For much of my early career, I believed the myth of the linear career path: success was a straight line from A to Z, carefully plotted by staying on track. It was what I saw around me—people staying in the same job for decades, achieving the definition of success I was taught to aspire to. But what happens when you realise that track isn’t taking you where you want to go?
For me, that realisation was terrifying—and liberating. After my first real job, I was dissatisfied and felt I had missed the ‘train.’ I was in a different country, had made significant life commitments there, but couldn’t find a way to feel fulfilled. I felt like I had wasted precious years living someone else’s life.
It was only when I laid out all my options and entertained them seriously that I realised what I wanted to do: learn enough to become a founder. I wanted to know what zero-to-one was and experience it myself. I wanted to create. To do that, I had to widen the search space and rethink my career.
Life is like a journey. You need to change directions a few times to get where you want to go.
Hell Yeah or No, Derek Sivers
This shift taught me something profound: success isn’t about staying on one track but about navigating the right path for you. Since then, I use the left-hand side of the Double Diamond Framework, representing divergence and convergence on the problem space. Let’s call it a lozenge, to be fancier…
Picture a lozenge: it starts wide, representing exploration and possibility, and then narrows to a single point, symbolising focus and commitment to a path forward. When I face big decisions, I follow this two-step process:
- Open the solution space: allow time for exploration, experimentation, and broad thinking to uncover new options. Here I embrace uncertainty and let my curiosity drive me, mapping out potential paths.
- Close down on a path forward: commit to a decision, eliminate alternatives, and set clear goals to stay accountable. Step by step, I start eliminating options until the path forward is clear.
I timebox the process, which helps me embrace it confidently while keeping guardrails in place to avoid analysis-paralysis. Once a decision is made, I’m all-in, never looking back.
Derek Sivers captures this perfectly in his book Hell Yeah or No:
Eventually, your focus on something will pay off. Because you’re successful, you will be overwhelmed with opportunities and offers. You’ll want to do them all. But this is when you need to switch strategies again. This is when you need to say ‘hell yeah or no’ to avoid drowning.
It’s all about widening the funnel to explore what’s right, then closing it down by elimination. That’s the best way to avoid becoming Buridan’s Donkey – paralysed by indecision.
This framework has helped me move forward with confidence and purpose, even when the path ahead wasn’t linear or clear, and success isn’t guaranteed.
