I’m doing a casual decision-making presentation at Lane Cove Library on 13th October (6:15-7:30pm), and I’d love you to come along.
But first, let me tell you about the career change that spurred my life long study into taking calculated risks.
career change without losing your head
In 2018, I was asking myself the same question many professionals are asking today: should I change careers to AI?
I had a comfortable job in software testing. I could easily provide value and command respect without stretching myself too much. The work felt predictable, the income was stable, and I knew exactly what was expected of me each day.
But I had this growing sense that the landscape was shifting. AI and machine learning were becoming more than just buzzwords, and I started wondering if I could create a career in the safe release of artificial intelligence (now known as AI alignment).
The scariest part wasn’t just wondering if I was making the right career change – it was the thought of throwing away a very stable and easy source of income on something that might not pan out.
After running it through my fledgling decision making process, I made the jump.
decisions I didn’t know I was making
Years later, when I started studying decision-making as a skill, I realised something profound about career changes: If I had chosen to stay in my software testing career, I was unintentionally choosing to not catch the AI train.
Instead, I would be unintentionally choosing to run after the train after it had already left the station.
Or maybe …unintentionally choosing to get hit by the AI train as it started to gather speed.

This is what I call an “unintentional decision,” and it’s particularly relevant for anyone wondering whether they should change careers to AI or any emerging field. We think we’re avoiding risk by not choosing, but we’re actually making a choice – we’re just not conscious of it.
Every day we don’t upskill, we’re choosing to become less relevant.
Every quarter we don’t explore new opportunities, we’re choosing to stay exactly where we are while industries transform around us.
The comfortable choice often disguises itself as “no choice at all,” but when it comes to career change decisions, staying put may be the riskiest decision we can make.
the decisions all around us
This insight changed how I see everything. We’re surrounded by decisions – some obvious, many hidden. The question isn’t whether we’re making decisions; it’s whether we’re making them intentionally.
Are you choosing to develop new skills, or are you unintentionally choosing to let your skills stagnate? Are you deciding to have that difficult conversation, or are you inadvertently deciding to let resentment build?
When we start seeing the decisions that are being made all around us – both intentionally and unintentionally – we begin to realise the optionality we actually have in our lives. And that realisation is incredibly empowering.
takeaways
This is not just about career changes. This is about the contracts we make with ourselves. Committing to complete a certain course. Deciding to have monthly check-ins with our goals. Choosing to prioritise one project over another.
What am I choosing by not choosing?
What decision am I making by default?
Sometimes the answer is that you’re consciously choosing stability, and that’s perfectly valid. But sometimes you discover you’ve been sleep-walking through choices that could reshape your entire trajectory.
come and chat
You’ll find these hard-won lessons in From Dilemmas to Decisions, but, more importantly, I’ve found that talking through real examples with people makes these concepts come alive.
That’s why I’m hosting a casual chat at Lane Cove Library* on Monday, 13th October from 6:15-7:30pm.
We’ll dig into practical decision-making insights you can use immediately, and I’d love to hear about the decisions you’re wrestling with – both the obvious ones and the hidden ones.**
I’ll be sharing the key frameworks from the book, but really, I’m hoping for an engaging conversation about how we can all become more intentional about the choices shaping our lives.
If you’re wondering what you need to do to stay relevant in this rapidly changing landscape, considering whether you should change careers to AI, or simply curious about spotting the unintentional decisions in your own life, come along.
Hope to see you there.
*at previous events they have also provided snacks and beverages. So they might for this one too 🤞🏾
**if you couldn’t make it, but are still interested, let me know.
