KPIs at work? If so, which ones? Is it more about winning the respect of colleagues or having influence in the wider professional world? And what about outside of work? Are you going on enough vacations? Are you reading enough books? Do you have enough friends? Do you have enough fun? Social media, with its carefully curated, pitch-perfect versions of your acquaintances’ lives, would tell you it’s all of these things, and more. Most of us are aware that’s not realistic, so what are we supposed to be aiming for?

Let’s turn to some experts. “Success in life could be defined as the continued expansion of happiness and the progressive realisation of worthy goals.” (That’s Mr Deepak Chopra in his 1994 book The Seven Spiritual Laws Of Success). “The real mantra of success is sustainability and growth.” (That’s Mr Steven Covey in the foreword to his hugely popular, genre-defining 1989 book The 7 Habits Of Highly Effective People. Side note: if success were a number, it would be the number seven, clearly.) Both these thoughts suggest that success is something that is worked towards, not necessarily achieved. That’s all well and good, but I’m a needy millennial. I need to feel successful. How do I do it?

“Recognition boosts everyone’s self-esteem, but learning how to credit and value yourself without needing the presence of others is very helpful,” says Ms Mary Spillane, a London-based executive coach who has worked with businesses including the BBC, IBM and BMW. “Many people don’t hear praise and therefore don’t feel the recognition they have earned. Others don’t need to feel successful and are driven by other things: learning, growing, doing something new, or for others.”

So, the wine quiz scenario. Valid? Grown-up? Healthy? “Human beings benefit from having goals and working towards them and celebrating when they are achieved, for sure,” says Ms Spillane. But goal-driven thinking has its pitfalls, too. “Because success can be fleeting,” she adds, “you have to keep working at it, or exploring areas of your life that have suffered because you have focused too much on one aspect.”

It’s about goals, then. And goals upon goals. Always growing. Never ending. The thing about goals, though, is that it’s not always clear who is defining them, and how, and what they mean. This is what struck me when, for the purposes of this piece, I started asking my friends about their successes. I wanted to know if any of them had ever felt successful or whether that’s just a myth, or not exactly the point.

The most interesting conversation was with a friend – let’s call him Mr Smith – who has been incredibly successful since his early twenties when, in his first job, he quickly became the top performer at a 50-person recruitment firm in the City. If anyone should have a feeling of having achieved goals, I thought, it would and should be him. But he says his early employment, goal-driven as it was, was something of a nightmare. “The sole focus of the firm was to produce revenue,” he says. “Our targets were annual, monthly, weekly, daily and, I kid you not, hourly. I set myself the target of becoming top biller and then I’d allow myself to quit.”

But he didn’t quit. “My main driver wasn’t money,” he says. “Instead, it turned out that I hated letting people down on a professional front. At the time, I was being told that, as the company was struggling, certain, newer employees would likely lose their jobs if I didn’t continue to bring in more and more money.”

When he did finally leave, it was because the pressure had made him develop severe, physical anxiety symptoms. But what about hitting the targets? Wasn’t smashing them exciting? Wasn’t it inspiring? “At no point did I find my early success in my industry galvanising,” he says. “All I wanted each week or month was to have my head above water and not let management down.”

Mr Smith now runs his own successful business in the same sector. It’s enabled him to focus on what he has discovered is important to him – delivering satisfaction to clients, nurturing colleagues and sharing the fruits of success with the whole business in the form of benefits, such as “more freedom” and “more flexibility”. You never see those words in a Google Analytics report, do you?

The learning here is that meeting goals, in and of itself, doesn’t necessarily lead to that feeling, that idea, that sense of contentment, that we might think of when we hear the word “success”. This is where all the metrics, all the KPIs, that we encounter in our day-to-day lives can become a little disheartening. They are informative, certainly, indicative, maybe. But are they meaningful_?_

In her book How To Be Happy At Work, Ms Annie McKee argues that workers (and by inference, people ) should focus on “vision”, not “goals”, despite what is written on their HR-approved performance plan. “In our hypercompetitive, achievement-oriented workplaces, setting and achieving goals has become the main event,” she writes, “not something we do on the road to something bigger and more meaningful. A narrow focus on goal attainment is so prevalent in our collective psyche that sometimes all we do is set and try to achieve small, measurable goals at work. Success has come to be defined by many people – and many managers – as goal achievement, rather than movement towards a hopeful vision of a fulfilling future.”

This idea points towards some uncomfortable truths. The pursuit of success is the same as the pursuit of meaning, which seems way more complex, and one concept doesn’t work without the other. What’s more, that meaning is a personal thing. The only person who can define what is meaningful for an individual is that individual.

For me, that’s a bit terrifying. I can’t help thinking, what, no badge? But, really, that fear is a shirking of responsibility. The idea that we’re responsible for our own successes is not a new one, but it’s typically linked to concerns around performance. It’s the idea that if we work harder, longer and strive towards an externally set standard of excellence in all aspects of our lives, success will be ours.

But there’s a lot more to be said for a different kind of success-hacking; that is, the reality that a person is never going to be – or feel – successful unless they decide for themselves, irrespective of what the world wants, what success looks like. For some, that might be money, power, recognition, admiration. For others, it might be raising a family, or helping friends, or promoting a particular political or social cause. For me, it is knowing the difference between a chablis and a sancerre, which seems completely ridiculous. But it’s certainly a starting point. And that’s OK, isn’t it? Please tell me it’s OK.