Estimated reading time: 7 minutes
Key Takeaways
- Entrepreneurs need to choose courage over comfort rather than being crazy risk takers.
- Staying in the comfort zone can lead to stagnation and missed opportunities; challenge yourself to grow.
- Bold actions drive innovation and inspire others, making courage essential in business.
- Building psychological safety can support courageous choices in personal and professional contexts.
- Reflect on where you feel stuck and how to push your comfort zone with consistent small steps.
There is a bit of a misconception that entrepreneurs are crazy risk takers and that’s not really true; what is true is that we must choose courage over comfort.
In this week’s episode, we look at…
- The dangers of playing it too safe and staying stagnant in our ‘comfort zones’ as we miss out on important opportunities
- The benefits that come from stretching our comfort zones to challenge ourselves and grow beyond what we think is possible
- The power of taking bold action to drive innovation and creativity and to become a role model for others
Tune in to hear more about choosing courage over comfort.
*Resources mentioned during the episode*
Free Assessment – Download this free assessment to consider what ‘success’ means to you across different areas of your life, evaluate where you are today, and prioritise the right goals to get you to where you want to be. https://onestepoutside.com/what-is-success/
Courage over comfort
There’s a misconception that entrepreneurs are crazy risk takers. That’s not really true. What is true is that building anything worthwhile requires choosing courage over comfort – consistently, not just once.
This applies whether you’re running your own business, leading a team, or navigating what comes next in your career. The capacity to tolerate uncertainty, show up vulnerably, and take action before you feel ready – these aren’t personality traits you either have or don’t. They’re choices you make, repeatedly, over time.
Why playing it safe is more expensive than it looks
The comfort zone has real advantages – we talked about that in the episode on comfort versus complacency. There are seasons when stability is exactly right.
But there’s a version of playing it safe that’s quietly costly. When you stay in the stagnation zone – not because you’re genuinely content, but because taking the next step feels too uncertain – you’re not standing still. You’re drifting. Missing opportunities. Slowly losing touch with what you’re actually capable of.
From a business perspective, the correlation between taking risks and innovative thinking is clear. The companies that couldn’t disrupt themselves – Kodak, Blockbuster, Nokia – aren’t cautionary tales about ambition. They’re cautionary tales about the cost of staying too comfortable for too long. The same applies to individuals. If you’re sitting on a draft book, a business idea, an opinion you’re afraid to share – you’re not just delaying the thing. You’re not finding out what you could do.
And with AI reshaping so many industries right now, the cost of playing it safe is higher than ever. Adding real, distinctive value – the kind that can’t be easily replicated – requires courage. It requires putting something genuinely yours into the world.
The moment of inertia
Here’s what I’ve noticed from the times I’ve pushed myself out of my comfort zone – quitting my job, launching a podcast, publishing a book, starting a coaching practice. The scary moment is never when you’re doing the thing. It’s the moment just before.
A friend and I did three bungee jumps in New Zealand. On the highest one, she stood at the edge with her arms up, ready to go – and then I watched her hands cover her face. That moment of I’m not sure I can do this. And then she jumped. And then I jumped. And once you’re flying, the feeling isn’t fear – it’s why didn’t I do this sooner?
That gap between standing at the edge and jumping – that’s where most of us lose the most time. The jump itself is almost never as bad as the waiting.
Courage isn’t the absence of fear
Brené Brown’s work on vulnerability is worth naming here. Daring greatly isn’t about being fearless. It’s about deciding the thing matters enough to do it anyway.
And there’s a counterpart to individual courage worth acknowledging: psychological safety. Amy Edmondson’s research on this shows that being courageous requires a context where vulnerability is met with trust, not attack. Whether that’s in a relationship, a team, or a community – the environment you’re in either supports your courage or undermines it. Choosing who you’re around matters as much as choosing to be brave.
The comfort zone shrinks if you let it
One thing I’ve noticed after a decade of running my own business: what felt courageous when I started has become mundane. Sending a newsletter. Recording a podcast. Speaking on stage. These things required courage once. Now they’re routine.
That’s not a bad thing – it means the comfort zone expanded. But it also means the work of courage doesn’t stop. The zone shrinks back around you if you stop pushing it. What used to stretch you becomes comfortable. And then you have to find the next edge.
I’m at that point myself – a decade since I left my corporate job, asking what the next decade looks like. What’s the new vision? Where’s the next edge? That’s not a crisis – it’s the natural rhythm of growth.
Where to start
The call to action here is a simple reflection. Two questions worth sitting with:
Where are you stagnating right now – not comfortable, but stuck? That’s the place where the cost of staying is quietly accumulating.
Where do you need to show up with more courage – in your business, your work, your relationships, your creative life? What would that take?
You don’t have to leap. Sometimes a leap is necessary – there are moments of no return where the small steps aren’t enough. But most of the time, one step outside your comfort zone, taken consistently, is enough to start moving. The comfort zone is more malleable than it feels. Find the thinner point in the membrane and push through.
Everything you’ve ever wanted is one step outside your comfort zone. Not a giant leap. One step.
If you’re at the edge of something – a business decision, a career pivot, a change you’ve been circling for a while – and you want to think it through with someone, the free Solopreneur Diagnostic is a good starting point. Five minutes to see where you are and what might be holding you back.
And if you want to make the leap alongside a small group of established solopreneurs doing the same, Off Script is the community built for that.
Choosing courage over comfort means deciding to take action – in your business, career, or life – even when staying where you are feels safer. It doesn’t require being fearless. It requires recognising that playing it safe has its own costs: stagnation, missed opportunities, and the slow erosion of what you’re capable of.
Your comfort zone doesn’t stay the same size if you stop pushing it – it shrinks. What once felt familiar and manageable becomes smaller over time if you don’t keep stretching it. Growth, innovation, and fulfilment all require operating at the edge of what feels comfortable rather than retreating from it.
Start with small, consistent steps rather than dramatic leaps. The moment of inertia – just before you act – is almost always the hardest part. Once you’re doing the thing, it’s rarely as scary as the waiting. Build courage by acting repeatedly in small ways, and let the experience of surviving those moments compound over time.
Courage is taking calculated risks in service of something that matters to you – with awareness of what you’re risking and why. Recklessness is acting without that awareness, letting the pendulum swing so far that you land in the panic zone rather than the growth zone. The goal is the growth zone – stretched and challenged, not overwhelmed.
Most of the time, small consistent steps are enough – and more sustainable. But there are moments of no return where the incremental approach isn’t working and a bigger commitment is needed. The signal is usually that you’ve been taking small steps for a while without meaningful movement, or that a decision point has arrived where staying and going are both significant choices.
