The biggest risk I’ve ever taken wasn’t stepping onto a big stage or calling out the gaps in our startup funding system. It happened long before that. Quietly, almost imperceptibly, when I walked away from a job I genuinely loved.
I was in a well-paid, intellectually fascinating role, surrounded by people who made me laugh every day. The work stretched me. The pace suited me. The mission mattered. By all accounts, it was the kind of job you build your life around.
And that was precisely the problem.
At some point, the question that had been whispering in the background got too loud to ignore:
“What kind of life am I building around this job, and is it the one I actually want?”
When I finally admitted the answer might be “no,” it felt terrifying. Not because anything was wrong, but because everything was right… and I still wanted something different.
Choosing to leave wasn’t dramatic. There was no meltdown, no clash, no last-straw moment. It was a slow, deliberate decision made with full awareness of the privilege and the consequences: start again, build something from nothing, and trade certainty for possibility.
That decision became the foundation of GuessWorks and IfWeRaise, and the beginning of me taking my own life design seriously.
The Internal Risk Of Walking Away From “Good”
It’s easy to think of risk as something that pulls you away from danger. But sometimes the most courageous thing you can do is walk away from something good. Something comfortable. Something that could easily have kept you for a very long time.
Leaving meant giving up intellectual adrenaline on tap, a team I genuinely adored, and a level of financial safety that was deeply reassuring. It meant stepping into the unknown without the guarantee of success, relevance, or even clarity. But it also meant choosing myself. Not in the self-help sense, but in the very practical, structural sense. I was choosing to design my life with intention rather than inherit it by default.
When your internal direction is misaligned with your external reality, something eventually has to move. For me, staying would have meant shrinking. Leaving meant expanding
That decision became the beginning of GuessWorks and soon after, IfWeRaise. And at the time, it was my biggest act of life design. Life design isn’t about chasing constant freedom or avoiding structure; it’s about building the right structure for the life you want. It’s something I now speak about in depth on the Untangling Life Podcast: how to build systems that support who you are, not suppress it.
GuessWorks was my attempt to create a working life where thinking deeply, challenging assumptions, and designing better pathways weren’t side tasks squeezed between meetings, but the whole point.
Why Intentional Life Design Makes Better Leaders
Leaving my job forced me to consider something most leaders avoid: am I shaping my work, or is my work shaping me? That question isn’t just personal; it’s organisational. Leaders who ignore the architecture of their own lives often replicate that lack of intention inside their teams. The result is a culture built around urgency rather than clarity, pressure rather than purpose, and activity rather than impact.
True innovation requires space to think. It requires systems that support curiosity, experimentation, and reflection. When leaders design their own lives with intention, not perfection, but intention, they tend to design better environments for the people around them. They’re less reactive, more thoughtful, and (crucially) more honest.
Calculated Risk Vs. Reckless Hope
Leaving a stable, stimulating job to start a company may look reckless from the outside, but it wasn’t. Recklessness is acting without awareness of the consequences. Calculated risk is acting with full awareness, including the parts that scare you. Before I left, I interrogated everything: my finances, my support network, my worst-case scenarios, the skills I could fall back on, and the kind of life I genuinely wanted to build.
What ultimately made the decision clear wasn’t confidence - it was alignment. When your internal direction is misaligned with your external reality, something eventually has to move. For me, staying would have meant shrinking. Leaving meant expanding.
Rewarding Courage Without Making It Conditional
One of the most subtle but damaging behaviours inside organisations is only rewarding courage when it results in success. That turns bravery into a retrospective performance metric rather than a cultural value. People quickly learn that taking risks is only “sage” when the outcome is guaranteed, which is not real risk-taking at all.
If leaders want courageous teams, they need to reward the decision, not just the result. Recognise the person who raised the uncomfortable truth. Celebrate the thoughtful experiment even when it doesn’t land perfectly. Honour the integrity of the choice, not the neatness of the outcome. That’s how you build a culture where innovation becomes consistent, not accidental.
How Fear Shows Up In Leadership
Fear doesn’t often announce itself as fear. It shows up in behaviours: micromanagement disguised as “high standards,” endless meetings that postpone decisions, defensiveness masquerading as expertise, hiring for sameness instead of diversity, and prioritising optics over outcomes. Fear shrinks leaders into the smallest, safest version of themselves.
The leaders who grow, and help others grow, are the ones who treat fear as data. They ask: What am I afraid of losing? What story am I telling myself? Is this discomfort a sign to stop or a sign to pay attention? Courage doesn’t eliminate fear. It reframes it.
What Failure Has Taught Me
Since starting GuessWorks and IfWeRaise, I’ve made decisions that didn’t land the way I hoped. Programmes that needed redesign. Partnerships that didn’t quite fit. Strategies that looked great in theory but unravelled in practice. And each time, the lesson was the same: Failure is information. It’s not a verdict.
Failure has taught me that resilience is the speed at which you recover clarity, not the volume of effort you can endure. It’s taught me that iteration is the discipline that separates progress from stagnation. And it’s taught me that trust grows fastest when leaders are transparent about what didn’t work, not just when everything is going well.
Resilience is the speed at which you recover clarity, not the volume of effort you can endure.
How I Prepare For Bold Decisions Now
People assume bravery comes from adrenaline. I find it comes from preparation. When I’m about to make a big call, I do three things:
- I get brutally clear on the “why.”
If the purpose is shallow (ego, optics, pressure), the risk won’t hold. If the purpose is deep (fairness, impact, integrity), the fear becomes manageable.
- I create my own “floor.”
I ask: What’s the minimum support system I need so this won’t break me if it goes wrong? For me, that includes my inner circle, data I trust, and a plan for the morning after.
- I imagine the version of myself I’m trying to grow into.
The question isn’t “Can I do this?” It’s “Will doing this make me a leader I’m proud of?”
Once that’s clear, I move. Not because I feel fearless, but because I feel responsible.
The Real Reward
Leaving my job to start GuessWorks and IfWeRaise wasn’t just a career decision. It was a personal turning point that fundamentally reshaped how I lead, work, and design my life. The reward hasn’t simply been the business itself; it’s been the life built around it. A life more grounded in intention, clarity, curiosity, and the courage to choose alignment over autopilot.
Bold leadership isn’t about fearless leaps; it’s about refusing to stay in places that no longer fit who you’re becoming. That, to me, is what courage really looks like.
Want to hear more about this? Check out Untangling Life on your favourite podcast channel, where Hattie Willis and Andy Ayim MBE invite you into their honest conversations about the breakthrough moments, the inevitable knots, and the universal "is this normal?" questions. Each week, they share practical tools and real-context stories to help you break free from limiting beliefs and move toward a life where your work and personal roles feel integrated and aligned.
You can find Hattie Willis on LinkedIn and Instagram.
Member discussion