The questions that guide me

The questions that guide me

An exclusive extract from Emma’s book, Winging It.

BY Emma Isaacs, 9 min READ

I’ve always believed that asking the right questions allows me to get to know others more deeply.

We’re often too busy talking and not asking enough intelligent questions, and as a result we miss out on the opportunity to truly connect.

One time I was having lunch with a girlfriend, Simone. Simone told me about the latest round of failed dates she’d had, and how exasperated she felt that she hadn’t found a partner yet. Like many of us, her life hadn’t eventuated into the expectation she had of it. She was on the other side of 40, and desperate (her words) to have a child. She was open to having a baby on her own, but was afraid and stuck as to which way to turn. Normally, we’d banter back and forth on this topic (it wasn’t new territory in our friendship, as this was the most important thing in her world) and then move on to the next subject. This time, I wanted it to be different.

‘Sim, we need to get real,’ I said. I paused, took a very deep breath, and asked her, ‘What are you really scared of?’
Simone burst into tears. She told me she was actually terrified of what other people would think if she were to have a baby on her own. She’d been raised in a very conservative family who had strong opinions on how a family should look, and she thought they’d be disappointed if she went it alone. Through tears, and a glass of champagne, we workshopped this together and by the end of the lunch she’d decided to set a plan in motion.

Today, Simone is the solo parent to a gorgeous baby boy who is adored not only by Simone, but by Simone’s family, too.
In the same way great questioning can open up a world of possibility for others, asking questions of ourselves from time to time can be incredibly helpful. Doing this promotes introspection, and ultimately helps us to decide what’s important and what’s not. Here are the ones I regularly ask myself, so I can always be lifting my game.


This question helps me remember that the only thing standing in the way of attempting something is the thought that I might fail at it. You too? We’d all try so much more if we weren’t scared of falling on our faces. It could be applying for a job you’ve had
your eye on, or asking someone out on a date, or even just starting back at the gym. An act of courage usually only takes a few seconds of ‘pain’ anyway and then it’s over. The challenges that scare us are often like needles – we dread them so much, but they’re never as bad as we imagine.

I use this question to really try to open my mind too, not just to get through everyday tasks. This question gently nudges me to think larger and aim higher. When I was contemplating moving overseas (I’ll get to that story soon) I pondered this question and it helped me decide right then and there that the move was the right thing for us.


Instead of writing a to-do list, I start each day with a fresh page in my notebook. At the top (instead of ‘to do’) I just write, ‘What would make today great?’ I try to imagine myself at the end of my day, having accomplished a few things and knowing that I’ve given my all, doing the important things that matter most.

It can be as simple as writing a card to someone I haven’t been in touch with for a while, or getting a major pitch in, or calling my mum, or booking a massage, or doing something that I know I’ve been putting off. It also helps me avoid falling into the busyness trap of trying to do too much. The goal is to run your day, not have the day run you. By setting it up from the outset, and being clear about your intention, you’re more likely to be inspired to achieve all that’s on your list.


This question sits on a sign above my desk, and is a constant reminder that life is short and the ‘perfect’ opportunity to start working towards a goal or dream you have may never arise. Too often we’re stuck in ‘We’ll get it done, one day’-mode, when we all know that one day may never come.

Nigella Lawson, the British food personality, spoke for Business Chicks a while back and I loved her take on this one. The emcee asked what Nigella’s best piece of advice was and she said, ‘Do it now.’ When prompted to explain a little deeper, Nigella said she was a fan of getting things done as soon as you think of them. She said we waste so much time thinking about a task or a project, or even an email, and that her advice would be to just get that thing done straight away.

So many of my tasks don’t make it to my to-do list as I just get them done when I think of them. Or I do them immediately, then afterwards I write them on the list so I can get the satisfaction of ticking them off. (I bet you’ve been guilty of this too.)


When it comes down to it, we’re all kind of the same. We have jobs, families, we eat, we sleep. It’s what we do outside of these things that makes us interesting and gets us remembered. My friend Narelle was once on a business trip in rural China, which
happened to coincide with her birthday. It took me loads of effort to track her down at her hotel and organise to have a chocolate

winging it

cake (her fave) delivered to her room. The language barrier with the hotel was strong, and it took some super-sleuthing on my end, but the surprise it gave her was worth the effort and she still talks about it to this day.


We only get one shot. Might as well go for it.


This is an extract from Winging It by Emma Isaacs. Available in bookstores and online now, Macmillan Australia, RRP $34.99.

Haven’t bought your copy yet? Whatcha waiting for? Order your copy of Winging It now.


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