Alex Soojung-Kim Pang, Ph.D.

I study people, technology, and the worlds they make

Want to reach your goals? Be oblique

John Kay may be my favorite business writer. For some time he’s been thinking about a concept he calls “obliquity,” which is the subject of a forthcoming book, Obliquity: Why Our Goals Are Best Achieved Indirectly. An essay from the Financial Times in 2004 explains the concept.

Obliquity is characteristic of systems that are complex, imperfectly understood, and change their nature as we engage with them…. [These are systems in which] the attempt to focus on simple, well defined objectives proved less successful than management with a broader, more comprehensive conception of objectives…. Obliquity is equally relevant to our businesses and our bodies, to the management of our lives and our national economies.

And yes, it is counterintuitive.

Isn’t it true that you must do better if you set out to maximise something – happiness, wealth, profit – than if you don’t? Surprisingly, the answer is no. Life is too complex and uncertain for us to be able to predict and follow the most direct perceived route to success. Our knowledge is always imperfect, and events are influenced by the unpredictability of other people and organisations. Instead, our objectives are best achieved by a more meandering approach that enables us to adapt our strategy to changing situations. And we learn about the nature of our objectives and the means of achieving them through a process of experiment and discovery.

Part of what’s brilliant about Kay’s argument is that it ranges very widely. He compares CEOs who think broadly versus those who focus more exclusively on profitability, and finds that the second are more likely to destroy value: as he puts it, “Obliquity gives rise to the profit-seeking paradox: the most profitable companies are not the most profit-oriented.” In forestry, it turns out that letting small fires burn helps protect forests from huge fires by clearing undergrowth. He talks about architecture and urban planning (“a house is not simply a machine for living in”), and the complexity and adaptability of biological systems (and how markets are like them). (Indeed, while he doesn’t trumpet this, Kay’s may be the best application of biological concepts to management and organizational theory around.)

Interesting stuff in theory, but what does it mean? Kay lays that out in a recent Management Today article:

  • Have objectives, but keep your approach flexible so that you can overcome unforeseen obstacles and take advantage of surprise opportunities.
  • Know that your knowledge is always imperfect and incomplete. Cast your net wide – always go fishing for more.
  • Don’t be afraid to change tack once you’ve started if you see a better course.
  • Meandering can lead to serendipitous discoveries and unexpected benefits.
  • Think laterally to solve problems: indirect solutions can often be the most effective answer.


  1. Interesting. We play a lot of gin, and there’s this odd fact that our younger son almost always beats our older son, who’s a very logical guy and good at most games, and can certainly beat his younger brother handily at things like chess – and usually at Catan, too – he’s just great at looking at the board setup and deciding that this is a game where it’ll be really useful to have, say, the sheep port, and making that happen, and the rest of us are toast. But his think-it-all-through-as-early-as-possible method doesn’t work for gin. It’s happened enough times now that we think it can’t just be luck anymore, and our hypothesis is that our younger son is just better at adapting his strategies during the game to changing circumstances than our older one. Sorta more oblique.

  2. Life is too complex and uncertain for us to be able to predict and follow the most direct perceived route to success. Our knowledge is always imperfect, and events are influenced by the unpredictability of other people and organisations. – This is so true. We always have to be ready for everything. Changes is constant in this word.

  3. I believe one of our fave authors, Nassem Taleb, has a forthcoming book on tinkering – how so many positive outcomes and inventions happen by accident. I believe he’ll indict rigid academic approaches as ways of stifling progress.

    Superfreakanmomics touches on this too. Inventing for the sake of inventing is the most productive way of creating useful technologies.

  4. Great stuff — this book should be quite interesting so long as it isn’t best described in a condensed short essay..or what you’ve said right here succinctly. Like The Black Swan and other business-philosophy books do — repeating examples over and over and over of a quite legible principle.

    Anyway — this point here is wonderful advice perhaps best for young students who think they must follow the now creaky stairs up to their first job, second job, third job and then wait basically to die. I found out, quite by accident, that a short rant-post I did some time ago has been put on reading lists for some colleges that echoes this theme (and conversations that are swirling around the failings of academia that I know you and I have had). Follow Curiosity Not Careers. All of this is good, great stuff I think for remaking the world in a more habitable way, it seems to me.

Comments are closed.

© 2018 Alex Soojung-Kim Pang, Ph.D.

Theme by Anders NorenUp ↑