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Why I’m doing this

“If you wish to improve, be content to appear clueless or stupid in extraneous matters–don’t wish to seem knowledgeable. And if some regard you as important, distrust yourself.”

– EPICTETUS, ENCHIRIDION, 13a (from The Daily Stoic by Ryan Holiday)


I’ve always been bad at conversation. If I have to keep a conversation going with someone I’m not comfortable with, I’m in Strugglesville. But I’ve always loved asking questions.

12 years ago, I was about to fly up from Melbourne to Sydney to interview Les Murray (the Soccer guy) for an article, and at the last minute, my girlfriend at the time gave me some advice: ‘Don’t ask any stupid questions. You do that a lot…’. In a split second, my confidence about the interview was shot and I also got extremely defensive. (I did actually ask some really dumb questions though. I’d go to an engagement party and ask the bride-to-be how she knew her future husband. Or ask things that a simple Wikipedia search would’ve answered in three seconds.)

Looking back now though, that was a huge compliment.

The writers I admire the most are John Safran, Neil Strauss, Louis Theroux and Tim Ferriss. And it’s because these guys ask ‘stupid’ questions. Questions coming from a position of true curiosity. The obvious questions that you want the answer to, but you yourself might be afraid to ask, for fear of looking like an idiot.

In Ryan Holiday‘s book, The Daily Stoic, he says, ‘One of the most powerful things you can do as a human being in our hyperconnected, 24/7 media world is say: “I don’t know”.’

Guys like Safran, Strauss, Theroux etc. acknowledge they don’t know something, so they ask about it. Simple as that. Without worrying whether people will think they’re dumb. That doesn’t happen enough.

If you ask someone a question that starts with ‘what…?’ (e.g. What do you do? What is that? What does it do?’ etc.), most of the time you get a pre-programmed response, straight off auto-pilot. You can leave things there, sure, but if you then genuinely ask them ‘Why?’, most of the time, you get a real response from within them, about their motivations, reasons and belief about that thing. And even if you don’t get it first time, asking again (and even again – ie. the rules of 3’s) will eventually get you to the truth, where you learn about them, it can actually help them learn more about themselves, and in turn it may even help you learn more about yourself. All because of one word.

This can be annoying, but it works. And really digging deep and thinking about why we actually do what we do is what helps you constantly become an even better version of yourself and live a better life.

So this site is dedicated to the ‘Why?’. And the stupid questions that get to the core of why you do what you do.

It’s also about daily routines, rituals and habits. Oh, and also, pyjamas.

That’s why I do it.

Yours in stupidity,