Are you thinking big enough?

Hint: you're probably not.

The other night I was reading through feedback from my recently finished, first ever group mentoring program, and I’ve been pondering one person’s response ever since. They wrote:

“I didn’t realise I was thinking so small until I heard what others in the group were working on and winning at. The last month together has helped me stop fixating on the next task and think bigger about my impossible dream”.

I’ve been thinking about this non-stop, not just because I believe it’s my sacred duty to take all product feedback and marinate on it for 5-7 business days, but also because I’ve been caught in the ‘thinking small’ trap many times myself. It’s that mental space where I only focus on tasks and outcomes that feel immediately achievable, safe or certain.

At first glance it seems limiting but thinking small is not always a bad thing. Sometimes focusing in on itty bitty actions is a smart strategy. Noting down an idea. Going to the event. Talking to a customer. Posting on LinkedIn. Winning your first client. Cashing in an invoice. Being laser focused on tangible steps feels achievable when the big picture is too much.

But while thinking small gets you started, at some point it becomes a liability. For me, that came after landing my first long term clients. Despite having 18 months of financial security I stayed in small-mode, unable to imagine a grander future for myself because my brain was scared to go there. It felt self indulgent, and subconsciously I wanted to prevent the brutal disappointment if and when I failed. And so, despite my newfound stability, instead of calmly declining opportunities that weren’t aligned with my non-existent vision, I said yes to everything. Every client, every project, every request to pick my brain, every 30 minute coffee catch up, every event invitation, every distraction, every literal thing. And I wasn’t saying yes because #abundance but because short-term busy-work felt cosy and safe.

It wasn’t until I found a mentor who expanded my realm of possibility and began intensely journaling about what my future could look like, that I started creating space in my calendar to dream. I started saying ‘thanks but no thanks’ to others so I could think bigger and say yes to myself. Pretty soon after, I started this newsletter. Then I diversified my income. Then I built a digital product. Then I hit a certain revenue target. The more I believed, the braver I became, the bolder I acted, the bigger I stepped, and a larger storyline began to make itself known.

This is what I now know to be true:

• Thinking small and acting small helps you get going. It gives you something manageable to focus on when anything else feels paralysing

• Thinking big and acting small helps you build momentum. This is when you start to conceptualise a bigger vision while still executing in small, consistent steps

• Thinking big and acting big helps you scale beyond yourself. With more resources (time, money, people etc.) you can now take larger risks and bigger swings

If you find yourself thinking small as a default not a strategy, it’s time to broaden your mind. You must to connect with others who expand your worldview. You must ask ‘where is this taking me?’ rather than ‘what’s next on my list?’. You must create the space to dream, to hope, to wonder. To name what you want. To write it down and speak it out loud. You must take a deep breath and ask yourself:

What is my impossible dream?

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A riff on how I’ve been thinking bigger in my portfolio career (and how I’m dealing with the setbacks and rejection that comes with that) and why it’s important to surround yourself with people who help you see your potential:

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🫶🏼 When you’re ready, here are three ways I can help:

• Free Training: Stabilise, Systemise and Scale Your Portfolio Career in 2025: learn the inbound and outbound acquisition strategies to generate a consistent flow of leads and grow your income, and the workflows to that will help you increase capacity beyond your time.

• The Portfolio Career Operating System: a fully fledged system for people who do multiple things and want to do them well. I’m talking Sales, Marketing, Content, Product, Clients, Ops, Finances and Admin.

• Portfolio Career Mentoring: 1-1 sessions to help you get started and build a career that sits at the intersection of freedom, creative fulfilment, meaning and money.

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