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Alain De Botton encounters office life. Photograph: Phil Fisk

Is Alain de Botton the biggest pseud and poseur of all time, or a brilliant writer who asks intriguing questions? The Guardian has always been pretty clear on the matter: "He's an absolute pair-of-aching balls of a man - a slapheaded, ruby-lipped pop philosopher who's forged a lucrative career stating the bleeding obvious." But then he has fans like Edmund White, Roger Scruton, John Banville, Jan Morris and John Updike, who called him "dazzling". The weird thing is I find it possible to hold both views about de Botton almost simultaneously - I can flip between the two while reading just one paragraph of his writing. His new book is called The Pleasures and Sorrows of Work, and immediately provokes the furious question, what do you know about work? De Botton is the son of a fabulously wealthy Swiss financier, has never worked in a factory or shop in his life, and only briefly worked in an office, part-time, when he was making TV documentaries. So when he remarks playfully - playfully being his default setting - that a lot of the jobs people do seem rather futile, I want to shake him and say: "Not if you have to feed a family." At his dilettante worst, he can sound like Prince Charles asking why we can't all be crofters. But then being infuriating and provocative is part of his job.

Meeting him produces the same sort of confusion. On the one hand he is friendly, charming and polite; on the other, there is something almost repellent about his politeness. In his autobiographical Essays in Love, he quotes his girlfriend saying that he "used politeness as an aggressive defence" and I know what she meant. His response to any critical remark is "Interesting", as if you have made a good debating point. Armed with his Cambridge double first, backed by a phalanx of trusty philosophers - Plato, Seneca, Montaigne, Nietzsche, Schopenhauer - ready to rush to his aid with a supportive quote, it is incredibly difficult to get past his cool defences.

The Pleasures and Sorrows of Work is brilliant on the scenery of work - the shipping lanes, the warehouses, the pylons, the office atria, the airports - less good on the people. He seems to regard them more as ants. But when I tell him this, he says, "Interesting" and proceeds to explain why I am wrong: "It's not a portrait of individuals at work so much. It's more about the processes of industrial civilisation - to be pretentious." Or when I tell him that he is unnecessarily cruel about some of the people he encounters, such as a careers counsellor, he says: "I don't know. He was actually a very nice man, but I think in an impossible job. So rather than being mean about him, I think it was more the wider set-up in which he's operating." Really? So then why did he need to print a photograph of the man's modest suburban semi and tell us that "at most times of the day - even in the early morning - the place smelt powerfully of freshly boiled cabbage"?

And yet, the book is enormously engaging, even lovable, at times. There is a brilliant scene towards the end when de Botton is in Mojave and finds a sort of elephants' graveyard of decaying airplanes. He asks the security man at the gate if he can walk around and the man tells him to fuck off. De Botton delivers a great soliloquy about Goethe and the 18th-century German passion for Ruinenlust, and tells him that "the disintegrating Continental Airlines 747 visible outside your window seems the equivalent, for myself, of what the Coliseum in Rome must have been for the young Edward Gibbon." Whereupon the man tells him to fuck off again and threatens to shoot him. So then de Botton offers $20 bills and the man lets him in. But it shows a much tougher side of de Botton than one normally glimpses. Did it really happen like that? "More or less. I was in a rather desperate mood and he was in a rather desperate mood, the whole mood of the place was extreme, maybe I was having a nervous breakdown. Having come all this way, I just thought: better do it. I think of myself as quite a shy person. But when I'm curious about something I'll go quite far to satisfy my curiosity."

De Botton spent two years and presumably a lot of money researching the book, travelling from the Maldives to French Guiana as well as the US and Europe, with a photographer in tow. He says it was two years of extreme discomfort, both physically (horrible hotels) and psychologically, being stared at as the stranger in the workplace. "It was a real challenge, because as a writer I normally spend most of my time in a study, comfortably, and I suppose I wanted to give myself that kick of discomfort - to discover worlds I didn't know."

It was also difficult to set up. He had to write to 15 seafood importers before he found one who'd let him accompany a tuna all the way from a fishing boat in the Maldives to a British supermarket shelf. His plan was to make a TV series to accompany the book, but it was too hard to get access. "It was incredibly hard to get in anywhere. These PR people surround you and won't allow you to be alone in a room with anyone."

Why did he want to write about work? "Partly I think as a kind of intellectual challenge because I think that work doesn't appear in books as much as it should, or in novels anyway - people fall in love and have sex and that's all they ever do, they never go to the office. Or they're a writer or a psychoanalyst or something. And in television dramas, they're always doctors or lawyers - there's quite a standard vision of what work is. But work is so much more varied than that. I think my book is in praise of the enormous ingenuity that human beings bring to the job of being busy."

The irony is that de Botton is one of the few writers who could afford never to work. His father left a huge trust fund (well over £200m) that he could tap if he ever needed to, but he prefers to live by his writing. His father, Gilbert de Botton, was a Jewish banker, born in Egypt, who moved to Switzerland as head of Rothschild Bank, then founded Global Asset Management in 1983 with £1m capital and sold it to UBS in 1999 for £420m. He was a supremely cultured man who collected late Picassos and was the only person ever to be painted by both Freud and Bacon. He died in 2000 and has a room at Tate Modern named in his honour.

But he was, according to his son, a "tough" father. Having grown up penniless and stateless, entirely self-made, Gilbert never allowed his children, Alain and his sister Miel, to take anything for granted. "He was a cruel tyrant as a domestic figure, hugely overbearing, and there were constant attempts to make sure that we understood the value of absolutely everything. So in many ways we were less privileged than children in an ordinary middle-class family. I saw my friends getting a large cheque or a car when they turned 18, but this was not something I was ever going to grow up with, and in fact I was going to grow up with a huge chip on my shoulder."

His father, having spent his childhood in Egypt when it was a British protectorate, also had an exaggerated respect for English education and sent Alain to board at the Dragon School in Oxford when he was only eight. He spoke no English, having grown up in Switzerland: "It was miserable. I was foreign and Jewish, with a funny name, and was very small and hated sport, a real problem at an English prep school. So the way to get round it was to become the school joker, which I did quite effectively - I was always fooling around to make the people who would otherwise dump me in the loo laugh."

He failed to get into Eton, but went to Harrow and then Cambridge, getting a double first in history before doing a master's in philosophy and starting a PhD. But he found Cambridge a disappointment. He went there hoping to fall in love, to make hundreds of friends, and to be taught by brilliant teachers. "None of those things happened - I didn't fall in love in a transforming way, I wasn't taught brilliantly and I didn't make hundreds of friends. But it was a good time for thinking and working out what I wanted to do. I didn't find the history course particularly challenging, so I just spent all my time reading things that were not on the course syllabus. And started writing." The result was his first, brilliantly original Essays in Love, published when he was just 23.

How did his father feel about Alain becoming a writer? "Very conflicted. He was a big reader, he wanted to write, he was passionate about writing, his greatest heroes were writers - and one of the ways in which we could communicate was through books. I think in a way it made him very happy, but also totally envious, so I'd get very odd responses from him. I wrote four books in his lifetime and with each one he would manage to say something absolutely vile - I remember him in earshot saying: 'I don't think he's succeeded with this one' - and it was tough to hear. But then I learnt that he'd sent copies of my books to his friends, so ... it was a strange and schizophrenic, very troubled, relationship."

After Essays in Love, de Botton published another two semi-autobiographical semi-novels, The Romantic Movement (1994) and Kiss & Tell (1995), which he says he now prefers to forget. It was his next book, How Proust Can Change Your Life (1997), that made him a world bestseller, thanks to a rave review from John Updike in The New Yorker. Proust and its successor, The Consolations of Philosophy (2000), established what de Botton was really about - writing what were effectively self-help books designed to encourage readers to think for themselves and not regurgitate received ideas. He restored philosophy to a lay audience, much to the fury of academic philosophers who always wanted to keep the subject as dry and impenetrable as possible.

Was he attracted to philosophy by a need to think through his own problems? "Yes. My writing always came out of a very personal place, out of an attempt to stay sane. I might not have understood that, or admitted that once, but actually now I think, well why not? Yes, it is self-therapy. And if other people find value in it, it's precisely on that basis. So I'm the opposite of an academic who comes at knowledge from a desire to find out exactly what Plato thought. My view is: OK, let's find out what Plato thought because he might make a difference to me, to you, he might tell us something that is of use."

Although de Botton seems very confident now - he turns 40 this year - he says any confidence is recently gained. As a child, he was too shy to look anyone in the eye. As a teenager, he was "quite puppyishly keen to make friends and never quite understanding why that didn't happen. I was an incredibly lonely, very alienated, teenager." Also, he started losing his hair very young, at 20, which reinforced his anxieties and made him even less confident with girls. It also made him think about ageing, which is unusual at 20. He thinks it matured him psychologically, but he still had a long way to go. He had a pattern of falling in love with girls but then going off them when they showed signs of loving him back. The problem was only solved with two years of psychotherapy in his early 30s. "I learnt a lot. I learnt to stop fantasising about the perfect job or the perfect relationship because that can actually be an excuse for not living. I was full of youthful romanticism, which teeters on solipsism and a kind of narcissism. So I think I possibly wouldn't have been able to get married and have children if I hadn't had some of those very earth-shattering conversations."

He met his wife Charlotte in 2001 in a typically quirky de Bottonian way. He was talking with friends late at night and someone asked him to describe his ideal girlfriend, so he did, in great detail, and "miraculously one person in the room took note of this and introduced me to Charlotte the very next weekend." It was miraculous, given the specificity of his demands. He said his ideal girlfriend had to be a doctor's daughter who grew up outside London and worked in business or science, all of which Charlotte was. "She was a businesswoman, she'd started her own company, she knew how to create an Excel spreadsheet or run a payroll - she can do all these things that I can't do."

Why a doctor's daughter? "I like the values associated with a medical family - common sense, being practical but also thoughtful." And why growing up outside London? "Oh, you know, a suspicion of metropolitan values and, in me, an Orwellian desire for something more grounded. I think partly because I'd observed in my parents' life a kind of unpleasantness that can come at the top of society. My father, because he needed to find investors in his business, had to spend a lot of time sucking up to rich people. And I rather ran away from that. I was interested in the idea of 'the normal', and I thought the country was more normal."

Did he say that his ideal girlfriend had to be Jewish? "No. I preferred not Jewish. I think I might have gone so far as to say that she must have had a Christian education, which indeed she had." Why? "Oh, you know, the exoticism. Because it was so taboo! My parents said if you marry a Christian, they will turn round one day and call you a dirty Jew - that's what all good Jewish children are brought up thinking." His father was dead by then, but would he have been furious at his only son marrying out? "He probably would have made a disparaging remark. My sister married a non-Jew and there was quite a lot of fuss."

De Botton says in Proust, "What is fascinating about marriage is why anyone wants to get married." So why did he? "I think people want to get married to end their emotional uncertainty. In a way, they want to end powerful feelings, or certainly the negative ones. To me, that was the promise of marriage, that it would answer all those questions about love once and for all. And also the depth of the commitment, knowing that the other person has also taken this enormous risk, that you've jumped off a cliff holding each other. And I was very keen by the time I got married, at 32, to have children." He has two sons, Samuel and Saul.

Despite being firmly settled in England, he still comes over as foreign, and his books often sell better abroad than they do here. But he writes and speaks perfect English so the foreignness is a bit of a mystery. Partly, it's his exquisite manners and neat appearance, but also a constant need for deep, meaningful conversations. He says his wife often gets irritated when he launches one at breakfast and she says: "Look, I can't deal with this now, save it for later." But he has a friend in Australia who will ring up and say without preamble, "What is shyness?", which is his idea of a good conversation. At dinner parties he likes to launch a topic - "What is the best form of government?" - rather than making small talk. Or he asks people questions until they get irritated. He complains: "There is a coldness in English social life. No one reveals anything, says anything that is in any way naked, vulnerable, interesting, honest, and that does frustrate me."

So what will de Botton do next? He has already started his next book. But he is keen to move beyond books, to develop other projects, especially The School of Life that he set up last year in Bloomsbury. It is a former shop with books for sale on the ground floor and a big salon downstairs where he and his fellow teachers hold seminars on subjects such as Love, Politics, Work. The aim of the school is to teach "ideas to live by" or, he says, "to inspire people to change their lives through culture". Doesn't it attract loads of nutters? "That was a fear at the beginning and there are a few who want to come in every day and sit and talk, but it's only maybe 10 people who've caused trouble." He hopes that eventually there can be Schools of Life all round the world - they have already had offers to open branches in New York and Australia, but feel they want to "road-test" the idea a bit longer.

Does he have some secret desire to be an entrepreneur, to make a fortune like his father? He admits to envying friends who have started their own businesses and "like most people, I'm gripped by Dragons' Den. And to some extent this School is a kind of attempt to do that." I assumed he learnt about business from his father but he says, on the contrary, "he mystified it. He made it seem like something I'd never get my head round - don't go near this, this is my patch. So he made jokes about my inability to understand maths, and, sure enough, I soon fell into line and didn't understand anything about maths. So it's an area that now, as an adult, I'm tremendously curious about - something I might have a talent for that got suppressed. That's why I look at entrepreneurs and think, hey, perhaps I deserve to be at this table, too. And also I'm often struck by the fear that books don't do very much. I think they're the most important things in the world, but I also think who's going to read them, and could one get the message across in another way, maybe on the web, or by making a film, or getting involved in the School? And that's where the entrepreneurship comes in - how can you spread ideas? What I want to do is make a difference."

• The Pleasures and Sorrows of Work by Alain de Botton is published by Hamish Hamilton on 2 April, price £18.99