Why Wouldn't Ya?

Why Wouldn't Ya?

Oct 08, 2026

“If you’re not playful, it won’t be fun. And if it’s not fun, it won’t work!”

imageI’ve been thinking about the whys and why nots of life lately, as I move through transitions and versions of myself. I see people stay where they’ve always been, and I see myself get stuck in places too. But I also see myself throwing myself in to new adventures and experiences, and others being brave and bold as they do the same.

It got me thinking about the comfort zone. I know I’ve written a lot about it, but when life is throwing a lot around, comfort seems like your best friend. It’s like a safety net… until it’s not. Somehow, it can morph from a safety net into a trap that’s really hard to get out of. I don’t think we always notice when that happens.

I used to say I became a tour guide because I wanted to get paid to travel (and that was true). But these days, I think more about what people take home after travelling with me. The photos, obviously. Probably some sand in their shoes and hopefully all their belongings. But what else? A little more confidence? A deeper connection to the places we’ve visited? More wonder and awe at the world around them?

I can’t decide what an experience will mean to someone else, but I can pay attention to what I bring to it. What’s your why? comes up in a lot of things I do: in business, in the entrepreneurial world, in personal development. Or maybe it’s just in my head, like that annoying kid asking, “But why?”

One of my best mates and I spun it around one year at a festival, and it became, “Well, why wouldn’t ya?”

Why do we choose the lives we choose? The relationships we stay in, the things we say yes to, the dreams we keep putting off? Why do we keep doing something long after it’s stopped feeling right? Or pack up a perfectly reasonable life and start again, without much idea of what comes next?

But also, why wouldn’t we? If you’re happy and content, growing and loving your life in its current state, there might be plenty of reasons why you wouldn’t do the new thing. Plenty of reasons why you chose what you’re doing now, and why you keep choosing it.

I suppose the question becomes more important when we’re not entirely happy with our choices. When we want growth, change or movement, but we feel stuck. When we’re grasping at things to numb our feelings rather than feel them. Or when we’re scared of what a new version of life might look like because it’s so different from the one we chose in the past, and it might mean letting go of things we’ve loved. That doesn’t mean those things were wrong. They might have been right for who we were then, but no longer fit who we’re becoming. We can love what they meant to us and still let them go. We can’t take everything with us forever and ever - that'd be heavy!

Fear and excitement can show up in our bodies with similar sensations. A racing heart, butterflies, a whole lot of energy. How we understand what’s happening can change how we meet it. A base jumper might stand on the edge of a cliff and feel excited, whereas I imagine most people would feel fear. Their experience, preparation and what they’re expecting from that leap would be heaps different too.

I see versions of this all the time. Things I’d happily do are out of the question for someone else. Things other people seem to do easily can feel really daunting to me! We don’t all have the same comfort zone, and that’s part of the beauty of humanity.

I spent years living out of my backpack, learning languages and diving into different cultures. Drop me in a country where I don’t speak the language and I love it. There’s something about having to find another way to connect that I enjoy.

Was going overseas scary? I think I’m a bit weird, because I didn’t really think about it that much before it happened. I still don't. I bought the ticket, got on the plane, and I suppose I lived in the moment for those years. I didn’t really miss home because there were so many new and exciting things happening. Coming home was actually the hardest part.

I could’ve easily left again, but staying, although it was hard, became a catalyst for a new version of me. Going somewhere unfamiliar wasn’t necessarily the thing that stretched me most. Sometimes staying put does.

Looking back, I can see a thread through all my different jobs and places. Curiosity. Connection. Having a go. Finding out what happens when we step beyond what we already know. I wasn’t always consciously thinking about my why, but in hindsight, I’ve accumulated plenty of them along the way!

Different jobs, people, places and experiences have been an important part of getting to know myself. But it was the things inside myself that I found more challenging. Letting people in, being vulnerable and allowing myself to be seen when I didn’t know how someone would respond—that was way scarier!

Packing up and leaving Adelaide after COVID was another big one.

There were plenty of honest answers to that why, but honestly, that one was more of a why wouldn’t I? Money, freedom, travel, a change of scenery, the chance to spend more time outside. The life I’d built in Adelaide made sense for the years I lived it. My grandparents, Pokes, teaching and some really great mates. There was a lot there that I loved.

But it stopped making sense for me. My reasons for staying were becoming more about others than myself. It was time, again, to choose me.

I keep coming back to fear and love, a thread I’ve taken from don Miguel Ruiz’s teachings. When I look beneath the reasons I give for my decisions, those two tend to be hanging around somewhere. Am I doing this because I love it, because I’m curious, because something in me wants to grow? Or because I’m scared of disappointing someone, being alone, getting it wrong or losing what I already have?

Sometimes it’s a bit of both. I can love the possibility of something and be scared shitless of doing it. Feeling all those feels doesn’t automatically mean I’m heading in the wrong direction.

Our alarm bells don’t only ring when something is life-threatening. They can also ring when we’re uncomfortable, facing uncertainty or stepping outside our comfort zone. The feeling is real, even when the thing we’re facing isn’t an immediate physical danger. I think it’s important to get curious about the difference, while remembering that some fears are responding to real risks and experiences.

Comfort has its place. Sometimes we need to rest and feel supported. But sometimes growth asks us to feel a little awkward, be a beginner or have the conversation we’ve been avoiding. Be curious.

And I know, fear can be quite convincing! It can sound like being sensible (sometimes suspiciously boring), keeping everyone happy or waiting for the right time. That magical time when we’re completely ready and nothing could possibly go wrong. I’m still waiting to meet that time. I am pretty sure it's mythical.

Meanwhile, there’s now. And now… and even now. Not everything needs to happen this minute, but I do have to notice when “not yet” keeps becoming “never.”

As I’ve got older, I’ve realised that money alone doesn’t give me enough reason to keep doing a job. The work needs to mean something to me. I’m grateful to work for Intrepid because I see care for people and places in the work we do. I doubt I’d still be guiding if I felt I was working for a company that consistently put profit ahead of both.

And I’ve also come to feel that, for my why to stay meaningful and sustainable, it needs an element of service. Something beyond what I get out of it. A way of bringing my presence, passion, energy and heart to the people and places I encounter. It needs to be bigger than me, while still leaving room for me.

That sense of contribution can live in all sorts of places. Raising a child, making something, caring for a neighbour or just listening properly when a friend is having a shit day. Doing a job with care, even when nobody’s watching. We don’t all need to change careers or move into a van to find meaning in what we do!

I don’t need every decision to come with a profound explanation either (even though my writing maybe suggest I do!) Sometimes I go for a swim because it’s hot and it feels good. Often, I say yes just because it sounds fun. Playfulness has been behind some of the best things I’ve done, and I don’t want to get so caught up in finding my purpose that I forget to enjoy being alive.

But when something keeps niggling, when I’m exhausted, resentful or wondering how the fuck I ended up here, why is a pretty useful place to begin. What am I getting from this? What am I giving? Does it still matter to me? Am I choosing it, or am I scared of what might happen if I choose something else?

And if there’s something I keep wanting to try, something that feels exciting but a little beyond the edges of the life I know, maybe it’s worth asking, “Well, why wouldn’t ya?”

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