For decades the image of the outsider has been that of the uncompromising maverick – the lone wolf, a Hollywood hero, a winner. More recently, gurus such as Malcolm Gladwell have confirmed this advantageous view. When it comes to success, says the zeitgeist, being a misfit fits.

Great news – if only it were true. In reality being an outsider is – nearly always – a one-way ticket to exclusion. Alienation, isolation, poor-confidence (often hidden by a veneer of “cool”) and depression are the more likely results of feeling like you don’t belong – a grim fate made all the worse by success-gurus convincing outsiders their traits are bankable. Ultimately, the world’s still run by insiders with “successful outsiders” usually little more than “eccentric insiders”. Indeed, for every genuine outsider success story – David Bowie, perhaps, or Tracey Emin – there are 100s of disaffected, disillusioned and unhappy misfits who’ve never reached their potential.

That’s the bad news. The good news is that outsiders can forge an edge… a unique (often creative) and dynamic outlook that can (if honed) generate genuine success. Yet outsiders must go on a mission – first “finding meaning” for their life, before developing skills and attributes that bust through those glass ceilings or, better still, ignore other people’s ceilings altogether.

If outsiders can overcome the negative baggage they’ve acquired (often in childhood or adolescence) they can harness their unique qualities to win: on their own terms.

The Outside Edge is both a timely-tale of our era – uncovering the truth about misfits and individuality – and a redemption story.

“This is not another quaint book about how outsiders have an edge. This is a subversive manual for how outsiders can carve an edge for themselves with hard work, creativity and the right mental framework,” Ryan Holiday, author of The Obstacle Is The Way.

“This stopped me in my tracks. Robert has articulated and explained something which to many of us is just a feeling of outsider-ness. More than that he has explained what to do about it,” Richard Newton, bestselling author of The Little Book of Thinking Big.

“Ignore trendy commentators telling you being an outsider’s advantageous: it’s actually highly disabling. Kelsey gets on top of the issues to find a practical (and uncompromising) way through. With Kelsey’s help – being an outsider won’t f*** you up,” Oliver James, author of They F*** You Up and Affluenza.

“This is a thorough investigation into a neglected and often misunderstood area. Empathising with outsiders isn’t always easy – they are the (often self-declared) ‘misfits’ after all. And, as Kelsey points out, outsiders themselves are prone to ‘distorted empathy’ (i.e. identifying with the bad guy). Yet this makes Kelsey’s highly readable text and positive methodology all the more noteworthy,” Roman Krznaric, author of Empathy: Why it Matters, and How to Get it, and The Wonderbox: Curious Histories of How to Live.

“Robert’s book is a brilliant resource for anyone who feels stuck in the ‘grey zone’ or is working in the area of people development. It helps to explain why people behave in the way that they do and provides many practical ideas and tips to help them and/or others make the changes they need to find meaning and purpose,” Lindsey Agness, founder and managing director of The Change Corporation and author of Change Your Life with NLP.

“This is a book that totally resonates. Outsiders tend not to be positive thinkers and pessimists can find themselves feeling shut out. Kelsey not only understands this, but finds a way through. The Outside Edge is defensive pessimism in action. Bravo!” Julie K. Norem Ph.D, author, The Positive Power of Negative Thinking.

“This is an excellent read packed with both cautionary tales and optimistic insight, for anyone who’s ever felt on the periphery. It’s revealing, compelling and highly practical – not least in offering life-skills to those without the innate advantages of the insider,” Helena Pozniak, life-skills writer for the Daily Telegraph, The Guardian, The Independent and elsewhere.

“The Outside Edge is a terrific book for anyone who ever felt they didn’t belong. The author has written a highly personal analysis of how outsiders can succeed in work and in life. He has drawn upon a vast range of references across psychology, self-help, literature, philosophy and business to provide advice and encouragement to readers who feel they are not a member of the club. Kelsey has found fulfilment in middle age by building his own company and becoming a husband and father, and describes his journey – trying to be cool but feeling constantly alienated – brilliantly. I found The Outside Edge to be both pragmatic and uplifting. If you are looking for an enjoyable guide to both meaning and purpose in the 21st century, then I strongly recommend this title,” Luke Johnson, Sunday Times columnist, author of Start It Up and Chairman of the Centre for Entrepreneurs.

“As Kelsey so eloquently demonstrates, outsiders are often highly creative, and are usually best placed pursuing entrepreneurial ambitions – something that certainly chimes with my own outlook. What’s unique about this book, however, is Kelsey’s explanation of the sometimes discomforting reasons why people become estranged from their tribe. It’s message is uncompromisingly positive, although it also deals well with the genuine struggles outsiders face,” Michael Jacobsen, serial entrepreneur and author of The Business of Creativity.

“I can’t believe how many excellent insights Kelsey has drawn from such diverse and wise sources. With his characteristic honesty and ability to reflect on personal experience, he has created an inspiring and practical guide for outsiders. Kelsey’s books have the rare quality of encouraging the reader to reach beyond current limitations without over-promising, denying our vulnerability, or pretending that life isn’t sometimes (often) unpredictable, random, and difficult. The Outside Edge is a book outsiders will certainly appreciate if we want to increase our chances of success and well-being, however we define them, in a world made, and dominated, by insiders,” Ian Aspin, author of How to Be a Super Human: Using the Amazing Power of Social Networks

“Having helped generate 60 startups in six years, I’ve seen many outsiders succeed – on their own terms – as entrepreneurs. To make the most of their unique perspective, however, outsiders must acquire a degree of self-awareness as well as certain specific skills: knowledge that’s expressed brilliantly in this book, which I heartily recommend,”

Martin Bjergegaard, co-founder of Rainmaking and Startupbootcamp and best-selling author of Winning without Losing.

INTRODUCTION – Debunking the Outsider Myth

“If you really want to hear about it, the first thing you’ll probably want to know is where I was born, and what my lousy childhood was like, and how my parents were occupied and all before they had me, and all that David Copperfield kind of crap, but I don’t feel like going into it, if you really want to know the truth.”

Holden Caulfield’s sleep-deprived meanderings around 1940s New York provide the narrative for probably the most enduring treatise to adolescent alienation ever written. J.D. Salinger’s Catcher in the Rye (1951) is an exploration of the contradictions, shallowness and fakery of adult life – as seen through the eyes of a 16-year old outsider. According to Caulfield, everyone he encounters is a “phony” – pursuing thinly-disguised self-interest via artificial conventions and a veneer of amiability. It’s a world he despises for its hypocrisy and materialistic insincerity. Seeking depth and purity, Cauflield clings to uncorrupted icons such as his kid sister or the ducks in Central Park.

It’s a private and lonely rebellion: insightful yet naïve, sensitive yet hateful, individualistic yet aching to be understood. Defiant and insolent despite his inner confusion, Caulfield’s inarticulate musings express both the hopes and despair of youth so authentically they’ve made Salinger’s antihero the torchbearer for generations of tortured souls, me included. Like millions before and since, I identified with Caulfield’s mix of cynicism and angst – even mimicking his train journey into Manhattan through adolescent forays down the Essex commuter line into London’s Liverpool Street Station.

Clutching a day-return ticket, I’d wander the backstreets of the East End: collar up, cigarette in mouth, hands in pocket – the sheer misery of the streets around Petticoat Lane and Spitalfields markets (then, when shut, full of rubbish and winos) reflecting my lonely discomfort at the straightened adulthood I saw ahead of me.

Oh, how I loved Salinger for giving voice to my lonely disaffection.

Salinger’s false promise

Yet there’s a problem with this vision. While Manhattan and central London are obvious comparatives – and Caulfield and I suffered the same mix or angst and alienation – we had little in common. Unbeknown to me, Caulfield had an edge. He was being thrown out of Pencey Prep, an exclusive private school that had equipped him well despite his inability to complete a history paper or enjoy the college football games.

The tutors knew him and even cared for his welfare, and he was captain of the school fencing team. Meanwhile, I was one more mass-produced nobody from a “bog standard” state education system that expected, and planned for, low attainment. No one looked out for me and I was captain of nothing. So while Caulfield’s alienation came from his fear and rejection of the expectations driven by his expensive education, mine came from an altogether different source: exclusion.

In fact, Caulfield was no outsider. He was an insider with attitude. It’s a crucial divide, and one giving him an edge over the likes of me, who was simply on the edge: as denoted by our behaviour once in the big city. Caulfield confidently bluffed his way into expensive Midtown hotels – blagging alcoholic drinks and dancing with 30-something female tourists – while I kicked around closed markets, maybe engaging a homeless bum in a doorway or nursing a mug of tea in an East End “caff”.

Of course, Catcher in the Rye is fiction, although Salinger’s early adulthood somewhat mirrors that of Caulfield, with the added guilt of benefiting from self-made immigrant parents. Yet this theme of the romantic outsider being – in reality – an elite rejectionist, and therefore someone with an edge over less advantaged outsiders, is repeated time and again. A British literary hero of the rebellious classes is George Orwell (1903-50), a man disavowing imperial conformity to chronicle the poor and downtrodden of the inter-war years. As social commentary Orwell’s writing is explosive – not least his ability to experience the life of an alienated down-and-out or itinerate salesman.

And, like Salinger, Orwell’s work has survived through decades of change by tapping into social exclusion via his own alienation. An alienation, what’s more, that ran deep enough to reject the affected-revolutionary rhetoric of his fellow bohemians. Indeed, Orwell is a hero of intellectual heretics from both ends of the political spectrum – surely the mark of a true outsider?

Except that Orwell was no outsider. An Old Etonian – and part of the imperial governing-class – Orwell, like Caulfield, had an edge over his fellow rejectionists. And he also had the indulgence of choice. Tired of roughing it, Orwell would return to his parents’ seaside residence in the smart Suffolk resort of Southwold. Here, he could eat well, pursue love interests and perhaps be fitted for a new suit – all while damning the bourgeoisie for their selfish mores, petty snobberies and hypocritical values.

In terms of experiential reportage, Ernest Hemingway (1899-1961) is America’s outsider hero. A rugged and individualistic “man’s man”, Hemingway repudiated societal boundaries by seeking novelty through adventure. His reportage is legendary although, again, Hemingway was no outsider. He was the well-educated son of a doctor and musician. And those masculine survivor skills were learnt from his father at the family’s second home in rural Michigan: a weekend retreat away from the smart-gatherings of upper middle-class suburban Chicago.

As with Orwell, Hemingway pursued extreme individualism out of choice. Again, his expensively-honed skills and family connections gave him the edge required for him to profitably pursue macho dreams that indulged his love of European sophistication, hardcore naturalism and the adrenalin of war.

Gladwell’s myth exposed

As outsiders, Orwell and Hemingway make poor role-models. They renounced conventional attitudes not despite their privileges but because of them – relying on the edge their advantages give them in order to succeed as outsiders. Meanwhile, anybody forsaking such norms without such an edge will find such individualism a far harder slog. In fact, they’ll likely find it impossible.

Of course, to the observer, such rejection looks and acts outwardly the same. Orwell the tramp looks much like the next guy sleeping under Waterloo Bridge. Yet they couldn’t be further apart. Given Orwell’s privileges, he has an incentive to sleep rough – not so the outcast beside him, for whom a good Suffolk breakfast, a fitting at Denny’s and a mild disagreement with one’s publisher are the pursuits of someone from another planet.

Such is the gap between the advantaged and the disadvantaged outsider – such is the edge some have and others lack. Not that you’d know it from reading Malcolm Gladwell. In his book – David and Goliath: Underdogs, Misfits and the Art of Battling Giants (2013) – that modern-day sage explores the art of success for those without the advantages of the insider. And as the book’s title suggests, Gladwell uses that famous biblical battle as his exemplar.

History perceives the underdog to be the shepherd-boy misfit David. Yet, according to Gladwell, David possessed hidden advantages over the warrior-giant Goliath due to his ability to generate new solutions by breaking the rules. Goliath prepared for a straight fight based on his traditional assumptions and military knowledge, and expected to win based on his size. Meanwhile, the outsider David – by refusing armour – ignored convention: instead employing his shepherd’s slingshot to fell the colossus.

Life’s full of such examples, opines Gladwell – proving that the disadvantaged or excluded can break convention simply by turning it on its head. Dyslexics succeed due to their highly-developed listening skills, he says, while those educated in larger class sizes – something most educationalists think detrimental – benefit from shared learning and collaboration. From the American Revolution to Vietnam, from the Civil Rights movement to Northern Ireland, Gladwell finds history littered with underdogs that were expected to lose due to their disadvantages, yet who overcame obstacles through guile, guts and creativity. Most often – like David and his agile slingshooting – they won because their perceived disadvantages were in fact advantages, giving them an edge over their rivals.

Great news. If only it were true.

Unfortunately, it’s a myth: the outsider myth – a modern day fallacy that says, to succeed, you have to go against the tide. Be different. In reality, however, it’s an option open only to a well-educated elite pursuing their expensively-acquired advantages over the rest of us. Of course, underdogs can succeed, just as outsiders can change the world. Yet any “misfit” thinking success assured simply because they’re “not like other people” is likely to find themselves on the wrong side of history. From 5,000 years of records, Gladwell picks the winners while ignoring the countless occasions outsiders were crushed and forgotten by those utilizing their inherent advantages – their edge – over the rest of us.

For Gladwell, disadvantages – such as low educational attainment and social exclusion – are not disadvantages at all. They encourage co-operation, flair and imagination. Yet I think this a cruel trick to play on the millions of people feeling alienated from conventional pursuits while lacking the gilded opportunities of an Orwell or Hemingway, or even a Caulfield. Society’s changed since Salinger wrote of Caulfield’s bleary-eyed New York wanderings, and even since I kicked around the East End. But it hasn’t changed enough to accommodate all those encouraged to think their outsider angst and misfit rage a sure-sign their “gift” is bankable.

The soundtrack of working-class rebellion

Not so, shout the optimists. The world’s full of disadvantaged outsiders that made it due to their unique outlook. Take rock-‘n’-roll. Isn’t that the soundtrack to working class rebellion going right back to white kids playing black rhythms to shock their parents in 1950s America? On this side of the pond, pop-music (at least until the 1990s) was virtually defined by alienation: not least in the spawning of multiple musical tribes such as punks, mods, casuals, rude boys or new romantics. Surely, each of these cultural insurgencies contained significant elements of working class rebellion, didn’t they? And their revolutionary leaders – whether Ozzy Osbourne, Paul Weller, Johnny Rotten, Terry Hall or Steve Strange – were all authentic working class heroes, weren’t they?

Indeed they were. Yet look closely and those preaching anarchy were just as often recoiling from middle-class expectations – from “making plans for Nigel” – than the limits of working-class aspiration. Sure, the odd back-street band won a deal from the moneymen – producing dancehall fodder for the masses. But nearly all those 1970s superbands – the likes of Genesis, Pink Floyd, Queen, Fleetwood Mac, and even The Clash – can trace their heritage back to Britain’s fee-paying “public” schools, again proving that rebellion is facilitated by, not despite, the advantages of privilege.

A peculiarly-British twist? Not at all. While researching this book news came of Lou Reed’s death. A sad loss, not least because, along with his band (the Velvet Underground), he was emblematic of the rebellion pop-music engendered for so many. Reed was billed as an outsider – a label confirmed by his obituaries: The New York Times even running the headline “Outsider Whose Dark Lyrical Vision Helped Shape Rock ‘n’ Roll”.

Yet Lou Reed’s rejection of society owes more to his advantages than any sense of working class rebellion. The son of an accountant, Reed – as the child of successful New York Jewry – led a rather similar, well-educated, adolescence to Salinger. In other words, he was an idiosyncratic member of an elitist club. And this made Reed’s rebellion towards the drug-addled dens of New York’s underworld a choice, although his sense of rejection was compounded by his parent’s ham-fisted efforts to “cure” his bisexual “urges”.

In fact, just about everywhere you look for rebellion you find highly-educated people with expensively-honed talents pursuing “exclusion” as a means of self-expression – something true of music, the arts and literature. And it’s even true in business. After all, revolutionary techies Bill Gates (of Microsoft) and Mark Zuckerberg (of Facebook) had wealthy parents and a good college education – seemingly necessary requisites for breaking the mould via entrepreneurial success. Even Richard Branson, the UK’s best-known entrepreneurial rebel – and one of the moneymen supporting British pop – is the privately-educated son of a barrister.

Can disadvantaged outsiders prosper?

Stop me if I’m ranting, because the message here isn’t one of class envy or “chippiness”. At least not deliberately. My concern is for the outsider and the fact there’s a gulf – despite appearances – between the tools available, and therefore the outcomes, for advantaged against disadvantaged outsiders: for those with or without the edge of privilege.

Yet the central premise of this book is not the bemoaning of this reality. It’s to establish how disadvantaged outsiders can develop that edge. While disagreeing with Gladwell’s claim that our disadvantages and/or alienation can work in our favour, my aim here is to help make that very prospect a reality: to give genuine outsiders (not just eccentric elitists) the edge required to help them succeed.

Indeed, for every Salinger there’s a D.H. Lawrence or Alan Sillitoe: both born to semi-literate Nottinghamshire fathers – one a miner the other a bicycle-factory worker. Yet both became era-defining writers. In fact, Sillitoe’s The Loneliness of the Long Distance Runner (1959) stands alongside Catcher in the Rye as a treatise to, this time working class, alienation and rebellion.

For every Lou Reed there’s a David Bowie (the Brixton-born son of a waitress and charity worker); or Andy Warhol (Reed’s mentor and patron, and the son of an immigrant Pennsylvanian miner); or Tracey Emin (a teenage rape victim from the wrong part of Kent with cross-Romany/Turk-Cypriot parentage).

And for every Richard Branson there’s Apple’s Steve Jobs (the adopted son of a garage mechanic); or omni-inventor Thomas Edison (the near-deaf youngest child of a political refugee); or Starbucks’ Howard Schultz (the son of a Brooklyn truck driver).

Yet don’t be fooled. The Edisons and the Emins – as well as the Bowies and Warhols – are far from the norm. Insiders are the norm. It’s their world, with advantaged outsiders no more than insiders with an attitude – though still utilizing the edge gained from their inherent advantages in pursuit of their (usually creative) self-expression. Disadvantaged outsiders have to make it despite their sometimes highly-disabling attributes, not because of them. Gladwell’s wrong on this one, though that’s where this book comes in.

Making rebellion count

Being a disadvantaged outsider is usually a one-way ticket to economic and social exclusion: a message as true of race, gender, age and sexuality as it is for class. Forget the noise that anything’s possible – rebellion’s end for those without the edge of inherited or acquired privilege (in whatever form) more usually involves confusion, isolation, failure and surrender. More outsiders commit suicide than conquer the world using their original perspective: a depressing conclusion that every word in this book is aimed at preventing.

If we’re to avoid such a fate, we must forge an edge for ourselves: one that helps us cut through the discrimination and barriers we face (both seen and unseen). As stated, those that feel alienated – not by their guilty advantages but due to the lack of them – can break conventions. And this can, if successful, lead to revolutionary change. Many advances in all human fields have been brought about by those “thinking outside the box” – most often due to their exclusion from those “inside the box”. We look at the world as if watching a play unfold, allowing us to observe and understand it in ways not available to the players themselves.

This is a unique vantage point. It’s also one offering genuine outsiders an even sharper edge than all those eccentric insiders utilizing their inherent social booty: as long as we can calculate a singular direction and hone the skills required to progress. If we can develop that unique perspective and – importantly – find a way of getting others to listen, then rebellion’s end could well bring about revolutionary change. And that sure beats kicking around the East End with the weight of the world on your shoulders.