The Underrated Art of ‘Winging It’: Why It’s Every Entrepreneur’s Winning Secret


According to the fantastic, deeply introverted and highly in-demand Dr Jason Fox.


In a world of ‘just do it’, Dr. Jason Fox is a guy who espouses the hidden benefits of doubt. As a result, Fortune 500 companies like Microsoft, PepsiCo, McDonald’s and a swathe of others regularly hire him to speak to (and inspire) their staff.

“Personally, as a raging introvert, I find the world of motivational speaking is often so extroverted and fraught with alpha males talking about big, hairy, audacious goals. A lot of my work is looking at, ‘How do we tap into the benefit of self-doubt and how do we make progress without setting clear goals and without having clear conviction?” Jason tells Collective Hub. “How do we take an approach that’s much more meandering and embracing the fuzzy sense of where we’re going, rather than a clear sense of where we’re going?’”

Jason has learnt to capitalise on his introverted nature by scheduling catch-ups in advance with people he wants to connect with, focusing more on one-on-one conversations and building plenty of time to recharge into his schedule.

“I work particularly in the space of companies that are looking to progress through uncharted territory. You’re looking at leadership development where you can’t set a specific goal. You can’t just follow work that’s been done before and increase performance on past results. You’re looking to do something that’s completely new. The zero-to-one stuff,” explains Jason. “One of the first things I help businesses see is where default thinking is getting in the way of meaningful progress.”

“I refer to this as the Curse of Efficiency. We become so good at finding these time-saving efficiencies that it actually robs us of the ability to think deeper, to think more thoroughly, to build in space for curiosity and empathy. What happens instead is we have a whole heap of templates and defaults that we refer to that save us time and are a lot easier – we don’t have to think as much – but in the process bring us closer to irrelevance.

“A great example of this is someone who builds a highly automated email campaign for new clients and invests time to get all the efficiencies sorted out and has this goal of being able to set and forget. And so you have these efficiencies established but because you’re not thinking about it actively any more, you’re possibly losing empathy with what the client’s needs are. And you’re not actually pioneering any more; you’re stagnating or at least being complacent in the work that’s already being done. And that can lead you closer to irrelevance if you’re not careful.”

Catch Dr. Jason Fox as he hosts a Collective 101 Masterclass on Design Thinking in Melbourne. Aug 2 

As Australia’s 2016 Keynote Speaker of the Year, it’s clear there’s a lot of thought and research behind everything Jason does; even down to the clothes he wears. This is a man obsessed with timeless fashion items: think pocket squares, waistcoats, etched leather Alexander McQueen shoes. Yes, he cuts a dapper figure, but it’s not just because he’s partial to the odd three-piece suit. He cites a psychology paper that talks about a concept called enclothed cognition, and how “the clothes you wear influence your thinking and how you interact with people.”

And once you think about it, it ties in nicely with Jason’s bigger-picture philosophy (including the wonderful illustrations in his latest book).

“In my world, I’m dealing a lot with the future and these emerging technologies. My branding could easily be really futuristic; all digital and lots of blues and technology based. But I like the Renaissance thinking. The Leonardo da Vinci-style thinking. That curiosity. That wonder. The kind of old-school science where we’re asking big questions about the universe and our role and the meaning of life. That spirit is what I try to bring in to the very modern context of the future of work.”

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