How to Have the Uncomfortable Conversations in Your Life


It’s what makes us Human.

Talking to people. Sometimes talking to yourself.

By ‘talking to yourself’ I mean asking questions of yourself; challenging yourself and doing some introspective work.

Of course, it could also be actually talking to yourself…

I do this often, especially when I’m cooking or about to eat. Basically, I talk to my food a lot.


While many of us are guilty of not having these important conversations with ourselves about progression, growth and personal accountability, we’re often guilty of not having conversations with others that could alleviate issues, create opportunities, remove tension and uncomfortable situations, or just make good stuff happen in general, whatever it may be.

That was a long sentence.


We might be so blind to it, that on occasion we might not even contemplate that a conversation is there to be had.

I’ll call that unconscious ignorance.

hy businessman

Other times we might simply be choosing not to have the conversation that’s needed.

Let’s call this conscious ignorance.


The difference between these too is awareness, as it often is in life. The initial way out of the first is to have an uncomfortable conversation with yourself… Reflect upon situations and interactions and ask yourself “Could I have said something there? Could I have facilitated the conversation? Furthered it? Improved it? Could saying something have supported myself and others involved?”

Portrait of a man looking in the mirror

That will help you gain awareness for next time.

Then you’re in the field of choosing not to be ignorant.

Choice brings options. However, don’t over-think it and get caught in that head of yours. STOP the thinking!

Then start… the uncomfortable conversation.

Simply force yourself to start having the conversation you need to have, which is relevant to the situation you’re in.

Of course, we can specifically work at increasing your Social Intelligence, and with that your communication skills across the board, but you can’t let that be a rationalisation for not embracing these more uncomfortable conversations, ala “I’m no good and communicating…”

Bullshit. That’s a story in your head.

We learn by doing, so if by nothing else, you’ll improve your communication skills the more you lean into these courageous conversations. Competence creates confidence.


You’ll screw things up from time to time. That’s great – from that you can reflect and learn for next time.

This is how life goes; do, learn, do again, learn, do again but better… and so on. 

It starts by giving yourself permission to mess it up.


Simply lean-in to those more awkward moments and you’ll start to improve.

Once we stop thinking about what could go wrong and instead think about what could go right, we can start having the conversations, We find that the vague worst case scenario we let float like a grey cloud in our mind, just isn’t that bad.

Nor does it even come to fruition that much.

If you really feel fear or dread over a conversation, then try entering it asking the other person to support you in it. Say “I need/want to discuss something, but I’m finding it difficult to do so. Could you support me and provide a safe space for me to share without fear of judgement?”

To get your head around that, put yourself int he shoes of someone receiving that request. What would you do? Chances are you’d say “Yes, of course!” and see that act alone as courageous.


It starts with you deciding to embrace that uncomfortable feeling (you know the one), accepting that everything in life can’t be nice and feel good, and through discomfort and unease we lay a foundation for growth.


At the end of the day, whatever it is – asking for support, speaking to your boss about pay/treatment/workload, bringing up sex with your partner, calling your mate out on sexist chat – if you don’t do it, nothing will change. You’ll feel regret and frustration.

We teach others how to treat us by the way we act and communicate. When you start setting boundaries or standard for conversation, this doesn’t go unnoticed. However, the converse is true also; never take a stand, and it’ll be expected.

If you give yourself permission to not be concerned over what other people might think, over rejection then you’ll actually go into these conversations lighter and more resilient; ready for whatever happens, knowing that you win, or you learn. This is where growth and confidence come; competence breeds confidence.

Conversation remember, it’s what makes us HU-MAN 🙂


*Edit – we originally posted this in regards to getting support for the kickstarter campaign – we nailed that, and created/released seven episodes of the show, then held an event in August 2016….

We’re now running two new events March 2017…

This exact topic is something we’ll be covering and digging into at the upcoming Beyond The Beers Live Event in Brisbane – Saturday, September 16th.

For more info about what you’ll gain from a day like this, check out the page to get tickets here.

And remember not to keep this to yourselfshare the event (or show if you’re outside Australia) with those men in your life who could benefit from this content and the show in supporting them getting more out of life.

By | 2017-08-10T03:59:53+00:00 May 13th, 2016|Man skills, Social Intelligence|0 Comments

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