How I Learned to Stop Worrying and Love Asking Questions

Most of us would say that deep down we struggle with self-esteem. We don’t ask questions, we beat ourselves up, and we miss out on opportunities because when it comes down to it we suspect that we’re just not good enough.

I think this is true for almost all humans, but the writers of The Confidence Gap put forward a pretty compelling argument that women typically feel this even more than men, and that it limits them in a variety of insidious ways. It’s a really complex issue, so when the organisers of Girl Geek Dinners Melbourne asked me to speak on the topic of the Confidence Gap, I wondered how I could contribute to the discussion in any meaningful way.

I’d never thought about the confidence gap in relation to my own self-esteem, and had never thought about it in relation to my gender, but on reflection I realised I did have something to share. It just happened to be a whole lot more personal than I’m usually comfortable getting with a big bunch of strangers.

You can listen to the full talk below, but the cliff notes are that in my 20s I realised that poor self-esteem was limiting me in all sorts of ways. I couldn’t really control the negative voice in my head, but I could start behaving like a confident person and hopefully achieve the same results. So I spent some time modelling people I felt had the whole confidence thing figured out, and looking for the differences between their behaviour and mine. And the difference was clear and startling. The two big differences were:

  • They asked questions and didn’t worry about sounding stupid
  • They went out looking for new opportunities and experiences and didn’t worry about failing. They knew that if they worked hard they’d succeed.

I realised I had a whole lifetime of opposing behaviour, so I set two simple rules for myself, and determined to follow them no matter how I felt. They were:

  • If I don’t know, I always ask, even if I think it makes me look stupid
  • I will take on any challenge offered to me, and try not to worry about failure.

You’ll notice these rules are in present tense, and that’s because, nearly a decade later, I still follow them. They sound simple, but for me they were a game changer. It’s still a challenge, and it’s still a work in progress, but I credit them with most of the success I’ve had to date (paired with hard work and a good sprinkling of luck).

I’ve spoken on this topic a couple of times and it’s become clear to me that we need to start talking about this stuff more. What seems to resonate with the people who have listened to this talk is not my self-imposed rules so much as the acknowledgement that we all battle with self-worth.

Have a candid conversation with anyone you think has it all figured out and you’ll soon learn that in their mind they’re still figuring it all out. In fact I’d wager every hyper-successful person you admire has the same worries and fears we all do. They just find their own ways to work around them.
If you haven’t already, I think you should too.

You can listen to my talk here, and check out the slides below! I hope you find it useful. :-)

And here are the presentation slides:


Cyan Ta'eed co-founded Envato when she was 25, and since then has developed and run most of the teams in the business at one time or another (excluding finance which would have been a very bad idea). She's passionate about community, product development, and diversity in tech.

In her spare time she runs around with her two little boys, talks shop with her husband, Collis, and tries to load them all into planes to explore a new city as often as possible.

You can follow Cyan on Twitter here: @cyantaeed.


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