As a conversational icebreaker, the ubiquitous question, "So what do you do?" has never been much good. It's vaguely annoying to be asked it, but somehow far more frustrating to hear yourself asking it: perhaps uniquely in the field of small talk, it's both boringly predictable and likely to offend, whether because the other person's embarrassed about their job situation or because you're already supposed to know what they do. (The Queen once asked it of Brian May, but then she asks it of almost everyone, which is fair enough in her job – so long as she doesn't ask some of her closest relatives.) But I'm not the first to note that the problem's getting worse: in troubled economic times, "What do you do?" is far more likely to draw attention to the fact that someone's out of a job, or tolerating one they're not proud of. Which, to stretch the shipping metaphor, makes the question less of an icebreaker and more of a (self-esteem) destroyer.
Self-help writers and business gurus seem fixated on promoting alternatives to WDYD, apparently in the belief that impressive conversational gambits are a sure-fire way to win customers, friends, job opportunities and lovers. "Don't ask, 'What do you do for a living?', ask what they like to do for fun," counsels one motivational speaker, Christine Cashen. If that makes you cringe, consider the questions others recommend: "What's important to you?", "What makes you feel keenly alive?", or the infuriatingly zany, "Which is better: the power of flight or the power of invisibility?" It's true that any of these might elicit more interesting answers, while making the asker seem excitingly unconventional. But they miss the point of small talk, which is to establish a connection in a non-intimidating way. "What makes you feel keenly alive?" may avoid the downsides of WDYD, but only at the cost of making the answerer feel like they've been buttonholed by a scary oddball.
One modification I'm grudgingly willing to endorse is the question the blogger Ben Casnocha recommends as a follow-up to WDYD: "What does that entail on a day-to-day basis?" I've tried this, and it works. Specifics, it seems, are more interesting for asker and answerer.
If you find yourself stumped when asked what you do, Casnocha also notes, that may be a good thing: "Generally, the harder it is to explain to someone you've just met at a cocktail party what it is you do on a day-to-day basis, the more interesting the work you're engaged in." Indeed, this might be pretty decent careers advice: look for work that can't be easily defined. "If a job can be defined, it can be automated or outsourced," notes the economist Arnold Kling, echoing Daniel Pink's book A Whole New Mind. Pink argues that "information age" work – lawyer, software engineer, accountant – is now as imperilled by automation as factory jobs once were. Perhaps only the hard-to-define "creative" element of work, whether in white-collar jobs or skilled manual roles, is what's safe. Work that makes for awkward small talk may be the work of the future.
If all else fails, though, I advise answering WDYD in the manner advised by the radical anti-job site whywork.org: "I am presently too prosperous to work." Then saunter off. You'll have made your point, even if nobody's quite sure what it is.
• Help!, by Oliver Burkeman, is out now in paperback, published by Canongate Books at £7.99. To order a copy for £6.39, visit the Guardian Bookshop.
oliver.burkeman@theguardian.com; twitter.com/oliverburkeman
