Why Playing Small Is The Riskiest Move You Can Make

Introduction
Hey there, and welcome back. This blog is where I talk all things mindset, motivation, and making big things happen in your small business.
I’m Jenny, and today I’m talking about something that holds so many small business owners back: playing small.
Here’s the truth – staying in your comfort zone, avoiding calculated risk taking, and waiting for the ‘right time’ might feel safe… but in reality? It’s the biggest risk you can make.
If you’ve been holding yourself back, shrinking from your priority goals, or hesitating on making that bold move for fear of failure – this post is for you. Let’s get into it.

Once Up A Time
I remember the first time I made a real ‘risky’ move in my business. I’d been playing it safe for months, doing the work, but not really putting myself out there in a big way, because I felt the level of risk involved in doing that was too great.
And then, I had this opportunity – one of those ‘now or never’ moments. The kind of moment that makes you feel like you might actually throw up.
I could have said, Nah, I’m not ready. I could have stayed where I was, comfortable, unseen, safe. But I didn’t. I jumped. And that single decision changed everything.
It was the moment I had the opportunity to take a bigger financial risk for the first time, and invest in some paid ads for my business – even though at that point my business was not making any real money.
I had to take a leap of faith, consider whether running paid ads was one of those kinds of risks I was willing to take, or continue to stay small and stuck in my business.
I took the risk. And it paid off.
Those first ads (that I ran myself) brought the first REAL revenue to my business, and showed me the potential for paid ads moving forwards.
Had I not taken that leap of faith, I might still be here now, not understanding the power of paid ads to get money and people in to my business, and still feeling stuck.
Here’s what I realised in that moment where I decided on the risky decision to run my first ads: The successful people who get ahead in business? They’re the ones who take risks.
Most people think taking risks is dangerous. But let me ask you this – what’s actually riskier:
- Launching your offer, even if it flops… or spending years waiting for the ‘right time’ and never doing it at all?
- Posting that video, even if it feels awkward… or staying invisible and hoping people might magically find you?
- Investing in support, even if it scares you… or trying to DIY everything and staying stuck for years?
Fear of Failure
Fear of failure is keeping you small. And small doesn’t get you to 40k a month revenue success (this is the life changing goal I work on with ladies in my community).
Women inside that community see positive outcomes when they become bigger risk takers – because they take greater action.
Not all risks are created equal, and not all risks result in great outcomes (which is why we are so risk averse).
But trying to remain in your comfort zone and keep the status quo in your business, is a sure fire way to fail.

Reframing Risk: What If It Works?
Here’s the thing – every time you feel afraid to take a leap, I want you to ask yourself this: What if it works?
What if that post you’re scared to publish brings in your next big client? Or that launch that feels ‘too big’ changes everything for you? What if taking that step leads to the breakthrough you’ve been waiting for?
Because staying stuck, waiting for the perfect moment? That’s a guarantee for zero results. Growth only happens on the other side of risk.
And another question to ask yourself when you’re considering taking smart risks in your business is “Am I 100% willing to accept the responsibility for and the outcome of this risk, no matter what that outcome is?” If you can start to answer “yes” to this question, risk taking becomes if not comfortable, certainly easier.
Practical Steps to Start Taking More Risks
If risk-taking doesn’t come naturally to you, here’s how you can start shifting into that bold, unstoppable mindset:
- Start with Small Risks Daily – Get comfortable with discomfort. It is essential that you do this in your business, because no business is built off the back of comfort zones. So say yes to that podcast interview. Post that opinionated take. Make the offer. Each small risk builds your tolerance for bigger ones.
- Separate Fear from Facts – Question is the risk actually dangerous, or is your brain just overthinking? Nine times out of ten, the worst-case scenario isn’t nearly as bad as we think.
- Surround Yourself with Big Thinkers – If you’re around people who play small, you’ll play small. Join communities where bold moves are the norm – like my community inside 40k Club.
- Ask Yourself: Who Do I Want to Be? – The version of you who’s hitting monthly 40k revenue goals – how does she make decisions? What risks does she take? Does she play small and stay in her comfort zone? Or does she step out boldly and start taking the calculated risks her business needs for growth? Start acting like her now.
Conclusion
Here’s what I want you to take away today: The only way to grow is to leap. Playing small might feel safe, but it’s actually the fastest way to stay stuck.
You don’t need permission to grow. You don’t need more time to grow. You just need to decide that risky decisions will be part of your future strategy.
If you’re serious about taking your business to the next level, my community 40k Club exists to get you out of your comfort zone and building a business roadmap tailored to YOU (and yes – doing that will come with risks).
If you’re tired of guessing and waiting and feeling stuck, come and join the best membership where you start to build strategy that actually gets you to your goals.
Related Articles
If this blog post was of use, and has pushed you to step up to a whole new level, you might also find the following blog posts useful.
And stay tuned, because there are more motivational and helpful small business blog posts on the way!
Discipline – Your Secret Weapon In Business
The Courage To Keep Going In Your Business When No-One Is Watching